nitromethane profile

nitromethane: structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

nitromethane : A primary nitroalkane that is methane in which one of the hydrogens is replace by a nitro group. A polar solvent (b.p. 101 degreeC), it is an important starting material in organic synthesis. It is also used as a fuel for rockets and radio-controlled models. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

ID Source	ID
PubMed CID	6375
CHEMBL ID	276924
CHEBI ID	77701
MeSH ID	M0052653

Synonym
AKOS009031372
nitro-methane
ch2no2
inchi=1/ch3no2/c1-2(3)4/h1h
NCGC00091494-01
ai3-00111
nitrometan [polish]
einecs 200-876-6
ccris 1205
nsc 428
un1261
hsdb 106
wln: wn1
75-52-5
nitrometan
methane, nitro-
nsc-428
nitrocarbol
nitromethane
nsc428
nitromethane, puriss., absolute, over molecular sieve (h2o <=0.01%), >=98.5% (gc)
nitromethane [un1261] [flammable liquid]
nitromethane, reagent grade, 96%
CHEMBL276924
chebi:77701 ,
FT-0659976
N0239
N0019
N0209
A838443
NCGC00091494-02
C19275
NCGC00258376-01
tox21_200822
dtxcid40977
dtxsid2020977 ,
cas-75-52-5
unii-ru5wg8c3f4
ru5wg8c3f4 ,
ec 200-876-6
methane, nitro-,ion(1-) (8ci,9ci)
nitromethane [iarc]
nitromethane [usp-rs]
nitromethane [hsdb]
nitromethane [mi]
nitromethane [inci]
nitromethane, acs
nitro- methane
no2ch3
nitro methane
ch3no2
meno2
23717-53-5
un 1261
nitro fuel (salt/mix)
F1908-0092
BR1297
mfcd00007400
nitromethane, saj first grade, >=90.0%
nitromethane, acs reagent, >=95%
nitromethane, for hplc, >=96%
nitromethane, analytical standard
nitromethane, reagentplus(r), >=99.0%
nitromethane, hplc grade
nitromethane, 99.0%
Q407733
STL185630
nitrometane
nitromethane (15n)
nmt(fire protection guide to hazardous materials. 13 ed. quincy, ma: national fire protection association, 2002., p. 49-109)
nitromethane (iarc)
nitromethane (usp-rs)

Excerpt	Reference	Relevance
"Nitromethane is a known toxicant and suspected human carcinogen. "	( Nitromethane Exposure from Tobacco Smoke and Diet in the U.S. Population: NHANES, 2007-2012. Blount, BC; Capella, KM; De Jesús, VR; Espenship, MF; Geldner, NB; Rasio, JP; Reese, CM; Rey deCastro, B; Silva, LK; Smith, MM; Woodford, AM, 2019)	3.4
"Nitromethane (CH3NO2) is an important organic chemical raw material with a wide variety of applications as well as one of the most common pollutants. "	( Highly sensitive amperometric biosensor based on electrochemically-reduced graphene oxide-chitosan/hemoglobin nanocomposite for nitromethane determination. Wang, S; Wen, W; Wen, Y; Zhang, X, 2016)	2.08
"Halonitromethanes (HNMs) are a class of nitrogenous disinfection by-products (N-DBPs) that have so far received little attention and focused largely on trichloronitromethane. "	( Solvent-minimized extraction for determining halonitromethanes and trihalomethanes in water. Gallego, M; Montesinos, I, 2012)	1.19
"Halonitromethanes (HNMs) are a recently identified class of disinfection by-products (DBPs) in drinking water. "	( Mutagenicity in Salmonella of halonitromethanes: a recently recognized class of disinfection by-products in drinking water. DeMarini, DM; Kundu, B; Matthews, PP; Richard, AM; Richardson, SD; Swartz, PD, 2004)	1.16
"Bromonitromethane is an inefficient suicide substrate for glucose oxidase (in contrast to the case of CH(3)CCl=NO(2)(-) and D-amino acid oxidase) because, in the enzyme-substrate encounter step, the required ionization states of enzyme (EH(0)(+), pK(a) approximately 3.5) and substrate (CHBr=NO(2)(-), pK(a) approximately 8.3) cannot be highly populated simultaneously. "	( Active site generation of a protonically unstable suicide substrate from a stable precursor: glucose oxidase and dibromonitromethane. Bright, HJ; Porter, DJ; Voet, JG, 2000)	1.03

Excerpt	Reference	Relevance
"Nitromethane has been shown to interfere with the determination of serum creatinine through the Jaffe reaction."	( Apparent elevated creatinine after ingestion of nitromethane: interference with the Jaffe reaction. Killorn, E; Lim, RK; Rieder, M, 2011)	1.35
"Nitromethane has wide industrial and commercial application as a polar solvent for adhesives and acrylics as well as explosive fuel. "	( Occupational allergic contact dermatitis to nitromethane. Fowler, JF; Webb, KG, 2002)	2.02
"Nitromethane has several properties that make it an interesting solvent for capillary electrophoresis especially for lipophilic analytes that are not sufficiently soluble in water: freezing and boiling points are suitable for laboratory conditions, low viscosity leads to favourable electrophoretic mobilities, or an intermediate dielectric constant enables dissolution of electrolytes. "	( Nitromethane as solvent in capillary electrophoresis. Kenndler, E; Porras, SP; Rosés, M; Subirats, X, 2005)	3.21

Excerpt	Reference	Relevance
"Nitromethane can cause a false elevation of serum creatinine concentration as measured by the widely used Jaffe colorimetric method."	( Creatinine elevation associated with nitromethane exposure: a marker of potential methanol toxicity. Clark, RF; Cook, MD, 2007)	1.33

Excerpt	Reference	Relevance
" However, data on toxic effect from in vivo experiment is limited."	( Comparative toxicity of chloro- and bromo-nitromethanes in mice based on a metabolomic method. Wu, B; Xian, Q; Yin, J; Zhang, XX, 2017)	0.72

Excerpt	Relevance	Reference
" The removal efficiency was affected by initial NDMA concentration; higher NDMA dosing required higher ozone utilization."	( Reinvestigation on the ozonation of N-nitrosodimethylamine: Influencing factors and degradation mechanism. Li, Y; Lv, J; Song, Y, 2013)	0.39
" 1B is not appropriate, based on the fact that rat mammary and harderian tumors are likely not relevant to humans and lung and liver tumors reported in mice were equivocal in their dose-response and statistical significance."	( Hazard characterization of carcinogenicity, mutagenicity, and reproductive toxicity for short chain primary nitroalkanes. Garnick, L; Gillie, C; Kozal, J; Maier, A; Monnot, A; Quinn, J; Spencer, P, 2021)	0.62

Role	Description
EC 4.3.1.3 (histidine ammonia-lyase) inhibitor	An EC 4.3.1.* (ammonia-lyase) inhibitor that interferes with the action of histidine ammonia-lyase (EC 4.3.1.3).
polar aprotic solvent	A solvent with a comparatively high relative permittivity (or dielectric constant), greater than ca. 15, and a sizable permanent dipole moment, that cannot donate suitably labile hydrogen atoms to form strong hydrogen bonds.
explosive	A substance capable of undergoing rapid and highly exothermic decomposition.
NMR chemical shift reference compound	Any compound that produces a peak used to reference an NMR spectrum during data pre-processing.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Class	Description
primary nitroalkane	A nitroalkane in which the nitro group is attached to a terminal carbon. Major microspecies at pH 7.3.
volatile organic compound	Any organic compound having an initial boiling point less than or equal to 250 degreeC (482 degreeF) measured at a standard atmospheric pressure of 101.3 kPa.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathway	Proteins	Compounds
alkylnitronates degradation	3	50

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
thyroid stimulating hormone receptor	Homo sapiens (human)	Potency	30.6379	0.0016	28.0151	77.1139	AID1259385
nuclear factor erythroid 2-related factor 2 isoform 1	Homo sapiens (human)	Potency	48.5577	0.0006	27.2152	1,122.0200	AID743219
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Assay ID	Title	Year	Journal	Article
AID212400	Toxicity determined using Tadpole Narcosis Test	1991	Journal of medicinal chemistry, May, Volume: 34, Issue:5	Using theoretical descriptors in quantitative structure-activity relationships: some toxicological indices.
AID736767	Inhibition of Escherichia coli MetAP expressed in Escherichia coli BL21(lambdaDE3) using Met-AMC as substrate at 10 uM incubated for 30 mins prior to substrate addition measured for 15 mins fluorometric analysis	2013	Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3	Chemical, biochemical and microbiological properties of a brominated nitrovinylfuran with broad-spectrum antibacterial activity.
AID736763	Inhibition of Dengue virus NS2B-NS3 protease expressed in Escherichia coli BL21(lambdaDE3) using Abz-NleKRRS-3-(NO2)Y as substrate at 50 uM incubated for 15 mins prior to substrate addition measured for 15 mins by fluorometric analysis	2013	Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3	Chemical, biochemical and microbiological properties of a brominated nitrovinylfuran with broad-spectrum antibacterial activity.
AID343683	Octanol-water partition coefficient, log P of the compound	2008	Journal of medicinal chemistry, Jul-10, Volume: 51, Issue:13	Toward prediction of alkane/water partition coefficients.
AID736366	Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 after 20 to 24 hrs by broth microdilution assay	2013	Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3	Chemical, biochemical and microbiological properties of a brominated nitrovinylfuran with broad-spectrum antibacterial activity.
AID736771	Inhibition of Escherichia coli MurA expressed in Escherichia coli BL21(lambdaDE3) using UNAG and PEP as substrate incubated for 10 mins prior to PEP addition measured after 60 mins by spectrophotometric analysis	2013	Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3	Chemical, biochemical and microbiological properties of a brominated nitrovinylfuran with broad-spectrum antibacterial activity.
AID736367	Antibacterial activity against Escherichia coli ATCC 25922 after 20 to 24 hrs by broth microdilution assay	2013	Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3	Chemical, biochemical and microbiological properties of a brominated nitrovinylfuran with broad-spectrum antibacterial activity.
AID736758	Cytotoxicity against human A431 cells after 72 hrs by crystal violet staining method	2013	Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3	Chemical, biochemical and microbiological properties of a brominated nitrovinylfuran with broad-spectrum antibacterial activity.
AID736381	Half life of the compound in tris buffer at pH 7.8	2013	Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3	Chemical, biochemical and microbiological properties of a brominated nitrovinylfuran with broad-spectrum antibacterial activity.
AID736770	Inhibition of Escherichia coli MurA C115D mutant expressed in Escherichia coli BL21(lambdaDE3) using UNAG and PEP as substrate incubated for 10 mins prior to PEP addition measured after 60 mins by spectrophotometric analysis	2013	Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3	Chemical, biochemical and microbiological properties of a brominated nitrovinylfuran with broad-spectrum antibacterial activity.
AID19262	Aqueous solubility	2000	Bioorganic & medicinal chemistry letters, Jun-05, Volume: 10, Issue:11	Prediction of drug solubility from Monte Carlo simulations.
AID736757	Cytotoxicity against human MeWo cells after 72 hrs by crystal violet staining method	2013	Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3	Chemical, biochemical and microbiological properties of a brominated nitrovinylfuran with broad-spectrum antibacterial activity.
AID736756	Cytotoxicity against human Calu6 cells after 72 hrs by crystal violet staining method	2013	Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3	Chemical, biochemical and microbiological properties of a brominated nitrovinylfuran with broad-spectrum antibacterial activity.
AID736760	Cytotoxicity against human HaCaT cells after 72 hrs by crystal violet staining method	2013	Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3	Chemical, biochemical and microbiological properties of a brominated nitrovinylfuran with broad-spectrum antibacterial activity.
AID736755	Cytotoxicity against human CaSki cells after 72 hrs by crystal violet staining method	2013	Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3	Chemical, biochemical and microbiological properties of a brominated nitrovinylfuran with broad-spectrum antibacterial activity.
AID736765	Inhibition of human MetAP2 expressed in Escherichia coli BL21(lambdaDE3) using Met-AMC as substrate at 10 uM incubated for 30 mins prior to substrate addition measured for 15 mins fluorometric analysis	2013	Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3	Chemical, biochemical and microbiological properties of a brominated nitrovinylfuran with broad-spectrum antibacterial activity.
AID343684	Alkane-water partition coefficient, log P of the compound	2008	Journal of medicinal chemistry, Jul-10, Volume: 51, Issue:13	Toward prediction of alkane/water partition coefficients.
AID736759	Cytotoxicity against human Flow 2002 cells after 72 hrs by crystal violet staining method	2013	Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3	Chemical, biochemical and microbiological properties of a brominated nitrovinylfuran with broad-spectrum antibacterial activity.
AID736380	Half life of the compound in citrate buffer at pH 6	2013	Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3	Chemical, biochemical and microbiological properties of a brominated nitrovinylfuran with broad-spectrum antibacterial activity.
AID736375	Induction of GSH-adduct formation in citrate buffer at100 uM by RP-LC/MS analysis	2013	Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3	Chemical, biochemical and microbiological properties of a brominated nitrovinylfuran with broad-spectrum antibacterial activity.
AID736374	Induction of GSSG formation in citrate buffer at 100 uM by RP-LC/MS analysis	2013	Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3	Chemical, biochemical and microbiological properties of a brominated nitrovinylfuran with broad-spectrum antibacterial activity.
AID736768	Inhibition of Staphylococcus aureus MurA2 expressed in Escherichia coli BL21(lambdaDE3) using UNAG and PEP as substrate incubated for 10 mins prior to PEP addition measured after 60 mins by spectrophotometric analysis	2013	Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3	Chemical, biochemical and microbiological properties of a brominated nitrovinylfuran with broad-spectrum antibacterial activity.
AID736764	Inhibition of thrombin (unknown origin) expressed in Escherichia coli BL21(lambdaDE3) using Boc-Val-Pro-Arg-AMC as substrate at 25 uM incubated for 15 mins prior to substrate addition measured for 10 mins by fluorometric analysis	2013	Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3	Chemical, biochemical and microbiological properties of a brominated nitrovinylfuran with broad-spectrum antibacterial activity.
AID736762	Antibacterial activity against methicillin-sensitive Staphylococcus aureus ATCC 25923 after 20 to 24 hrs by broth microdilution assay	2013	Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3	Chemical, biochemical and microbiological properties of a brominated nitrovinylfuran with broad-spectrum antibacterial activity.
AID736753	Cytotoxicity against human SW707 cells after 72 hrs by crystal violet staining method	2013	Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3	Chemical, biochemical and microbiological properties of a brominated nitrovinylfuran with broad-spectrum antibacterial activity.
AID736761	Antibacterial activity against methicillin-resistant Staphylococcus aureus NCTC 10442 after 20 to 24 hrs by broth microdilution assay	2013	Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3	Chemical, biochemical and microbiological properties of a brominated nitrovinylfuran with broad-spectrum antibacterial activity.
AID736766	Inhibition of human MetAP1 expressed in Escherichia coli BL21(lambdaDE3) using Met-AMC as substrate at 10 uM incubated for 30 mins prior to substrate addition measured for 15 mins fluorometric analysis	2013	Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3	Chemical, biochemical and microbiological properties of a brominated nitrovinylfuran with broad-spectrum antibacterial activity.
AID736754	Cytotoxicity against human Capan1 cells after 72 hrs by crystal violet staining method	2013	Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3	Chemical, biochemical and microbiological properties of a brominated nitrovinylfuran with broad-spectrum antibacterial activity.
AID736769	Inhibition of Pseudomonas aeruginosa MurA expressed in Escherichia coli BL21(lambdaDE3) using UNAG and PEP as substrate incubated for 10 mins prior to PEP addition measured after 60 mins by spectrophotometric analysis	2013	Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3	Chemical, biochemical and microbiological properties of a brominated nitrovinylfuran with broad-spectrum antibacterial activity.
AID23443	Partition coefficient (logP)	1985	Journal of medicinal chemistry, Mar, Volume: 28, Issue:3	Use of physicochemical parameters in distance geometry and related three-dimensional quantitative structure-activity relationships: a demonstration using Escherichia coli dihydrofolate reductase inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	19 (9.31)	18.7374
1990's	15 (7.35)	18.2507
2000's	66 (32.35)	29.6817
2010's	91 (44.61)	24.3611
2020's	13 (6.37)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	4 (1.94%)	6.00%
Case Studies	22 (10.68%)	4.05%
Observational	0 (0.00%)	0.25%
Other	180 (87.38%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
monoisopropanolamine monoisopropanolamine: possible industrial pollutant; structure. 1-aminopropan-2-ol : Any amino alcohol that is propan-2-ol substituted by an amino group at position 1.	1.96	1	amino alcohol; secondary alcohol	Escherichia coli metabolite
ethylene dichloride ethylene dichloride: RN given refers to 1,2-isomer; structure given in first source. 1,2-dichloroethane : A member of the class of chloroethanes substituted by two chloro groups at positions 1 and 2.	3.49	2	chloroethanes	hepatotoxic agent; mutagen; non-polar solvent
1,2,4-trichlorobenzene 1,2,4-trichlorobenzene : A trichlorobenzene with chloro substituents at positions 1, 2 and 4.	3.07	1	trichlorobenzene
acetic acid Acetic Acid: Product of the oxidation of ethanol and of the destructive distillation of wood. It is used locally, occasionally internally, as a counterirritant and also as a reagent. (Stedman, 26th ed). acetic acid : A simple monocarboxylic acid containing two carbons.	2.4	2	monocarboxylic acid	antimicrobial food preservative; Daphnia magna metabolite; food acidity regulator; protic solvent
acetaldehyde Acetaldehyde: A colorless, flammable liquid used in the manufacture of acetic acid, perfumes, and flavors. It is also an intermediate in the metabolism of alcohol. It has a general narcotic action and also causes irritation of mucous membranes. Large doses may cause death from respiratory paralysis.. acetaldehyde : The aldehyde formed from acetic acid by reduction of the carboxy group. It is the most abundant carcinogen in tobacco smoke.. aldehyde : A compound RC(=O)H, in which a carbonyl group is bonded to one hydrogen atom and to one R group.. acetyl group : A group, formally derived from acetic acid by dehydroxylation, which is fundamental to the biochemistry of all forms of life. When bound to coenzyme A, it is central to the metabolism of carbohydrates and fats.	7.52	2	aldehyde	carcinogenic agent; EC 3.5.1.4 (amidase) inhibitor; electron acceptor; Escherichia coli metabolite; human metabolite; mouse metabolite; mutagen; oxidising agent; Saccharomyces cerevisiae metabolite; teratogenic agent
acetamide acetimidic acid : A carboximidic acid that is acetic acid in which the carbonyl oxygen is replaced by an imino group.	2	1	acetamides; carboximidic acid; monocarboxylic acid amide; N-acylammonia
acetone methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).	4.01	4	ketone body; methyl ketone; propanones; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; human metabolite; polar aprotic solvent
adenine [no description available]	2	1	6-aminopurines; purine nucleobase	Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
ammonium hydroxide azane : Saturated acyclic nitrogen hydrides having the general formula NnHn+2.	2.1	1	azane; gas molecular entity; mononuclear parent hydride	EC 3.5.1.4 (amidase) inhibitor; metabolite; mouse metabolite; neurotoxin; NMR chemical shift reference compound; nucleophilic reagent; refrigerant
benzaldehyde [no description available]	2.74	3	benzaldehydes	EC 3.1.1.3 (triacylglycerol lipase) inhibitor; EC 3.5.5.1 (nitrilase) inhibitor; flavouring agent; fragrance; odorant receptor agonist; plant metabolite
benzene [no description available]	3.49	2	aromatic annulene; benzenes; volatile organic compound	carcinogenic agent; environmental contaminant; non-polar solvent
benzoic acid Benzoic Acid: A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid.. benzoic acid : A compound comprising a benzene ring core carrying a carboxylic acid substituent.. aromatic carboxylic acid : Any carboxylic acid in which the carboxy group is directly bonded to an aromatic ring.	2	1	benzoic acids	algal metabolite; antimicrobial food preservative; drug allergen; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 3.1.1.3 (triacylglycerol lipase) inhibitor; human xenobiotic metabolite; plant metabolite
benzyl alcohol Benzyl Alcohol: A colorless liquid with a sharp burning taste and slight odor. It is used as a local anesthetic and to reduce pain associated with LIDOCAINE injection. Also, it is used in the manufacture of other benzyl compounds, as a pharmaceutic aid, and in perfumery and flavoring.. hydroxytoluene : Any member of the class of toluenes carrying one or more hydroxy substituents.. benzyl alcohol : An aromatic alcohol that consists of benzene bearing a single hydroxymethyl substituent.. aromatic alcohol : Any alcohol in which the alcoholic hydroxy group is attached to a carbon which is itself bonded to an aromatic ring.. aromatic primary alcohol : Any primary alcohol in which the alcoholic hydroxy group is attached to a carbon which is itself bonded to an aromatic ring.	3.07	1	benzyl alcohols	antioxidant; fragrance; metabolite; solvent
betaine glycine betaine : The amino acid betaine derived from glycine.	2.05	1	amino-acid betaine; glycine derivative	fundamental metabolite
bromide Bromides: Salts of hydrobromic acid, HBr, with the bromine atom in the 1- oxidation state. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)	3.33	6	halide anion; monoatomic bromine
1-butanol 1-Butanol: A four carbon linear hydrocarbon that has a hydroxy group at position 1.. butan-1-ol : A primary alcohol that is butane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It it produced in small amounts in humans by the gut microbes.	3.5	2	alkyl alcohol; primary alcohol; short-chain primary fatty alcohol	human metabolite; mouse metabolite; protic solvent
carbon monoxide Carbon Monoxide: Carbon monoxide (CO). A poisonous colorless, odorless, tasteless gas. It combines with hemoglobin to form carboxyhemoglobin, which has no oxygen carrying capacity. The resultant oxygen deprivation causes headache, dizziness, decreased pulse and respiratory rates, unconsciousness, and death. (From Merck Index, 11th ed). carbon monoxide : A one-carbon compound in which the carbon is joined only to a single oxygen. It is a colourless, odourless, tasteless, toxic gas.	2.85	3	carbon oxide; gas molecular entity; one-carbon compound	biomarker; EC 1.9.3.1 (cytochrome c oxidase) inhibitor; human metabolite; ligand; metabolite; mitochondrial respiratory-chain inhibitor; mouse metabolite; neurotoxin; neurotransmitter; P450 inhibitor; probe; signalling molecule; vasodilator agent
formic acid formic acid: RN given refers to parent cpd. formic acid : The simplest carboxylic acid, containing a single carbon. Occurs naturally in various sources including the venom of bee and ant stings, and is a useful organic synthetic reagent. Principally used as a preservative and antibacterial agent in livestock feed. Induces severe metabolic acidosis and ocular injury in human subjects.	1.96	1	monocarboxylic acid	antibacterial agent; astringent; metabolite; protic solvent; solvent
methane Methane: The simplest saturated hydrocarbon. It is a colorless, flammable gas, slightly soluble in water. It is one of the chief constituents of natural gas and is formed in the decomposition of organic matter. (Grant & Hackh's Chemical Dictionary, 5th ed). methane : A one-carbon compound in which the carbon is attached by single bonds to four hydrogen atoms. It is a colourless, odourless, non-toxic but flammable gas (b.p. -161degreeC).	8.58	199	alkane; gas molecular entity; mononuclear parent hydride; one-carbon compound	bacterial metabolite; fossil fuel; greenhouse gas
coumarin 2H-chromen-2-one: coumarin derivative	2.04	1	coumarins	fluorescent dye; human metabolite; plant metabolite
2-cresol 2-cresol: RN given refers to parent cpd. o-cresol : A cresol that is phenol substituted by a methyl group at position 2. It is a minor urinary metabolite of toluene.	3.07	1	cresol	human xenobiotic metabolite
salicylic acid Scalp: The outer covering of the calvaria. It is composed of several layers: SKIN; subcutaneous connective tissue; the occipitofrontal muscle which includes the tendinous galea aponeurotica; loose connective tissue; and the pericranium (the PERIOSTEUM of the SKULL).	2	1	monohydroxybenzoic acid	algal metabolite; antifungal agent; antiinfective agent; EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor; keratolytic drug; plant hormone; plant metabolite
3-cresol 3-cresol: RN given refers to parent cpd. m-cresol : A cresol with the methyl substituent at position 3. It is a minor urinary metabolite of toluene.	3.47	2	cresol	human xenobiotic metabolite
2-nitropropane 2-nitropropane: RN given refers to cpd with locant for nitro moiety in 2 position. 2-nitropropane : A secondary nitroalkane that is propane in which a hydrogen at position 2 has been replaced by a nitro group. Mainly used as a solvent (b.p. 120degreeC).	2.41	2	secondary nitroalkane	carcinogenic agent; hepatotoxic agent; polar aprotic solvent; xenobiotic
propionaldehyde propionaldehyde: may cause respiratory irritation; RN given refers to parent cpd; structure. propanal : An aldehyde that consists of ethane bearing a formyl substituent. The parent of the class of propanals.	2	1	alpha-CH2-containing aldehyde; propanals	Escherichia coli metabolite
4-nitrobenzaldehyde 4-nitrobenzaldehyde: RN given refers to parent cpd. 4-nitrobenzaldehyde : A C-nitro compound that is benzaldehyde substituted at the para-position with a nitro group.	2.44	2	benzaldehydes; C-nitro compound
dibenzofuran Dibenzofurans: Compounds that include the structure of dibenzofuran.. dibenzofurans : Any organic heterotricyclic compound based on a dibenzofuran skeleton and its substituted derivatives thereof.. dibenzofuran : A mancude organic heterotricyclic parent that consists of a furan ring flanked by two benzene rings ortho-fused across the 2,3- and 4,5-positions.	2	1	dibenzofurans; mancude organic heterotricyclic parent; polycyclic heteroarene	xenobiotic
cytosine [no description available]	2	1	aminopyrimidine; pyrimidine nucleobase; pyrimidone	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
alanine [no description available]	2	1	alpha-amino acid; amino acid zwitterion	fundamental metabolite
dimethylamine [no description available]	2.08	1	methylamines; secondary aliphatic amine	metabolite
dimethyl sulfoxide Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.	2.46	2	sulfoxide; volatile organic compound	alkylating agent; antidote; Escherichia coli metabolite; geroprotector; MRI contrast agent; non-narcotic analgesic; polar aprotic solvent; radical scavenger
hexachlorocyclohexane Lindane: An organochlorine insecticide made up of greater than 99% gamma-Hexachlorocyclohexane. It has been used as a pediculicide and scabicide, and shown to cause cancer.. beta-hexachlorocyclohexane : The beta-isomer of hexachlorocyclohexane.	2	1	chlorocyclohexane
glycine [no description available]	6.97	1	alpha-amino acid; amino acid zwitterion; proteinogenic amino acid; serine family amino acid	EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor; fundamental metabolite; hepatoprotective agent; micronutrient; neurotransmitter; NMDA receptor agonist; nutraceutical
indole [no description available]	2.42	2	indole; polycyclic heteroarene	Escherichia coli metabolite
kynurenine Kynurenine: A metabolite of the essential amino acid tryptophan metabolized via the tryptophan-kynurenine pathway.. kynurenine : A ketone that is alanine in which one of the methyl hydrogens is substituted by a 2-aminobenzoyl group.	1.99	1	aromatic ketone; non-proteinogenic alpha-amino acid; substituted aniline	human metabolite
methanol Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.	5.19	15	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
acetanilide acetanilide: a phenylacetamide; use ACETANILIDES for the plural group meaning of the singular term. N-phenylacetamide : A member of the class of acetamides that is acetamide in which one of the hydrogens attached to the nitrogen is substituted by a phenyl group.	2	1	acetamides; anilide	analgesic
naphthalene [no description available]	3.49	2	naphthalenes; ortho-fused bicyclic arene	apoptosis inhibitor; carcinogenic agent; environmental contaminant; mouse metabolite; plant metabolite; volatile oil component
nitrates Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.	2.94	4	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species
nitrites Nitrites: Salts of nitrous acid or compounds containing the group NO2-. The inorganic nitrites of the type MNO2 (where M=metal) are all insoluble, except the alkali nitrites. The organic nitrites may be isomeric, but not identical with the corresponding nitro compounds. (Grant & Hackh's Chemical Dictionary, 5th ed)	3.14	5	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species	human metabolite
nitrous oxide Nitrous Oxide: Nitrogen oxide (N2O). A colorless, odorless gas that is used as an anesthetic and analgesic. High concentrations cause a narcotic effect and may replace oxygen, causing death by asphyxia. It is also used as a food aerosol in the preparation of whipping cream.. dinitrogen oxide : A nitrogen oxide consisting of linear unsymmetrical molecules with formula N2O. While it is the most used gaseous anaesthetic in the world, its major commercial use, due to its solubility under pressure in vegetable fats combined with its non-toxicity in low concentrations, is as an aerosol spray propellant and aerating agent for canisters of 'whipped' cream.	2.07	1	gas molecular entity; nitrogen oxide	analgesic; bacterial metabolite; food packaging gas; food propellant; general anaesthetic; greenhouse gas; inhalation anaesthetic; NMDA receptor antagonist; raising agent; refrigerant; vasodilator agent
1-octanol 1-Octanol: A colorless, slightly viscous liquid used as a defoaming or wetting agent. It is also used as a solvent for protective coatings, waxes, and oils, and as a raw material for plasticizers. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed). octan-1-ol : An octanol carrying the hydroxy group at position 1.	3.07	1	octanol; primary alcohol	antifungal agent; bacterial metabolite; fuel additive; kairomone; plant metabolite
4-nitrophenol 4-nitrophenol: RN given refers to parent cpd. mononitrophenol : A nitrophenol that is phenol carrying a single nitro substituent at unspecified position.. 4-nitrophenol : A member of the class of 4-nitrophenols that is phenol in which the hydrogen that is para to the hydroxy group has been replaced by a nitro group.	3.07	1	4-nitrophenols	human xenobiotic metabolite; mouse metabolite
phenanthrene phenanthrene : A polycyclic aromatic hydrocarbon composed of three fused benzene rings which takes its name from the two terms 'phenyl' and 'anthracene.'	3.07	1	ortho-fused polycyclic arene; ortho-fused tricyclic hydrocarbon; phenanthrenes	environmental contaminant; mouse metabolite
phenol [no description available]	3.49	2	phenols	antiseptic drug; disinfectant; human xenobiotic metabolite; mouse metabolite
1-propanol 1-Propanol: A colorless liquid made by oxidation of aliphatic hydrocarbons that is used as a solvent and chemical intermediate.. propan-1-ol : The parent member of the class of propan-1-ols that is propane in which a hydrogen of one of the methyl groups is replaced by a hydroxy group.	3.49	2	propan-1-ols; short-chain primary fatty alcohol	metabolite; protic solvent
pyridine azine : An organonitrogen compound of general structure RCH=N-N=CHR or RR'C=N-N=CRR'.	4	4	azaarene; mancude organic heteromonocyclic parent; monocyclic heteroarene; pyridines	environmental contaminant; NMR chemical shift reference compound
dimethyl sulfide dimethyl sulfide: structure. dimethyl sulfide : A methyl sulfide in which the sulfur atom is substituted by two methyl groups. It is produced naturally by some marine algae.. methyl sulfide : Any aliphatic sulfide in which at least one of the organyl groups attached to the sulfur is a methyl group.	2	1	aliphatic sulfide	algal metabolite; bacterial xenobiotic metabolite; EC 3.5.1.4 (amidase) inhibitor; Escherichia coli metabolite; marine metabolite
succinic acid Succinic Acid: A water-soluble, colorless crystal with an acid taste that is used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. (Hawley's Condensed Chemical Dictionary, 12th ed, p1099; McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed, p1851). succinic acid : An alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. It is an intermediate metabolite in the citric acid cycle.	2	1	alpha,omega-dicarboxylic acid; C4-dicarboxylic acid	anti-ulcer drug; fundamental metabolite; micronutrient; nutraceutical; radiation protective agent
2-mercaptoacetate [no description available]	1.96	1	sulfur-containing carboxylic acid
toluene methylbenzene : Any alkylbenzene that is benzene substituted with one or more methyl groups.	3.49	2	methylbenzene; toluenes; volatile organic compound	cholinergic antagonist; fuel additive; neurotoxin; non-polar solvent
trimethylamine [no description available]	2	1	methylamines; tertiary amine	Escherichia coli metabolite; human xenobiotic metabolite
uracil 2,4-dihydroxypyrimidine: a urinary biomarker for bipolar disorder	2	1	pyrimidine nucleobase; pyrimidone	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; prodrug; Saccharomyces cerevisiae metabolite
urea pseudourea: clinical use; structure. isourea : A carboximidic acid that is the imidic acid tautomer of urea, H2NC(=NH)OH, and its hydrocarbyl derivatives.	2.39	2	isourea; monocarboxylic acid amide; one-carbon compound	Daphnia magna metabolite; Escherichia coli metabolite; fertilizer; flour treatment agent; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
1-anilino-8-naphthalenesulfonate 1-anilino-8-naphthalenesulfonate: RN given refers to parent cpd. 8-anilinonaphthalene-1-sulfonic acid : A naphthalenesulfonic acid that is naphthalene-1-sulfonic acid substituted by a phenylamino group at position 8.	2.25	1	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
5,5-dimethyl-1-pyrroline-1-oxide 5,5-dimethyl-1-pyrroline-1-oxide: do not confuse with DMPO (4',5'-dihydroxy-7-methoxy-4-phenyl-5,2'-oxidocoumarin). 5,5-dimethyl-1-pyrroline N-oxide : A member of the class of 1-pyrroline nitrones (1-pyrroline N-oxides) resulting from the formal N-oxidation of 5,5-dimethyl-1-pyrroline. Used as a spin trap for the study of radicals formed by enzymatic acetaldehyde oxidation.	1.99	1	1-pyrroline nitrones	neuroprotective agent; spin trapping reagent
phenytoin [no description available]	2	1	imidazolidine-2,4-dione	anticonvulsant; drug allergen; sodium channel blocker; teratogenic agent
acetaminophen Acetaminophen: Analgesic antipyretic derivative of acetanilide. It has weak anti-inflammatory properties and is used as a common analgesic, but may cause liver, blood cell, and kidney damage.. paracetamol : A member of the class of phenols that is 4-aminophenol in which one of the hydrogens attached to the amino group has been replaced by an acetyl group.	2	1	acetamides; phenols	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; cyclooxygenase 3 inhibitor; environmental contaminant; ferroptosis inducer; geroprotector; hepatotoxic agent; human blood serum metabolite; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
theophylline [no description available]	2.42	2	dimethylxanthine	adenosine receptor antagonist; anti-asthmatic drug; anti-inflammatory agent; bronchodilator agent; drug metabolite; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; fungal metabolite; human blood serum metabolite; immunomodulator; muscle relaxant; vasodilator agent
amitriptyline Amitriptyline: Tricyclic antidepressant with anticholinergic and sedative properties. It appears to prevent the re-uptake of norepinephrine and serotonin at nerve terminals, thus potentiating the action of these neurotransmitters. Amitriptyline also appears to antagonize cholinergic and alpha-1 adrenergic responses to bioactive amines.. amitriptyline : An organic tricyclic compound that is 10,11-dihydro-5H-dibenzo[a,d][7]annulene substituted by a 3-(dimethylamino)propylidene group at position 5.	2.04	1	carbotricyclic compound; tertiary amine	adrenergic uptake inhibitor; antidepressant; environmental contaminant; tropomyosin-related kinase B receptor agonist; xenobiotic
aspirin Aspirin: The prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5). acetylsalicylate : A benzoate that is the conjugate base of acetylsalicylic acid, arising from deprotonation of the carboxy group.. acetylsalicylic acid : A member of the class of benzoic acids that is salicylic acid in which the hydrogen that is attached to the phenolic hydroxy group has been replaced by an acetoxy group. A non-steroidal anti-inflammatory drug with cyclooxygenase inhibitor activity.	2	1	benzoic acids; phenyl acetates; salicylates	anticoagulant; antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; EC 1.1.1.188 (prostaglandin-F synthase) inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; plant activator; platelet aggregation inhibitor; prostaglandin antagonist; teratogenic agent
atrazine [no description available]	2	1	chloro-1,3,5-triazine; diamino-1,3,5-triazine	environmental contaminant; herbicide; xenobiotic
baclofen [no description available]	2.77	3	amino acid zwitterion; gamma-amino acid; monocarboxylic acid; monochlorobenzenes; primary amino compound	central nervous system depressant; GABA agonist; muscle relaxant
barbital 5,5-diethylbarbituric acid : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by two ethyl groups. Formerly used as a hypnotic (sleeping aid).	2	1	barbiturates	drug allergen
benzamide benzamide : An aromatic amide that consists of benzene bearing a single carboxamido substituent. The parent of the class of benzamides.	2	1	benzamides
benzocaine Benzocaine: A surface anesthetic that acts by preventing transmission of impulses along NERVE FIBERS and at NERVE ENDINGS.. dextran sulfate sodium : An organic sodium salt of dextran sulfate. It induces colitis in mice.. benzocaine : A benzoate ester having 4-aminobenzoic acid as the acid component and ethanol as the alcohol component. A surface anaesthetic, it is used to suppress the gag reflex, and as a lubricant and topical anaesthetic on the larynx, mouth, nasal cavity, respiratory tract, oesophagus, rectum, urinary tract, and vagina.	2	1	benzoate ester; substituted aniline	allergen; antipruritic drug; sensitiser; topical anaesthetic
bay h 4502 bifonazole : A racemate comprising equimolar amounts of R- and S-bifonazole. It is a broad spectrum antifungal drug used for the treatment of fungal skin and nail infections.. 1-[biphenyl-4-yl(phenyl)methyl]imidazole : A member of the class of imidazoles carrying an alpha-(biphenyl-4-yl)benzyl substituent at position 1.	2	1	biphenyls; imidazoles
bromazepam Bromazepam: One of the BENZODIAZEPINES that is used in the treatment of ANXIETY DISORDERS.	2	1	organic molecular entity
caffeine [no description available]	2.42	2	purine alkaloid; trimethylxanthine	adenosine A2A receptor antagonist; adenosine receptor antagonist; adjuvant; central nervous system stimulant; diuretic; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; environmental contaminant; food additive; fungal metabolite; geroprotector; human blood serum metabolite; mouse metabolite; mutagen; plant metabolite; psychotropic drug; ryanodine receptor agonist; xenobiotic
chlorpromazine Chlorpromazine: The prototypical phenothiazine antipsychotic drug. Like the other drugs in this class chlorpromazine's antipsychotic actions are thought to be due to long-term adaptation by the brain to blocking DOPAMINE RECEPTORS. Chlorpromazine has several other actions and therapeutic uses, including as an antiemetic and in the treatment of intractable hiccup.. chlorpromazine : A substituted phenothiazine in which the ring nitrogen at position 10 is attached to C-3 of an N,N-dimethylpropanamine moiety.	2	1	organochlorine compound; phenothiazines; tertiary amine	anticoronaviral agent; antiemetic; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; phenothiazine antipsychotic drug
4-cresol 4-cresol: RN given refers to parent cpd. p-cresol : A cresol that consists of toluene substituted by a hydroxy group at position 4. It is a metabolite of aromatic amino acid metabolism produced by intestinal microflora in humans and animals.	2	1	cresol	Escherichia coli metabolite; human metabolite; uremic toxin
desipramine Desipramine: A tricyclic dibenzazepine compound that potentiates neurotransmission. Desipramine selectively blocks reuptake of norepinephrine from the neural synapse, and also appears to impair serotonin transport. This compound also possesses minor anticholinergic activity, through its affinity to muscarinic receptors.. desipramine : A dibenzoazepine consisting of 10,11-dihydro-5H-dibenzo[b,f]azepine substituted on nitrogen with a 3-(methylamino)propyl group.	2.42	2	dibenzoazepine; secondary amino compound	adrenergic uptake inhibitor; alpha-adrenergic antagonist; antidepressant; cholinergic antagonist; drug allergen; EC 3.1.4.12 (sphingomyelin phosphodiesterase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; H1-receptor antagonist; serotonin uptake inhibitor
diazepam Diazepam: A benzodiazepine with anticonvulsant, anxiolytic, sedative, muscle relaxant, and amnesic properties and a long duration of action. Its actions are mediated by enhancement of GAMMA-AMINOBUTYRIC ACID activity.. diazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a chloro group at position 7, a methyl group at position 1 and a phenyl group at position 5.	2	1	1,4-benzodiazepinone; organochlorine compound	anticonvulsant; anxiolytic drug; environmental contaminant; sedative; xenobiotic
ddt 1,1-bis(p-chlorophenyl)-2,2,2-trichloroethane: structure in first source	2	1	benzenoid aromatic compound; chlorophenylethane; monochlorobenzenes; organochlorine insecticide	bridged diphenyl acaricide; carcinogenic agent; endocrine disruptor; persistent organic pollutant
diuron Diuron: A pre-emergent herbicide.. diuron : A member of the class of 3-(3,4-substituted-phenyl)-1,1-dimethylureas that is urea in which both of the hydrogens attached to one nitrogen are substituted by methyl groups, and one of the hydrogens attached to the other nitrogen is substituted by a 3,4-dichlorophenyl group.	2	1	3-(3,4-substituted-phenyl)-1,1-dimethylurea; dichlorobenzene	environmental contaminant; mitochondrial respiratory-chain inhibitor; photosystem-II inhibitor; urea herbicide; xenobiotic
valproic acid Valproic Acid: A fatty acid with anticonvulsant and anti-manic properties that is used in the treatment of EPILEPSY and BIPOLAR DISORDER. The mechanisms of its therapeutic actions are not well understood. It may act by increasing GAMMA-AMINOBUTYRIC ACID levels in the brain or by altering the properties of VOLTAGE-GATED SODIUM CHANNELS.. valproic acid : A branched-chain saturated fatty acid that comprises of a propyl substituent on a pentanoic acid stem.	2.04	1	branched-chain fatty acid; branched-chain saturated fatty acid	anticonvulsant; antimanic drug; EC 3.5.1.98 (histone deacetylase) inhibitor; GABA agent; neuroprotective agent; psychotropic drug; teratogenic agent
ether Ether: A mobile, very volatile, highly flammable liquid used as an inhalation anesthetic and as a solvent for waxes, fats, oils, perfumes, alkaloids, and gums. It is mildly irritating to skin and mucous membranes.. ether : An organooxygen compound with formula ROR, where R is not hydrogen.. diethyl ether : An ether in which the oxygen atom is linked to two ethyl groups.	9.2	5	ether; volatile organic compound	inhalation anaesthetic; non-polar solvent; refrigerant
fenbufen fenbufen: structure; RN given refers to parent cpd	2	1	4-oxo monocarboxylic acid; biphenyls	non-steroidal anti-inflammatory drug
fluconazole Fluconazole: Triazole antifungal agent that is used to treat oropharyngeal CANDIDIASIS and cryptococcal MENINGITIS in AIDS.. fluconazole : A member of the class of triazoles that is propan-2-ol substituted at position 1 and 3 by 1H-1,2,4-triazol-1-yl groups and at position 2 by a 2,4-difluorophenyl group. It is an antifungal drug used for the treatment of mucosal candidiasis and for systemic infections including systemic candidiasis, coccidioidomycosis, and cryptococcosis.	2	1	conazole antifungal drug; difluorobenzene; tertiary alcohol; triazole antifungal drug	environmental contaminant; P450 inhibitor; xenobiotic
fluorouracil Fluorouracil: A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.. 5-fluorouracil : A nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth.	2.03	1	nucleobase analogue; organofluorine compound	antimetabolite; antineoplastic agent; environmental contaminant; immunosuppressive agent; radiosensitizing agent; xenobiotic
flurbiprofen Flurbiprofen: An anti-inflammatory analgesic and antipyretic of the phenylalkynoic acid series. It has been shown to reduce bone resorption in periodontal disease by inhibiting CARBONIC ANHYDRASE.. flurbiprofen : A monocarboxylic acid that is a 2-fluoro-[1,1'-biphenyl-4-yl] moiety linked to C-2 of propionic acid. A non-steroidal anti-inflammatory, analgesic and antipyretic, it is used as a pre-operative anti-miotic as well as orally for arthritis or dental pain.	2	1	fluorobiphenyl; monocarboxylic acid	antipyretic; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug
fomepizole Fomepizole: A pyrazole and competitive inhibitor of ALCOHOL DEHYDROGENASE that is used for the treatment of poisoning by ETHYLENE GLYCOL or METHANOL.. fomepizole : A member of the class of pyrazoles that is 1H-pyrazole substituted by a methyl group at position 4.	2.44	2	pyrazoles	antidote; EC 1.1.1.1 (alcohol dehydrogenase) inhibitor; protective agent
halothane [no description available]	1.96	1	haloalkane; organobromine compound; organochlorine compound; organofluorine compound	inhalation anaesthetic
ibuprofen Midol: combination of cinnamedrine, phenacetin, aspirin & caffeine	2	1	monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; environmental contaminant; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; radical scavenger; xenobiotic
lidocaine Lidocaine: A local anesthetic and cardiac depressant used as an antiarrhythmia agent. Its actions are more intense and its effects more prolonged than those of PROCAINE but its duration of action is shorter than that of BUPIVACAINE or PRILOCAINE.. lidocaine : The monocarboxylic acid amide resulting from the formal condensation of N,N-diethylglycine with 2,6-dimethylaniline.	2	1	benzenes; monocarboxylic acid amide; tertiary amino compound	anti-arrhythmia drug; drug allergen; environmental contaminant; local anaesthetic; xenobiotic
imipramine Imipramine: The prototypical tricyclic antidepressant. It has been used in major depression, dysthymia, bipolar depression, attention-deficit disorders, agoraphobia, and panic disorders. It has less sedative effect than some other members of this therapeutic group.. imipramine : A dibenzoazepine that is 5H-dibenzo[b,f]azepine substituted by a 3-(dimethylamino)propyl group at the nitrogen atom.	2.42	2	dibenzoazepine	adrenergic uptake inhibitor; antidepressant; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
indomethacin Indomethacin: A non-steroidal anti-inflammatory agent (NSAID) that inhibits CYCLOOXYGENASE, which is necessary for the formation of PROSTAGLANDINS and other AUTACOIDS. It also inhibits the motility of POLYMORPHONUCLEAR LEUKOCYTES.. indometacin : A member of the class of indole-3-acetic acids that is indole-3-acetic acid in which the indole ring is substituted at positions 1, 2 and 5 by p-chlorobenzoyl, methyl, and methoxy groups, respectively. A non-steroidal anti-inflammatory drug, it is used in the treatment of musculoskeletal and joint disorders including osteoarthritis, rheumatoid arthritis, gout, bursitis and tendinitis.	2	1	aromatic ether; indole-3-acetic acids; monochlorobenzenes; N-acylindole	analgesic; drug metabolite; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; gout suppressant; non-steroidal anti-inflammatory drug; xenobiotic metabolite; xenobiotic
indoprofen Indoprofen: A drug that has analgesic and anti-inflammatory properties. Following reports of adverse reactions including reports of carcinogenicity in animal studies it was withdrawn from the market worldwide. (From Martindale, The Extra Pharmacopoeia, 30th ed, p21). indoprofen : A monocarboxylic acid that is propionic acid in which one of the hydrogens at position 2 is substituted by a 4-(1-oxo-1,3-dihydroisoindol-2-yl)phenyl group. Initially used as an anti-inflammatory and analgesic, it was withdrawn from the market due to causing severe gastrointestinal bleeding. It has been subsequently found to increase production of the survival motor neuron protein.	2	1	gamma-lactam; isoindoles; monocarboxylic acid	EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug
2-propanol 2-Propanol: An isomer of 1-PROPANOL. It is a colorless liquid having disinfectant properties. It is used in the manufacture of acetone and its derivatives and as a solvent. Topically, it is used as an antiseptic.. propan-2-ol : A secondary alcohol that is propane in which one of the hydrogens attached to the central carbon is substituted by a hydroxy group.	4.04	4	secondary alcohol; secondary fatty alcohol	protic solvent
ketoprofen Ketoprofen: An IBUPROFEN-type anti-inflammatory analgesic and antipyretic. It is used in the treatment of rheumatoid arthritis and osteoarthritis.. ketoprofen : An oxo monocarboxylic acid that consists of propionic acid substituted by a 3-benzoylphenyl group at position 2.	2	1	benzophenones; oxo monocarboxylic acid	antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-steroidal anti-inflammatory drug; xenobiotic
lorazepam Lorazepam: A benzodiazepine used as an anti-anxiety agent with few side effects. It also has hypnotic, anticonvulsant, and considerable sedative properties and has been proposed as a preanesthetic agent.	2	1	benzodiazepine
mirtazapine Mirtazapine: A piperazinoazepine tetracyclic compound that enhances the release of NOREPINEPHRINE and SEROTONIN through blockage of presynaptic ALPHA-2 ADRENERGIC RECEPTORS. It also blocks both 5-HT2 and 5-HT3 serotonin receptors and is a potent HISTAMINE H1 RECEPTOR antagonist. It is used for the treatment of depression, and may also be useful for the treatment of anxiety disorders.	2.04	1	benzazepine; tetracyclic antidepressant	alpha-adrenergic antagonist; anxiolytic drug; H1-receptor antagonist; histamine antagonist; oneirogen; serotonergic antagonist
nevirapine Nevirapine: A potent, non-nucleoside reverse transcriptase inhibitor used in combination with nucleoside analogues for treatment of HIV INFECTIONS and AIDS.. nevirapine : A dipyridodiazepine that is 5,11-dihydro-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepine which is substituted by methyl, oxo, and cyclopropyl groups at positions 4, 6, and 11, respectively. A non-nucleoside reverse transcriptase inhibitor with activity against HIV-1, it is used in combination with other antiretrovirals for the treatment of HIV infection.	2	1	cyclopropanes; dipyridodiazepine	antiviral drug; HIV-1 reverse transcriptase inhibitor
nifedipine Nifedipine: A potent vasodilator agent with calcium antagonistic action. It is a useful anti-anginal agent that also lowers blood pressure.	2	1	C-nitro compound; dihydropyridine; methyl ester	calcium channel blocker; human metabolite; tocolytic agent; vasodilator agent
oxazepam Oxazepam: A benzodiazepine used in the treatment of anxiety, alcohol withdrawal, and insomnia.. oxazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a chloro group at position 7, a hydroxy group at position 3 and phenyl group at position 5.	2	1	1,4-benzodiazepinone; organochlorine compound	anxiolytic drug; environmental contaminant; xenobiotic
perphenazine Perphenazine: An antipsychotic phenothiazine derivative with actions and uses similar to those of CHLORPROMAZINE.. perphenazine : A phenothiazine derivative in which the phenothiazine tricycle carries a chloro substituent at the 2-position and a 3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl group at N-10.	2	1	N-(2-hydroxyethyl)piperazine; N-alkylpiperazine; organochlorine compound; phenothiazines	antiemetic; dopaminergic antagonist; phenothiazine antipsychotic drug
phenacetin Saridon: contains phenacetin, caffeine, propyphenazone & pyrithyldione	2	1	acetamides; aromatic ether	cyclooxygenase 3 inhibitor; non-narcotic analgesic; peripheral nervous system drug
phenobarbital Phenobarbital: A barbituric acid derivative that acts as a nonselective central nervous system depressant. It potentiates GAMMA-AMINOBUTYRIC ACID action on GABA-A RECEPTORS, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations.. phenobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and phenyl groups.	2	1	barbiturates	anticonvulsant; drug allergen; excitatory amino acid antagonist; sedative
phenolphthalein Phenolphthalein: An acid-base indicator which is colorless in acid solution, but turns pink to red as the solution becomes alkaline. It is used medicinally as a cathartic.	2	1	phenols
piracetam Piracetam: A compound suggested to be both a nootropic and a neuroprotective agent.	2.03	1	organonitrogen compound; organooxygen compound
potassium iodide Potassium Iodide: An inorganic compound that is used as a source of iodine in thyrotoxic crisis and in the preparation of thyrotoxic patients for thyroidectomy. (From Dorland, 27th ed). potassium iodide : A metal iodide salt with a K(+) counterion. It is a scavenger of hydroxyl radicals.	1.98	1	potassium salt	expectorant; radical scavenger
procaine Procaine: A local anesthetic of the ester type that has a slow onset and a short duration of action. It is mainly used for infiltration anesthesia, peripheral nerve block, and spinal block. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1016).. procaine : A benzoate ester, formally the result of esterification of 4-aminobenzoic acid with 2-diethylaminoethanol but formed experimentally by reaction of ethyl 4-aminobenzoate with 2-diethylaminoethanol.	2	1	benzoate ester; substituted aniline; tertiary amino compound	central nervous system depressant; drug allergen; local anaesthetic; peripheral nervous system drug
promazine Promazine: A phenothiazine with actions similar to CHLORPROMAZINE but with less antipsychotic activity. It is primarily used in short-term treatment of disturbed behavior and as an antiemetic.. promazine : A phenothiazine deriative in which the phenothiazine tricycle has a 3-(dimethylaminopropyl) group at the N-10 position.	2	1	phenothiazines; tertiary amine	antiemetic; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; H1-receptor antagonist; muscarinic antagonist; phenothiazine antipsychotic drug; serotonergic antagonist
pyrilamine Pyrilamine: A histamine H1 antagonist. It has mild hypnotic properties and some local anesthetic action and is used for allergies (including skin eruptions) both parenterally and locally. It is a common ingredient of cold remedies.. mepyramine : An ethylenediamine derivative that is ethylenediamine in which one of the amino nitrogens is substituted by two methyl groups and the remaining amino nitrogen is substituted by a 4-methoxybenzyl and a pyridin-2-yl group.	2.04	1	aromatic ether; ethylenediamine derivative	H1-receptor antagonist
risperidone Risperidone: A selective blocker of DOPAMINE D2 RECEPTORS and SEROTONIN 5-HT2 RECEPTORS that acts as an atypical antipsychotic agent. It has been shown to improve both positive and negative symptoms in the treatment of SCHIZOPHRENIA.. risperidone : A member of the class of pyridopyrimidines that is 2-methyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one carrying an additional 2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl group at position 2.	2.04	1	1,2-benzoxazoles; heteroarylpiperidine; organofluorine compound; pyridopyrimidine	alpha-adrenergic antagonist; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; H1-receptor antagonist; psychotropic drug; second generation antipsychotic; serotonergic antagonist
rolipram [no description available]	7.07	1	pyrrolidin-2-ones	antidepressant; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor
thioridazine Thioridazine: A phenothiazine antipsychotic used in the management of PHYCOSES, including SCHIZOPHRENIA.. thioridazine : A phenothiazine derivative having a methylsulfanyl subsitituent at the 2-position and a (1-methylpiperidin-2-yl)ethyl] group at the N-10 position.	2	1	phenothiazines; piperidines	alpha-adrenergic antagonist; dopaminergic antagonist; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; first generation antipsychotic; H1-receptor antagonist; serotonergic antagonist
trifluoperazine [no description available]	2	1	N-alkylpiperazine; N-methylpiperazine; organofluorine compound; phenothiazines	antiemetic; calmodulin antagonist; dopaminergic antagonist; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor; EC 5.3.3.5 (cholestenol Delta-isomerase) inhibitor; phenothiazine antipsychotic drug
triflupromazine Triflupromazine: A phenothiazine used as an antipsychotic agent and as an antiemetic.. triflupromazine : A member of the class of phenothiazines that is 10H-phenothiazine having a trifluoromethyl subsitituent at the 2-position and a 3-(dimethylamino)propyl group at the N-10 position.	2	1	organofluorine compound; phenothiazines; tertiary amine	anticoronaviral agent; antiemetic; dopaminergic antagonist; first generation antipsychotic
trimethoprim Trimethoprim: A pyrimidine inhibitor of dihydrofolate reductase, it is an antibacterial related to PYRIMETHAMINE. It is potentiated by SULFONAMIDES and the TRIMETHOPRIM, SULFAMETHOXAZOLE DRUG COMBINATION is the form most often used. It is sometimes used alone as an antimalarial. TRIMETHOPRIM RESISTANCE has been reported.. trimethoprim : An aminopyrimidine antibiotic whose structure consists of pyrimidine 2,4-diamine and 1,2,3-trimethoxybenzene moieties linked by a methylene bridge.	1.96	1	aminopyrimidine; methoxybenzenes	antibacterial drug; diuretic; drug allergen; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; environmental contaminant; xenobiotic
corticosterone [no description available]	2	1	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone	human metabolite; mouse metabolite
carbachol Carbachol: A slowly hydrolyzed CHOLINERGIC AGONIST that acts at both MUSCARINIC RECEPTORS and NICOTINIC RECEPTORS.	1.96	1	ammonium salt; carbamate ester	cardiotonic drug; miotic; muscarinic agonist; nicotinic acetylcholine receptor agonist; non-narcotic analgesic
prednisone Prednisone: A synthetic anti-inflammatory glucocorticoid derived from CORTISONE. It is biologically inert and converted to PREDNISOLONE in the liver.. prednisone : A synthetic glucocorticoid drug that is particularly effective as an immunosuppressant, and affects virtually all of the immune system. Prednisone is a prodrug that is converted by the liver into prednisolone (a beta-hydroxy group instead of the oxo group at position 11), which is the active drug and also a steroid.	2	1	11-oxo steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	adrenergic agent; anti-inflammatory drug; antineoplastic agent; immunosuppressive agent; prodrug
carbon tetrachloride Carbon Tetrachloride: A solvent for oils, fats, lacquers, varnishes, rubber waxes, and resins, and a starting material in the manufacturing of organic compounds. Poisoning by inhalation, ingestion or skin absorption is possible and may be fatal. (Merck Index, 11th ed). tetrachloromethane : A chlorocarbon that is methane in which all the hydrogens have been replaced by chloro groups.	3.07	1	chlorocarbon; chloromethanes	hepatotoxic agent; refrigerant
chloramphenicol Amphenicol: Chloramphenicol and its derivatives.	7.44	2	C-nitro compound; carboxamide; diol; organochlorine compound	antibacterial drug; antimicrobial agent; Escherichia coli metabolite; geroprotector; Mycoplasma genitalium metabolite; protein synthesis inhibitor
aspartic acid Aspartic Acid: One of the non-essential amino acids commonly occurring in the L-form. It is found in animals and plants, especially in sugar cane and sugar beets. It may be a neurotransmitter.. aspartic acid : An alpha-amino acid that consists of succinic acid bearing a single alpha-amino substituent. L-aspartic acid : The L-enantiomer of aspartic acid.	2.03	1	aspartate family amino acid; aspartic acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; mouse metabolite; neurotransmitter
cyanides Cyanides: Inorganic salts of HYDROGEN CYANIDE containing the -CN radical. The concept also includes isocyanides. It is distinguished from NITRILES, which denotes organic compounds containing the -CN radical.. cyanides : Salts and C-organyl derivatives of hydrogen cyanide, HC#N.. isocyanide : The isomer HN(+)#C(-) of hydrocyanic acid, HC#N, and its hydrocarbyl derivatives RNC (RN(+)#C(-)).. cyanide : A pseudohalide anion that is the conjugate base of hydrogen cyanide.	6.96	1	pseudohalide anion	EC 1.9.3.1 (cytochrome c oxidase) inhibitor
adenosine diphosphate Adenosine Diphosphate: Adenosine 5'-(trihydrogen diphosphate). An adenine nucleotide containing two phosphate groups esterified to the sugar moiety at the 5'-position.	1.98	1	adenosine 5'-phosphate; purine ribonucleoside 5'-diphosphate	fundamental metabolite; human metabolite
aniline [no description available]	9	4	anilines; primary arylamine
dimethylnitrosamine Dimethylnitrosamine: A nitrosamine derivative with alkylating, carcinogenic, and mutagenic properties. It causes serious liver damage and is a hepatocarcinogen in rodents.	2.4	2	nitrosamine	geroprotector; mutagen
phenylalanine Phenylalanine: An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE.. L-phenylalanine : The L-enantiomer of phenylalanine.. phenylalanine : An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.	1.96	1	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; phenylalanine; proteinogenic amino acid	algal metabolite; EC 3.1.3.1 (alkaline phosphatase) inhibitor; Escherichia coli metabolite; human xenobiotic metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
chloroform Chloroform: A commonly used laboratory solvent. It was previously used as an anesthetic, but was banned from use in the U.S. due to its suspected carcinogenicity.. chloroform : A one-carbon compound that is methane in which three of the hydrogens are replaced by chlorines.	3.47	2	chloromethanes; one-carbon compound	carcinogenic agent; central nervous system drug; inhalation anaesthetic; non-polar solvent; refrigerant
bromoacetate [no description available]	1.96	1
dimethylformamide Dimethylformamide: A formamide in which the amino hydrogens are replaced by methyl groups.. N,N-dimethylformamide : A member of the class of formamides that is formamide in which the amino hydrogens are replaced by methyl groups.	3.07	1	formamides; volatile organic compound	geroprotector; hepatotoxic agent; polar aprotic solvent
mannitol [no description available]	2	1	mannitol	allergen; antiglaucoma drug; compatible osmolytes; Escherichia coli metabolite; food anticaking agent; food bulking agent; food humectant; food stabiliser; food thickening agent; hapten; metabolite; osmotic diuretic; sweetening agent
4-toluenesulfonamide 4-toluenesulfonamide: RN given refers to parent cpd. toluene-4-sulfonamide : A sulfonamide that is benzenesulfonamide bearing a methyl group at position 4.	2	1	sulfonamide
histidine Histidine: An essential amino acid that is required for the production of HISTAMINE.. L-histidine : The L-enantiomer of the amino acid histidine.. histidine : An alpha-amino acid that is propanoic acid bearing an amino substituent at position 2 and a 1H-imidazol-4-yl group at position 3.	2.37	2	amino acid zwitterion; histidine; L-alpha-amino acid; polar amino acid zwitterion; proteinogenic amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
n-pentanol n-pentanol: RN given refers to parent cpd. pentan-1-ol : A short-chain primary fatty alcohol that is pentane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It has been isolated from Melicope ptelefolia.	3.07	1	pentanol; short-chain primary fatty alcohol	human metabolite; plant metabolite
1,1,1-trichloroethane Trichloroethanes: Chlorinated ethanes which are used extensively as industrial solvents. They have been utilized in numerous home-use products including spot remover preparations and inhalant decongestant sprays. These compounds cause central nervous system and cardiovascular depression and are hepatotoxic. Include 1,1,1- and 1,1,2-isomers.. 1,1,1-trichloroethane : A member of the class of chloroethanes carrying three chloro substituents at position 1.	3.77	3	chloroethanes	polar solvent
methyl bromide methyl bromide: used in ionization chambers, degreasing wool, extracting oils; insect fumigant; high concentrations can produce pulmonary edema,narcosis; chronic exposure can cause CNS depression,kidney injury; RN given refers to parent cpd; structure. bromomethane : A one-carbon compound in which the carbon is attached by single bonds to three hydrogen atoms and one bromine atom. It is produced naturally by marine algae.	3.47	2	bromohydrocarbon; bromomethanes; methyl halides	algal metabolite; fumigant insecticide; marine metabolite
ethane Ethane: A two carbon alkane with the formula H3C-CH3.. ethane : An alkane comprising of two carbon atoms.	4.74	9	alkane; gas molecular entity	plant metabolite; refrigerant
ethylene Plastipore: high density polyethylene sponge biocompatible material; used as posts in dental bridges	1.96	1	alkene; gas molecular entity	plant hormone; refrigerant
acetylene [no description available]	1.96	1	alkyne; gas molecular entity; terminal acetylenic compound
methyl chloride Methyl Chloride: A hydrocarbon used as an industrial solvent. It has been used as an aerosal propellent, as a refrigerant and as a local anesthetic. (From Martindale, The Extra Pharmacopoeia, 31st ed, p1403). chlorocarbon : Compounds consisting wholly of chlorine and carbon.. chloromethane : A one-carbon compound that is methane in which one of the hydrogens is replaced by a chloro group.	2.4	2	chloromethanes; methyl halides	marine metabolite; mutagen; refrigerant
methyl iodide methyl iodide: RN given refers to unlabeled cpd with MF of CH3-I. iodomethane : A member of the class of iodomethanes that is methane in which one of the hydrogens is replaced by iodine.	1.96	1	iodomethanes; methyl halides	fumigant insecticide
methylamine methyl group : An alkyl group that is the univalent group derived from methane by removal of a hydrogen atom.	2.71	3	methylamines; one-carbon compound; primary aliphatic amine	mouse metabolite
propane Propane: A three carbon alkane with the formula H3CCH2CH3.	9.23	5	alkane; gas molecular entity	food propellant
methylacetylene methylacetylene: structure	1.96	1	alkyne; gas molecular entity; terminal acetylenic compound
ethyl chloride Ethyl Chloride: A gas that condenses under slight pressure. Because of its low boiling point ethyl chloride sprayed on skin produces an intense cold by evaporation. Cold blocks nerve conduction. Ethyl chloride has been used in surgery but is primarily used to relieve local pain in sports medicine.. chloroethane : The simplest and least toxic member of the class of chloroethanes, that is ethane in which a single hydrogen is substituted by a chlorine. A colourless gas at room temperature and pressure (boiling point 12degreeC), it is used as a mild topical anaesthetic to numb the skin prior to ear piercing, skin biopsies, etc., and is also used in the treatment of sports injuries. It was formerly used in the production of tetraethyllead.	3.78	3	chloroethanes	antipruritic drug; inhalation anaesthetic; local anaesthetic
ethylamine ethylamine : A two-carbon primary aliphatic amine.	2.38	2	primary aliphatic amine	human metabolite
acetonitrile acetonitrile: RN given refers to unlabeled cpd. acetonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a methyl group.	4.62	8	aliphatic nitrile; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent
methylene chloride Methylene Chloride: A chlorinated hydrocarbon that has been used as an inhalation anesthetic and acts as a narcotic in high concentrations. Its primary use is as a solvent in manufacturing and food technology.. dichloromethane : A member of the class of chloromethanes that is methane in which two of the hydrogens have been replaced by chlorine. A dense, non-flammible colourless liquid at room temperature (b.p. 40degreeC, d = 1.33) which is immiscible with water, it is widely used as a solvent, a paint stripper, and for the removal of caffeine from coffee and tea.	3.78	3	chloromethanes; volatile organic compound	carcinogenic agent; polar aprotic solvent; refrigerant
difluoromethane difluoromethane: structure given in first source	1.96	1	fluoromethanes	refrigerant
formaldoxime formaldoxime: structure in first source. nitrone : A nitrogen ylide obtained by oxygenation of any imine.	2.06	1
2-propylamine 2-propylamine: RN given refers to parent cpd	1.96	1	alkylamines; primary aliphatic amine
1,1-dichloroethane [no description available]	3.47	2	organochlorine compound
1,1-difluoroethane [no description available]	1.96	1
1,1-difluoroethylene 1,1-difluoroethylene: structure	1.96	1	olefinic compound; organofluorine compound
dichlorofluoromethane [no description available]	1.96	1
fluorocarbon 22 [no description available]	1.96	1	hydrochlorofluorocarbon
tert-butyl alcohol tert-Butyl Alcohol: An isomer of butanol that contains a tertiary butyl group that consists of three methyl groups, each separately attached to a central (tertiary) carbon.. tert-butanol : A tertiary alcohol alcohol that is isobutane substituted by a hydroxy group at position 2.	3.49	2	tertiary alcohol	human xenobiotic metabolite
tert-amyl alcohol 2-methylbutan-2-ol : A tertiary alcohol that is propan-1-ol in which both of the hydrogens at position 1 have been replaced by methyl groups.	3.07	1	aliphatic alcohol; tertiary alcohol	protic solvent
trifluoroethanol Trifluoroethanol: A non-aqueous co-solvent that serves as tool to study protein folding. It is also used in various pharmaceutical, chemical and engineering applications.	1.96	1	fluoroalcohol
chloropicrin chloropicrin: major descriptor (66-85); on-line search HYDROCARBONS, CHLORINATED (66-85); Index Medicus search CHLOROPICRIN (66-85). chloropicrin : A C-nitro compound that is nitromethane in which all three hydrogens are replaced by chlorines. It is a severe irritant, and can cause immediate, severe inflammation of the eyes, nose and throat, and significant injuries to the upper and lower respiratory tract. Formerly stockpiled as a chemical warfare agent, it has been widely used in the US as a soil fumigant, particularly for strawberry crops. It is not approved for use within the European Union.	8.23	5	C-nitro compound; one-carbon compound; organochlorine compound	antifungal agrochemical; fumigant insecticide; nematicide
freon 114 Freon 114: InChIKey: DDMOUSALMHHKOS-UHFFFAOYSA-N	1.96	1
perfluoroethane [no description available]	1.96	1	fluoroalkane; fluorocarbon	refrigerant
isobutyl alcohol isobutyl alcohol: RN given refers to parent cpd	3.5	2	alkyl alcohol; primary alcohol	Saccharomyces cerevisiae metabolite
propylene dichloride propylene dichloride: Russian drug; structure. 1,2-dichloropropane : A chloroalkane that is propane in which a hydrogen from each of two adjacent carbons has been replaced by chlorines.	3.07	1	chloroalkane; volatile organic compound
2-butanol 2-butanol: RN given is for parent cpd without isomeric designation. butan-2-ol : A secondary alcohol that is butane substituted by a hydroxy group at position 2.	3.07	1	secondary alcohol
methylethyl ketone methylethyl ketone: solvent; colorless synthetic resins, smokeless powders; may be irritating to eyes, mucous membranes; may be toxic in high concentrations; structure. butanone : Any ketone that is butane substituted by an oxo group at unspecified position.. butan-2-one : A dialkyl ketone that is a four-carbon ketone carrying a single keto- group at position C-2.	3.77	3	butanone; dialkyl ketone; methyl ketone; volatile organic compound	bacterial metabolite; polar aprotic solvent
1,1,2-trichloroethane 1,1,2-trichloroethane: RN given refers to cpd with locants as specified. 1,1,2-trichloroethane : A member of the class of chloroethanes that is ethane substituted by chloro groups at positions 1, 1 and 2.	3.07	1	chloroethanes
trichloroethylene Trichloroethylene: A highly volatile inhalation anesthetic used mainly in short surgical procedures where light anesthesia with good analgesia is required. It is also used as an industrial solvent. Prolonged exposure to high concentrations of the vapor can lead to cardiotoxicity and neurological impairment.. triol : A chemical compound containing three hydroxy groups.	3.77	3	chloroethenes	inhalation anaesthetic; mouse metabolite
n-methylacetamide N-methylacetamide: RN given refers to parent cpd. N-methylacetamide : A monocarboxylic acid amide that is the N-methyl derivative of acetamide.	1.96	1	acetamides; monocarboxylic acid amide	metabolite
methyl acetate methyl acetate : An acetate ester resulting from the formal condensation of acetic acid with methanol. A low-boiling (57 degreeC) colourless, flammable liquid, it is used as a solvent for many resins and oils.	2.38	2	acetate ester; methyl ester; volatile organic compound	EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor; fragrance; polar aprotic solvent
nitroethane nitroethane : A nitroalkane that is ethane substituted by a nitro group.	4.81	10	primary nitroalkane
1,1,2,2-tetrachloroethane 1,1,2,2-tetrachloroethane: see also record for tetrachloroethane. 1,1,2,2-tetrachloroethane : A member of the class of chloroethanes that is ethane substituted by chloro groups at positions 1, 1, 2 and 2.	3.07	1	chloroethanes
fluorene [no description available]	2	1	ortho-fused polycyclic arene; ortho-fused tricyclic hydrocarbon
1,2,3-trichlorobenzene trichlorobenzene: commercial grade of trichlorobenzene containing 70% 1,2,4-trichlorobenzene & 30% 1,2,3-trichlorobenzene; see also record for 1,2,4-trichlorobenzene. trichlorobenzene : Any member of the class of chlorobenzenes carrying three chloro substituents at unspecified positions.. 1,2,3-trichlorobenzene : A trichlorobenzene carrying chloro substituents at positions 1, 2 and 3.	3.07	1	trichlorobenzene
hexamethylbenzene hexamethylbenzene : A methylbenzene that is benzene in which all six hydrogens have been replaced by methyl groups.	2	1	methylbenzene
2-nitrotoluene nitrotoluene : Any member of the class of toluenes bearing one or more nitro substituents on the benzene ring.	3.07	1	mononitrotoluene	carcinogenic agent; environmental contaminant
picric acid picric acid: used as antiseptic, astringent & stimulant for epitheliazation; structure. picric acid : A C-nitro compound comprising phenol having three nitro substtituents at the 2-, 4- and 6-positions.	2.47	2	C-nitro compound	antiseptic drug; explosive; fixative
thymol Thymol: A phenol obtained from thyme oil or other volatile oils used as a stabilizer in pharmaceutical preparations, and as an antiseptic (antibacterial or antifungal) agent.. thymol : A phenol that is a natural monoterpene derivative of cymene.	3.07	1	monoterpenoid; phenols	volatile oil component
salicylaldehyde o-hydroxybenzaldehyde: structure in first source	2.07	1	hydroxybenzaldehyde	nematicide; plant metabolite
quinoxalines quinoxaline : A naphthyridine in which the nitrogens are at positions 1 and 4.	7.47	2	mancude organic heterobicyclic parent; naphthyridine; ortho-fused heteroarene
quinoline [no description available]	3.79	3	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinolines
diphenyl diphenyl: RN given refers to unlabeled cpd; structure	2	1	aromatic fungicide; benzenes; biphenyls	antifungal agrochemical; antimicrobial food preservative
benzidine benzidine: RN given refers to parent cpd. benzidine : A member of the class of biphenyls that is 1,1'-biphenyl in which the hydrogen at the para-position of each phenyl group has been replaced by an amino group.	2	1	biphenyls; substituted aniline	carcinogenic agent
methyl benzoate methyl benzoate : A benzoate ester obtained by condensation of benzoic acid and methanol.	2	1	benzoate ester; methyl ester	insect attractant; metabolite
benzothiazole benzothiazole: structure. benzothiazole : An organic heterobicyclic compound that is a fusion product between benzene and thiazole. The parent of the class of benzothiazoles.	2.04	1	benzothiazoles	environmental contaminant; plant metabolite; xenobiotic
2-xylene 2-xylene: RN given refers to parent cpd. o-xylene : A xylene substituted by methyl groups at positions 1 and 2.	3.07	1	xylene
2-dichlorobenzene 2-dichlorobenzene: structure. 1,2-dichlorobenzene : A dichlorobenzene carrying chloro substituents at positions 1 and 2.	3.07	1	dichlorobenzene	hepatotoxic agent; metabolite
1,2,4,5-tetrachlorobenzene 1,2,4,5-tetrachlorobenzene : A tetrachlorobenzene carrying chloro groups at positions 1, 2, 4 and 5.	3.07	1	tetrachlorobenzene
1,2,3-trichloropropane [no description available]	7.02	1	organochlorine compound
diethyl ketone diethyl ketone: RN given refers to unlabeled parent cpd. pentan-3-one : A pentanone that is pentane carrying an oxo group at position 3. It has been isolated from Triatoma brasiliensis and Triatoma infestans.	3.07	1	pentanone	animal metabolite
cyclopentanol [no description available]	3.07	1	cyclopentanols
ethyl 2-methylpropanoate ethyl isobutyrate : A fatty acid ethyl ester obtained by the formal condensation of isobutyric acid with ethanol.	3.07	1	fatty acid ethyl ester	plant metabolite
benzotrifluoride alpha,alpha,alpha-trifluorotoluene: structure in first source. (trifluoromethyl)benzene : A fluorohydrocarbon that is fluoroform in which the hydrogen is substituted by a phenyl group.	2	1	(trifluoromethyl)benzenes; fluorohydrocarbon	environmental contaminant; NMR chemical shift reference compound; solvent
benzenesulfonamide [no description available]	1.96	1	sulfonamide
butylphen butylphen: irritant; structure. 4-tert-butylphenol : A member of the class of phenols that is phenol substituted with a tert-butyl group at position 4.	3.49	2	phenols	allergen
acetophenone acetophenone : A methyl ketone that is acetone in which one of the methyl groups has been replaced by a phenyl group.	3.79	3	acetophenones	animal metabolite; photosensitizing agent; xenobiotic
nitrobenzene nitrobenzene : A nitroarene consisting of benzene carrying a single nitro substituent. An industrial chemical used widely in the production of aniline.	4.19	5	nitroarene; nitrobenzenes
3-nitrotoluene [no description available]	1.96	1	mononitrotoluene
carvone carvone: an oxidized derivative of limonene; RN given refers to cpd without isomeric designation; L-carvone has spearmint flavor, D-carvone has dill/caraway flavor. carvone : A p-menthane monoterpenoid that consists of cyclohex-2-enone having methyl and isopropenyl substituents at positions 2 and 5, respectively.	2	1	botanical anti-fungal agent; carvones	allergen
3-dinitrobenzene dinitrobenzene : Any member of the class of nitrobenzenes that consists of a benzene ring substituted by two nitro groups. A closed class.. 1,3-dinitrobenzene : A dinitrobenzene that is benzene disubstituted at positions 1 and 3 with nitro groups.	1.96	1	dinitrobenzene	neurotoxin
ethylbenzene [no description available]	2	1	alkylbenzene
benzonitrile benzonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a phenyl group.	2.42	2	benzenes; nitrile
4-cyanopyridine 4-cyanopyridine: spectroscopic probe for cytochrome P450 BM3	2.04	1
anisole anisole : A monomethoxybenzene that is benzene substituted by a methoxy group.	4	4	monomethoxybenzene	plant metabolite
methylphenylsulfide thioanisole : An aryl sulfide that is thiophenol in which the hydrogen of the thiol group has been replaced by a methyl group.	1.96	1	aryl sulfide; benzenes
ethyl propionate ethyl propionate: cholesterol gallstone solvent. ethyl propionate : A propanoate ester of ethanol.	3.07	1	propanoate ester	metabolite
diethyl malonate diethyl malonate: isomer of diethylmalonic acid; one of most used compounds in drug synthesis, don't confuse with ethylmalonic acid	2.08	1	dicarboxylic acid
ethyl butyrate ethyl butyrate : A butyrate ester resulting from the formal condensation of the hydroxy group of ethanol with the carboxy group of butyric acid.	3.07	1	butyrate ester	plant metabolite
2,4-dimethylphenol 2,4-dimethylphenol: RN given refers to parent cpd. 2,4-xylenol : A member of the class of phenols that phenol substituted by methyl groups at positions 2 and 4.	3.07	1	aromatic fungicide; phenols	disinfectant; volatile oil component
4-chloroaniline 4-chloroaniline: RN given refers to parent cpd; structure. 4-chloroaniline : A chloroaniline in which the chloro atom is para to the aniline amino group.	2	1	chloroaniline; monochlorobenzenes
1,2-epoxybutane 1,2-epoxybutane: RN given refers to cpd with unspecified isomeric designation	2	1	epoxide
1-bromopropane 1-bromopropane: used as a solvent. 1-bromopropane : A bromoalkane that is propane carrying a bromo substituent at position 1.	2	1	bromoalkane; bromohydrocarbon	neurotoxin; solvent
1-butene but-1-ene : A butene with unsaturation at position 1.	1.96	1	butene
propylamine propylamine : A member of the class of alkylamines that is propane substituted by an amino group at C-1.	1.96	1	alkylamines
propionitrile propionitrile: structure. propionitrile : A nitrile that is acrylonitrile in which the carbon-carbon double bond has been reduced to a single bond.	2	1	aliphatic nitrile; volatile organic compound	polar aprotic solvent
acrylonitrile [no description available]	1.96	1	aliphatic nitrile; volatile organic compound	antifungal agent; carcinogenic agent; fungal metabolite; mutagen; polar aprotic solvent
methyl formate methyl formate: RN given refers to parent cpd. methyl formate : A formate ester resulting from the formal condensation of formic acid with methanol. A low-boiling (31.5 degreeC) colourless, flammable liquid, it has been used as a fumigant and larvicide for tobacco and food crops.	3.07	1	formate ester; methyl ester; volatile organic compound	fumigant; insecticide; polar aprotic solvent; refrigerant
2-pentanone pentanone : Any ketone that is pentane substituted by an oxo group at unspecified position.	3.07	1	methyl ketone; pentanone	plant metabolite
3-hydroxybutanal [no description available]	2.48	2
1-nitropropane 1-nitropropane : A nitroalkane that is propane substituted at C-1 by a nitro group.	3.58	2	primary nitroalkane
methyl isobutyl ketone [no description available]	3.07	1	ketone
3-xylene m-xylene : A xylene carrying methyl groups at positions 1 and 3.	3.07	1	xylene
3-chloroaniline 3-chloroaniline: RN given refers to parent cpd	1.96	1
methyl malonate methyl malonate: do not confuse with methylmalonate, i.e., malonic acid substituted with a methyl group on C2; structure	2.03	1
1,3,5-trichlorobenzene 1,3,5-trichlorobenzene: structure in first source. 1,3,5-trichlorobenzene : A trichlorobenzene carrying chloro substituents at positions 1, 3 and 5.	3.07	1	trichlorobenzene
bromobenzene [no description available]	2.38	2	bromoarene; bromobenzenes; volatile organic compound	hepatotoxic agent; mouse metabolite; non-polar solvent
chlorobenzene [no description available]	3.77	3	monochlorobenzenes	solvent
cyclohexanol Cyclohexanols: Monohydroxy derivatives of cyclohexanes that contain the general formula R-C6H11O. They have a camphorlike odor and are used in making soaps, insecticides, germicides, dry cleaning, and plasticizers.. cyclohexanols : An alcohol in which one or more hydroxy groups are attached to a cyclohexane skeleton.	3.07	1	cyclohexanols; secondary alcohol	solvent
cyclohexanone [no description available]	3.07	1	cyclohexanones	human xenobiotic metabolite
thiophenol thiophenol : A thiol in which the sulfanyl group is attached to a phenyl group.	1.96	1	aryl thiol
2-chloropyridine 2-chloropyridine: structure given in first source	2.04	1	monochloropyridine
propyl acetate propyl acetate: affects aggression without affecting motor activity; RN given refers to parent cpd. propyl acetate : An acetate ester obtained by the formal condensation of acetic acid with propanol.	3.07	1	acetate ester	fragrance; plant metabolite
pentane Pentanes: Five-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives.. pentane : A straight chain alkane consisting of 5 carbon atoms.	3.49	2	alkane; volatile organic compound	non-polar solvent; refrigerant
1-pentene 1-pentene: structure in first source	3.07	1
butyl chloride butyl chloride: structure	3.07	1
dicyanmethane malononitrile : A dinitrile that is methane substituted by two cyano groups.	2.78	3	aliphatic nitrile; dinitrile
dimethoxymethane dimethoxymethane : An acetal that is the dimethyl acetal derivative of formaldehyde.	2	1	acetal; diether
ethyl vinyl ether ethyl vinyl ether: structure	1.96	1
ethyl formate ethyl formate : A formate ester resulting from the formal condensation of formic acid with ethanol.. ethoxycarbonyl group : An organyl group of formula -COOEt.	3.07	1	ethyl ester; formate ester	fumigant; plant metabolite
pyrroles 1H-pyrrole : A tautomer of pyrrole that has the double bonds at positions 2 and 4.. pyrrole : A five-membered monocyclic heteroarene comprising one NH and four CH units which forms the parent compound of the pyrrole group of compounds. Its five-membered ring structure has three tautomers. A 'closed class'.. azole : Any monocyclic heteroarene consisting of a five-membered ring containing nitrogen. Azoles can also contain one or more other non-carbon atoms, such as nitrogen, sulfur or oxygen.	1.96	1	pyrrole; secondary amine
tetrahydrofuran oxolane : A cyclic ether that is butane in which one hydrogen from each methyl group is substituted by an oxygen.	3.79	3	cyclic ether; oxolanes; saturated organic heteromonocyclic parent; volatile organic compound	polar aprotic solvent
furan furan : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing four carbons and one oxygen, with formula C4H4O. It is a toxic, flammable, low-boiling (31degreeC) colourless liquid.	2.44	2	furans; mancude organic heteromonocyclic parent; monocyclic heteroarene	carcinogenic agent; hepatotoxic agent; Maillard reaction product
thiophenes Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.	2	1	mancude organic heteromonocyclic parent; monocyclic heteroarene; thiophenes; volatile organic compound	non-polar solvent
isobutyl acetate isobutyl acetate : The acetate ester of isobutanol.	3.07	1	acetate ester	Saccharomyces cerevisiae metabolite
n-hexane hexane : An unbranched alkane containing six carbon atoms.	2	1	alkane; volatile organic compound	neurotoxin; non-polar solvent
2-ethoxyethanol 2-ethoxyethanol : A hydroxyether that is the ethyl ether derivative of ethylene glycol.	1.96	1	glycol ether; primary alcohol	protic solvent; teratogenic agent
cyclohexane Cyclohexane: C6H12. cyclohexane : An alicyclic hydrocarbon comprising a ring of six carbon atoms; the cyclic form of hexane, used as a raw material in the manufacture of nylon.	2	1	cycloalkane; volatile organic compound	non-polar solvent
cyclohexene cyclohexene : A cycloalkene that is cylohexane with a single double bond.	2	1	cycloalkene
morpholine [no description available]	2	1	morpholines; saturated organic heteromonocyclic parent	NMR chemical shift reference compound
2-octanone 2-octanone : A methyl ketone that is octane substituted by an oxo group at position 2.	3.07	1	methyl ketone	metabolite
1-hexanol 1-hexanol: RN given refers to parent cpd. hexanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of six carbon atoms.. hexan-1-ol : A primary alcohol that is hexane substituted by a hydroxy group at position 1.	3.07	1	hexanol; primary alcohol	alarm pheromone; antibacterial agent; fragrance; plant metabolite
heptanol Heptanol: A colorless liquid with a fragrant odor. It is used as an intermediate, solvent and in cosmetics.. heptanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of seven carbon atoms.. heptan-1-ol : A primary alcohol that is heptane substituted by a hydroxy group at position 1. It has been isolated from Capillipedium parviflorum.	3.07	1	heptanol; primary alcohol	flavouring agent; fragrance; gap junctional intercellular communication inhibitor; plant metabolite
propylene propylene: structure	1.96	1	alkene; gas molecular entity	refrigerant; xenobiotic
dimethyl ether dimethyl ether : An ether in which the oxygen atom is connected to two methyl groups.	1.96	1	ether
2,2,2-trichloroethanol [no description available]	1.96	1	chloroethanol	mouse metabolite
tetrafluoroethylene tetrafluoroethylene: RN given refers to parent cpd; structure	2	1	fluorocarbon
trinitrotoluene Trinitrotoluene: A 2,4,6-trinitrotoluene, which is an explosive chemical that can cause skin irritation and other toxic consequences.. 2,4,6-trinitrotoluene : A trinitrotoluene having the nitro groups at positions 2, 4 and 6.	2.35	2	trinitrotoluene	explosive
isoquinoline [no description available]	2.04	1	azaarene; isoquinolines; mancude organic heterobicyclic parent; ortho-fused heteroarene
ethyl-p-hydroxybenzoate ethyl-p-hydroxybenzoate: structure	2	1	ethyl ester; paraben	antifungal agent; antimicrobial food preservative; phytoestrogen; plant metabolite
cyclopentanone [no description available]	3.07	1	cyclopentanones	Maillard reaction product
triethylamine [no description available]	2.41	1	tertiary amine
cyclonite cyclonite: explosive & convulsant; structure. 1,3,5-trinitro-1,3,5-triazinane : An N-nitro compound that is 1,3,5-triazinane in which all three of the hydrogens attached to the nitrogens have been replaced by nitro groups. It is widely used in both industrial and military explosives.	2.42	2	1,3,5-triazinanes; N-nitro compound	explosive
3-nitrobenzoic acid 3-nitrobenzoic acid: RN given refers to parent cpd	2	1
2-naphthol 2-naphthol: RN given refers to parent cpd. 2-naphthol : A naphthol carrying a hydroxy group at position 2.. naphthols : Any hydroxynaphthalene derivative that has a single hydroxy substituent.	3.49	2	naphthol	antinematodal drug; genotoxin; human urinary metabolite; human xenobiotic metabolite; mouse metabolite; radical scavenger
zephiramine [no description available]	2.02	1
ethyl acetate ethyl acetate : The acetate ester formed between acetic acid and ethanol.	4	4	acetate ester; ethyl ester; volatile organic compound	EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor; metabolite; polar aprotic solvent; Saccharomyces cerevisiae metabolite
mesityl oxide mesityl oxide: solvent for extraction of nitrocellulose, many resins, & tellurium; structure	2.08	1	olefinic compound
ethyl acetoacetate ethyl acetoacetate: RN given refers to unlabeled parent cpd. ethyl acetoacetate : An ethyl ester resulting from the formal condensation of the carboxy group of acetoacetic acid with ethanol.	2.08	1	ethyl ester	antibacterial agent; flavouring agent; plant metabolite
dibutyl ether [no description available]	3.07	1
cycloguanil cycloguanil: the active metabolite of proguanil; antifolate drug; structure in first source. cycloguanil : A triazine in which a 1,6-dihydro-1,3,5-triazine ring is substituted at N-1 by a 4-chlorophenyl group, at C-2 and -4 by amino groups and at C-6 by gem-dimethyl groups. A dihydrofolate reductase inhibitor, it is a metabolite of the antimalarial drug proguanil.	1.96	1	triazines	antifolate; antiinfective agent; antimalarial; antiparasitic agent; antiprotozoal drug; EC 1.5.1.3 (dihydrofolate reductase) inhibitor
cinnoline cinnoline: structure in first source. cinnoline : An azaarene that is the 1,2-diaza analogue of naphthalene. The parent of the class of cinnolines.	2.04	1	azaarene; cinnolines; mancude organic heterobicyclic parent; ortho-fused heteroarene
benzoxazoles 1,3-benzoxazole : A benzoxazole in which the benzene ring is fused to a 1,3-oxazole ring across positions 4 and 5.. benzoxazole : Compounds based on a fused 1,2- or 1,3-oxazole and benzene bicyclic ring skeleton.	2.04	1	1,3-benzoxazoles; mancude organic heterobicyclic parent
isoxazoles Isoxazoles: Azoles with an OXYGEN and a NITROGEN next to each other at the 1,2 positions, in contrast to OXAZOLES that have nitrogens at the 1,3 positions.. isoxazole : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing three carbon atoms and an oxygen and nitrogen atom adjacent to each other. It is the parent of the class of isoxazoles.. isoxazoles : Oxazoles in which the N and O atoms are adjacent.	7.11	1	isoxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
oxazoles Oxazoles: Five-membered heterocyclic ring structures containing an oxygen in the 1-position and a nitrogen in the 3-position, in distinction from ISOXAZOLES where they are at the 1,2 positions.. 1,3-oxazole : A five-membered monocyclic heteroarene that is an analogue of cyclopentadiene with O in place of CH2 at position 1 and N in place of CH at position 3.. oxazole : An azole based on a five-membered heterocyclic aromatic skeleton containing one N and one O atom.	2.01	1	1,3-oxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
12-crown-4 12-crown-4: structure in first source. 12-crown-4 : A crown ether that is cyclododecane in which the carbon atoms at positions 1, 4, 7 and 10 have been replaced by oxygen atoms.	7.06	1	crown ether; saturated organic heteromonocyclic parent
ephedrine Ephedrine: A phenethylamine found in EPHEDRA SINICA. PSEUDOEPHEDRINE is an isomer. It is an alpha- and beta-adrenergic agonist that may also enhance release of norepinephrine. It has been used for asthma, heart failure, rhinitis, and urinary incontinence, and for its central nervous system stimulatory effects in the treatment of narcolepsy and depression. It has become less extensively used with the advent of more selective agonists.. (-)-ephedrine : A phenethylamine alkaloid that is 2-phenylethanamine substituted by a methyl group at the amino nitrogen and a methyl and a hydroxy group at position 2 and 1 respectively.	2	1	phenethylamine alkaloid; phenylethanolamines	bacterial metabolite; environmental contaminant; nasal decongestant; plant metabolite; sympathomimetic agent; vasoconstrictor agent; xenobiotic
thiocyanate thiocyanate: RN given refers to parent cpd. thiocyanate : A pseudohalide anion obtained by deprotonation of the thiol group of thiocyanic acid.	2.07	1	pseudohalide anion; sulfur molecular entity	human metabolite
diethyl sulfide ethyl sulfide : An aliphatic sulfide in which the sulfur atom is bonded to at least one ethyl group.. diethyl sulfide : An ethyl sulfide compound having two ethyl groups attached to a sulfur atom.	1.96	1	ethyl sulfide
1,1,1-trichloro-2,2,2-trifluoroethane [no description available]	1.96	1
2-fluoroethanol [no description available]	1.96	1
cyanogen cyanogen: structure. oxalonitrile : A dinitrile that is ethane substituted by two cyano groups.	2.03	1	dinitrile; pseudohalogen
fluorobenzenes Fluorobenzenes: Derivatives of BENZENE that contain FLUORINE.. monofluorobenzene : The simplest member of the class of monofluorobenzenes that is benzene carrying a single fluoro substituent.. fluorobenzenes : Any fluoroarene that is a benzene or a substituted benzene carrying at least one fluoro group.	2.38	2	monofluorobenzenes	NMR chemical shift reference compound
propadiene [no description available]	2.4	2	allenes
pinane pinane: RN given refers to cpd without isomeric designation. pinane : A monoterpene that is bicyclo[3.1.1]heptane substituted by methyl groups at positions 2, 6 and 6.	2.11	1	carbobicyclic compound; monoterpene; terpenoid fundamental parent	plant metabolite
dimethylacetylene dimethylacetylene: structure in source	1.96	1
tetranitromethane [no description available]	2.33	2	organonitrogen compound
flavone flavone: RN given refers to unlabeled cpd; structure given in first source. flavone : The simplest member of the class of flavones that consists of 4H-chromen-4-one bearing a phenyl substituent at position 2.	2.04	1	flavones	metabolite; nematicide
4-chloroacetanilide 4-chloroacetanilide : Acetamide substituted on nitrogen by a para-chlorophenyl group.	2	1	acetamides; monochlorobenzenes
Ethyl pentanoate ethyl valerate: a green apple flavoring agent	3.07	1	fatty acid ester
1-chloropropane 1-chloropropane: structure in first source	2	1
1,3-dichlorobenzene 1,3-dichlorobenzene : A dichlorobenzene carrying chloro substituents at positions 1 and 3.	3.07	1	dichlorobenzene
2,3-dichlorophenol dichlorophenol : Any chlorophenol carrying chloro substituents.	2	1
potassium carbonate potassium carbonate : A potassium salt that is the dipotassium salt of carbonic acid.	2.02	1	carbonate salt; potassium salt	catalyst; fertilizer; flame retardant
nitrosobenzene [no description available]	1.96	1	benzenes; nitroso compound	xenobiotic metabolite
iodobenzene iodobenzene: RN given refers to unlabeled parent cpd	1.96	1
mercuric cyanide [no description available]	6.96	1	mercury coordination entity
fluoromethane fluoromethane: RN given refers to parent cpd. fluorocarbon : Compounds consisting wholly of fluorine and carbon.. fluoromethane : A member of the class of fluoromethanes that is methane in which a single hydrogen is substituted by a fluorine atom.	1.96	1	fluorohydrocarbon; fluoromethanes; methyl halides	refrigerant
diisopropylnitrosamine [no description available]	1.96	1
ferrocin c N-methyl-2-quinolone: structure in first source	2.04	1
pentachlorobenzene pentachlorobenzene: structure. pentachlorobenzene : A member of the class of pentachlorobenzenes that is benzene in which five of the hydrogens are replaced by chlorines. Now classed as a persistent organic pollutant under the Stockholm Convention.	3.07	1	pentachlorobenzenes	persistent organic pollutant
n,n-dimethylbenzamide [no description available]	2.04	1
methyl butyrate [no description available]	2	1	fatty acid ester
methyl nitrite [no description available]	6.98	1
2-hexanol hexan-2-ol : A hexanol in which the hydroxy group is at position 2.	3.07	1	hexanol; secondary alcohol	human metabolite; plant metabolite; semiochemical
amyl acetate amyl acetate: sources do not specify n-isomer. pentyl acetate : An acetate ester of pentanol.	3.07	1	acetate ester	metabolite
1,2,3,4-tetrachlorobenzene 1,2,3,4-tetrachlorobenzene : A tetrachlorobenzene carrying chloro groups at positions 1, 2 , 3 and 4.. tetrachlorobenzene : Any member of the class of chlorobenzenes carrying four chloro groups at unspecified positions.	3.07	1	tetrachlorobenzene
1,2,3,5-tetrachlorobenzene 1,2,3,5-tetrachlorobenzene : A tetrachlorobenzene carrying chloro groups at positions 1, 2, 3 and 5.	3.07	1	tetrachlorobenzene
succindialdehyde [no description available]	2.11	1	aldehyde
formal glycol [no description available]	2	1	cyclic acetal; dioxolane
methylnitrosourea Methylnitrosourea: A nitrosourea compound with alkylating, carcinogenic, and mutagenic properties.. N-methyl-N-nitrosourea : A member of the class of N-nitrosoureas that is urea in which one of the nitrogens is substituted by methyl and nitroso groups.	1.96	1	N-nitrosoureas	alkylating agent; carcinogenic agent; mutagen; teratogenic agent
triphenylphosphine oxide triphenylphosphine oxide: used in the extraction, separation & spectrophotometric determination of cadmium & mercury in environmental samples. triphenylphosphane oxide : A phosphine oxide in which the substituents on phosphorus are three phenyl groups.	2.04	1	phosphine oxide	NMR chemical shift reference compound
diphenyl sulfoxide diphenyl sulfoxide: electron acceptor for liver aldehyde oxidase	2.04	1	sulfoxide
4-acetylpyridine [no description available]	2.04	1
methyl phenyl sulfoxide (methylsulfinyl)benzene : A sulfoxide resulting from the formal oxidation of the sulfur atom of thioanisole.	2.39	2	benzenes; sulfoxide
cadmium sulfide [no description available]	7.05	1	cadmium molecular entity
hydrofluoric acid Hydrofluoric Acid: Hydrofluoric acid. A solution of hydrogen fluoride in water. It is a colorless fuming liquid which can cause painful burns.. hydrogen fluoride : A diatomic molecule containing covalently bonded hydrogen and fluorine atoms.. organofluorine compound : An organofluorine compound is a compound containing at least one carbon-fluorine bond.	2.1	1	hydrogen halide; mononuclear parent hydride	NMR chemical shift reference compound
tricarballylic acid tricarballylic acid: RN given refers to parent cpd. tricarballylic acid : A tricarboxylic acid that is glutaric acid in which one of the beta-hydrogens is substituted by a carboxy group.	2.06	1	tricarboxylic acid
methyl tert-butyl ether methyl tert-butyl ether: used to dissolve gallstones; gasoline additive. methyl tert-butyl ether : An ether having methyl and tert-butyl as the two alkyl components.	2.07	1	ether	fuel additive; metabolite; non-polar solvent
2,5-dihydrofuran 2,5-dihydrofuran: structure in first source	1.96	1
2-tert-butylhydroquinone 2-tert-butylhydroquinone: an anticarcinogenic and chemopreventive agent. 2-tert-butylhydroquinone : A member of the class of hydroquinones in which one of the ring hydrogens of hydroquinone is replaced by a tert-butyl group.	2	1	hydroquinones	food antioxidant
decachlorobiphenyl decachlorobiphenyl: structure. decachlorobiphenyl : A polychlorobiphenyl that is biphenyl in which all of the hydrogens are replaced by chlorines.	2	1	pentachlorobenzenes; polychlorobiphenyl
octogen octogen: an explosive compound, contaminant in waste water; structure given in third source. octogen : A tetrazocane that is 1,3,5,7-tetrazocane in which the hydrogen atom attached to each of the nitrogens is replaced by a nitro group.	2	1	N-nitro compound; tetrazocane	explosive
2,2-bis(bromomethyl)-1,3-propanediol 2,2-bis(bromomethyl)-1,3-propanediol: structure given in first source	7.02	1	primary alcohol
mannose mannopyranose : The pyranose form of mannose.	2.63	3	D-aldohexose; D-mannose; mannopyranose	metabolite
carbonates Carbonates: Salts or ions of the theoretical carbonic acid, containing the radical CO2(3-). Carbonates are readily decomposed by acids. The carbonates of the alkali metals are water-soluble; all others are insoluble. (From Grant & Hackh's Chemical Dictionary, 5th ed). carbonates : Organooxygen compounds that are salts or esters of carbonic acid, H2CO3.	2.02	1	carbon oxoanion
4,6-diamino-2,2-dimethyl-1,2-dihydro-1-phenyl-s-triazine 4,6-diamino-2,2-dimethyl-1,2-dihydro-1-phenyl-s-triazine: structure in first source	1.96	1
dimethylnitramine [no description available]	2.46	2
diaveridine diaveridine: RN given refers to parent cpd; structure. diaveridine : An aminopyrimidine in which the pyrimidine ring carries amino substituents at C-2 and C-4 and a 3,4-dimethoxybenzyl group at C-5. A folic acid antagonist, it is used as a synergist with sulfonamides against the parasitic Eimeria species.	1.96	1	aminopyrimidine	antiparasitic agent; drug allergen
ammonium nitrate ammonium nitrate: structure. ammonium nitrate : The ammonium salt of nitric acid.	2.71	3	ammonium salt; inorganic molecular entity; inorganic nitrate salt	explosive; fertilizer; oxidising agent
tert-nitrosobutane [no description available]	1.98	1
mercury Mercury: A silver metallic element that exists as a liquid at room temperature. It has the atomic symbol Hg (from hydrargyrum, liquid silver), atomic number 80, and atomic weight 200.59. Mercury is used in many industrial applications and its salts have been employed therapeutically as purgatives, antisyphilitics, disinfectants, and astringents. It can be absorbed through the skin and mucous membranes which leads to MERCURY POISONING. Because of its toxicity, the clinical use of mercury and mercurials is diminishing.. mercury(0) : Elemental mercury of oxidation state zero.	1.96	1	elemental mercury; zinc group element atom	neurotoxin
palladium Palladium: A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.. palladium : Chemical element (nickel group element atom) with atomic number 46.	3.48	7	metal allergen; nickel group element atom; platinum group metal atom
platinum Platinum: A heavy, soft, whitish metal, resembling tin, with atomic number 78, atomic weight 195.084, symbol Pt. It is used in manufacturing equipment for laboratory and industrial use. It occurs as a black powder (platinum black) and as a spongy substance (spongy platinum) and may have been known in Pliny's time as alutiae.	2.41	1	elemental platinum; nickel group element atom; platinum group metal atom
argon Argon: A noble gas with the atomic symbol Ar, atomic number 18, and atomic weight 39.948. It is used in fluorescent tubes and wherever an inert atmosphere is desired and nitrogen cannot be used.	2.05	1	monoatomic argon; noble gas atom; p-block element atom	food packaging gas; neuroprotective agent
gold Gold: A yellow metallic element with the atomic symbol Au, atomic number 79, and atomic weight 197. It is used in jewelry, goldplating of other metals, as currency, and in dental restoration. Many of its clinical applications, such as ANTIRHEUMATIC AGENTS, are in the form of its salts.	2.11	1	copper group element atom; elemental gold
helium Helium: A noble gas with the atomic symbol He, atomic number 2, and atomic weight 4.003. It is a colorless, odorless, tasteless gas that is not combustible and does not support combustion. It was first detected in the sun and is now obtained from natural gas. Medically it is used as a diluent for other gases, being especially useful with oxygen in the treatment of certain cases of respiratory obstruction, and as a vehicle for general anesthetics.	7.06	1	monoatomic helium; noble gas atom; s-block element atom	food packaging gas
phosphine phosphane : The simplest phosphine, consisting of a single phosphorus atom with three hydrogens attached.. phosphine : Phosphane (PH3) and compounds derived from it by substituting one, two or three hydrogen atoms by hydrocarbyl groups: RPH2, R2PH, R3P (R =/= H) are called primary, secondary and tertiary phosphines, respectively. A specific phosphine is preferably named as a substituted phosphane.	7.05	1	mononuclear parent hydride; phosphanes; phosphine	carcinogenic agent; fumigant insecticide
bromine Bromine: A halogen with the atomic symbol Br, atomic number 35, and atomic weight 79.904. It is a volatile reddish-brown liquid that gives off suffocating vapors, is corrosive to the skin, and may cause severe gastroenteritis if ingested.	2.43	2	diatomic bromine
barium sulfate Barium Sulfate: A compound used as an x-ray contrast medium that occurs in nature as the mineral barite. It is also used in various manufacturing applications and mixed into heavy concrete to serve as a radiation shield.. barium sulfate : A metal sulfate with formula BaO4S. Virtually insoluble in water at room temperature, it is mostly used as a component in oil well drilling fluid it occurs naturally as the mineral barite.	2.07	1	barium salt; inorganic barium salt; metal sulfate	radioopaque medium
deuterium Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	2.41	1	dihydrogen
chlorine Chlorine: An element with atomic symbol Cl, atomic number 17, and atomic weight 35, and member of the halogen family.	8.49	7	diatomic chlorine; gas molecular entity	bleaching agent
cupric bromide [no description available]	2.07	1
thallium chloride thallium chloride: RN given refers to unlabeled parent cpd	1.98	1	inorganic chloride; thallium molecular entity
desmedipham desmedipham: structure. desmedipham : A carbamate ester that is phenylcarbamic acid in which the hydrogen of the hydroxy group has been replaced by a 3-[(ethoxycarbonyl)amino]phenyl group. It is an agrochemical used as a herbicide.	2	1	carbamate ester	agrochemical; environmental contaminant; herbicide; xenobiotic
galactose aldohexose : A hexose with a (potential) aldehyde group at one end.	1.96	1
ozone Ozone: The unstable triatomic form of oxygen, O3. It is a powerful oxidant that is produced for various chemical and industrial uses. Its production is also catalyzed in the ATMOSPHERE by ULTRAVIOLET RAY irradiation of oxygen or other ozone precursors such as VOLATILE ORGANIC COMPOUNDS and NITROGEN OXIDES. About 90% of the ozone in the atmosphere exists in the stratosphere (STRATOSPHERIC OZONE).. ozone : An elemental molecule with formula O3. An explosive, pale blue gas (b.p. -112degreeC) that has a characteristic, pungent odour, it is continuously produced in the upper atmosphere by the action of solar ultraviolet radiation on atmospheric oxygen. It is an antimicrobial agent used in the production of bottled water, as well as in the treatment of meat, poultry and other foodstuffs.	8.71	9	elemental molecule; gas molecular entity; reactive oxygen species; triatomic oxygen	antiseptic drug; disinfectant; electrophilic reagent; greenhouse gas; mutagen; oxidising agent; tracer
chloramine [no description available]	2.77	3	halide
menthone menthone : The trans-stereoisomer of p-menthan-3-one.. (-)-menthone : A menthone that is cyclohexanone substituted by a methyl and an isopropyl group at positions 5 and 2 respectively (the 2S,5R-stereoisomer).	2	1	menthone
tiletamine hydrochloride Cyclohexanones: Cyclohexane ring substituted by one or more ketones in any position.. cyclohexanones : Any alicyclic ketone based on a cyclohexane skeleton and its substituted derivatives thereof.	2.06	1
thiamphenicol [no description available]	2.13	1	monocarboxylic acid amide; sulfone	antimicrobial agent; immunosuppressive agent
phenyl acetate phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.	2.95	4	benzenes; phenyl acetates
acetylacetone acetylacetone : A beta-diketone that is pentane in which the hydrogens at positions 2 and 4 are replaced by oxo groups.	2.02	1	beta-diketone
butyl acetate butyl acetate: structure. butyl acetate : The acetate ester of butanol.	3.07	1	acetate ester	metabolite
1,4-dioxane 1,4-dioxane: dehydrating agent; polar solvent miscible both with water & most organic solvents. dioxane : Any member of the class of dioxanes that is a cyclohexane in which two carbon atoms are replaced by oxygen atoms.. 1,4-dioxane : A dioxane with oxygen atoms at positions 1 and 4.	2.04	1	dioxane; volatile organic compound	carcinogenic agent; metabolite; NMR chemical shift reference compound; non-polar solvent
chloroprene Chloroprene: Toxic, possibly carcinogenic, monomer of neoprene, a synthetic rubber; causes damage to skin, lungs, CNS, kidneys, liver, blood cells and fetuses. Synonym: 2-chlorobutadiene.	2	1	chloroolefin
tetrachloroethylene Tetrachloroethylene: A chlorinated hydrocarbon used as an industrial solvent and cooling liquid in electrical transformers. It is a potential carcinogen.	1.96	1	chlorocarbon; chloroethenes	nephrotoxic agent
dimethylacetamide hallucinogen : Drugs capable of inducing illusions, hallucinations, delusions, paranoid ideations and other alterations of mood and thinking.. N,N-dimethylacetamide : A member of the class of acetamides that is acetamide in which the hydrogens attached to the N atom have been replaced by two methyl groups respectively. Metabolite observed in cancer metabolism.	2	1	acetamides; monocarboxylic acid amide	human metabolite
pyrene pyrene: structure in Merck Index, 9th ed, #7746. pyrene : An ortho- and peri-fused polycyclic arene consisting of four fused benzene rings, resulting in a flat aromatic system.	2.41	2	ortho- and peri-fused polycyclic arene	fluorescent probe; persistent organic pollutant
alkenes [no description available]	2.8	3
azides Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.	1.96	1	pseudohalide anion	mitochondrial respiratory-chain inhibitor
15-crown-5 15-crown-5 : A saturated organic heteromonocyclic parent that is cyclopentadecane in which the carbon atoms at positions 1, 4, 7, 10 and 13 have been replaced by oxygen atoms to give a crown ether.	7.06	1	crown ether; saturated organic heteromonocyclic parent
nitroacetic acid nitroacetic acid: inhibits succinate dehydrogenase; RN given refers to parent cpd	2.44	2
fenoxycarb fenoxycarb: used against mosquitoes (Diptera:Culicidae); structure given in first source. fenoxycarb : A carbamate ester that is the O-ethyl carbamate of 2-(4-phenoxyphenoxy)ethylamine.	2	1	aromatic ether; carbamate ester	environmental contaminant; insecticide; juvenile hormone mimic; xenobiotic
adenosine quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit	2.01	1	adenosines; purines D-ribonucleoside	analgesic; anti-arrhythmia drug; fundamental metabolite; human metabolite; vasodilator agent
trichloroacetamide [no description available]	1.96	1
aristeromycin aristeromycin: RN given refers to (1R-(1alpha,2alpha,3beta,5alpha)-isomer	2.01	1
fenclofenac fenclofenac: RN given refers to parent cpd	2	1	aromatic ether
anthranil 2,1-benzoxazole : A benzoxazole in which the benzene ring is fused to a 1,2-oxazole ring across positions 3 and 4.	2.04	1	2,1-benzoxazoles; mancude organic heterobicyclic parent
trifluoroacetamide [no description available]	1.96	1
bromonitromethane bromonitromethane: structure in first source	7.52	2
5-iodouracil 5-iodouracil: RN given refers to parent cpd. 5-iodouracil : An organoiodine compound consisting of uracil having an iodo substituent at the 5-position.	1.96	1	organoiodine compound	antimetabolite
4-methoxybenzonitrile 4-methoxybenzonitrile: RN given refers to parent cpd	2.04	1
2,6-difluoropyridine [no description available]	2.04	1
n,n'-dibutylurea N,N'-dibutylurea: structure in first source	2.02	1
1-benzylimidazole 1-benzylimidazole: inhibits human thromboxane synthetase	2.04	1
imidazo(1,2-a)pyridine imidazo(1,2-a)pyridine: structure	2.07	1
2,4-diamino-5-benzylpyrimidine 2,4-diamino-5-benzylpyrimidine: structure given in first source	1.96	1
bromates Bromates: Negative ions or salts derived from bromic acid, HBrO3.	2.08	1	bromine oxoanion; monovalent inorganic anion
6-chloroindole [no description available]	2.04	1	indoles
cobalt Cobalt: A trace element that is a component of vitamin B12. It has the atomic symbol Co, atomic number 27, and atomic weight 58.93. It is used in nuclear weapons, alloys, and pigments. Deficiency in animals leads to anemia; its excess in humans can lead to erythrocytosis.. cobalt(1+) : A monovalent inorganic cation obtained from cobalt.. cobalt atom : A cobalt group element atom that has atomic number 27.	2.08	1	cobalt group element atom; metal allergen	micronutrient
florfenicol florfenicol: structure given in first source. florfenicol : A carboxamide that is the N-dichloroacetyl derivative of (1R,2S)-2-amino-3-fluoro-1-[4-(methanesulfonyl)phenyl]propan-1-ol. A synthetic veterinary antibiotic that is used for treatment of bovine respiratory disease and foot rot; also used in aquaculture.	2.13	1	organochlorine compound; organofluorine compound; secondary alcohol; secondary carboxamide; sulfone	antimicrobial agent
paliperidone 3-{2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl}-9-hydroxy-2-methyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one : A member of the class of pyridopyrimidines that is 9-hydroxy-2-methyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one carrying an additional 2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl group at position 2.. paliperidone : A racemate comprising equimolar amounts of (R)- and (S)-paliperidone. Paliperidone is the primary active metabolite of the older antipsychotic risperidone and is used for treatment of schizophrenia.	2.04	1	1,2-benzoxazoles; heteroarylpiperidine; organofluorine compound; pyridopyrimidine; secondary alcohol
flavin semiquinone flavin semiquinone: chromophore found in methanol oxidase	2	1
1,n(6)-ethenoadenosine diphosphate 1,N(6)-ethenoadenosine diphosphate: polarized fluorescence reagents	1.98	1
l 663581 L 663581: structure given in first source; partial agonist at the benzodiazepine receptor	2.04	1
proline Proline: A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons.. proline : An alpha-amino acid that is pyrrolidine bearing a carboxy substituent at position 2.	7.45	2	amino acid zwitterion; glutamine family amino acid; L-alpha-amino acid; proline; proteinogenic amino acid	algal metabolite; compatible osmolytes; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
naproxen Naproxen: An anti-inflammatory agent with analgesic and antipyretic properties. Both the acid and its sodium salt are used in the treatment of rheumatoid arthritis and other rheumatic or musculoskeletal disorders, dysmenorrhea, and acute gout.. naproxen : A methoxynaphthalene that is 2-methoxynaphthalene substituted by a carboxy ethyl group at position 6. Naproxen is a non-steroidal anti-inflammatory drug commonly used for the reduction of pain, fever, inflammation and stiffness caused by conditions such as osteoarthritis, kidney stones, rheumatoid arthritis, psoriatic arthritis, gout, ankylosing spondylitis, menstrual cramps, tendinitis, bursitis, and for the treatment of primary dysmenorrhea. It works by inhibiting both the COX-1 and COX-2 enzymes.	2	1	methoxynaphthalene; monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; environmental contaminant; gout suppressant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
hydroxyl radical Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.	2.08	1	oxygen hydride; oxygen radical; reactive oxygen species
camphora camphora: a component of Guanxingao, a kind of traditional Chinese rubber electuary medicine which is able to either cure or guard against coronary heart disease and angina pectoris. (R)-camphor : The (R)- enantiomer of camphor.	2	1	camphor
singlet oxygen Singlet Oxygen: An excited state of molecular oxygen generated photochemically or chemically. Singlet oxygen reacts with a variety of biological molecules such as NUCLEIC ACIDS; PROTEINS; and LIPIDS; causing oxidative damages.	1.99	1	chalcogen; monoatomic oxygen; nonmetal atom	macronutrient
carbodiimides Carbodiimides: Compounds with the general formula RN=C=NR, where R is a hydrocarbyl group.. methanediimine : A carbodiimide in which both nitrogens are unsubstituted.	1.96	1	carbodiimide
asenapine asenapine : A racemate consisting of equal amounts of (R,R)- and (S,S)-asenapine. Used as its maleate salt for the acute treatment of schizophrenia and acute treatment of manic or mixed episodes associated with bipolar I disorder with or without psychotic features.. (S,S)-asenapine : A 5-chloro-2-methyl-2,3,3a,12b-tetrahydrodibenzo[2,3:6,7]oxepino[4,5-c]pyrrole in which both of the stereocentres have S configuration.	2.04	1	5-chloro-2-methyl-2,3,3a,12b-tetrahydrodibenzo[2,3:6,7]oxepino[4,5-c]pyrrole
org 4428 [no description available]	2.04	1
alpha-aminooxy-beta-phenylpropionic acid alpha-aminooxy-beta-phenylpropionic acid: inhibits phenylalanine ammonia-lyase; RN given refers to (S)-isomer	1.96	1
pyrenesulfonyl azide pyrenesulfonyl azide: used as lipohilic photolabel	1.96	1
atropine tropan-3alpha-yl 3-hydroxy-2-phenylpropanoate : A tropane alkaloid that is (1R,5)-8-methyl-8-azabicyclo[3.2.1]octane substituted by a (3-hydroxy-2-phenylpropanoyl)oxy group at position 3.	2	1
anabasine Anabasine: A piperidine botanical insecticide.. (S)-anabasine : The (S)-enantiomer of anabasine.. anabasine : A pyridine alkaloid that is pyridine substituted by a piperidin-2-yl group at position 3.	2.07	1	anabasine
o-iodoxybenzoic acid o-iodoxybenzoic acid: structure in first source. 1-hydroxy-1,3-dioxobenziodoxole : A benziodoxole compound having hydroxy and oxo substituents at the 1-position and an oxo substituent at the 3-position. It is a mild and efficient hypervalent iodine synthetic reagent used to carry out several selective oxidation reactions.	2.07	1	benziodoxole	EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor; oxidising agent
arabinose [no description available]	2.33	2	L-arabinose	Escherichia coli metabolite; mouse metabolite
tartaric acid tartaric acid: RN given refers to cpd with unspecified isomeric designation. D-tartaric acid : The D-enantiomer of tartaric acid.	2.03	1	tartaric acid	Escherichia coli metabolite
(+)-limonene (4R)-limonene : An optically active form of limonene having (4R)-configuration.	2	1	limonene	plant metabolite
griseofulvin Griseofulvin: An antifungal agent used in the treatment of TINEA infections.. griseofulvin : An oxaspiro compound produced by Penicillium griseofulvum. It is used by mouth as an antifungal drug for infections involving the scalp, hair, nails and skin that do not respond to topical treatment.	2.44	2	1-benzofurans; antibiotic antifungal drug; benzofuran antifungal drug; organochlorine compound; oxaspiro compound	antibacterial agent; Penicillium metabolite
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	2.08	1	cyclodextrin
alpha-cyclodextrin alpha-cyclodextrin : A cycloamylose composed of six alpha-(1->4) linked D-glucopyranose units.	7	1	cyclodextrin
cocaine Cocaine: An alkaloid ester extracted from the leaves of plants including coca. It is a local anesthetic and vasoconstrictor and is clinically used for that purpose, particularly in the eye, ear, nose, and throat. It also has powerful central nervous system effects similar to the amphetamines and is a drug of abuse. Cocaine, like amphetamines, acts by multiple mechanisms on brain catecholaminergic neurons; the mechanism of its reinforcing effects is thought to involve inhibition of dopamine uptake.. cocaine : A tropane alkaloid obtained from leaves of the South American shrub Erythroxylon coca.	2	1	benzoate ester; methyl ester; tertiary amino compound; tropane alkaloid	adrenergic uptake inhibitor; central nervous system stimulant; dopamine uptake inhibitor; environmental contaminant; local anaesthetic; mouse metabolite; plant metabolite; serotonin uptake inhibitor; sodium channel blocker; sympathomimetic agent; vasoconstrictor agent; xenobiotic
fosfomycin Fosfomycin: An antibiotic produced by Streptomyces fradiae.. fosfomycin : A phosphonic acid having an (R,S)-1,2-epoxypropyl group attached to phosphorus.	2.08	1	epoxide; phosphonic acids	antimicrobial agent; EC 2.5.1.7 (UDP-N-acetylglucosamine 1-carboxyvinyltransferase) inhibitor
diethylstilbestrol Diethylstilbestrol: A synthetic nonsteroidal estrogen used in the treatment of menopausal and postmenopausal disorders. It was also used formerly as a growth promoter in animals. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), diethylstilbestrol has been listed as a known carcinogen. (Merck, 11th ed). diethylstilbestrol : An olefinic compound that is trans-hex-3-ene in which the hydrogens at positions 3 and 4 have been replaced by p-hydroxyphenyl groups.	2	1	olefinic compound; polyphenol	antifungal agent; antineoplastic agent; autophagy inducer; calcium channel blocker; carcinogenic agent; EC 1.1.1.146 (11beta-hydroxysteroid dehydrogenase) inhibitor; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; endocrine disruptor; xenoestrogen
1,1-diamino-2,2-dinitroethylene 1,1-diamino-2,2-dinitroethylene: structure in first source	7.02	1
glycosides [no description available]	2.04	1
benzylideneacetone benzylideneacetone: RN given refers to cpd without isomeric; structure in Merck Index, 9th ed, #1153. trans-benzylideneacetone : The trans-isomer of benzylideneacetone. It acts as an inhibitor of the enzyme phospholipase A2 (EC 3.1.1.4) of insects like diamond back moth.. benzylideneacetone : An enone in which a phenyl ring is attached to the beta-carbon atom of but-3-en-2-one. Although both cis- and trans-isomers are possible for the alpha,beta-unsaturated ketone, only the trans-isomer is observed.	2.04	1	benzylideneacetone	bacterial metabolite; EC 3.1.1.4 (phospholipase A2) inhibitor; flavouring agent; fragrance
prolinol prolinol: RN given refers to cpd without isomeric designation; structure. prolinol : An amino alcohol formed by reduction of the amino acid proline.	2.08	1
flavin-adenine dinucleotide Flavin-Adenine Dinucleotide: A condensation product of riboflavin and adenosine diphosphate. The coenzyme of various aerobic dehydrogenases, e.g., D-amino acid oxidase and L-amino acid oxidase. (Lehninger, Principles of Biochemistry, 1982, p972)	2	1	flavin adenine dinucleotide; vitamin B2	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; prosthetic group
cotinine Cotinine: The N-glucuronide conjugate of cotinine is a major urinary metabolite of NICOTINE. It thus serves as a biomarker of exposure to tobacco SMOKING. It has CNS stimulating properties.. (-)-cotinine : An N-alkylpyrrolidine that consists of N-methylpyrrolidinone bearing a pyridin-3-yl substituent at position C-5 (the 5S-enantiomer). It is an alkaloid commonly found in Nicotiana tabacum.	2.21	1	N-alkylpyrrolidine; pyridines; pyrrolidin-2-ones; pyrrolidine alkaloid	antidepressant; biomarker; human xenobiotic metabolite; plant metabolite
sulindac Sulindac: A sulfinylindene derivative prodrug whose sulfinyl moiety is converted in vivo to an active NSAID analgesic. Specifically, the prodrug is converted by liver enzymes to a sulfide which is excreted in the bile and then reabsorbed from the intestine. This helps to maintain constant blood levels with reduced gastrointestinal side effects.. sulindac : A monocarboxylic acid that is 1-benzylidene-1H-indene which is substituted at positions 2, 3, and 5 by methyl, carboxymethyl, and fluorine respectively, and in which the phenyl group of the benzylidene moiety is substituted at the para position by a methylsulfinyl group. It is a prodrug for the corresponding sulfide, a non-steroidal anti-inflammatory drug, used particularly in the treatment of acute and chronic inflammatory conditions.	2	1	monocarboxylic acid; organofluorine compound; sulfoxide	analgesic; antineoplastic agent; antipyretic; apoptosis inducer; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; prodrug; tocolytic agent
2-thiopyridine 2-thiopyridine: RN given refers to parent cpd. pyridine-2-thiol : Pyridine substituted at C-2 by a sulfanyl group.	1.98	1	aryl thiol; pyridines	allergen; fluorescence quencher
thiourea Thiourea: A photographic fixative used also in the manufacture of resins. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), this substance may reasonably be anticipated to be a carcinogen (Merck Index, 9th ed). Many of its derivatives are ANTITHYROID AGENTS and/or FREE RADICAL SCAVENGERS.. thiourea : The simplest member of the thiourea class, consisting of urea with the oxygen atom substituted by sulfur.	8.28	6	one-carbon compound; thioureas; ureas	antioxidant; chromophore
1-butyl-3-methylimidazolium tetrafluoroborate [no description available]	2.05	1
lithium Lithium: An element in the alkali metals family. It has the atomic symbol Li, atomic number 3, and atomic weight [6.938; 6.997]. Salts of lithium are used in treating BIPOLAR DISORDER.	7.06	1	alkali metal atom
n-ethylthiourea [no description available]	1.96	1	thioureas
5-nitroso-salicylate 5-nitroso-salicylate: metabolite of 5-aminosalicylic acid	1.96	1	hydroxybenzoic acid
calixarenes Calixarenes: Phenolic metacyclophanes derived from condensation of PHENOLS and ALDEHYDES. The name derives from the vase-like molecular structures. A bracketed [n] indicates the number of aromatic rings.. calixarenes : Originally macrocyclic compounds capable of assuming a basket (or "calix") shaped conformation. They are formed from p-hydrocarbyl phenols and formaldehyde. The term now applies to a variety of derivatives by substitution of the hydrocarbon cyclo{oligo[(1,3-phenylene)methylene]}.. calixarene : A macrocycle composed of 1,3-phenylene groups linked by methylene groups. The number of 1,3-phenylene units in the macrocycle is denoted by the "n" in calix[n]arene name.	2.25	1
dinoprostone prostaglandin E2 : Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.	2	1	prostaglandins E	human metabolite; mouse metabolite; oxytocic
codeine [no description available]	2	1	morphinane alkaloid; organic heteropentacyclic compound	antitussive; drug allergen; environmental contaminant; opioid analgesic; opioid receptor agonist; prodrug; xenobiotic
morphine Meconium: The thick green-to-black mucilaginous material found in the intestines of a full-term fetus. It consists of secretions of the INTESTINAL GLANDS; BILE PIGMENTS; FATTY ACIDS; AMNIOTIC FLUID; and intrauterine debris. It constitutes the first stools passed by a newborn.	2	1	morphinane alkaloid; organic heteropentacyclic compound; tertiary amino compound	anaesthetic; drug allergen; environmental contaminant; geroprotector; mu-opioid receptor agonist; opioid analgesic; plant metabolite; vasodilator agent; xenobiotic
cesium Cesium: A member of the alkali metals. It has an atomic symbol Cs, atomic number 50, and atomic weight 132.91. Cesium has many industrial applications, including the construction of atomic clocks based on its atomic vibrational frequency.	7.04	1	alkali metal atom
thallium Thallium: A heavy, bluish white metal, atomic number 81, atomic weight [204.382; 204.385], symbol Tl.. thallium : A metallic element first identified and named from the brilliant green line in its flame spectrum (from Greek thetaalphalambdalambdaomicronsigma, a green shoot).	1.98	1	boron group element atom
cysteine Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.	1.99	1	cysteinium	fundamental metabolite
phosphorus Phosphorus: A non-metal element that has the atomic symbol P, atomic number 15, and atomic weight 31. It is an essential element that takes part in a broad variety of biochemical reactions.	2.03	1	monoatomic phosphorus; nonmetal atom; pnictogen	macronutrient
2-bromo-5-(2-bromo-2-nitrovinyl)furan 2-bromo-5-(2-bromo-2-nitrovinyl)furan: structure in first source	2.08	1
oxalates Oxalates: Derivatives of OXALIC ACID. Included under this heading are a broad variety of acid forms, salts, esters, and amides that are derived from the ethanedioic acid structure.	2.06	1
nifuroxime 5-nitro-2-furaldehyde oxime: structure in first source	2	1
nitrofurantoin Nitrofurantoin: A urinary anti-infective agent effective against most gram-positive and gram-negative organisms. Although sulfonamides and antibiotics are usually the agents of choice for urinary tract infections, nitrofurantoin is widely used for prophylaxis and long-term suppression.. nitrofurantoin : An imidazolidine-2,4-dione that is hydantoin substituted at position 1 by a [(5-nitro-2-furyl)methylene]amino group. An antibiotic that damages bacterial DNA.	2	1	imidazolidine-2,4-dione; nitrofuran antibiotic; organonitrogen heterocyclic antibiotic; organooxygen heterocyclic antibiotic	antibacterial drug; antiinfective agent; hepatotoxic agent
mannich bases Mannich Bases: Ketonic amines prepared from the condensation of a ketone with formaldehyde and ammonia or a primary or secondary amine. A Mannich base can act as the equivalent of an alpha,beta unsaturated ketone in synthesis or can be reduced to form physiologically active amino alcohols.	2.08	1
aluminum oxide Aluminum Oxide: An oxide of aluminum, occurring in nature as various minerals such as bauxite, corundum, etc. It is used as an adsorbent, desiccating agent, and catalyst, and in the manufacture of dental cements and refractories.	2.02	1
horsfiline horsfiline: structure in first source	7.1	1
coerulescine coerulescine: structure in first source	7.1	1
1,4-dihydroquinoline 1,4-dihydroquinoline: structure in first source	2.1	1
chitosan [no description available]	2.49	2
lithium perchlorate lithium perchlorate: stabilizes DNA-polycation complex; RN given refers to parent compound	2.96	4
piperidines Piperidines: A family of hexahydropyridines.	2.02	1
ascorbic acid Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.	1.99	1	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent
warfarin Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.	2.43	2	benzenes; hydroxycoumarin; methyl ketone
cobamamide cobamamide : A member of the class of cobalamins that is vitamin B12 in which the cyano group is replaced by a 5'-deoxyadenos-5'-yl moiety. It is one of the two metabolically active form of vitamin B12.	2.01	1
haloperidol diphenylprolinol silyl ether: structure in first source	2.13	1
deoxyguanosine [no description available]	2.02	1	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
guanine [no description available]	2	1	2-aminopurines; oxopurine; purine nucleobase	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
sapropterin sapropterin: RN given refers to parent cpd; co-factor required for catalytic activity of nitric oxide synthases. (6R)-5,6,7,8-tetrahydrobiopterin : A 5,6,7,8-tetrahydrobiopterin in which the stereocentre at position 6 has R-configuration.. sapropterin : A tetrahydropterin that is 2-amino-5,6,7,8-tetrahydropteridin-4(3H)-one in which a hydrogen at position 6 is substituted by a 1,2-dihydroxypropyl group (6R,1'R,2'S-enantiomer).	1.99	1	5,6,7,8-tetrahydrobiopterin	coenzyme; cofactor; diagnostic agent; human metabolite
allopurinol Allopurinol: A XANTHINE OXIDASE inhibitor that decreases URIC ACID production. It also acts as an antimetabolite on some simpler organisms.. allopurinol : A bicyclic structure comprising a pyrazole ring fused to a hydroxy-substituted pyrimidine ring.	2	1	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger
imidacloprid imidacloprid: systemic & contact insecticide exhibiting low mammalian toxicity; structure given in first source; it is one of the neonicotinoid insecticides, which acts as an antagonist by binding to postsynaptic nicotinic receptors in the insect central nervous system. imidacloprid : An imidazolidine that is N-nitroimidazolidin-2-imine bearing a (6-chloro-3-pyridinyl)methyl substituent at position 1.	2.07	1	imidacloprid; imidazolidines; monochloropyridine	environmental contaminant; genotoxin; neonicotinoid insectide; nicotinic acetylcholine receptor agonist; xenobiotic

Condition	Relationship Strength	Studies
Encephalopathy, Toxic [description not available]	2.51	2
Brain Disorders [description not available]	2.31	1
Brain Diseases Pathologic conditions affecting the BRAIN, which is composed of the intracranial components of the CENTRAL NERVOUS SYSTEM. This includes (but is not limited to) the CEREBRAL CORTEX; intracranial white matter; BASAL GANGLIA; THALAMUS; HYPOTHALAMUS; BRAIN STEM; and CEREBELLUM.	2.31	1
Acute Kidney Failure [description not available]	2.97	4
Acute Kidney Injury Abrupt reduction in kidney function. Acute kidney injury encompasses the entire spectrum of the syndrome including acute kidney failure; ACUTE KIDNEY TUBULAR NECROSIS; and other less severe conditions.	2.97	4
Breast Cancer [description not available]	2.21	1
Cancer of Prostate [description not available]	2.21	1
Breast Neoplasms Tumors or cancer of the human BREAST.	2.21	1
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	2.21	1
Dizzyness [description not available]	2.11	1
Daytime Sleepiness [description not available]	2.11	1
Dizziness An imprecise term which may refer to a sense of spatial disorientation, motion of the environment, or lightheadedness.	2.11	1
Disorders of Excessive Somnolence Disorders characterized by hypersomnolence during normal waking hours that may impair cognitive functioning. Subtypes include primary hypersomnia disorders (e.g., IDIOPATHIC HYPERSOMNOLENCE; NARCOLEPSY; and KLEINE-LEVIN SYNDROME) and secondary hypersomnia disorders where excessive somnolence can be attributed to a known cause (e.g., drug affect, MENTAL DISORDERS, and SLEEP APNEA SYNDROME). (From J Neurol Sci 1998 Jan 8;153(2):192-202; Thorpy, Principles and Practice of Sleep Medicine, 2nd ed, p320)	2.11	1
Poisoning Used with drugs, chemicals, and industrial materials for human or animal poisoning, acute or chronic, whether the poisoning is accidental, occupational, suicidal, by medication error, or by environmental exposure.	8.14	5
Metabolic Acidosis [description not available]	2.04	1
Acidosis A pathologic condition of acid accumulation or depletion of base in the body. The two main types are RESPIRATORY ACIDOSIS and metabolic acidosis, due to metabolic acid build up.	2.04	1
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	2.05	1
Corynebacterium diphtheriae Infection [description not available]	1.92	1
Diphtheria A localized infection of mucous membranes or skin caused by toxigenic strains of CORYNEBACTERIUM DIPHTHERIAE. It is characterized by the presence of a pseudomembrane at the site of infection. DIPHTHERIA TOXIN, produced by C. diphtheriae, can cause myocarditis, polyneuritis, and other systemic toxic effects.	6.92	1
Kidney Diseases Pathological processes of the KIDNEY or its component tissues.	2.06	1
Electrolytes Substances that dissociate into two or more ions, to some extent, in water. Solutions of electrolytes thus conduct an electric current and can be decomposed by it (ELECTROLYSIS). (Grant & Hackh's Chemical Dictionary, 5th ed)	2.73	3
Allergic Contact Dermatitis [description not available]	7.01	1
Dermatitis, Occupational A recurrent contact dermatitis caused by substances found in the work place.	2.01	1
Hand Dermatosis [description not available]	2.01	1
Hand Dermatoses Skin diseases involving the HANDS.	2.01	1
Dermatitis, Allergic Contact A contact dermatitis due to allergic sensitization to various substances. These substances subsequently produce inflammatory reactions in the skin of those who have acquired hypersensitivity to them as a result of prior exposure.	2.01	1
Cancer of Liver [description not available]	2.02	1
Liver Neoplasms Tumors or cancer of the LIVER.	2.02	1
Cerebellar Diseases Diseases that affect the structure or function of the cerebellum. Cardinal manifestations of cerebellar dysfunction include dysmetria, GAIT ATAXIA, and MUSCLE HYPOTONIA.	2.04	1
Convulsions, Grand Mal [description not available]	2.44	2
Absence Status [description not available]	2.04	1
Epilepsy, Tonic-Clonic A generalized seizure disorder characterized by recurrent major motor seizures. The initial brief tonic phase is marked by trunk flexion followed by diffuse extension of the trunk and extremities. The clonic phase features rhythmic flexor contractions of the trunk and limbs, pupillary dilation, elevations of blood pressure and pulse, urinary incontinence, and tongue biting. This is followed by a profound state of depressed consciousness (post-ictal state) which gradually improves over minutes to hours. The disorder may be cryptogenic, familial, or symptomatic (caused by an identified disease process). (From Adams et al., Principles of Neurology, 6th ed, p329)	2.44	2
Status Epilepticus A prolonged seizure or seizures repeated frequently enough to prevent recovery between episodes occurring over a period of 20-30 minutes. The most common subtype is generalized tonic-clonic status epilepticus, a potentially fatal condition associated with neuronal injury and respiratory and metabolic dysfunction. Nonconvulsive forms include petit mal status and complex partial status, which may manifest as behavioral disturbances. Simple partial status epilepticus consists of persistent motor, sensory, or autonomic seizures that do not impair cognition (see also EPILEPSIA PARTIALIS CONTINUA). Subclinical status epilepticus generally refers to seizures occurring in an unresponsive or comatose individual in the absence of overt signs of seizure activity. (From N Engl J Med 1998 Apr 2;338(14):970-6; Neurologia 1997 Dec;12 Suppl 6:25-30)	2.04	1
Methemoglobinemia The presence of methemoglobin in the blood, resulting in cyanosis. A small amount of methemoglobin is present in the blood normally, but injury or toxic agents convert a larger proportion of hemoglobin into methemoglobin, which does not function reversibly as an oxygen carrier. Methemoglobinemia may be due to a defect in the enzyme NADH methemoglobin reductase (an autosomal recessive trait) or to an abnormality in hemoglobin M (an autosomal dominant trait). (Dorland, 27th ed)	2.04	1
Diseases, Occupational [description not available]	2.38	2
Atherosclerotic Parkinsonism [description not available]	1.96	1
Parkinson Disease, Secondary Conditions which feature clinical manifestations resembling primary Parkinson disease that are caused by a known or suspected condition. Examples include parkinsonism caused by vascular injury, drugs, trauma, toxin exposure, neoplasms, infections and degenerative or hereditary conditions. Clinical features may include bradykinesia, rigidity, parkinsonian gait, and masked facies. In general, tremor is less prominent in secondary parkinsonism than in the primary form. (From Joynt, Clinical Neurology, 1998, Ch38, pp39-42)	1.96	1
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	2.37	2
Amino Acid Metabolism Disorders, Inborn [description not available]	1.95	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	3.29	2
Actinic Reticuloid Syndrome [description not available]	1.99	1
Blunt Injuries [description not available]	1.99	1
Crush Syndrome Severe systemic manifestation of trauma and ischemia involving soft tissues, principally skeletal muscle, due to prolonged severe crushing. It leads to increased permeability of the cell membrane and to the release of potassium, enzymes, and myoglobin from within cells. Ischemic renal dysfunction secondary to hypotension and diminished renal perfusion results in acute tubular necrosis and uremia.	1.99	1
Rhabdomyolysis Necrosis or disintegration of skeletal muscle often followed by myoglobinuria.	6.99	1
Autoimmune Demyelinating Disease, Peripheral [description not available]	2	1
Benign Neoplasms [description not available]	2.92	1
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	2.92	1
Experimental Neoplasms [description not available]	2	1
Peripheral Nerve Diseases [description not available]	2	1
Peripheral Nervous System Diseases Diseases of the peripheral nerves external to the brain and spinal cord, which includes diseases of the nerve roots, ganglia, plexi, autonomic nerves, sensory nerves, and motor nerves.	2	1
Acute Liver Injury, Drug-Induced [description not available]	1.97	1
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	1.97	1
Chemical and Drug Induced Liver Injury A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.	1.97	1

nitromethane

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