Compounds > nitroguanidine
Page last updated: 2024-11-13

nitroguanidine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

nitroguanidine: RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

nitroguanidine : An N-nitro compound that is guanidine in which one of the hydrogens is replaced by a nitro group. It can exist in distinct tautomeric forms, as 1-nitroguanidine (a nitroimine) or 2-nitroguanidine (a nitroamine); in both solid and in solution, the nitroimine form predominates. [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]

Cross-References

ID SourceID
PubMed CID86287517
CHEMBL ID3187135
CHEBI ID39180
SCHEMBL ID107616
MeSH IDM0157672

Synonyms (47)

Synonym
nitroguanidine, wetted or picrite, wetted with not <20% water, by mass
ec 209-143-5
nitroguanidine or picrite, dry or wetted with <20% water, by mass [un0282] [explosive 1.1d]
nay6kwl67f ,
nitroguanidine or picrite, dry or wetted with <20% water, by mass
unii-nay6kwl67f
nitroguanidine, wetted or picrite, wetted with not <20% water, by mass [un1336] [flammable solid]
n-nitroguanidine
nsc41036
guanidine, 1-nitro-
1-nitroguanidine
picrite (the explosive)
556-88-7
nitroguanidine
picrite
guanidine, 1-nitro- (wet)
wln: wnmyzum
nsc-41036
n''-nitroguanidine
guanidine, nitro-
nitroguanidine or picrite, dry or wetted with < 20% water, by mass
hsdb 5693
un1336
n(1)-nitroguanidine
einecs 209-143-5
un0282
ai3-16306
CHEBI:39180 ,
AKOS005111009
N0206
NCGC00248865-01
cas-556-88-7
tox21_200886
dtxsid4024222 ,
NCGC00258440-01
dtxcid204222
FT-0632385
1-nitroguanidine [hsdb]
n-nitroguanidine [mi]
SCHEMBL107616
1-nitroguanidine wetted with not less than 25% water
W-105552
CHEMBL3187135
mfcd00007039
nitroguanidine (wetted with 25% water)
nitroguanidine 100 microg/ml in acetonitrile
VS-08107

Research Excerpts

Overview

Nitroguanidine (NQ) is a constituent of gas generators for automobile airbags, smokeless pyrotechnics, insecticides, propellants, and new insensitive munitions formulations applied by the military. It is currently being considered as a TNT replacement in explosive formulations.

ExcerptReferenceRelevance
"Nitroguanidine (NQ) is an emerging contaminant being used by the military as a constituent of new insensitive munitions. "( Reductive transformation of the insensitive munitions compound nitroguanidine by different iron-based reactive minerals.
Chorover, J; Field, JA; Menezes, O; Niu, XZ; Rios-Valenciana, EE; Romero, J; Root, RA; Sierra-Alvarez, R, 2022)		2.4
"Nitroguanidine (NQ) is a constituent of gas generators for automobile airbags, smokeless pyrotechnics, insecticides, propellants, and new insensitive munitions formulations applied by the military. "( Elucidating the mechanisms associated with the anaerobic biotransformation of the emerging contaminant nitroguanidine.
Blubaum, C; Field, JA; Krzmarzick, MJ; Menezes, O; Rios-Valenciana, EE; Romero, J; Sierra-Alvarez, R, 2023)		2.57
"Nitroguanidine (NQ) is an energetic material that is used as a key ingredient of triple-base propellants and is currently being considered as a TNT replacement in explosive formulations. "( Aerobic mineralization of nitroguanidine by Variovorax strain VC1 isolated from soil.
Ampleman, G; Halasz, A; Hawari, J; Manno, D; Perreault, NN; Thiboutot, S, 2012)		2.12
"Nitroguanidine is a chemical of low toxicity (LD50 greater than 5 g/kg); it is quantitatively absorbed from the gastrointestinal tract, distributed throughout the body, and rapidly excreted in the urine."( The fate of nitroguanidine in the rat.
Ho, B; Kincannon, LC; Korte, DW; Simboli, PB; Tillotson, JA, 1988)		1.38

Toxicity

ExcerptReferenceRelevance
" Without photodegradation, DNAN was more toxic (median lethal concentration [LC50] = 43 mg/L) than the other 2 constituents and it contributed predominantly to the toxicity of IMX-101 (LC50 = 206 mg/L) based on toxic units."( Aquatic toxicity of photo-degraded insensitive munition 101 (IMX-101) constituents.
Bednar, AJ; Gust, KA; Jordan, SM; Kennedy, AJ; Melby, NL; Moores, LC; Poda, AR, 2017)		0.46
" Identification of principal toxic agents in the UV-degraded NQ product mixture remains a critical data gap."( Effect of UV-light exposure duration, light source, and aging on nitroguanidine (NQ) degradation product profile and toxicity.
Acrey, B; Amar, SK; George, GW; Gust, KA; Jones, SJ; Kennedy, AJ; Moores, LC; Rabalais, L; Zetterholm, SG, 2022)		0.96

Bioavailability

ExcerptReferenceRelevance
" The bioavailability of orally administered NG was 100%; the kinetics of NG in the blood was not dose dependent."( The fate of nitroguanidine in the rat.
Ho, B; Kincannon, LC; Korte, DW; Simboli, PB; Tillotson, JA, 1988)		0.65

Dosage Studied

ExcerptRelevanceReference
" The kinetics of [14C]NG in the blood of the dosed animals was followed."( The fate of nitroguanidine in the rat.
Ho, B; Kincannon, LC; Korte, DW; Simboli, PB; Tillotson, JA, 1988)		0.65
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
nitroguanidineAn N-nitro compound that is guanidine in which one of the hydrogens is replaced by a nitro group. It can exist in distinct tautomeric forms, as 1-nitroguanidine (a nitroimine) or 2-nitroguanidine (a nitroamine); in both solid and in solution, the nitroimine form predominates.
one-carbon compoundAn organic molecular entity containing a single carbon atom (C1).
nitroguanidineAn N-nitro compound that is guanidine in which one of the hydrogens is replaced by a nitro group. It can exist in distinct tautomeric forms, as 1-nitroguanidine (a nitroimine) or 2-nitroguanidine (a nitroamine); in both solid and in solution, the nitroimine form predominates.
one-carbon compoundAn organic molecular entity containing a single carbon atom (C1).
[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]

Protein Targets (2)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency49.33860.003041.611522,387.1992AID1159552; AID1159555
retinoid X nuclear receptor alphaHomo sapiens (human)Potency42.96470.000817.505159.3239AID1159527
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (1)

Assay IDTitleYearJournalArticle
AID1135359Ionization constant, pKa of the compound1977Journal of medicinal chemistry, Jul, Volume: 20, Issue:7
Cyanoguanidine-thiourea equivalence in the development of the histamine H2-receptor antagonist, cimetidine.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (39)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (10.26)18.7374
1990's2 (5.13)18.2507
2000's4 (10.26)29.6817
2010's16 (41.03)24.3611
2020's13 (33.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 47.50

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index47.50 (24.57)
Research Supply Index3.71 (2.92)
Research Growth Index5.22 (4.65)
Search Engine Demand Index69.65 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (47.50)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (2.50%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other39 (97.50%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
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.		2.110alkyl alcohol;
one-carbon compound;
primary alcohol;
volatile organic compound		amphiprotic solvent;
Escherichia coli metabolite;
fuel;
human metabolite;
mouse metabolite;
Mycoplasma genitalium 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.		2.0510isourea;
monocarboxylic acid amide;
one-carbon compound		Daphnia magna metabolite;
Escherichia coli metabolite;
fertilizer;
flour treatment agent;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
pimagedine
pimagedine: diamine oxidase & nitric oxide synthase inhibitor; an advanced glycosylation end product inhibitor; used in the treatment of diabetic complications; structure. aminoguanidine : A one-carbon compound whose unique structure renders it capable of acting as a derivative of hydrazine, guanidine or formamide.		2.0310guanidines;
one-carbon compound		EC 1.14.13.39 (nitric oxide synthase) inhibitor;
EC 1.4.3.4 (monoamine oxidase) inhibitor
cimetidine
Cimetidine: A histamine congener, it competitively inhibits HISTAMINE binding to HISTAMINE H2 RECEPTORS. Cimetidine has a range of pharmacological actions. It inhibits GASTRIC ACID secretion, as well as PEPSIN and GASTRIN output.. cimetidine : A member of the class of guanidines that consists of guanidine carrying a methyl substituent at position 1, a cyano group at position 2 and a 2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl group at position 3. It is a H2-receptor antagonist that inhibits the production of acid in stomach.		1.9510aliphatic sulfide;
guanidines;
imidazoles;
nitrile		adjuvant;
analgesic;
anti-ulcer drug;
H2-receptor antagonist;
P450 inhibitor
guanidine
Guanidine: A strong organic base existing primarily as guanidium ions at physiological pH. It is found in the urine as a normal product of protein metabolism. It is also used in laboratory research as a protein denaturant. (From Martindale, the Extra Pharmacopoeia, 30th ed and Merck Index, 12th ed) It is also used in the treatment of myasthenia and as a fluorescent probe in HPLC.. guanidine : An aminocarboxamidine, the parent compound of the guanidines.		7.3420carboxamidine;
guanidines;
one-carbon compound
kynurenic acid
Kynurenic Acid: A broad-spectrum excitatory amino acid antagonist used as a research tool.. kynurenic acid : A quinolinemonocarboxylic acid that is quinoline-2-carboxylic acid substituted by a hydroxy group at C-4.		2.110monohydroxyquinoline;
quinolinemonocarboxylic acid		G-protein-coupled receptor agonist;
human metabolite;
neuroprotective agent;
nicotinic antagonist;
NMDA receptor antagonist;
Saccharomyces cerevisiae metabolite
ethylene oxide
Ethylene Oxide: A colorless and flammable gas at room temperature and pressure. Ethylene oxide is a bactericidal, fungicidal, and sporicidal disinfectant. It is effective against most micro-organisms, including viruses. It is used as a fumigant for foodstuffs and textiles and as an agent for the gaseous sterilization of heat-labile pharmaceutical and surgical materials. (From Reynolds, Martindale The Extra Pharmacopoeia, 30th ed, p794). oxirane : A saturated organic heteromonocyclic parent that is a three-membered heterocycle of two carbon atoms and one oxygen atom.		2.0810gas molecular entity;
oxacycle;
saturated organic heteromonocyclic parent		allergen;
mouse metabolite;
mutagen
propylene oxide
propylene oxide: structure. 1,2-epoxypropane : An epoxide that is oxirane substituted by a methyl group at position 2.		2.0810epoxide
trifluoroacetic acid
Trifluoroacetic Acid: A very strong halogenated derivative of acetic acid. It is used in acid catalyzed reactions, especially those where an ester is cleaved in peptide synthesis.. trifluoroacetic acid : A monocarboxylic acid that is the trifluoro derivative of acetic acid.		2.110fluoroalkanoic acidhuman xenobiotic metabolite;
NMR chemical shift reference compound;
reagent
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.		2.7530trinitrotolueneexplosive
2,4-dinitroanisole
2,4-dinitroanisole : A member of the class of dinitroanisoles that is 2-nitroanisole in which the hydrogen para to the methoxy group is replaced by a second nitro group.		3.7490dinitroanisolesexplosive
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.		2.98401,3,5-triazinanes;
N-nitro compound		explosive
thiazoles
[no description available]		2.44201,3-thiazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene
cyanamide
Cyanamide: A cyanide compound which has been used as a fertilizer, defoliant and in many manufacturing processes. It often occurs as the calcium salt, sometimes also referred to as cyanamide. The citrated calcium salt is used in the treatment of alcoholism.. cyanamide : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by an amino group.		2.4110nitrile;
one-carbon compound		EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor
dicyandiamido
dicyandiamido: RN given refers to parent cpd; structure. cyanoguanidine : A guanidine in which one of the amino hydrogens of guanidine itself is substituted by a cyano group. It is used in the manufacture of fertilizers, pharmaceuticals, explosives, oil well drilling muds, and dyestuffs.		1.9510guanidines;
nitrile		curing agent;
explosive;
fertilizer;
flame retardant;
nitrification inhibitor
hesperidin
Hesperidin: A flavanone glycoside found in CITRUS fruit peels.. hesperidin : A disaccharide derivative that consists of hesperetin substituted by a 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.		2.41103'-hydroxyflavanones;
4'-methoxyflavanones;
dihydroxyflavanone;
disaccharide derivative;
flavanone glycoside;
monomethoxyflavanone;
rutinoside		mutagen
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.		210N-nitro compound;
tetrazocane		explosive
azides
Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.		3.3110pseudohalide anionmitochondrial respiratory-chain inhibitor
triazoles
Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.		3.941101,2,3-triazole
thiamethoxam
Thiamethoxam: A nitro-oxazine and thiazole derivative that is used as a broad spectrum neonicotinoid insecticide.. thiamethoxam : An oxadiazane that is tetrahydro-N-nitro-4H-1,3,5-oxadiazin-4-imine bearing (2-chloro-1,3-thiazol-5-yl)methyl and methyl substituents at positions 3 and 5 respectively.		2.44201,3-thiazoles;
2-nitroguanidine derivative;
organochlorine compound;
oxadiazane		antifeedant;
carcinogenic agent;
environmental contaminant;
neonicotinoid insectide;
xenobiotic
thiacloprid
thiacloprid: structure in first source. (Z)-thiacloprid : The (Z)-stereoisomer of thiacloprid.. thiacloprid : A nitrile that is cyanamide in which the hydrogens are replaced by a 1,3-thiazolidin-2-ylidene group which in turn is substituted by a (6-chloropyridin-3-yl)methyl group at the ring nitrogen.		2.610monochloropyridine;
nitrile;
thiazolidines		environmental contaminant;
neonicotinoid insectide;
xenobiotic
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.		7.610amino 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
imidaclothiz
imidaclothiz: an insecticide; structure in first source		2.610
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.		2.0310anabasine
cellulose triacetate
cellulose triacetate: for hemodialysis filtration		2.1710
nitroarginine
Nitroarginine: An inhibitor of nitric oxide synthetase which has been shown to prevent glutamate toxicity. Nitroarginine has been experimentally tested for its ability to prevent ammonia toxicity and ammonia-induced alterations in brain energy and ammonia metabolites. (Neurochem Res 1995:200(4):451-6). N(gamma)-nitro-L-arginine : An L-arginine derivative that is L-arginine in which the terminal nitrogen of the guanidyl group is replaced by a nitro group.		2.110guanidines;
L-arginine derivative;
N-nitro compound;
non-proteinogenic L-alpha-amino acid
1,1-diamino-2,2-dinitroethylene
1,1-diamino-2,2-dinitroethylene: structure in first source		2.1710
metiamide
Metiamide: A histamine H2 receptor antagonist that is used as an anti-ulcer agent.		1.9510imidazoles
1,3-dimethylthiourea
[no description available]		1.9510
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.		1.9510one-carbon compound;
thioureas;
ureas		antioxidant;
chromophore
burimamide
Burimamide: An antagonist of histamine that appears to block both H2 and H3 histamine receptors. It has been used in the treatment of ulcers.		1.9510imidazoles
nitenpyram
nitenpyram: a nitromethylene neonicotinoid insecticide; structure in first source. (E)-nitenpyram : A nitenpyram in which the double bond has E configuration.. nitenpyram : A C-nitro compound consisting of 2-nitroethene-1,1-diamine where one of the nitrogens bears ethyl and (6-chloro-3-pyridinyl)methyl while the other nitrogen carries a methyl group.		2.0310chloropyridyl insecticide;
nitenpyram
nitrovin
Nitrovin: An antibacterial growth promoter used in animal feeds.		1.9910C-nitro compound;
furans
cellulose
DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.		2.1710glycoside
chitosan
[no description available]		2.1710
5-nitro-1,2,4-triazol-3-one
5-nitro-1,2,4-triazol-3-one: impact-insensitive explosive; structure in first source		3.7490
methylnitronitrosoguanidine
Methylnitronitrosoguanidine: A nitrosoguanidine derivative with potent mutagenic and carcinogenic properties.. N-methyl-N'-nitro-N-nitrosoguanidine : An N-nitroguanidine compound having nitroso and methyl substituents at the N'-position		2.7620nitroso compoundalkylating agent
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.		2.5120imidacloprid;
imidazolidines;
monochloropyridine		environmental contaminant;
genotoxin;
neonicotinoid insectide;
nicotinic acetylcholine receptor agonist;
xenobiotic
ConditionIndicatedRelationship StrengthStudiesTrials
Cancer of Stomach
[description not available]		02.7620
Stomach Neoplasms
Tumors or cancer of the STOMACH.		02.7620
Innate Inflammatory Response
[description not available]		02.3110
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		02.3110
Caries, Dental
[description not available]		02.0310
Dental Caries
Localized destruction of the tooth surface initiated by decalcification of the enamel followed by enzymatic lysis of organic structures and leading to cavity formation. If left unchecked, the cavity may penetrate the enamel and dentin and reach the pulp.		02.0310