Compounds > methacrylonitrile

Page last updated: 2024-12-06

methacrylonitrile

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Description

methacrylonitrile: lacrimator; preparation of polymers & homopolymers; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID Source	ID
PubMed CID	31368
CHEMBL ID	1529759
MeSH ID	M0052191

Synonyms (72)

Synonym
nsc 20659
126-98-7
2-methylpropenenitrile
2-cyano-1-propene
isopropenylnitrile
nsc-24145
2-propenenitrile, 2-methyl-
2-methyl-2-propenenitrile
.alpha.-methacrylonitrile
2-cyanopropene
nsc24145
2-methylacrylonitrile
methylacrylonitrile
isopropene cyanide
methacrylonitrile
2-cyanopropene-1
usaf st-40
.alpha.-methylacrylonitrile
wln: ncy1 & u1
un3079
einecs 204-817-5
ccris 4841
rcra waste number u152
hsdb 5613
methyl acrylonitrile
rcra waste no. u152
ai3-52399
nsc 24145
nsc20659
25067-61-2
nsc-20659
propenoic acid,2-methyl,nitrile methacryl nitrile
inchi=1/c4h5n/c1-4(2)3-5/h1h2,2h
NCGC00090742-01
methacrylonitrile, 99%
NCGC00090742-02
methacrylonitrile-15n
204523-22-8
2-methylprop-2-enenitrile
AKOS000121392
NCGC00090742-03
NCGC00090742-04
unii-04s4k38612
methacrylonitrile, inhibited [un3079] [flammable liquid]
ec 204-817-5
methacrylonitrile, inhibited
04s4k38612 ,
tox21_303172
dtxcid104176
cas-126-98-7
NCGC00256956-01
dtxsid1024176 ,
NCGC00258906-01
tox21_201354
BBL011404
M0089
STL146508
methylacrylonitrile [hsdb]
methacrylonitrile [mi]
isobutenenitrile
methacrylnitrile
2-methyl-acrylonitrile
propenenitrile, 2-methyl
1-methyl-1-cyanoethylene
ch2c(ch3)cn
CHEMBL1529759
methacrylonitrile, stabilized
mfcd00001872
methacrylonitrile (stabilized with hydroquinone monomethyl ether)
Q2088171
methacrylonitrile (15n)
EN300-21169

Research Excerpts

Overview

Methacrylonitrile (MAN) is an industrial chemical used to manufacture plastics and elastomers. It is structurally similar to the known rat carcinogen and suspected human carcinogen acrylonitile (AN) Methacryonitrile is an unsaturated aliphatic nitrile.

Excerpt	Reference	Relevance
"Methacrylonitrile is an unsaturated aliphatic nitrile. "	( Characterization of the toxicity, mutagenicity, and carcinogenicity of methacrylonitrile in F344 Rats and B6C3F1 mice. Ghanayem, BI; Nyska, A, 2003)	1.99
"Methacrylonitrile (MeAN) is a plastic monomer. "	( Effect of methacrylonitrile on membrane bound enzymes of rat brain. Devaraj, SN; Unnisa, AZ, )	1.98
"Methacrylonitrile (MAN) is an industrial chemical used to manufacture plastics and elastomers. "	( Investigation of methacrylonitrile metabolism and the metabolic basis for the differences in its toxicity in rats and mice. Burka, LT; Ghanayem, BI; Sanchez, IM, 1994)	2.07
"Methacrylonitrile (MAN) is a widely used industrial chemical. "	( Single dose blood toxicokinetics of methacrylonitrile in the F344 rat. Demby, KB; Ghanayem, BI; Sanchez, IM, 1993)	2
"Methacrylonitrile (MAN) is a widely used aliphatic nitrile and is structurally similar to the known rat carcinogen and suspected human carcinogen acrylonitrile (AN). "	( Role of cytochrome P-450 2E1 in methacrylonitrile metabolism and disposition. Burka, LT; Chanas, B; Ghanayem, BI; Gonzalez, FJ; Sanders, JM, 1999)	2.03
"Methacrylonitrile is an unsaturated aliphatic nitrile. "	( Toxicology and carcinogenesis studies of methacrylonitrile (CAS No. 126-98-7) in F344/N rats and B6C3F1 mice (gavage studies). , 2001)	2.02
"Methacrylonitrile is an aliphatic nitrile used extensively in the preparation of homo- and copolymers, elastomers, and plastics and as a chemical intermediate in the preparation of acids, amides, esters, and other nitriles. "	( NTP technical report on the toxicity studies of methacrylonitrile (CAS No. 126-98-7). Administered by gavage to F344/N rats and B6C3F1 mice. Ghanayem, BI, 2000)	2.01

Effects

Excerpt	Reference	Relevance
"Methacrylonitrile has been given by a variety of routes to mammalian species to study its toxic effects."	( Toxicology of methacrylonitrile. Farooqui, MY; Mumtaz, MM, 1991)	1.36

Toxicity

Excerpt	Reference	Relevance
"When rats were exposed for 30 min to methacrylonitrile at concentrations between 3180 and 5700 ppm, the clinical symptoms observed suggested a toxic activity of metabolically formed cyanide."	( Effect of antidotes of the acute toxicity of methacrylonitrile. Bolt, HM; Peter, H, 1985)	0.8
" LD50 of MAN is 200 to 230 mg/kg in rats and 17 mg/kg in mice."	( Investigation of methacrylonitrile metabolism and the metabolic basis for the differences in its toxicity in rats and mice. Burka, LT; Ghanayem, BI; Sanchez, IM, 1994)	0.63
"5 LD50 doses of the nitriles by gavage and they were observed for 12 It for cholinomimetic and central nervous system effects."	( Effect of dosing vehicle on the toxicity and metabolism of unsaturated aliphatic nitriles. Farooqui, MY; Piper, J; Tamez, A; Ybarra, B, )	0.13
" In rats, no treatment-related maternal clinical signs or mortality were observed, nor was there any adverse effect on maternal body weight or food or water consumption."	( Evaluation of the developmental toxicity of methacrylonitrile in Sprague-Dawley rats and New Zealand white rabbits. George, JD; Heindel, JJ; Hunter, ES; Marr, MC; Myers, CB; Price, CJ; Schwetz, BA, 1996)	0.56

Bioavailability

Excerpt	Reference	Relevance
"87 mmol/kg) of 2-14C-MAN or 2-14C-AN to male F344 rats, both chemicals were well absorbed from the GI tract and distributed to all major tissues."	( Comparative metabolism and disposition of acrylonitrile and methacrylonitrile in rats. Ahmed, AE; Burka, LT; Ghanayem, BI; Sanchez, IM, 1994)	0.53

Dosage Studied

Excerpt	Relevance	Reference
" All the three species showed a dose-response relationship in metabolism of MeAN to cyanide."	( Methacrylonitrile: in vivo metabolism to cyanide in rats, mice, and gerbils. Deleon, JH; Diaz, RG; Farooqui, MY, )	1.57
" Investigating the effect of dosing vehicle on MAN disposition in rats revealed that administration of 115 mg MAN/kg in oil resulted in the death of rats within 24 hr after treatment."	( Effects of dose, strain, and dosing vehicle on methacrylonitrile disposition in rats and identification of a novel-exhaled metabolite. Burka, LT; Ghanayem, BI; Sanchez, IM, )	0.39
" MAN elimination was almost complete within 24 hr after dosing and the tissue concentrations of MAN-derived radioactivity were, with the exception of the urinary bladder, consistently higher in rats than in mice."	( Investigation of methacrylonitrile metabolism and the metabolic basis for the differences in its toxicity in rats and mice. Burka, LT; Ghanayem, BI; Sanchez, IM, 1994)	0.63
" Blood samples were collected at various time points after dosing and serum MAN concentrations were measured."	( Single dose blood toxicokinetics of methacrylonitrile in the F344 rat. Demby, KB; Ghanayem, BI; Sanchez, IM, 1993)	0.56
"The effect of dosing vehicle on toxicity and metabolism of unsaturated aliphatic nitriles was investigated in male Sprague-Dawley rats."	( Effect of dosing vehicle on the toxicity and metabolism of unsaturated aliphatic nitriles. Farooqui, MY; Piper, J; Tamez, A; Ybarra, B, )	0.13
"Timed-pregnant Sprague-Dawley (CD) outbred rats and New Zealand White rabbits were dosed by gavage with methacrylonitrile (MACR) in distilled water during major organogenesis."	( Evaluation of the developmental toxicity of methacrylonitrile in Sprague-Dawley rats and New Zealand white rabbits. George, JD; Heindel, JJ; Hunter, ES; Marr, MC; Myers, CB; Price, CJ; Schwetz, BA, 1996)	0.77
" In the 2-year study, survival of all dosed groups of rats was similar to that of the vehicle control groups."	( Toxicology and carcinogenesis studies of methacrylonitrile (CAS No. 126-98-7) in F344/N rats and B6C3F1 mice (gavage studies). , 2001)	0.58

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (10)

Potency Measurements

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Chain A, TYROSYL-DNA PHOSPHODIESTERASE	Homo sapiens (human)	Potency	3.5481	0.0040	23.8416	100.0000	AID485290
GLI family zinc finger 3	Homo sapiens (human)	Potency	64.6282	0.0007	14.5928	83.7951	AID1259369
AR protein	Homo sapiens (human)	Potency	64.6282	0.0002	21.2231	8,912.5098	AID743040
glucocorticoid receptor [Homo sapiens]	Homo sapiens (human)	Potency	21.4864	0.0002	14.3764	60.0339	AID588532; AID720691
estrogen nuclear receptor alpha	Homo sapiens (human)	Potency	20.0466	0.0002	29.3054	16,493.5996	AID588514; AID743069
peroxisome proliferator-activated receptor delta	Homo sapiens (human)	Potency	28.1838	0.0010	24.5048	61.6448	AID588535
aryl hydrocarbon receptor	Homo sapiens (human)	Potency	30.6379	0.0007	23.0674	1,258.9301	AID743085
activating transcription factor 6	Homo sapiens (human)	Potency	0.1836	0.1434	27.6121	59.8106	AID1159516
thyroid hormone receptor beta isoform 2	Rattus norvegicus (Norway rat)	Potency	68.5896	0.0003	23.4451	159.6830	AID743065
nuclear factor erythroid 2-related factor 2 isoform 1	Homo sapiens (human)	Potency	0.0172	0.0006	27.2152	1,122.0200	AID651741
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (38)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	7 (18.42)	18.7374
1990's	18 (47.37)	18.2507
2000's	10 (26.32)	29.6817
2010's	2 (5.26)	24.3611
2020's	1 (2.63)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 36.44

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.

Metric	This Compound (vs All)
Research Demand Index	36.44 (24.57)
Research Supply Index	3.81 (2.92)
Research Growth Index	4.80 (4.65)
Search Engine Demand Index	48.45 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (36.44)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	1 (2.27%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	43 (97.73%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
acetone methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).	2.39	2	ketone body; methyl ketone; propanones; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; human metabolite; polar aprotic solvent
benzene [no description available]	2	1	aromatic annulene; benzenes; volatile organic compound	carcinogenic agent; environmental contaminant; non-polar solvent
glycine [no description available]	2.11	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
ethoxyquin Ethoxyquin: Antioxidant; also a post-harvest dip to prevent scald on apples and pears.. ethoxyquin : A quinoline that is 1,2-dihydroquinoline bearing three methyl substituents at position 2, 2 and 4 as well as an ethoxy substituent at position 6.	2	1	aromatic ether; quinolines	antifungal agrochemical; food antioxidant; genotoxin; geroprotector; herbicide; Hsp90 inhibitor; neuroprotective agent; UDP-glucuronosyltransferase activator
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.	2.67	3	barbiturates	anticonvulsant; drug allergen; excitatory amino acid antagonist; sedative
proadifen Proadifen: An inhibitor of drug metabolism and CYTOCHROME P-450 ENZYME SYSTEM activity.	2.67	3	diarylmethane
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.	4.17	5	pseudohalide anion	EC 1.9.3.1 (cytochrome c oxidase) inhibitor
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.	1.96	1	bromohydrocarbon; bromomethanes; methyl halides	algal metabolite; fumigant insecticide; marine 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.	2.41	2	aliphatic nitrile; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent
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]	3.68	10	aliphatic nitrile; volatile organic compound	antifungal agent; carcinogenic agent; fungal metabolite; mutagen; polar aprotic solvent
n-butyronitrile [no description available]	2	1	aliphatic nitrile
allyl cyanide TL 350: structure given in first source. allyl cyanide : An aliphatic nitrile that is hydrogen cyanide in which the hydrogen has been replaced by an allyl group.	2.39	2	aliphatic nitrile; olefinic compound	antifeedant; neurotoxin; plant metabolite
sodium cyanide Sodium Cyanide: A highly poisonous compound that is an inhibitor of many metabolic processes and is used as a test reagent for the function of chemoreceptors. It is also used in many industrial processes.. sodium cyanide : A cyanide salt containing equal numbers of sodium cations and cyanide anions.	2	1	cyanide salt; one-carbon compound; sodium salt	EC 1.15.1.1 (superoxide dismutase) inhibitor
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	2	1	acetylcysteine; L-cysteine derivative; N-acetyl-L-amino acid	antidote to paracetamol poisoning; antiinfective agent; antioxidant; antiviral drug; ferroptosis inhibitor; geroprotector; human metabolite; mucolytic; radical scavenger; vulnerary
silver Silver: An element with the atomic symbol Ag, atomic number 47, and atomic weight 107.87. It is a soft metal that is used medically in surgical instruments, dental prostheses, and alloys. Long-continued use of silver salts can lead to a form of poisoning known as ARGYRIA.	7.6	1	copper group element atom; elemental silver	Escherichia coli metabolite
chromates Chromates: Salts of chromic acid containing the CrO(2-)4 radical.. chromate(2-) : A chromium oxoanion resulting from the removal of two protons from chromic acid.	1.96	1	chromium oxoanion; divalent inorganic anion	oxidising agent
2-chloroacrylonitrile 2-chloroacrylonitrile: structure given in first source	2.41	2
n-acetylneuraminic acid N-Acetylneuraminic Acid: An N-acyl derivative of neuraminic acid. N-acetylneuraminic acid occurs in many polysaccharides, glycoproteins, and glycolipids in animals and bacteria. (From Dorland, 28th ed, p1518). N-acetylneuraminic acid : An N-acylneuraminic acid where the N-acyl group is specified as acetyl.	1.99	1	N-acetylneuraminic acids	antioxidant; bacterial metabolite; EC 3.2.1.18 (exo-alpha-sialidase) inhibitor; human metabolite; mouse metabolite
crotononitrile crotononitrile: RN given refers to cpd without isomeric designation	2.39	2	nitrile
nadp [no description available]	2.39	2
bilirubin [no description available]	1.99	1	biladienes; dicarboxylic acid	antioxidant; human metabolite; mouse metabolite
2-pentenenitrile 2-pentenenitrile: RN given refers to parent cpd	2.02	1
silicon Silicon: A trace element that constitutes about 27.6% of the earth's crust in the form of SILICON DIOXIDE. It does not occur free in nature. Silicon has the atomic symbol Si, atomic number 14, and atomic weight [28.084; 28.086].	2.02	1	carbon group element atom; metalloid atom; nonmetal atom

Condition	Relationship Strength	Studies
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	3.09	5
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	3.09	5
Diseases, Occupational [description not available]	1.92	1
Fetal Resorption The disintegration and assimilation of the dead FETUS in the UTERUS at any stage after the completion of organogenesis which, in humans, is after the 9th week of GESTATION. It does not include embryo resorption (see EMBRYO LOSS).	1.99	1
Abnormalities, Drug-Induced Congenital abnormalities caused by medicinal substances or drugs of abuse given to or taken by the mother, or to which she is inadvertently exposed during the manufacture of such substances. The concept excludes abnormalities resulting from exposure to non-medicinal chemicals in the environment.	2.4	2
Hyperplasia An increase in the number of cells in a tissue or organ without tumor formation. It differs from HYPERTROPHY, which is an increase in bulk without an increase in the number of cells.	1.99	1
Hepatocellular Carcinoma [description not available]	1.99	1
Cancer of Liver [description not available]	1.99	1
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	1.99	1
Liver Neoplasms Tumors or cancer of the LIVER.	1.99	1
Extravascular Hemolysis [description not available]	1.99	1
Hemolysis The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.	1.99	1
Abortion, Veterinary Premature expulsion of the FETUS in animals.	1.98	1
Anasarca [description not available]	1.98	1
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	1.98	1
Acute Disease Disease having a short and relatively severe course.	1.96	1

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