Page last updated: 2024-12-06

n-amyl-n-methylnitrosamine

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

Description

N-amyl-N-methylnitrosamine is a potent carcinogen that has been extensively studied for its role in the development of various cancers, particularly esophageal and stomach cancer. It is a volatile, colorless liquid that is readily absorbed through the skin and respiratory tract. The compound is formed through the nitrosation of N-amylamine in the presence of nitrite, a process that can occur in the environment and in the human body. N-amyl-N-methylnitrosamine has been detected in tobacco smoke, processed meats, and other food products. Studies have shown that exposure to N-amyl-N-methylnitrosamine increases the risk of developing cancer, and its presence in various products has raised concerns about its potential for human health. Research into this compound focuses on understanding its mechanisms of action, identifying sources of exposure, and developing strategies to minimize exposure and reduce its carcinogenic effects.'

N-methyl-N-pentylnitrosamine : A nitrosamine that has methyl and pentyl substituents. It is a potent oesophageal carcinogen. [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 CID25805
CHEMBL ID352469
CHEBI ID140674
SCHEMBL ID4540276
MeSH IDM0083920

Synonyms (38)

Synonym
brn 1925624
n-amyl-n-methylnitrosamine
methyl-n-amylnitrosamine
n-methyl-n-nitrosopentylamine
pentylamine, n-methyl-n-nitroso-
methyl-n-pentylnitrosamine
ccris 3059
methylamylnitrosamin [german]
n-nitroso-n-methyl-n-amylamine
nitrosomethyl-n-pentylamine
nitrosomethyl-n-amylamine
methylamylnitrosamine
n-nitrosomethyl-n-amylamine
1-pentanamine, n-methyl-n-nitroso-
n-methyl-n-pentylnitrosamine
AMN ,
methylamylnitrosamin
mnan
CHEBI:140674
13256-07-0
n-methyl-n-pentylnitrous amide
FT-0662136
CHEMBL352469
unii-u9d5pxj785
u9d5pxj785 ,
AKOS015913828
SCHEMBL4540276
methylpentylnitrosoamine
1-methyl-2-oxo-1-pentylhydrazine #
KSFCDINBDBFFSI-UHFFFAOYSA-N
n-nitroso-n-methylamylamine
methylpentylnitrosamine
DTXSID30157617
J-006189
Q6823932
n-methyl-n-nitroso-1-pentanamine
methyl-n-pentylnitrosamine, n-
n-nitroso-n-methyl-n-pentylamine

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" Clearance of NMAA (25 mg/kg) from rat blood had a half-life of 21 min."( Metabolism of the oesophageal carcinogen N-nitrosomethylamylamine: changes with age, clearance from blood and DNA alkylation.
Ji, C; Krokos, C; Makary, M; Mirvish, SS; Schut, HA, 1987
)
0.27

Dosage Studied

ExcerptRelevanceReference
" For examining the modifying effects of 'initiation' treatment of test compounds, groups of animals were fed the diets containing 1000 ppm diosmin and 1000 ppm hesperidin, and the diet containing both compounds (900 ppm diosmin and 100 ppm hesperidin) for 13 weeks, starting 7 days before the MNAN dosing and then switched to the basal diet."( Modulation of N-methyl-N-amylnitrosamine-induced rat oesophageal tumourigenesis by dietary feeding of diosmin and hesperidin, both alone and in combination.
Fukutani, K; Hara, A; Kakumoto, M; Kawabata, K; Makita, H; Mori, H; Ogawa, H; Satoh, K; Sumida, T; Tanaka, T, 1997
)
0.3
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
carcinogenic agentA role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.
[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]

Drug Classes (1)

ClassDescription
nitrosamineN-Nitroso amines, compounds of the structure R2NNO. Compounds RNHNO are not ordinarily isolable, but they, too, are nitrosamines. The name is a contraction of N-nitrosoamine and, as such, does not require the N locant.
[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]

Bioassays (7)

Assay IDTitleYearJournalArticle
AID617975Mutagenic activity in Salmonella Typhimurium TA1535 at 100 uM after 2 hrs by plate-incorporating method in presence of Fe2+-H2O22011Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18
Isolation and structural identification of a direct-acting mutagen derived from N-nitroso-N-methylpentylamine and Fenton's reagent with copper ion.
AID617974Mutagenic activity in Salmonella Typhimurium TA1535 at 100 uM after 2 hrs by plate-incorporating method in presence of Cu2+-H2O22011Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18
Isolation and structural identification of a direct-acting mutagen derived from N-nitroso-N-methylpentylamine and Fenton's reagent with copper ion.
AID226732The compound was modelled in silico for carcinogenic potency; + = Carcinogen1982Journal of medicinal chemistry, Jul, Volume: 25, Issue:7
Computer-assisted studies of structure-activity relationships of N-nitroso compounds using pattern recognition.
AID617979Mutagenic activity in Salmonella Typhimurium TA1535 at 100 uM after 2 hrs by plate-incorporating method in presence of Fe2+-Cu2+-H2O2 and nitric oxide2011Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18
Isolation and structural identification of a direct-acting mutagen derived from N-nitroso-N-methylpentylamine and Fenton's reagent with copper ion.
AID617977Mutagenic activity in Salmonella Typhimurium TA1535 at 100 uM after 2 hrs by plate-incorporating method in presence of H2O22011Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18
Isolation and structural identification of a direct-acting mutagen derived from N-nitroso-N-methylpentylamine and Fenton's reagent with copper ion.
AID617976Mutagenic activity in Salmonella Typhimurium TA1535 at 100 uM after 2 hrs by plate-incorporating method in presence of Cu2+-Fe2+2011Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18
Isolation and structural identification of a direct-acting mutagen derived from N-nitroso-N-methylpentylamine and Fenton's reagent with copper ion.
AID617978Mutagenic activity in Salmonella Typhimurium TA1535 at 100 uM after 2 hrs by plate-incorporating method in presence of Fe2+-Cu2+-H2O22011Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18
Isolation and structural identification of a direct-acting mutagen derived from N-nitroso-N-methylpentylamine and Fenton's reagent with copper ion.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (53)

TimeframeStudies, This Drug (%)All Drugs %
pre-199024 (45.28)18.7374
1990's21 (39.62)18.2507
2000's7 (13.21)29.6817
2010's1 (1.89)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.07

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index10.07 (24.57)
Research Supply Index4.01 (2.92)
Research Growth Index4.08 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.07)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other54 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]