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Details

Stereochemistry ACHIRAL
Molecular Formula C11H9N3
Molecular Weight 183.2093
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 2-AMINO-9H-PYRIDO(2,3-B)INDOLE

SMILES

NC1=NC2=C(C=C1)C3=C(N2)C=CC=C3

InChI

InChIKey=FJTNLJLPLJDTRM-UHFFFAOYSA-N
InChI=1S/C11H9N3/c12-10-6-5-8-7-3-1-2-4-9(7)13-11(8)14-10/h1-6H,(H3,12,13,14)

HIDE SMILES / InChI

Molecular Formula C11H9N3
Molecular Weight 183.2093
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

PubMed

PubMed

TitleDatePubMed
Effect of Cytochrome P450 Reductase Deficiency on 2-Amino-9H-pyrido[2,3-b]indole Metabolism and DNA Adduct Formation in Liver and Extrahepatic Tissues of Mice.
2015-12-21
DNA adducts of the tobacco carcinogens 2-amino-9H-pyrido[2,3-b]indole and 4-aminobiphenyl are formed at environmental exposure levels and persist in human hepatocytes.
2013-09-16
Naturally occurring food toxins.
2010-09
Identification of carcinogen DNA adducts in human saliva by linear quadrupole ion trap/multistage tandem mass spectrometry.
2010-07-19
Simultaneous determination of six non-polar heterocyclic amines in meat samples by supercritical fluid extraction-capillary electrophoresis under fluorimetric detection.
2010-07
Suitability of ionic liquids as mobile-phase additives in HPLC with fluorescence and UV detection for the determination of heterocyclic aromatic amines.
2010-02
Biomonitoring of carcinogenic heterocyclic aromatic amines in hair: a validation study.
2009-08
The impact of NAT2 acetylator genotype on mutagenesis and DNA adducts from 2-amino-9H-pyrido[2,3-b]indole.
2009-04
Effect of 2-amino-9H-pyrido[2,3-b]indole (AalphaC), a carcinogenic heterocyclic amine present in food, on atherosclerotic plaque development in apoE deficient mice.
2009-03-10
Ethanol Does Not Promote MeIQx-initiated Rat Colon Carcinogenesis Based on Evidence from Analysis of a Colon Cancer Surrogate Marker.
2009-03
Prospective study of dietary patterns and colorectal cancer among Singapore Chinese.
2008-11-04
Binding of heterocyclic aromatic amines by lactic acid bacteria: results of a comprehensive screening trial.
2008-03
Model studies of lignified fiber fermentation by human fecal microbiota and its impact on heterocyclic aromatic amine adsorption.
2007-11-01
Tobacco smoking and urinary levels of 2-amino-9H-pyrido[2,3-b]indole in men of Shanghai, China.
2007-08
Solid-matrix luminescence of heterocyclic aromatic amines in several new sugar-glass systems.
2007-04-15
Metabolites of the carcinogen 2-amino-alpha-carboline formed in male Sprague-Dawley rats in vivo and in rat hepatocyte and human HepG2 cell incubates.
2007-03
Differential effects of heterocyclic amines on poly(ADP-ribose) polymerase-1 and mono-ADP-ribosyltransferase A.
2006-09
Influence of lignification and feruloylation of maize cell walls on the adsorption of heterocyclic aromatic amines.
2006-03-08
Investigation of the separation of heterocyclic aromatic amines by reversed phase ion-pair liquid chromatography coupled with tandem mass spectrometry: the role of ion pair reagents on LC-MS/MS sensitivity.
2005-10-25
Quantitation of carcinogenic heterocyclic aromatic amines and detection of novel heterocyclic aromatic amines in cooked meats and grill scrapings by HPLC/ESI-MS.
2005-04-20
DNA adduct formation of 14 heterocyclic aromatic amines in mouse tissue after oral administration and characterization of the DNA adduct formed by 2-amino-9H-pyrido[2,3-b]indole (AalphaC), analysed by 32P_HPLC.
2005-03-15
Two food-borne heterocyclic amines: metabolism and DNA adduct formation of amino-alpha-carbolines.
2005-03
Analysis of alpha- and beta-carbolines in mainstream smoke of reference cigarettes by gas chromatography-mass spectrometry.
2004-08-13
Rapid biomonitoring of heterocyclic aromatic amines in human urine by tandem solvent solid phase extraction liquid chromatography electrospray ionization mass spectrometry.
2004-08
Syntheses of DNA adducts of two heterocyclic amines, 2-amino-3-methyl-9H-pyrido[2,3-b]indole (MeAalphaC) and 2-amino-9H-pyrido[2,3-b]indole (AalphaC) and identification of DNA adducts in organs from rats dosed with MeAalphaC.
2004-08
Relationship between content and activity of cytochrome P450 and induction of heterocyclic amine DNA adducts in human liver samples in vivo and in vitro.
2004-06
Excretion of metabolites in urine and faeces from rats dosed with the heterocyclic amine, 2-amino-9H-pyrido[2,3-b]indole (AalphaC).
2004-06
Investigation of the genotoxic effects of 2-amino-9H-pyrido[2,3-b]indole in different organs of rodents and in human derived cells.
2004-03-25
Prevention of heterocyclic amine-induced DNA damage in colon and liver of rats by different lactobacillus strains.
2003-12
Impact of five cytochrome p450 enzymes on the metabolism of two heterocyclic aromatic amines, 2-amino-9H-pyrido[2,3-b]indole (AalphaC) and 2-amino-3-methyl-9H-pyrido[2,3-b]indole (MeAalphaC).
2003-05
Probiotic mixture decreases DNA adduct formation in colonic epithelium induced by the food mutagen 2-amino-9H-pyrido[2,3-b]indole in a human-flora associated mouse model.
2003-04
The food mutagen 2-amino-9H-pyrido[2,3-b]indole (AalphaC) but not its methylated form (MeAalphaC) increases intestinal tumorigenesis in neonatally exposed multiple intestinal neoplasia mice.
2002-08
Effects of soy sauce and sugar on the formation of heterocyclic amines in marinated foods.
2002-07
Mutagenic and carcinogenic heterocyclic amines as affected by muscle types/skin and cooking in pan-roasted mackerel.
2002-03-25
In vitro metabolism of two heterocyclic amines, 2-amino-9H-pyrido[2,3-b]indole (A(alpha)C) and 2-amino-3-methyl-9H-pyridol2,3-b]indole (MeA(alpha)C) in human and rat hepatic microsomes.
2002-03
Antimutagenicity of Murdannia loriformis in the Salmonella mutation assay and its inhibitory effects on azoxymethane-induced DNA methylation and aberrant crypt focus formation in male F344 rats.
2002-02
Activation of amino-alpha-carboline, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine and a copper phthalocyanine cellulose extract of cigarette smoke condensate by cytochrome P-450 enzymes in rat and human liver microsomes.
1991-10-01
Carcinogenicity in mice and rats of heterocyclic amines in cooked foods.
1986-08
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:34:37 GMT 2025
Edited
by admin
on Mon Mar 31 18:34:37 GMT 2025
Record UNII
P0GZ1ICS6X
Record Status Validated (UNII)
Record Version
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Name Type Language
2-AMINO-.ALPHA.-CARBOLINE
Preferred Name English
2-AMINO-9H-PYRIDO(2,3-B)INDOLE
HSDB  
Systematic Name English
1H-PYRIDO(2,3-B)INDOL-2-AMINE
Systematic Name English
A-ALPHA-C
Common Name English
AAC
Common Name English
9H-PYRIDO(2,3-B)INDOLE, 2-AMINO-
Systematic Name English
9H-1,9-DIAZAFLUOREN-2-AMINE
Systematic Name English
9H-PYRIDO(2,3-B)INDOL-2-AMINE
Systematic Name English
AMINO-9H-PYRIDO(2,3-B)INDOLE, 2-
Systematic Name English
A.ALPHA.C
Common Name English
GLOB-P-2
Common Name English
2-AMINO-9H-PYRIDO(2,3-B)INDOLE [HSDB]
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID7020001
Created by admin on Mon Mar 31 18:34:37 GMT 2025 , Edited by admin on Mon Mar 31 18:34:37 GMT 2025
PRIMARY
FDA UNII
P0GZ1ICS6X
Created by admin on Mon Mar 31 18:34:37 GMT 2025 , Edited by admin on Mon Mar 31 18:34:37 GMT 2025
PRIMARY
CAS
26148-68-5
Created by admin on Mon Mar 31 18:34:37 GMT 2025 , Edited by admin on Mon Mar 31 18:34:37 GMT 2025
PRIMARY
PUBCHEM
62805
Created by admin on Mon Mar 31 18:34:37 GMT 2025 , Edited by admin on Mon Mar 31 18:34:37 GMT 2025
PRIMARY
MESH
C017822
Created by admin on Mon Mar 31 18:34:37 GMT 2025 , Edited by admin on Mon Mar 31 18:34:37 GMT 2025
PRIMARY
HSDB
7086
Created by admin on Mon Mar 31 18:34:37 GMT 2025 , Edited by admin on Mon Mar 31 18:34:37 GMT 2025
PRIMARY