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SML1723

Sigma-Aldrich

2-Amino-9H-pyrido[2-3-b]indole

≥98% (HPLC)

Synonym(s):

2-Amino-α-carboline, 9H-1,9-Diazafluoren-2-amine, 9H-Pyrido[2,3-b]indol-2-amine, AαC, AaC

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About This Item

Empirical Formula (Hill Notation):
C11H9N3
CAS Number:
26148-68-5
Molecular Weight:
183.21
MDL number:
MFCD00210750
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to light brown

solubility

DMSO: 20 mg/mL, clear

storage temp.

−20°C

SMILES string

NC(C=C1)=NC2=C1C(C=CC=C3)=C3N2

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)

InChI key

FJTNLJLPLJDTRM-UHFFFAOYSA-N

Biochem/physiol Actions

AαC (2-Amino-9H-pyrido[2-3-b]indole) is a potential human carcinogen, which is generated by the combustion of tobacco, or by pyrolysis of protein. AαC potentially contributes to liver or digestive tract cancers. Inside body AαC is metabolized to intermediates (possibly short-lived nitrenium ion of AαC) that react with DNA.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H340,H351

Hazard Classifications

Carc. 2 - Muta. 1B

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Mingjun Yao et al.
Journal of food protection, 365-376 (2020-01-24)
The effects of different grilling methods and tea marinades on the formation of heterocyclic amines (HCAs) and benzo[a]pyrene (BaP) in grilled chicken drumsticks were investigated. This study showed that both the grilling method and type of charcoal used in charcoal
Y Iwamoto et al.
Digestion, 31(1), 31-36 (1985-01-01)
The effects of antigastrin (SC-15396) on amylase release and 2-deoxyglucose uptake were studied in dispersed acini from mouse pancreas. Antigastrin at concentrations between 0.5 and 2 mM inhibited cholecystokinin (CCK)-stimulated amylase release and 2-deoxyglucose uptake in a dose-dependent fashion. Antigastrin
Khyatiben V Pathak et al.
The Journal of biological chemistry, 290(26), 16304-16318 (2015-05-09)
2-Amino-9H-pyrido[2,3-b]indole (AαC) is a carcinogenic heterocyclic aromatic amine formed during the combustion of tobacco. AαC undergoes bioactivation to form electrophilic N-oxidized metabolites that react with DNA to form adducts, which can lead to mutations. Many genotoxicants and toxic electrophiles react
Gwendoline Nauwelaërs et al.
Chemical research in toxicology, 26(9), 1367-1377 (2013-08-01)
Aromatic amines and structurally related heterocyclic aromatic amines (HAAs) are produced during the combustion of tobacco or during the high-temperature cooking of meat. Exposure to some of these chemicals may contribute to the etiology of several common types of human

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