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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

signalword

Danger

hcodes

H340,H351

Hazard Classifications

Carc. 2 - Muta. 1B

wgk_germany

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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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
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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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