AalphaC
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MedKoo CAT#: 563737

CAS#: 26148-68-5

Description: AalphaC is the most abundant carcinogenic heterocyclic aromatic amine (HAA) formed in mainstream tobacco smoke and is a liver carcinogen in rodents, but its carcinogenic potential in humans is not known.


Chemical Structure

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AalphaC
CAS# 26148-68-5

Theoretical Analysis

MedKoo Cat#: 563737
Name: AalphaC
CAS#: 26148-68-5
Chemical Formula: C11H9N3
Exact Mass: 183.08
Molecular Weight: 183.210
Elemental Analysis: C, 72.11; H, 4.95; N, 22.94

Price and Availability

Size Price Availability Quantity
5mg USD 260
25mg USD 620
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Synonym: AalphaC; Aalpha-C; Aalpha C; 2-Amino-alpha-carboline;

IUPAC/Chemical Name: 9H-Pyrido[2,3-b]indol-2-amine

InChi Key: FJTNLJLPLJDTRM-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: NC1=CC=C2C(NC3=C2C=CC=C3)=N1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 183.21 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Bellamri M, Le Hegarat L, Turesky RJ, Langouët S. Metabolism of the Tobacco Carcinogen 2-Amino-9H-pyrido[2,3-b]indole (AαC) in Primary Human Hepatocytes. Chem Res Toxicol. 2017 Feb 20;30(2):657-668. doi: 10.1021/acs.chemrestox.6b00394. Epub 2016 Dec 15. PMID: 27976871; PMCID: PMC5439433.


2: Pathak KV, Bellamri M, Wang Y, Langouët S, Turesky RJ. 2-Amino-9H-pyrido[2,3-b]indole (AαC) Adducts and Thiol Oxidation of Serum Albumin as Potential Biomarkers of Tobacco Smoke. J Biol Chem. 2015 Jun 26;290(26):16304-18. doi: 10.1074/jbc.M115.646539. Epub 2015 May 7. PMID: 25953894; PMCID: PMC4481229.


3: Liu X, Zhang T, Li X, Zhao G, Xie F. Effects of 2-amino-9H-pyrido[2,3-b]indole (AαC) metabolic bio-activation on oxidative DNA damage in human hepatoma G2 (HepG2) cells. Toxicol Mech Methods. 2018 Mar;28(3):230-237. doi: 10.1080/15376516.2017.1391363. Epub 2017 Nov 28. PMID: 29022416.


4: Hu K, Zhao G, Fu Y, Wang S, Yuan H, Xie F, Zhang S, Liu H, Liu M. Screening and identification of the main metabolites of 2-amino-9H-pyrido[2,3-b]indole (AαC) in liver microsomes and rat urine by using UPLC-Q-TOF-MS/MS. J Chromatogr B Analyt Technol Biomed Life Sci. 2017 Mar 1;1046:110-121. doi: 10.1016/j.jchromb.2017.01.038. Epub 2017 Jan 26. PMID: 28157663.


5: Frederiksen H, Frandsen H. Excretion of metabolites in urine and faeces from rats dosed with the heterocyclic amine, 2-amino-9H-pyrido[2,3-b]indole (AalphaC). Food Chem Toxicol. 2004 Jun;42(6):879-85. doi: 10.1016/j.fct.2004.01.011. PMID: 15110096.


6: Bellamri M, Yao L, Bonala R, Johnson F, Von Weymarn LB, Turesky RJ. Bioactivation of the tobacco carcinogens 4-aminobiphenyl (4-ABP) and 2-amino-9H-pyrido[2,3-b]indole (AαC) in human bladder RT4 cells. Arch Toxicol. 2019 Jul;93(7):1893-1902. doi: 10.1007/s00204-019-02486-7. Epub 2019 Jun 15. PMID: 31203411; PMCID: PMC6714057.


7: Tang Y, LeMaster DM, Nauwelaërs G, Gu D, Langouët S, Turesky RJ. UDP- glucuronosyltransferase-mediated metabolic activation of the tobacco carcinogen 2-amino-9H-pyrido[2,3-b]indole. J Biol Chem. 2012 Apr 27;287(18):14960-72. doi: 10.1074/jbc.M111.320093. Epub 2012 Mar 5. PMID: 22393056; PMCID: PMC3340249.


8: Cai T, Yao L, Turesky RJ. Bioactivation of Heterocyclic Aromatic Amines by UDP Glucuronosyltransferases. Chem Res Toxicol. 2016 May 16;29(5):879-91. doi: 10.1021/acs.chemrestox.6b00046. Epub 2016 Apr 18. PMID: 27032077; PMCID: PMC4868641.


9: Frederiksen H, Frandsen H, Pfau W. 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. Carcinogenesis. 2004 Aug;25(8):1525-33. doi: 10.1093/carcin/bgh156. Epub 2004 Apr 1. PMID: 15059926.


10: Baranczewski P, Gustafsson JA, Moller L. 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. Biomarkers. 2004 May-Jun;9(3):243-57. doi: 10.1080/13547500400010056. PMID: 15764290.


11: Steffensen IL, Paulsen JE, Alexander J. 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. Carcinogenesis. 2002 Aug;23(8):1373-8. doi: 10.1093/carcin/23.8.1373. PMID: 12151357.


12: Turesky RJ, Konorev D, Fan X, Tang Y, Yao L, Ding X, Xie F, Zhu Y, Zhang QY. 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. Chem Res Toxicol. 2015 Dec 21;28(12):2400-10. doi: 10.1021/acs.chemrestox.5b00405. Epub 2015 Dec 3. PMID: 26583703; PMCID: PMC4703101.


13: Konorev D, Koopmeiners JS, Tang Y, Franck Thompson EA, Jensen JA, Hatsukami DK, Turesky RJ. Measurement of the Heterocyclic Amines 2-Amino-9H-pyrido[2,3-b]indole and 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in Urine: Effects of Cigarette Smoking. Chem Res Toxicol. 2015 Dec 21;28(12):2390-9. doi: 10.1021/acs.chemrestox.5b00401. Epub 2015 Dec 3. PMID: 26574651; PMCID: PMC4699441.


14: Zhang L, Wang L, Li Y, Xia Y, Chang CM, Xia B, Sosnoff CS, Pine BN, deCastro BR, Blount BC. Evaluation of Tobacco Smoke and Diet as Sources of Exposure to Two Heterocyclic Aromatic Amines for the U.S. Population: NHANES 2013-2014. Cancer Epidemiol Biomarkers Prev. 2020 Jan;29(1):103-111. doi: 10.1158/1055-9965.EPI-19-0169. Epub 2019 Oct 1. PMID: 31575556; PMCID: PMC6954285.


15: Raman M, Nilsson U, Skog K, Lawther M, Nair B, Nyman M. Physicochemical characterisation of dietary fibre components and their ability to bind some process-induced mutagenic heterocyclic amines, Trp-P-1, Trp-P-2, AαC and MeAαC. Food Chem. 2013 Jun 15;138(4):2219-24. doi: 10.1016/j.foodchem.2012.11.111. Epub 2012 Dec 12. PMID: 23497879.


16: Snyderwine EG, Sadrieh N, King RS, Schut HA. Formation of DNA adducts of the food-derived mutagen 2-amino-9H-pyrido-[2,3-b]indole (A(alpha)C) and bioassay of mammary gland carcinogenicity in Sprague-Dawley rats. Food Chem Toxicol. 1998 Dec;36(12):1033-41. doi: 10.1016/s0278-6915(98)00088-x. PMID: 9862644.


17: Turesky RJ, Bendaly J, Yasa I, Doll MA, Hein DW. The impact of NAT2 acetylator genotype on mutagenesis and DNA adducts from 2-amino-9H-pyrido[2,3-b]indole. Chem Res Toxicol. 2009 Apr;22(4):726-33. doi: 10.1021/tx800473w. PMID: 19243127; PMCID: PMC2673018.


18: Zhang TT, Zhao G, Li X, Xie FW, Liu HM, Xie JP. Genotoxic and oxidative stress effects of 2-amino-9H-pyrido[2,3-b]indole in human hepatoma G2 (HepG2) and human lung alveolar epithelial (A549) cells. Toxicol Mech Methods. 2015 Mar;25(3):212-22. doi: 10.3109/15376516.2015.1025345. Epub 2015 Mar 23. PMID: 25798651.


19: Kataoka H, Hayatsu T, Hietsch G, Steinkellner H, Nishioka S, Narimatsu S, Knasmüller S, Hayatsu H. Identification of mutagenic heterocyclic amines (IQ, Trp-P-1 and AalphaC) in the water of the Danube river. Mutat Res. 2000 Mar 3;466(1):27-35. doi: 10.1016/s1383-5718(99)00235-1. PMID: 10751722.


20: Tang Y, Kassie F, Qian X, Ansha B, Turesky RJ. DNA adduct formation of 2-amino-9H-pyrido[2,3-b]indole and 2-amino-3,4-dimethylimidazo[4,5-f]quinoline in mouse liver and extrahepatic tissues during a subchronic feeding study. Toxicol Sci. 2013 Jun;133(2):248-58. doi: 10.1093/toxsci/kft077. Epub 2013 Mar 27. PMID: 23535364; PMCID: PMC3663563.