(S)-4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol

CAS: 197712-01-9

Ref. TR-M323790

Product Information

• Name: (S)-4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol
• Synonyms: (αS)-α-[3-(Methylnitrosoamino)propyl3-pyridinemethanol, (S)-α-[3-(Methylnitrosoamino)propyl]-3-pyridinemethanol, (S)-NNAL
• CAS: 197712-01-9

Description

Applications (S)-4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol is the S-enantiomer of 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) which is a major metabolite of 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (M325750). It is a tobacco specific N-nitrosamine (TSNA) and a potent pulmonary carcinogen. The R-enantiomer of 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol, (R)-NNAL, tends to be significantly more tumorigenic than the S-entiomer, (S)-NNAL.
References Yang, Y.Y., et al.: J. Chromatogr. A, 1218, 6505 (2011); Carmella, S.G., et al.: J. Cancer Res., 53, 721 (1993); Upadhyaya, P., et al.: Carcinogenesis, 20, 1577 (1999)

• Brand: TRC

Chemical properties

• Molecular weight: 209.245
• Formula: C₁₀H₁₅N₃O₂
• Color/Form: Pale Yellow to Pale Red Gel to Low-Melting Solid
• InChI: InChI=1S/C10H15N3O2/c1-13(12-15)7-3-5-10(14)9-4-2-6-11-8-9/h2,4,6,8,10,14H,3,5,7H2,1H3/t10-/m0/s1
• InChI key: InChIKey=OGRXKBUCZFFSTL-JTQLQIEISA-N
• SMILES: CN(CCC[C@H](O)c1cccnc1)N=O