A tobacco-specific nitrosamine
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(R,S)-N-Nitrosoanabasine

Item No. 44338

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-(1-nitroso-2-piperidinyl)-pyridine
CAS Number
37620-20-5
Synonyms
  • (R,S)-N’-Nitrosoanabasine
  • NAB
Molecular Formula
C10H13N3O
Formula Weight
191.2
Purity
≥98%
Formulation (Request formulation change)
A low-melting solid
Solubility(Learn about Variance in Solubility)
DMSO: Soluble: ≥ 10 mg/mlEthanol: Soluble: ≥ 10 mg/mlPBS (pH 7.2): Sparingly soluble: 1-10 mg/ml
SMILES
O=NN1CCCCC1C2=CC=CN=C2
InChi Code
InChI=1S/C10H13N3O/c14-12-13-7-2-1-5-10(13)9-4-3-6-11-8-9/h3-4,6,8,10H,1-2,5,7H2
InChi Key
BXYPVKMROLGXJI-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $159

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    10 mg

    $302

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    25 mg

    $954

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    50 mg

    $1,431

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    ENVIRONMENTAL TOXICOLOGY TOOLS & SERVICES
    Product Description

    (R,S)-N-Nitrosoanabasine (NAB) is a tobacco-specific N-nitrosamine (TSNA) that has been found in tobacco products and electronic cigarettes.1,2 It inhibits the metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK; Item No. 16414) into 4-oxo-4-(3-pyridyl) butanal (OPB), 4-hydroxy-1-(3-pyridyl)-1-butanone (HPB), and 4-oxo-4-(3-pyridyl) butanoic acid (OPBA) by the cytochrome P450 (CYP) isoform CYP2A13 with Ki values of 0.23, 0.87, and 0.5 µM, respectively.3 NAB is not carcinogenic in hamsters but is carcinogenic in mice.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kumar, R., Siddiqi, M., Tricker, A.R., et al. Tobacco-specific N-nitrosamines in tobacco and mainstream smoke of Indian cigarettes. Food Chem. Toxicol. 29(6), 405-407 (1991).

    2. Kim, H.-J., and Shin, H.-S. Determination of tobacco-specific nitrosamines in replacement liquids of electronic cigarettes by liquid chromatography-tandem mass spectrometry. J. Chromatogr. A 1291, 48-55 (2013).

    3. Liu, X., Zhang, J., Zhang, C., et al. The inhibition of cytochrome P450 2A13-catalyzed NNK metabolism by NAT, NAB and nicotine. Toxicol. Res. (Camb). 5(4), 1115-1121 (2016).

    4. Hilfrich, J., Hecht, S.S., and Hoffmann, D. A study of tobacco carcinogenesis. XV. Effects of N'-nitrosonornicotine and N'-nitrosoanabasine in Syrian golden hamsters. Cancer Lett. 2(3), 169-175 (1977).

    5. Hoffmann, D., Djordjevic, M.V., Rivenson, A., et al. A study of tobacco carcinogenesis. LI. Relative potencies of tobacco-specific N-nitrosamines as inducers of lung tumours in A/J mice. Cancer Lett. 71(1-3), 25-30 (1993).