A metabolite of nicotine
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trans-3'-Hydroxycotinine

Item No. 16100

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3R-hydroxy-1-methyl-5S-(3-pyridinyl)-2-pyrrolidinone
CAS Number
34834-67-8
Synonyms
  • 3HC
Molecular Formula
C10H12N2O2
Formula Weight
192.2
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
262 nm
SMILES
O=C1C(O)C[C@@H](C2=CC=CN=C2)N1C
InChi Code
InChI=1S/C10H12N2O2/c1-12-8(5-9(13)10(12)14)7-3-2-4-11-6-7/h2-4,6,8-9,13H,5H2,1H3/t8-,9?/m0/s1
InChi Key
XOKCJXZZNAUIQN-IENPIDJESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $63

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    5 mg

    $213

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    10 mg

    $363

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    Cayman Chemical
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    Product Description

    trans-3’-Hydroxycotinine (3HC) is a product of CYP2A6 metabolism of the primary nicotine metabolite, cotinine (Item No. 15314).1,2 Cotinine has a longer metabolic half-life compared to 3HC (16 hours vs. 5 hours).1 The ratio of 3HC to cotinine, termed the nicotine metabolite ratio, correlates with nicotine clearance from the body and is used as a biomarker of CYP2A6 activity.1 This measure of nicotine metabolism has been used to study tobacco and secondhand smoke exposure as well as to develop pharmacological intervention strategies for smoking cessation.1,3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Zhu, A.Z., Zhou, Q., Cox, L.S., et al. Variation in trans-3'-hydroxycotinine glucuronidation does not alter the nicotine metabolite ratio or nicotine intake. PLoS One 8(8), e70938 (2013).

    2. von Weymarn, L.B., Retzlaff, C., and Murphy, S.E. CYP2A6- and CYP2A13-catalyzed metabolism of the nicotine Δ5'(1')iminium ion. J. Pharmacol. Exp. Ther. 343(2), 307-315 (2012).

    3. Murphy, S.E., Wickham, K.M., Lindgren, B.R., et al. Cotinine and trans 3'-hydroxycotinine in dried blood spots as biomarkers of tobacco exposure and nicotine metabolism. J. Expo. Sci. Environ. Epidermiol. 23(5), 513-518 (2013).