An alkaloid and active metabolite of (–)-nicotine
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(−)-Cotinine

Item No. 15314

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-methyl-5S-(3-pyridinyl)-2-pyrrolidinone
CAS Number
486-56-6
Synonyms
  • NIH 10498
Molecular Formula
C10H12N2O
Formula Weight
176.2
Purity
≥98%
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=C1CC[C@@H](C2=CN=CC=C2)N1C
InChi Code
InChI=1S/C10H12N2O/c1-12-9(4-5-10(12)13)8-3-2-6-11-7-8/h2-3,6-7,9H,4-5H2,1H3/t9-/m0/s1
InChi Key
UIKROCXWUNQSPJ-VIFPVBQESA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    50 mg

    $63

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    250 mg

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    500 mg

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    Cayman Chemical
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    Product Description

    (−)-Cotinine is an alkaloid that has been found in tobacco and an active metabolite of (–)-nicotine (Item Nos. 29138 | 20887).1,2 It is formed from (–)-nicotine by the cytochrome P450 (CYP) isoforms CYP2A6 or CYP2A13 via a 5'-hydroxy nicotine or nicotine Δ5’(1’)iminium ion intermediate.2 Compared with (–)-nicotine, (–)-cotinine is a weak agonist of nicotinic acetylcholine receptors (nAChRs).3 It reduces the number of dsDNA breaks induced by the tobacco-specific nitrosamine carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK; Item No. 16414) in a comet assay using HepaRG cells at 1 and 10 µM.4 (−)-Cotinine (5 mg/kg) improves working memory and reduces immobility time in the forced swim test in a mouse model of chronic stress.5 It has been found as a contaminant in soils used to grow tobacco.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Huang, H.-Y., and Hsieh, S.-H. Analyses of tobacco alkaloids by cation-selective exhaustive injection sweeping microemulsion electrokinetic chromatography. J. Chromatogr. A 1164(1-2), 313-319 (2007).

    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. Tan, X., Vrana, K., and Ding, Z.-M. Cotinine: Pharmacologically active metabolite of nicotine and neural mechanisms for its actions. Behav. Neurosci. 15, 758252 (2021).

    4. Ordonez, P., Sierra, A.B., Camacho, O.M., et al. Nicotine, cotinine, and β-nicotyrine inhibit NNK-induced DNA-strand break in the hepatic cell line HepaRG. Toxicol. In Vitro 28(7), 1329-1337 (2014).

    5. Grizzell, J.A., Iarkov, A., Holmes, R., et al. Cotinine reduces depressive-like behavior, working memory deficits, and synaptic loss associated with chronic stress in mice. Behav. Brain Res. 268, 55-65 (2014).

    6. Zhou, P., Luo, Q., Bai, Y., et al. Tobacco cultivation leads to the accumulation of alkaloids in the soil and causes potential risks. Microchem. J. 208, 112431 (2025).