An alkaloid and neuronal nAChR agonist
Related Products
Active Metabolite(s)
15314(−)-Cotinine
Alternative(s)
20887(−)-Nicotine (tartrate)
Analytical Standard(s)
44503(−)-Nicotine (CRM)
Metabolite(s)
16100trans-3'-Hydroxycotinine
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(−)-Nicotine

Item No. 29138

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-[(2S)-1-methyl-2-pyrrolidinyl]-pyridine
CAS Number
54-11-5
Synonyms
  • L-Nicotine
  • (–)-(S)-Nicotine
Molecular Formula
C10H14N2
Formula Weight
162.2
Purity
≥95%
Formulation
An oil
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mlDMSO: 30 mg/mlEthanol: 50 mg/mlPBS (pH 7.2): 1 mg/ml
λmax
262 nm
SMILES
CN1CCC[C@H]1C2=CC=CN=C2
InChi Code
InChI=1S/C10H14N2/c1-12-7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6,8,10H,3,5,7H2,1H3/t10-/m0/s1
InChi Key
SNICXCGAKADSCV-JTQLQIEISA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 g

    $41

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    Cayman Chemical
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    Product Description

    (–)-Nicotine is an alkaloid that has been found in tobacco.1 It is an agonist at neuronal nicotinic acetylcholine receptors (nAChRs) and binds to α3β4 and α4β2 subunit-containing nAChRs with Ki values of 481 and 11.1 nM, respectively.1,2 Chronic exposure to (–)-nicotine results in increased expression of certain nAChRs, particularly α4β2 subunit-containing nAChRs.3 (–)-Nicotine has addictive properties.2,3 Formulations containing (–)-nicotine have been used as smoking cessation aids for the relief of nicotine withdrawal symptoms.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Clayton, P., Lu, A., and Bishop, L. The pyrolysis of (−)-(S)-nicotine: Racemization and decomposition. Chirality 22(4), 442-446 (2010).

    2. Zaveri, N., Jiang, F., Olsen, C., et al. Novel α3β4 nicotinic acetylcholine receptor-selective ligands. Discovery, structure-activity studies, and pharmacological evaluation. J. Med. Chem. 53(22), 8187-8191 (2010).

    3. Albuquerque, E.X., Pereira, E.F.R., Alkondon, M., et al. Mammalian nicotinic acetylcholine receptors: From structure to function. Physiol. Rev. 89(1), 73-120 (2009).