An alkaloid and neuronal nAChR agonist
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Active Metabolite(s)
15314(−)-Cotinine
Alternative(s)
29138(−)-Nicotine
Analytical Standard(s)
44503(−)-Nicotine (CRM)
Isomer(s)
16535(±)-Nicotine
Metabolite(s)
16100trans-3'-Hydroxycotinine
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(−)-Nicotine (tartrate)

Item No. 20887

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-[(2S)-1-methyl-2-pyrrolidinyl]-pyridine (2R,3R)-2,3-dihydroxybutanedioate
CAS Number
65-31-6
Synonyms
  • NSC 97238
Molecular Formula
C10H14N2 • 2C4H6O6
Formula Weight
462.4
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: 75 nMWater: 50 mg/ml
λmax
259 nm
SMILES
CN1CCC[C@H]1C2=CC=CN=C2.OC([C@H](O)[C@@H](O)C(O)=O)=O.OC([C@H](O)[C@@H](O)C(O)=O)=O
InChi Code
InChI=1S/C10H14N2.2C4H6O6/c1-12-7-3-5-10(12)9-4-2-6-11-8-9;2*5-1(3(7)8)2(6)4(9)10/h2,4,6,8,10H,3,5,7H2,1H3;2*1-2,5-6H,(H,7,8)(H,9,10)/t10-;2*1-,2-/m011/s1
InChi Key
RFEJUZJILGIRHQ-OMDKHLBYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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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).