An agonist at neuronal nicotinic acetylcholine receptors
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(±)-Nicotine

Item No. 16535

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-(1-methyl-2-pyrrolidinyl)-pyridine
CAS Number
22083-74-5
Synonyms
  • DL-Nicotine
Molecular Formula
C10H14N2
Formula Weight
162.2
Purity
≥98%
Formulation
A neat oil
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mlDMSO: 30 mg/mlEthanol: 50 mg/mlPBS (pH 7.2): 1 mg/ml
SMILES
CN1CCCC1C2=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
InChi Key
SNICXCGAKADSCV-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    100 mg

    $120

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    250 mg

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    500 mg

    $421

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    Cayman Chemical
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    Product Description

    (±)-Nicotine is the racemic mixture of the dominant alkaloid found in tobacco plants. It acts as an agonist at neuronal nicotinic acetylcholine receptors (nAChRs; Kis = 481 and 11.1 nM for α3β4 and α4β2 subtypes, respectively) and possesses addictive and teratogenic properties.1 (−)-(S)-Nicotine is significantly more active at binding nAChRs compared to the (+)-(R) antipode, thus nicotine is typically synthesized as (−)-(S)-nicotine with only 0.2-1% of the (+)-(R) isomer present.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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).

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