An active metabolite of nicotine and nAChR agonist
Related Products
Labeled Version(s)
35242(±)-Nornicotine-d4
Parent Compound(s)
16535(±)-Nicotine
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(±)-Nornicotine

Item No. 20505

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-(2-pyrrolidinyl)-pyridine
CAS Number
5746-86-1
Synonyms
  • DL-Nornicotine
  • (R,S)-Nornicotine
Molecular Formula
C9H12N2
Formula Weight
148.2
Purity
≥95%
Formulation (Request formulation change)
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
λmax
262 nm
SMILES
C1(C2CCCN2)=CC=CN=C1
InChi Code
InChI=1S/C9H12N2/c1-3-8(7-10-5-1)9-4-2-6-11-9/h1,3,5,7,9,11H,2,4,6H2
InChi Key
MYKUKUCHPMASKF-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    50 mg

    $41

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    100 mg

    $75

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    250 mg

    $178

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    500 mg

    $332

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    Product Description

    (±)-Nornicotine is an active metabolite of nicotine (Item No. 16535) and a nicotinic acetylcholine receptor (nAChR) agonist.1 It induces currents in Xenopus oocytes expressing human α7 nAChRs or α6 subunit-containing nAChRs (EC50s = 17 and 3.7 µM, respectively). (±)-Nornicotine promotes cell migration and destabilizes cell-cell junctions in EA.hy926 endothelial cells.2 It is self-administered in rats.3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Papke, R.L., Dwoskin, L.P., and Crooks, P.A. The pharmacological activity of nicotine and nornicotine on nAChRs subtypes: Relevance to nicotine dependence and drug discovery. J. Neurochem. 101(1), 160-167 (2007).

    2. Gagat, M., Grzanka, D., Izdebska, M., et al. Nornicotine impairs endothelial cell-cell adherens junction complexes in EA.hy926 cell line via structural reorganization of F-actin. Folia Histochem. Cytobiol. 51(3), 179-192 (2013).

    3. Bardo, M.T., Green, T.A., Crooks, P.A., et al. Nornicotine is self-administered intravenously by rats. Psychopharmacology (Berl) 146(3), 290-296 (1999).

    4. Hoffman, A.C., and Evans, S.E. Abuse potential of non-nicotine tobacco smoke components: Acetaldehyde, nornicotine, cotinine, and anabasine. Nicotine Tob. Res. 15(3), 622-632 (2013).