101832-65-9
Chemical Structure
(S)-Nornicotine hydrochloride
- CAS No.: 101832-65-9
- Formula:C9H13ClN2
- Molecular Weight:184.67
IUPAC Name: (S)-3-(pyrrolidin-2-yl)pyridine hydrochloride
InChIKey: JRTXSGXQWWLEEU-FVGYRXGTSA-N
SMILES: [H]Cl.C1([C@H]2NCCC2)=CC=CN=C1
Biological Activity: (S)-Nornicotine hydrochloride is a nicotine metabolite that crosses the blood-brain barrier. (S)-Nornicotine hydrochloride weakly inhibits human CYP2A6 with a Ki >300 μM. (S)-Nornicotine hydrochloride promotes dopamine release in rat striatal and nucleus accumbens slices and increases endogenous DOPAC overflow through a calcium-dependent nAChR pathway that is sensitive to Mecamylamine (HY-B1395A). (S)-Nornicotine hydrochloride reduces behavioral responses maintained by nicotine or sucrose, exerts analgesic effects in persistent inflammatory pain and neuropathic pain models, and enhances the analgesic effect of morphine. (S)-Nornicotine hydrochloride is useful for research on tobacco dependence and pain[1][2][3][4].
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(S)-Nornicotine hydrochloride | (S)-Nornicotine hydrochloride is a nicotine metabolite that crosses the blood-brain barrier. (S)-Nornicotine hydrochloride weakly inhibits human CYP2A6 with a Ki >300 μM. (S)-Nornicotine hydrochloride promotes dopamine release in rat striatal and nucleus accumbens slices and increases endogenous DOPAC overflow through a calcium-dependent nAChR pathway that is sensitive to Mecamylamine (HY-B1395A). (S)-Nornicotine hydrochloride reduces behavioral responses maintained by nicotine or sucrose, exerts analgesic effects in persistent inflammatory pain and neuropathic pain models, and enhances the analgesic effect of morphine. (S)-Nornicotine hydrochloride is useful for research on tobacco dependence and pain. | |||||||||||||||||||||
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References
- [1]. Dwoskin LP, et al. S(-)-nornicotine increases dopamine release in a calcium-dependent manner from superfused rat striatal slices. Journal of neurochemistry. 1993 Jun;60(6):2167-74.
- [2]. Stairs DJ, et al. Effects of nornicotine enantiomers on intravenous S(-)-nicotine self-administration and cardiovascular function in rats. Psychopharmacology. 2007 Feb;190(2):145-55.
- [3]. Holtman JR, et al. The analgesic and toxic effects of nornicotine enantiomers alone and in interaction with morphine in rodent models of acute and persistent pain. Pharmacology, biochemistry, and behavior. 2010 Jan;94(3):352-62.
- [4]. Denton TT, et al. Nicotine-related alkaloids and metabolites as inhibitors of human cytochrome P-450 2A6. Biochem Pharmacol. 2004 Feb 15;67(4):751-6. [Content Brief]
