494-97-3
Chemical Structure
(S)-Nornicotine
- CAS No.: 494-97-3
- Formula:C9H12N2
- Molecular Weight:148.21
IUPAC Name: (S)-3-(pyrrolidin-2-yl)pyridine
InChIKey: MYKUKUCHPMASKF-VIFPVBQESA-N
SMILES: C1([C@H]2NCCC2)=CC=CN=C1
Biological Activity: (S)-Nornicotine is a nicotine metabolite that crosses the blood-brain barrier. (S)-Nornicotine weakly inhibits human CYP2A6 with a Ki >300 μM. (S)-Nornicotine 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 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 is useful for research on tobacco dependence and pain[1][2][3][4].
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(S)-Nornicotine | 98.59% | (S)-Nornicotine is a nicotine metabolite that crosses the blood-brain barrier. (S)-Nornicotine weakly inhibits human CYP2A6 with a Ki >300 μM. (S)-Nornicotine 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 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 is useful for research on tobacco dependence and pain. | ||||||||||||||||||||
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(S)-Nornicotine (Standard) | ≥98% | (S)-Nornicotine (Standard) is the analytical standard of (S)-Nornicotine (HY-W040430). This product is intended for research and analytical applications. (S)-Nornicotine is a nicotine metabolite that crosses the blood-brain barrier. (S)-Nornicotine weakly inhibits human CYP2A6 with a Ki >300 μM. (S)-Nornicotine 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 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 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]
