Molecular structure of R-(+)-Nicotine, CAS Number: 25162-00-9
R-(+)-Nicotine (CAS 25162-00-9)
Alternate Names:
3-[(2R)-1-Methyl-2-pyrrolidinyl]pyridine; (+)-Nicotine; (R)-3-(1-Methylpyrrolidin-2-yl)pyridine
Application:
R-(+)-Nicotine is an unnatural isomer of nicotine
CAS Number:
25162-00-9
Molecular Weight:
162.23
Molecular Formula:
C10H14N2
Supplemental Information:
This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
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SDS & Certificate of Analysis
(+)-Nicotine is the unnatural isomer of Nicotine. This enantiomer is typically not found in tobacco plants, except for minute amounts. This is still seen in vitro to act similary as a AChR (nicotinic cholinergic receptor) agonist. The binding of nicotine to these receptors causes the release of a variety of neurotransmitters, including dopamine, norepinephrine, and serotonin, which are involved in the regulation of mood, behavior, and cognition.
R-(+)-Nicotine (CAS 25162-00-9) References
- The pyrolysis of (-)-(S)-nicotine: racemization and decomposition. | Clayton, P., et al. 2010. Chirality. 22: 442-6. PMID: 19644958
- (R)-nicotine biosynthesis, metabolism and translocation in tobacco as determined by nicotine demethylase mutants. | Cai, B., et al. 2013. Phytochemistry. 95: 188-96. PMID: 23849545
- Stereospecific in vivo N-methylation of nicotine in the guinea pig. | Cundy, KC., et al. 1985. Drug Metab Dispos. 13: 175-85. PMID: 2859165
- N-Methylnornicotinium ion, a new in vivo metabolite of R-(+)-nicotine. | Sato, M. and Crooks, PA. 1985. Drug Metab Dispos. 13: 348-53. PMID: 2861995
- In vitro characteristics of guinea pig lung aromatic azaheterocycle N-methyltransferase. | Cundy, KC. and Crooks, PA. 1985. Drug Metab Dispos. 13: 658-63. PMID: 2867867
- Isolation and characterization of N-methyl-N'-oxonicotinium ion, a new urinary metabolite of R-(+)-nicotine in the guinea pig. | Pool, WF., et al. 1986. Drug Metab Dispos. 14: 574-9. PMID: 2876864
- N-methylation of nicotine enantiomers by human liver cytosol. | Crooks, PA. and Godin, CS. 1988. J Pharm Pharmacol. 40: 153-4. PMID: 2897456
- Enantioselective metabolism during continuous administration of S-(-)- and R-(+)-nicotine isomers to guinea-pigs. | Nwosu, CG., et al. 1988. J Pharm Pharmacol. 40: 862-9. PMID: 2907579
- Enantiomeric composition of nicotine in tobacco leaf, cigarette, smokeless tobacco, and e-liquid by normal phase high-performance liquid chromatography. | Zhang, H., et al. 2018. Chirality. 30: 923-931. PMID: 29722457
- Species variation and stereoselectivity in the metabolism of nicotine enantiomers. | Nwosu, CG. and Crooks, PA. 1988. Xenobiotica. 18: 1361-72. PMID: 3245230
- Stereoselectivity in the N'-oxidation of nicotine isomers by flavin-containing monooxygenase. | Damani, LA., et al. 1988. Mol Pharmacol. 33: 702-5. PMID: 3380084
- Differences between the binding modes of enantiomers S/R-nicotine to acetylcholinesterase. | Yang, J., et al. 2019. RSC Adv. 9: 1428-1440. PMID: 35518031
- In vivo depletion of S-adenosyl-L-homocysteine and S-adenosyl-L-methionine in guinea pig lung after chronic S-(-)-nicotine administration. | Godin, CS. and Crooks, PA. 1986. Toxicol Lett. 31: 23-9. PMID: 3715913
- Responses recorded from the frog olfactory epithelium after stimulation with R(+)- and S(-)-nicotine. | Thürauf, N., et al. 1995. Chem Senses. 20: 337-44. PMID: 7552043
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AChR.Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
R-(+)-Nicotine, 25 mg | sc-219357 | 25 mg | $398.00 |