Chemistry:Nornicotine
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| IUPAC name
3-[(2S)-2-Pyrrolidinyl]pyridine
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| Other names
Demethylnicotine
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3D model (JSmol)
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PubChem CID
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| Properties | |
| C9H12N2 | |
| Molar mass | 148.209 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Nornicotine is an alkaloid found in various plants including Nicotiana, the tobacco plant. It is chemically similar to nicotine, but does not contain a methyl group.
It is a precursor to the carcinogen N-nitrosonornicotine that is produced during the curing and processing of tobacco.[1] Nornicotine can react in human saliva to form N-nitrosonornicotine,[2] a known type 1 carcinogen.[3]
Synthesis
There are several routes for the synthesis of nornicotine. One route is the demethylation of nicotine, which can be accomplished by reaction with silver oxide.[4]
[math]\displaystyle{ \mathrm{ \xrightarrow[H_2O]{Ag_2O} } }[/math] 
Another route is the partial reduction of 3-myosmine, which can be accomplished by standard catalytic hydrogenation conditions using palladium as a catalyst[5] or with sodium borohydride.[6] This reaction gives the racemic product.
[math]\displaystyle{ \mathrm{ \xrightarrow[H_2]{Pd/C} } }[/math] Pharmacology
Nornicotine possess high affinity for alpha-6 and alpha-7 subunits of nAChRs.[7] It also inhibits DAT in striatum via nAChR and releases dopamine in rats.[8][9][10]
References
- ↑ Siminszky, B. (2005). "Conversion of nicotine to nornicotine in Nicotiana tabacum is mediated by CYP82E4, a cytochrome P450 monooxygenase". Proceedings of the National Academy of Sciences 102 (41): 14919–24. doi:10.1073/pnas.0506581102. PMID 16192354.
- ↑ "Nornicotine nitrosation in saliva and its relation to endogenous synthesis of N'-nitrosonornicotine in humans". Nicotine & Tobacco Research 15 (2): 591–5. February 2013. doi:10.1093/ntr/nts172. PMID 22923602.
- ↑ "List of Classifications – IARC Monographs on the Identification of Carcinogenic Hazards to Humans". https://monographs.iarc.fr/list-of-classifications.
- ↑ Spaeth (1936). "Über dasd-Nor-nicotin". Chem. Ber. 69 (2): 250–251. doi:10.1002/cber.19360690207.
- ↑ Haines (1945). "Chemical Reactivity of Myosmine". J. Am. Chem. Soc. 67 (8): 1258–1260. doi:10.1021/ja01224a011.
- ↑ Dickerson, TJ; Janda, KD (2002). "Aqueous aldol catalysis by a nicotine metabolite". J. Am. Chem. Soc. 124 (13): 3220–1. doi:10.1021/ja017774f. PMID 11916401..
- ↑ "The pharmacological activity of icotine and nornicotine on nAChRs subtypes: relevance to nicotine dependence and drug discovery". Journal of Neurochemistry 101 (1): 160–7. April 2007. doi:10.1111/j.1471-4159.2006.04355.x. PMID 17241116.
- ↑ "Nornicotine inhibition of dopamine transporter function in striatum via nicotinic receptor activation". Synapse (New York, N.Y.) 61 (3): 157–65. March 2007. doi:10.1002/syn.20351. PMID 17146768.
- ↑ "Nornicotine, a nicotine metabolite and tobacco alkaloid: desensitization of nicotinic receptor-stimulated dopamine release from rat striatum". European Journal of Pharmacology 428 (1): 69–79. September 2001. doi:10.1016/s0014-2999(01)01283-3. PMID 11779039.
- ↑ "S(-)-nornicotine increases dopamine release in a calcium-dependent manner from superfused rat striatal slices". Journal of Neurochemistry 60 (6): 2167–74. June 1993. doi:10.1111/j.1471-4159.1993.tb03502.x. PMID 8492124.
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