Nornicotine

Nornicotine
Names
	IUPAC name 3-[(2S)-2-Pyrrolidinyl]pyridine
	Other names Demethylnicotine
Identifiers
CAS Number	494-97-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	82588;
ECHA InfoCard	100.165.066
PubChem CID	91462;
UNII	83H6L5QD8Z ;
	InChI 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/t9-/m0/s1 Key: MYKUKUCHPMASKF-VIFPVBQESA-N; InChI=1/C9H12N2/c1-3-8(7-10-5-1)9-4-2-6-11-9/h1,3,5,7,9,11H,2,4,6H2/t9-/m0/s1 Key: MYKUKUCHPMASKF-VIFPVBQEBM;
	SMILES n1cccc(c1)[C@H]2NCCC2;
Properties
Chemical formula	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]

\mathrm {\xrightarrow[{H_{2}O}]{Ag_{2}O}}

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.

\mathrm {\xrightarrow[{H_{2}}]{Pd/C}}

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. PMC 1253577. PMID 16192354.
Knezevich A, Muzic J, Hatsukami DK, Hecht SS, Stepanov I (February 2013). "Nornicotine nitrosation in saliva and its relation to endogenous synthesis of N'-nitrosonornicotine in humans". Nicotine & Tobacco Research. 15 (2): 591–5. doi:10.1093/ntr/nts172. PMC 3611998. PMID 22923602.
"List of Classifications – IARC Monographs on the Identification of Carcinogenic Hazards to Humans". monographs.iarc.fr. Retrieved 2020-07-22.
Spaeth (1936). Chem. Ber. 69: 250–251. Missing or empty |title= (help)
Haines (1945). "Chemical Reactivity of Myosmine". J. Am. Chem. Soc. 67: 1258–1260. doi:10.1021/ja01224a011.
Dickerson, TJ; Janda, KD (2002). "Aqueous aldol catalysis by a nicotine metabolite". J. Am. Chem. Soc. 124: 3220–1. doi:10.1021/ja017774f. PMID 11916401..

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[1] 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. PMC 1253577. PMID 16192354.

[:1-2] Knezevich A, Muzic J, Hatsukami DK, Hecht SS, Stepanov I (February 2013). "Nornicotine nitrosation in saliva and its relation to endogenous synthesis of N'-nitrosonornicotine in humans". Nicotine & Tobacco Research. 15 (2): 591–5. doi:10.1093/ntr/nts172. PMC 3611998. PMID 22923602.

[:2-3] "List of Classifications – IARC Monographs on the Identification of Carcinogenic Hazards to Humans". monographs.iarc.fr. Retrieved 2020-07-22.

[späth-4] Spaeth (1936). Chem. Ber. 69: 250–251. Missing or empty |title= (help)

[5] Haines (1945). "Chemical Reactivity of Myosmine". J. Am. Chem. Soc. 67: 1258–1260. doi:10.1021/ja01224a011.

[6] Dickerson, TJ; Janda, KD (2002). "Aqueous aldol catalysis by a nicotine metabolite". J. Am. Chem. Soc. 124: 3220–1. doi:10.1021/ja017774f. PMID 11916401..