Structural Formula Vector Image
Title: Nornicotine
CAS Registry Number: 494-97-3
CAS Name: 3-(2-Pyrrolidinyl)pyridine
Additional Names: 2-(3-pyridyl)pyrrolidine
Molecular Formula: C9H12N2
Molecular Weight: 148.20
Percent Composition: C 72.94%, H 8.16%, N 18.90%
Literature References: Occurs in ordinary tobacco, in other species of Nicotiana, and also in Duboisia hopwoodii F. Muell., Solanaceae. Synthesis: Mizogruchi, Chem. Pharm. Bull. 9, 818 (1961); M. Nakane, C. R. Hutchinson, J. Org. Chem. 43, 3922 (1978). Pharmacology: P. S. Larson, H. B. Haag, J. Pharmacol. Exp. Ther. 77, 343 (1943). Toxicity: P. S. Larson et al., Proc. Soc. Exp. Biol. Med. 58, 231 (1945). Review: Markwood, U.S. Dept. Agr. Bur. Entomol. Plant Quarantine E-561 (1942), Supplement by Roark, E-645 (1945).
Properties: Hygroscopic, somewhat viscous liquid, develops a slight amine odor, less pungent than that of nicotine. bp 270°; bp11 131°; bp3 105-107°. Hardly volatile with steam (difference from nicotine which is readily volatile). d420 1.0737. [a]D22 -89° (c = 100). nD20 1.5378. Miscible with water. Very sol in alcohol, chloroform, ether, petr ether, kerosene, oils. Less volatile and less easily oxidized than nicotine. LD50 in mice, rabbits (mg/kg): 21.7, >13.7 i.p.; 3.4, 3.0 i.v. (Larson et al.).
Boiling point: bp 270°; bp11 131°; bp3 105-107°
Optical Rotation: [a]D22 -89° (c = 100)
Index of refraction: nD20 1.5378
Density: d420 1.0737
Use: Agricultural or horticultural insecticide.

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