Title: Anatabine
CAS Registry Number: 581-49-7
CAS Name: 1,2,3,6-Tetrahydro-2,3¢-bipyridine
Additional Names: 2-(3-pyridyl)-1,2,3,6-tetrahydropyridine; 1,2,3,6-tetrahydro-2-(3-pyridyl)pyridine
Molecular Formula: C10H12N2
Molecular Weight: 160.22
Percent Composition: C 74.96%, H 7.55%, N 17.48%
Literature References: The most abundant of the minor alkaloids of tobacco: Späth, Kesztler, Ber. 70, 239, 704, 2450 (1937). Fresh Nicotiana tabacum, the species most commonly used for the production of cigarette tobacco, contains 3.9% anatabine. Configuration: Lukes et al., Collect. Czech. Chem. Commun. 27, 751 (1962). Total synthesis of dl-form: Quan et al., J. Org. Chem. 30, 2769 (1965). Biosynthesis: E. Leete, S. Slattery, J. Am. Chem. Soc. 98, 6326 (1976). Biomimetic synthesis: E. Leete, M. E. Mueller, ibid. 104, 6440 (1982).
Derivative Type: l-Form
Properties: Liquid. d419 1.091. bp10 145-146°. [a]D17 -177.8°. nD20 1.5676. Misc with water. Sol in alc, ether, benzene.
Boiling point: bp10 145-146°
Optical Rotation: [a]D17 -177.8°
Index of refraction: nD20 1.5676
Density: d419 1.091
Derivative Type: dl-Form
Properties: Liquid. bp6.5 136°.
Boiling point: bp6.5 136°
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