626. Anatabine
Nomenclature
CAS number: 581-49-7
(2S)-1,2,3,6-Tetrahydro-2,3′-bipyridine; 2-(3-pyridyl)-1,2,3,6-tetrahydropyridine; 1,2,3,6-tetrahydro-2-(3-pyridyl)pyridine. C10H12N2; mol wt 160.22.
C 74.96%, H 7.55%, N 17.48%.
Description and references
The most abundant of the minor alkaloids of tobacco: Spth, 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) DOI. Biosynthesis: E. Leete, S. Slattery, J. Am. Chem. Soc. 98, 6326 (1976) DOI PubMed. Biomimetic synthesis: E. Leete, M. E. Mueller, ibid. 104, 6440 (1982) DOI.
