862. Atisine

Nomenclature

CAS number: 466-43-3
(6R,6aR,8aS,9R,11S,12aR,12bS,12cS)-Decahydro-6-methyl-10-methylene-9H,12cH-8a,11-ethano-6,12b-propano-5H-benz[h]oxazolo[2,3-a]isoquinolin-9-ol; anthorine.
C22H33NO2; mol wt 343.50.
C 76.92%, H 9.68%, N 4.08%, O 9.32%.

Description and references

From roots of the “atis” plant, Aconitum heterophyllum Wall., and from A. anthora L., Ranunculaceae: Broughton, Blue Book of East India Cinchona Cultivation 1877. 133; Goris, Metin, Compt. Rend. 180, 968 (1925); Lawson, Topps, J. Chem. Soc. 1937, 1640. Structure: Wiesner et al., Chem. Ind. (London) 1954, 132; Pelletier, Jacobs, J. Am. Chem. Soc. 76, 4496 (1954). Structure and stereochemistry: Dvornik, Edwards, Can. J. Chem. 42, 137 (1964). Partial synthesis: Pelletier, Jacobs, J. Am. Chem. Soc. 78, 4144 (1956); Pelletier, Parthasarathy, Tetrahedron Lett. 1963, 205. Racemic synthesis and resolution: Nagata et al., J. Am. Chem. Soc. 85, 2342 (1963); eidem, ibid. 89, 1499 (1967); Masamune, ibid. 86, 291 (1964); Guthrie et al., Tetrahedron Lett. 1966, 4645. 13C-NMR study of C-20 epimers: N. V. Mody, S. W. Pelletier, Tetrahedron 34, 2421 (1978).

Chemical structure

Properties

Solid, mp 57-60°. Distills in high vacuum at a bath temp of 140°. Strong base: pK 12.2.

Derivative

Hydrochloride.
C22H33NO2.HCl; mol wt 379.96.
C 69.54%, H 9.02%, N 3.69%, O 8.42%, Cl 9.33%.

Properties

Flat needles from dil alc, dec 311-312°. [α]D25 +28°.