Title: Eburnamonine
CAS Registry Number: 474-00-0
CAS Name: Eburnamenin-14(15H)-one
Additional Names: (+)-cis-eburnamonine
Molecular Formula: C19H22N2O
Molecular Weight: 294.39
Percent Composition: C 77.52%, H 7.53%, N 9.52%, O 5.43%
Literature References: One of the Vinca alkaloids, naturally occurring as the (+)- and (±)-forms. Isoln of the (+)-form from Hunteria eburnea Pinchon, Apocynaceae: M. F. Bartlett et al., Compt. Rend. 249, 1259 (1959); of the (±)-form from Vinca minor L., Apocynaceae: J. Mokry et al., Experientia 17, 354 (1961). The (-)-form is obtained by acid hydrolysis of vincamine, q.v.: J. Trajanek et al., Tetrahedron Lett. 1961, 702; O. Clauder et al., ibid. 1962, 1147; eidem, HU 151295 (1964 to Gedeon Richter), C.A. 60, 14558e (1964). Structure and synthesis of the (±)-form: M. F. Bartlett, W. I. Taylor, Tetrahedron Lett. 20, 20 (1959); eidem, J. Am. Chem. Soc. 82, 5941 (1960); E. Wenkert, B. Wickberg, ibid. 87, 1580 (1965). Short synthesis of the (±)-form: E. Wenkert et al., ibid. 100, 4893 (1978); high yield total synthesis: J. L. Hermann et al., ibid. 101, 1540 (1979); T. Imanishi et al., Chem. Pharm. Bull. 30, 1521 (1982). Synthesis of the (-)-form: D. Cartier et al., Bull. Soc. Chim. Fr. 1976, 1961. Structural and biogenetic relationship to vincamine: J. Mokry et al., Tetrahedron Lett. 1962, 433. Pharmacology of the (-)-form: P. Lacroix et al., Arzneim.-Forsch. 29, 1094 (1979). Series of articles on the pharmacodynamics, metabolism, and therapeutic use of the (-)-form: Eur. Neurol. 17, Suppl. 1, 1-172 (1978). Reviews: W. I. Taylor in The Alkaloids vol. 8, R. H. F. Manske, Ed. (Academic Press, NewYork, 1965) pp 253-259; idem, ibid. vol. 11, pp 108-110 (1968).
Properties: Cryst, mp 174°. [a]D25 +89° (chloroform). uv max: 241, 268, 296, 302 nm (e 19800, 10200, 4800, 4800).
Melting point: mp 174°
Optical Rotation: [a]D25 +89° (chloroform)
Absorption maximum: uv max: 241, 268, 296, 302 nm (e 19800, 10200, 4800, 4800)
Derivative Type: (±)-Form
CAS Registry Number: 2580-88-3
Additional Names: (±)-Eburnamenin-14(15H)-one; vincanorine
Properties: Crystals from methanol, mp 201-202.5°. uv max (ethanol): 227, 287, 294 nm (log e 4.49, 3.89, 3.87).
Melting point: mp 201-202.5°
Absorption maximum: uv max (ethanol): 227, 287, 294 nm (log e 4.49, 3.89, 3.87)
Derivative Type: (-)-Form
CAS Registry Number: 4880-88-0
Additional Names: (3a,16a)-Eburnamenin-14(15H)-one; 16-oxoeburnane; vincamone
Manufacturers' Codes: CH-846
Trademarks: Cervoxan (Sorbio)
Properties: Solid, mp 168-170°; also reported as mp 177-178° (Cartier). [a]D25 -102° (chloroform) (Clauder); [a]D -100° (c = 0.783 in chloroform) (Cartier). uv max: 205, 240, 265, 290, 300 nm (log e 4.28, 4.16, 3.90, 3.59, 3.57).
Melting point: mp 168-170°; mp 177-178° (Cartier)
Optical Rotation: [a]D25 -102° (chloroform) (Clauder); [a]D -100° (c = 0.783 in chloroform) (Cartier)
Absorption maximum: uv max: 205, 240, 265, 290, 300 nm (log e 4.28, 4.16, 3.90, 3.59, 3.57)
Derivative Type: (-)-Form phosphate
CAS Registry Number: 94134-60-8
Trademarks: Eburnal (Chiesi)
Therap-Cat: The (-)-form as vasodilator.
Keywords: Vasodilator (Cerebral). |