9991. Vinpocetine

Nomenclature

CAS number: 42971-09-5
(3α,16α)-Eburnamenine-14-carboxylic acid ethyl ester; 3α,16α-apovincaminic acid ethyl ester; ethyl apovincamin-22-oate; RGH-4405; Cavinton (Thiemann).
C22H26N2O2; mol wt 350.45.
C 75.40%, H 7.48%, N 7.99%, O 9.13%.

Description and references

Deriv of vincamine, q.v., with vasodilating activity. Prepn: C. Lrincz et al., DE 2253750; eidem, US 4035370 (1973, 1977 both to Gedeon Richter); eidem, Arzneim.-Forsch. 26, 1907 (1976). Series of articles on pharmacology, biochemistry, metabolism, pharmacokinetics, clinical studies: ibid. 1908-1989. Toxicity studies: E. Pálosi, L. Szporny, ibid. 1926; E. Cholnoky, L. I. Dmk, ibid. 1939. HPLC studies: G. Szepesi, M. Gazdag, J. Chromatogr. 205, 57, 341 (1981). Evaluation of effectiveness as antimotion drug: E. I. Matsnev, D. Bodo, Aviat. Space Environ. Med. 55, 281 (1984). One-pot synthesis from vincamine: Y. Kuge et al., Synth. Commun. 24, 759 (1994).

Chemical structure

Properties

Crystals from benzene, mp 147-153° (dec). [α]D20 +114° (c = 1 in pyridine). uv max (96% ethanol): 229, 275, 315 nm (log ε 4.45, 4.08, 3.85). LD50 in mice, rats (mg/kg): 534, 503 orally; 240, 133.8 i.p.; 58.7, 42.6 i.v. (Pálosi, Szporny), also reported as 161.2 mg/kg i.p. in mice (Cholnoky, Dmk).

Therapeutic Category

Vasodilator (cerebral).

Keywords

Vasodilator (Cerebral)