Vincamine
Title: Vincamine
CAS Registry Number: 1617-90-9
CAS Name: (3a,14b,16a)-14,15-Dihydro-14-hydroxyeburnamenine-14-carboxylic acid methyl ester
Additional Names: 13a-ethyl-2,3,5,6,12,13,13a,13b-octahydro-12-hydroxy-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylic acid methyl ester
Trademarks: Angiopac (UCB); Arteriovinca (Farma-Lepori); Cetal (Warner-Lambert); Oxygeron (Will-Pharma); Pervincamine (Sanofi-Aventis); Vincafor (Pharmafarm); Vincagil (Sanofi-Aventis); Vincimax (Sanofi-Aventis); Vraap (Inverni)
Molecular Formula: C21H26N2O3
Molecular Weight: 354.44
Percent Composition: C 71.16%, H 7.39%, N 7.90%, O 13.54%
Literature References: Major indole alkaloid of Vinca minor L., Apocynaceae occurring naturally in the d-form: E. Schlittler, A. Furlenmeier, Helv. Chim. Acta 36, 2017 (1953); Pailer, Belohlav, Monatsh. Chem. 85, 1055 (1954); King et al., J. Chem. Soc. 1955, 4206; J. Trojanek et al., Collect. Czech. Chem. Commun. 26, 867 (1961). Isoln from Tabernaemontana rigida Miers, Apocynaceae: M. P. Cava et al., J. Org. Chem. 33, 1055 (1968). Structure: J. Trojanek et al., Tetrahedron Lett. 1961, 702; J. Mokry et al., ibid. 1962, 433; O. Clauder, ibid. 1147; Plat et al., Bull. Soc. Chim. Fr. 1962, 1082. Abs config: J. Trojanek et al., Chem. Ind. (London) 1965, 1261; Blaha et al., Collect. Czech. Chem. Commun. 33, 3833 (1968). X-ray determn of molecular structure: H. P. Weber, T. J. Petcher, J. Chem. Soc. Perkin Trans. 2 1973, 2001. Total synthesis: C. Szantay et al., Tetrahedron Lett. 1973, 191; eidem, Tetrahedron 33, 1803 (1977); P. Pfäffli et al., Helv. Chim. Acta 58, 1131 (1975); W. Oppolzer et al., ibid. 60, 1801 (1977); of dl-form: M. E. Kuehne, J. Am. Chem. Soc. 86, 2946 (1964); J. L. Herrmann et al., ibid. 96, 3702 (1974); K. H. Gibson, J. E. Saxton, Tetrahedron 33, 833 (1977); K. Irie, Y. Ban, Heterocycles 18, 255 (1982); T. R. Govindachari, S. Rajeswari, Indian J. Chem. 22B, 531 (1983). Synthesis of stereoisomers: J. Warnant et al., DE 2115718; eidem, US 3770724 (1971, 1973 both to Roussel-UCLAF); G. Rossey, A. Wick, J. Org. Chem. 47, 4725 (1982). HPLC determn: A. Amato et al., J. Chromatogr. 270, 387 (1983). Toxicity data: L. Szporny, K. Szász, Arch. Exp. Pathol. Pharmakol. 236, 296 (1959). Hypotensive activity in dogs and man: Z. Szabo, Z. Nagy, Arzneim.-Forsch. 10, 811 (1960). Clinical pharmacology: C. C. Lim et al., Br. J. Clin. Pharmacol. 9, 100 (1980). Clinical pharmacokinetics: H. Millart, D. Lamiable et al., Int. J. Clin. Pharmacol. Ther. Toxicol. 21, 581 (1983). Brief review: P. Cook, I. James, N. Engl. J. Med. 305, 1562 (1981).
Properties: Yellow crystals from acetone or methanol, mp 232-233°. [a]D23 +41° (in pyridine). uv max: 225, 278 nm (log e 4.14, 3.61). LD50 in mice (mg/kg): 75 i.v.; >1000 s.c. (Szporny, Szász); 1000 orally (Szabo, Nagy).
Melting point: mp 232-233°
Optical Rotation: [a]D23 +41° (in pyridine)
Absorption maximum: uv max: 225, 278 nm (log e 4.14, 3.61)
Toxicity data: LD50 in mice (mg/kg): 75 i.v.; >1000 s.c. (Szporny, Szász); 1000 orally (Szabo, Nagy)
 
Derivative Type: Hydrochloride
CAS Registry Number: 10592-03-7
Trademarks: Esberidin (Schaper & Brðmer)
Molecular Formula: C21H26N2O3.HCl
Molecular Weight: 390.90
Percent Composition: C 64.52%, H 6.96%, N 7.17%, O 12.28%, Cl 9.07%
 
Derivative Type: (±)-Form
Properties: Crystals from methanol, mp 228-229° (Gibson, Saxton).
Melting point: mp 228-229° (Gibson, Saxton)
 
NOTE: Other alkaloids found in the "vincamine fraction" of Vinca minor L. are: vincine, vincaminine and vincinine: Holubek et al., Tetrahedron Lett. 1963, 897.
Therap-Cat: Vasodilator.
Keywords: Vasodilator (Cerebral).

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