Title: Viquidil
CAS Registry Number: 84-55-9
CAS Name: (3R-cis)-3-(3-Ethenyl-4-piperidinyl)-1-(6-methoxy-4-quinolinyl)-1-propanone
Additional Names: quinicine; 1-(6-methoxy-4-quinolyl)-3-(3-vinyl-4-piperidyl)-1-propanone; chinicine; mequiverine; quinotoxine; quinotoxol
Manufacturers' Codes: LM-192
Molecular Formula: C20H24N2O2
Molecular Weight: 324.42
Percent Composition: C 74.04%, H 7.46%, N 8.63%, O 9.86%
Literature References: An isomer of quinine; occurs naturally as the d-form. Present in small quantities in cinchona barks; formed by heating quinine with glycerol at 180°: Howard, J. Chem. Soc. 24, 61 (1871); 25, 101 (1872); Miller, Rohde, Ber. 33, 3214 (1900); Howard, Chick, Pharm. J. 99, 143 (1917). Conversion to quinine: Rabe, Kindler, Ber. 51, 466 (1918). Partial synthesis: Prostenik, Prelog, Helv. Chim. Acta 26, 1965 (1943). Total synthesis: Woodward, Doering, J. Am. Chem. Soc. 66, 849 (1944); 67, 860 (1945); US 2500444 (1950 to Polaroid); Grethe et al., Helv. Chim. Acta 56, 1485 (1973). Review of synthesis, chemistry and pharmacology: Quevauviller et al., Ann. Pharm. Fr. 24, 39 (1966). Series of articles on pharmacology and metabolism: Arzneim.-Forsch. 22, 1334-1346 (1972).
Properties: Yellow viscous oil, [a]D +43°. Slightly sol in water; freely sol in alcohol, chloroform, ether.
Optical Rotation: [a]D +43°
Derivative Type: Hydrochloride
CAS Registry Number: 52211-63-9
Trademarks: Desclidium (Nattermann); Permiran (Laphal)
Molecular Formula: C20H24N2O2.HCl
Molecular Weight: 360.88
Percent Composition: C 66.56%, H 6.98%, N 7.76%, O 8.87%, Cl 9.82%
Properties: Yellow, odorless and bitter tasting powder, mp 184 ±4°. uv max (chloroform): 246, 355 nm. Sol in alc; sparingly sol in water. Practically insol in acetone.
Melting point: mp 184 ±4°
Absorption maximum: uv max (chloroform): 246, 355 nm
Therap-Cat: Vasodilator (cerebral).
Keywords: Vasodilator (Cerebral). |