7019. Papaverine

Nomenclature

CAS number: 58-74-2
1-[(3,4-Dimethoxyphenyl)methyl]-6,7-dimethoxyisoquinoline; 6,7-dimethoxy-1-veratrylisoquinoline.
C20H21NO4; mol wt 339.39.
C 70.78%, H 6.24%, N 4.13%, O 18.86%.

Description and references

Smooth muscle relaxant found in opium (0.8-1.0%). Synthesis: Pictet, Gams, Compt. Rend. 149, 210 (1909); Ber. 42, 2943 (1909). Review of commercial syntheses: Goldberg, Chem. Prod. Chem. News 17, 371 (1954). Improved synthetic procedures: Braz, Chizhov, Soviet Pharmaceutical Research 3, 90-93 (New York, 1958). Biosynthetic studies: Battersby, Harper, J. Chem. Soc. 1962, 3526; Brochmann-Hanssen et al., J. Pharm. Sci. 60, 1672 (1971). Pharmacology and toxicology: Preininger in The Alkaloids vol. 15, R. H. F. Manske, Ed. (Academic Press, New York, 1975) pp 209-223. Toxicity: S. Levis et al., Arch. Int. Pharmacodyn. 123, 264 (1960). Clinical effect on cerebral blood flow: H. L. Karpman, J. J. Sheppard, Angiology 26, 592 (1975). Clinical evaluation in intermittent claudication: Y. Sheino et al., ibid. 34, 257 (1983). Comprehensive description: M. S. Hifnawy, F. J. Muhtadi, Anal. Profiles Drug Subs. 17, 367-447 (1988).

Chemical structure

Properties

Triboluminescent, orthorhombic prisms from alcohol + ether, mp 147°. Sublimes at 135-140° at 11 mm pressure and 2 mm distance. d420 1.337. pK (25°) 8.07. uv max (ethanol): 239, 278-280, 314, 327 nm (log ε 4.83, 3.86, 3.60, 3.67). Almost insol in water. Sol in hot benzene, glacial acetic acid, acetone; slightly sol in chloroform, carbon tetrachloride, petr ether. Optimal pH for storage of papaverine solns: 2.0-2.8.

Derivative

Hydrochloride.

Nomenclature

CAS number: 61-25-6
Artegodan (Artesan); Cepaverin (Globopharm); Cerebid (Saron); Cerespan (USV); Dynovas (Mayrand); Optenyl (Stroschein); Pameion (Simes); Panergon (Mack, Illert.); Papital T.R. (Zemmer); Pavabid (HMR); Pavacen (Central Pharm.); Pavadel (Canright); Pavagen (Darby); Pavakey (Key); Pavased (Mallard); Spasmo-Nit (Stroschein); Therapav (Berlex); Vasal (Tutag); Vasospan (Ulmer).
C20H21NO4.HCl; mol wt 375.85.
C 63.91%, H 5.90%, N 3.73%, O 17.03%, Cl 9.43%.

Properties

Monoclinic rods from water, mp 220-225°. uv max (ethanol): 249-250, 280-282, 311 nm (log ε 4.69, 3.80, 3.82). One gram dissolves in about 40 ml water. Sol in alcohol and chloroform. Practically insol in ether. pH of 0.05 molar soln 3.9; pH of 2% aq soln 3.3. LD50 in mice, rats (mg/kg): 27.5, 20 i.v.; 150, 370 s.c. (Levis).

Derivative

Nitrite.

Nomenclature

CAS number: 132-40-1
C20H21NO4.HNO2; mol wt 386.40.
C 62.17%, H 5.74%, N 7.25%, O 24.84%.

Properties

Light yellow, crystalline powder. Slightly soluble in water or alcohol; freely sol in chloroform, acetone.

Therapeutic Category

Vasodilator (cerebral).

Keywords

Vasodilator (Cerebral)