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Substance Name: Papaverine [BAN]
RN: 58-74-2
UNII: DAA13NKG2Q
InChIKey: XQYZDYMELSJDRZ-UHFFFAOYSA-N

Note

  • An alkaloid found in opium but not closely related to the other opium alkaloids in its structure or pharmacological actions. It is a direct-acting smooth muscle relaxant used in the treatment of impotence and as a vasodilator, especially for cerebral vasodilation. The mechanism of its pharmacological actions is not clear, but it apparently can inhibit phosphodiesterases and it may have direct actions on calcium channels.

Molecular Formula

  • C20-H21-N-O4

Molecular Weight

  • 339.3889
 

Classification Codes

  • Cardiovascular Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data
  • Mutation Data
  • Phosphodiesterase Inhibitors
  • Urological Agents
  • Vasodilator Agents

Names and Synonyms

Name of Substance

  • Papaverine
  • Papaverine [BAN]

MeSH Heading

  • Papaverine

Synonyms

  • 1-((3,4-Dimethoxyphenyl)methyl)-6,7-dimethoxyisoquinoline
  • 5-21-06-00182 (Beilstein Handbook Reference)
  • 6,7-Dimethoxy-1-veratrylisoquinoline
  • BRN 0312930
  • EINECS 200-397-2
  • HSDB 3147
  • Isoquinoline, 1-((3,4-dimethoxyphenyl)methyl)-6,7-dimethoxy-
  • Isoquinoline, 6,7-dimethoxy-1-veratryl-
  • NSC 136630
  • Papanerin
  • Papanerine
  • Papaverin
  • Papaverina
  • Papaverina [Italian]
  • Papaverine
  • Robaxapap
  • UNII-DAA13NKG2Q

Systematic Names

  • Isoquinoline, 1-((3,4-dimethoxyphenyl)methyl)-6,7-dimethoxy-
  • Isoquinoline, 6,7-dimethoxy-1-veratryl- (8CI)
  • Papaverine

Registry Numbers

CAS Registry Number

  • 58-74-2

FDA UNII

  • DAA13NKG2Q

Related Registry Number

  • 61-25-6 (hydrochloride)

System Generated Number

  • 0000058742

Structure Descriptors

InChI

1S/C20H21NO4/c1-22-17-6-5-13(10-18(17)23-2)9-16-15-12-20(25-4)19(24-3)11-14(15)7-8-21-16/h5-8,10-12H,9H2,1-4H3

InChIKey

XQYZDYMELSJDRZ-UHFFFAOYSA-N

Smiles

c12c(cc(c(c2)OC)OC)ccnc1Cc1cc(c(cc1)OC)OC

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo subcutaneous 120mg/kg (120mg/kg)   "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931.
dog LDLo subcutaneous 120mg/kg (120mg/kg)   "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931.
frog LDLo parenteral 225mg/kg (225mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

CARDIAC: PULSE RATE

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Journal of Pharmacology and Experimental Therapeutics. Vol. 25, Pg. 35, 1925.
frog LDLo subcutaneous 140mg/kg (140mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
man TDLo intramuscular 1143ug/kg (1.143mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: COMA
European Journal of Clinical Pharmacology. Vol. 33, Pg. 651, 1988.
mouse LD50 intradermal 150mg/kg (150mg/kg) BEHAVIORAL: EXCITEMENT

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 59, Pg. 149, 1938.
mouse LD50 intramuscular 175mg/kg (175mg/kg)   Archivum Immunologiae et Therapiae Experimentalis. Vol. 15, Pg. 415, 1967.
mouse LD50 intraperitoneal 91mg/kg (91mg/kg)   United States Patent Document. Vol. #4738965,
mouse LD50 intravenous 25mg/kg (25mg/kg) BEHAVIORAL: EXCITEMENT

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 59, Pg. 149, 1938.
mouse LD50 oral 162mg/kg (162mg/kg)   Therapie. Vol. 14, Pg. 731, 1959.
mouse LD50 subcutaneous 170mg/kg (170mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 227, Pg. 129, 1955.
pigeon LDLo subcutaneous 150mg/kg (150mg/kg)   "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931.
rabbit LD50 intravenous 25mg/kg (25mg/kg) BEHAVIORAL: EXCITEMENT

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 59, Pg. 149, 1938.
rabbit LDLo oral 190mg/kg (190mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
rabbit LDLo subcutaneous 250mg/kg (250mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
rat LD50 intraperitoneal 59600ug/kg (59.6mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 1338, 1970.
rat LD50 intravenous 13300ug/kg (13.3mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 26, Pg. 2172, 1976.
rat LD50 oral 325mg/kg (325mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 1338, 1970.
rat LD50 subcutaneous 151mg/kg (151mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 1338, 1970.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 147.5 deg C   EXP
pKa Dissociation Constant 8.07 (none) 25 EXP
log P (octanol-water) 2.95 (none)   EXP
Water Solubility 35 mg/L 17 EXP
Vapor Pressure 7.49E-09 mm Hg 25 EST
Henry's Law Constant 7.51E-13 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.50E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.