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Substance Name: Cocaine hydrochloride [USP:JAN]
RN: 53-21-4
UNII: XH8T8T6WZH
InChIKey: PIQVDUKEQYOJNR-VZXSFKIWSA-N

Note

  • An alkaloid ester extracted from the leaves of plants including coca. It is a local anesthetic and vasoconstrictor and is clinically used for that purpose, particularly in the eye, ear, nose, and throat. It also has powerful central nervous system effects similar to the amphetamines and is a drug of abuse. Cocaine, like amphetamines, acts by multiple mechanisms on brain catecholaminergic neurons; the mechanism of its reinforcing effects is thought to involve inhibition of dopamine uptake.

Molecular Formula

  • C17-H21-N-O4.Cl-H

Molecular Weight

  • 339.8168
 

Classification Codes

  • Anesthetic (Topical)
  • Drug / Therapeutic Agent
  • Mutation Data
  • Reproductive Effect
  • Skin / Eye Irritant
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Names and Synonyms

Name of Substance

  • Cocaine hydrochloride [USP:JAN]

Synonyms

  • 1alpha-H,5alpha-H-Tropane-2beta-carboxylic acid, 3beta-hydroxy-,
  • 8-Azabicyclo(3.2.1)octane-2-carboxylic acid, 3-(benzoyloxy)-8-methyl-, methyl ester, hydrochloride, (1R-(exo,exo))-
  • Cocain-chlorhydrat
  • Cocain-chlorhydrat [German]
  • Cocaine chloride
  • Cocaine HCl
  • Cocaine hydrochloride
  • Cocaine muriate
  • EINECS 200-167-1
  • l-Cocaine hydrochloride
  • Methyl 3-beta-hydroxy-1-alpha-H,5-alpha-H-tropan-2-beta-carboxylate, benzoate (ester) HCl
  • Methyl 3beta-hydroxy-1alphaH,5alphaH-tropan-2beta-carboxylate, benzoate (ester) hydrochloride
  • NSC 25263
  • Sal de merck
  • UNII-XH8T8T6WZH

Systematic Names

  • 1-alpha-H,5-alpha-H-Tropane-2-beta-carboxylic acid, 3-beta-hydroxy-, methyl ester, benzoate (ester), hydrochloride
  • 1alphaH,5alphaH-Tropane-2beta-carboxylic acid, 3beta-hydroxy-, methyl ester, benzoate (ester), hydrochloride (8CI)
  • 8-Azabicyclo(3.2.1)octane-2-carboxylic acid, 3-(benzoyloxy)-8-methyl-, methyl ester, hydrochloride, (1R-(exo,exo))-
  • Cocaine hydrochloride

Registry Numbers

CAS Registry Number

  • 53-21-4

FDA UNII

  • XH8T8T6WZH

Related Registry Number

  • 50-36-2 (Parent)

System Generated Number

  • 0000053214

Molecular Formulas

Molecular Formula

  • C17-H21-N-O4.Cl-H

Molecular Formula Fragments

  • C17-H21-N-O4
  • Cl-H
  • COMPONENT

Structure Descriptors

InChI

1S/C17H21NO4.ClH/c1-18-12-8-9-13(18)15(17(20)21-2)14(10-12)22-16(19)11-6-4-3-5-7-11;/h3-7,12-15H,8-10H2,1-2H3;1H/t12-,13+,14-,15+;/m0./s1

InChIKey

PIQVDUKEQYOJNR-VZXSFKIWSA-N

Smiles

CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)c3ccccc3)C(=O)OC.Cl

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 intravenous 10mg/kg (10mg/kg)   Proceedings of the Society for Experimental Biology and Medicine. Vol. 35, Pg. 316, 1936.
dog LD50 intravenous 21mg/kg (21mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

AUTONOMIC NERVOUS SYSTEM: SYMPATHOMIMETIC
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 235, Pg. 328, 1978.
guinea pig LD50 intravenous 14562ug/kg (14.562mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 93, Pg. 388, 1948.
guinea pig LD50 subcutaneous 30mg/kg (30mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 93, Pg. 388, 1948.
mammal (species unspecified) LD50 subcutaneous 125mg/kg (125mg/kg)   Ceska a Slovenska Farmacie. Vol. 44, Pg. 210, 1995.
mouse LD50 intraperitoneal 68mg/kg (68mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 189, Pg. 198, 1971.
mouse LD50 intravenous 15mg/kg (15mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 105, Pg. 221, 1956.
mouse LD50 oral 96mg/kg (96mg/kg)   Research Progress in Organic-Biological and Medicinal Chemistry. Vol. 2, Pg. 279, 1970.
mouse LD50 subcutaneous 30mg/kg (30mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 8, Pg. 181, 1958.
rabbit LD50 intratracheal 30mg/kg (30mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Journal of Pharmacology and Experimental Therapeutics. Vol. 132, Pg. 87, 1961.
rabbit LD50 intravenous 12mg/kg (12mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 93, Pg. 388, 1948.
rabbit LD50 subcutaneous 78mg/kg (78mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 93, Pg. 388, 1948.
rat LD50 intraperitoneal 78mg/kg (78mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 8, Pg. 181, 1958.
rat LD50 intravenous 16380ug/kg (16.38mg/kg)   Pharmaceutical Archives. Vol. 11, Pg. 81, 1940.
rat LD50 subcutaneous 102mg/kg (102mg/kg)   Pharmaceutical Archives. Vol. 11, Pg. 81, 1940.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 290 dec deg C   EXP
log P (octanol-water) 0.100 (none)   EST
Water Solubility 7.14E+05 mg/L 25 EXP
Vapor Pressure 4.30E-11 mm Hg 25 EST
Henry's Law Constant 2.07E-18 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 4.70E-11 cm3/molecule-sec 25 EST

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