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Substance Name: Cocaine [USP:BAN]
RN: 50-36-2
UNII: I5Y540LHVR
InChIKey: ZPUCINDJVBIVPJ-LJISPDSOSA-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

Molecular Weight

  • 303.3559
 

Classification Codes

Classification Codes

  • Anesthetic (Topical)
  • Anesthetics
  • Anesthetics, Local
  • Cardiovascular Agents
  • Central Nervous System Agents
  • Central Nervous System Depressants
  • Dopamine Agents
  • Dopamine Uptake Inhibitors
  • Drug / Therapeutic Agent
  • Human Data
  • Membrane Transport Modulators
  • Neurotransmitter Agents
  • Neurotransmitter Uptake Inhibitors
  • Peripheral Nervous System Agents
  • Reproductive Effect
  • Sensory System Agents
  • Skin / Eye Irritant
  • Vasoconstrictor Agents

Superlist Classification Code

  • DEA Schedule II

Names and Synonyms

Name of Substance

  • Cocaine
  • Cocaine [USP:BAN]

MeSH Heading

  • Cocaine

Synonyms

  • (1R,2R,3S,5S)-2-Methoxycarbonyltropan-3-yl benzoate
  • 1-alpha-H,5-alpha-H-Tropane-2-beta-carboxylic acid, 3-beta-hydroxy-, methyl ester, benzoate
  • 1-Cocaine
  • 2-beta-Carbomethoxy-3-beta-benzoxytropane
  • 2-beta-Tropanecarboxylic acid, 3-beta-hydroxy-, methyl ester, benzoate (ester)
  • 2beta-Carbomethoxy-3beta-benzoxytropane
  • 3-(Benzoyloxy)-8-methyl-8-azabicyclo-(3.2.1)octane-2-carboxylic acid methyl ether
  • 3-Tropanylbenzoate-2-carboxylic acid methyl ester
  • 3beta-Hydroxy-1alphaH,5alphaH-tropane-2beta-carboxylic acid methyl ester benzoate
  • 8-Azabicyclo(3.2.1)octane-2-carboxylic acid, 3-(benzoyloxy)-8-methyl-, methyl ester, (1R-(exo,exo))-
  • Benzoylmethylecgonine
  • Bernice [Street Name]
  • Bernies
  • Blow [Street Name]
  • Burese
  • C Carrie
  • Cecil [Street Name]
  • Cholly [Street Name]
  • Cocaina
  • Cocaine
  • Cocaine, l-
  • Coke
  • Corine
  • Crack
  • Crack cocaine
  • Dama blanca
  • Ecgonine, methyl ester, benzoate (ester)
  • EINECS 200-032-7
  • Eritroxilina
  • Erytroxylin
  • Flake [Street Name]
  • Girl [Street Name]
  • Gold dust [Street Name]
  • Green gold [Street Name]
  • Happy dust [Street Name]
  • Happy trails [Street Name]
  • HER
  • HSDB 6469
  • Jam
  • Kokain
  • Kokan
  • Kokayeen
  • L-Cocaine
  • Lady [Street Name]
  • Leaf
  • Methyl 3-beta-hydroxy-1-alpha-H,5-alpha-H-tropane-2-beta-carboxylate benzoate (ester)
  • Methyl 3beta-hydroxy-1alphaH,5alphaH-tropane-2beta-carboxylate benzoate (ester)
  • Methyl Benzoylecgonine
  • Neurocaine
  • Nose candy
  • Pimp's drug
  • Rock [Street Name]
  • Snow
  • Star dust [Street Name]
  • Star-spangled powder
  • Toot [Street Name]
  • UNII-I5Y540LHVR
  • White girl or lady

Systematic Names

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

Superlist Names

  • Cocaine
  • DEA No. 9041

Registry Numbers

CAS Registry Number

  • 50-36-2

FDA UNII

  • I5Y540LHVR

Related Registry Number

  • 53-21-4 (hydrochloride)

System Generated Number

  • 0000050362

Structure Descriptors

InChI

1S/C17H21NO4/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/t12-,13+,14-,15+/m0/s1

InChIKey

ZPUCINDJVBIVPJ-LJISPDSOSA-N

Smiles

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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 7500ug/kg (7.5mg/kg) BEHAVIORAL: GENERAL ANESTHETIC "Nachprufung der Toxicitat von Novocain und Tutocain bei Chloralisierten Tieren, Dissertation," Barke, A., Pharmakologischen Institut der Tierarztlichen Hochschule zu Hannover, Fed. Rep. Ger., 1936Vol. -, Pg. -, 1936.
cat LDLo subcutaneous 16mg/kg (16mg/kg) BEHAVIORAL: GENERAL ANESTHETIC "Nachprufung der Toxicitat von Novocain und Tutocain bei Chloralisierten Tieren, Dissertation," Barke, A., Pharmakologischen Institut der Tierarztlichen Hochschule zu Hannover, Fed. Rep. Ger., 1936Vol. -, Pg. -, 1936.
cattle LDLo subcutaneous 180mg/kg (180mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1332, 1935.
chicken 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 LD50 intravenous 13mg/kg (13mg/kg) AUTONOMIC NERVOUS SYSTEM: SYMPATHOMIMETIC

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Archives Internationales de Pharmacodynamie et de Therapie. Vol. 235, Pg. 328, 1978.
dog LDLo subcutaneous 3500ug/kg (3.5mg/kg) BEHAVIORAL: GENERAL ANESTHETIC "Nachprufung der Toxicitat von Novocain und Tutocain bei Chloralisierten Tieren, Dissertation," Barke, A., Pharmakologischen Institut der Tierarztlichen Hochschule zu Hannover, Fed. Rep. Ger., 1936Vol. -, Pg. -, 1936.
domestic animals - goat/sheep LDLo subcutaneous 180mg/kg (180mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1332, 1935.
frog LDLo intraspinal 175mg/kg (175mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 45, Pg. 291, 1932.
frog LDLo subcutaneous 300mg/kg (300mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

CARDIAC: PULSE RATE

BEHAVIORAL: EXCITEMENT		 Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 144, Pg. 197, 1929.
guinea pig LD50 subcutaneous 31mg/kg (31mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 240, Pg. 523, 1961.
guinea pig LDLo intravenous 20mg/kg (20mg/kg)   Physiological Reviews. Vol. 12, Pg. 190, 1932.
human TCLo inhalation 3571ug/kg (3.571mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Annals of Emergency Medicine. Vol. 21, Pg. 772, 1992.
human TDLo intravenous 1786ug/kg (1.786mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Annals of Emergency Medicine. Vol. 21, Pg. 772, 1992.
human TDLo oral 714mg/kg (714mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"		 JAMA, Journal of the American Medical Association. Vol. 238, Pg. 1391, 1977.
infant TDLo intrapleural 2308ug/kg (2.308mg/kg) BEHAVIORAL: EXCITEMENT

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)		 Journal of Toxicology, Clinical Toxicology. Vol. 25, Pg. 419, 1987.
infant TDLo oral 25800ng/kg (0.0258mg/kg) BEHAVIORAL: IRRITABILITY

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)		 Pediatric Emergency Care. Vol. 8, Pg. 82, 1992.
man LDLo oral 7353ug/kg (7.353mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
man TCLo inhalation 7143ug/kg (7.143mg/kg) BEHAVIORAL: IRRITABILITY

GASTROINTESTINAL: NAUSEA OR VOMITING

KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION		 Lancet. Vol. 2, Pg. 1150, 1987.
man TDLo intravenous 14mg/kg/4D-I (14mg/kg) CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION American Journal of Medicine. Vol. 81, Pg. 699, 1986.
mouse LD50 intraperitoneal 59mg/kg (59mg/kg)   Klinische Wochenscrift. Vol. 31, Pg. 97, 1953.
mouse LD50 intravenous 16mg/kg (16mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: EXCITEMENT

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION		 Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 1275, 1966.
mouse LD50 oral 99mg/kg (99mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: EXCITEMENT		 Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 1275, 1966.
mouse LD50 subcutaneous 81mg/kg (81mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 1025, 1966.
mouse LD50 unreported 108mg/kg (108mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 53, Pg. 2S, 1957.
pigeon LDLo subcutaneous 60mg/kg (60mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1333, 1935.
rabbit LD50 intravenous 17mg/kg (17mg/kg)   Journal of Laboratory and Clinical Medicine. Vol. 15, Pg. 731, 1930.
rabbit LD50 unreported 20mg/kg (20mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 24, Pg. 1957, 1974.
rabbit LDLo oral 126mg/kg (126mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 78, 1973.
rabbit LDLo subcutaneous 50mg/kg (50mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 160, Pg. 53, 1931.
rat LD50 intraperitoneal 70mg/kg (70mg/kg)   Journal of Laboratory and Clinical Medicine. Vol. 15, Pg. 731, 1930.
rat LD50 intravenous 17500ug/kg (17.5mg/kg)   Journal of Laboratory and Clinical Medicine. Vol. 15, Pg. 731, 1930.
rat LD50 subcutaneous 250mg/kg (250mg/kg)   Journal of Laboratory and Clinical Medicine. Vol. 15, Pg. 731, 1930.
women TCLo inhalation 14600mg/kg/2Y (14600mg/kg) CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 American Journal of Medicine. Vol. 81, Pg. 699, 1986.
women TDLo intravenous 10mg/kg (10mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

MUSCULOSKELETAL: OTHER CHANGES		 American Journal of Medicine. Vol. 85, Pg. 579, 1988.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 98 deg C   EXP
pKa Dissociation Constant 8.61 (none) 15 EXP
log P (octanol-water) 2.3 (none)   EXP
Water Solubility 1800 mg/L 22 EXP
Vapor Pressure 1.91E-07 mm Hg 25 EXP
Henry's Law Constant 4.24E-11 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 5.30E-11 cm3/molecule-sec 25 EST

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