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Cocaine

Catalog No. DB00907 Name DrugBank
CAS Number 50-36-2 Website http://www.ualberta.ca/
M. F. C17H21NO4 Telephone (780) 492-3111
M. W. 303.35294 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 783

SYNONYMS

IUPAC name
methyl (2R,3S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
IUPAC Traditional name
cocaine
Brand Name
Cocaine
Synonyms
Moonrocks
Beta-Cocain
Flex
Candy
Isococaine
Star-Spangled Powder
Neurocaine
Lady
Isocaine
Gold Dust
Florida Snow
Eritroxilina
Dust
Bernice
Bernies
Blizzard
Cocaina
Coke
Zip
Yeyo
Trails
Prime Time
Pimp's Drug
Methyl Benzoylecgonine
Leaf
L-Cocaine
L-Cocain
Kokayeen
Kokain
Isococain
Happy Trails
Happy Dust
Goofball
Erytroxylin
Blast
Blow
Bouncing Powder
Cocaine Free Base
Cocaine-M
Coca
COC
D-pseudococaine
Corine
Cola
Cocktail
Toot
Toke
Sweet Stuff
Sugar
Star Dust
Snort
Sleighride
Rock
Line
Kokan
Kibbles N' Bits
Jam
Hell
Heaven
Happy Powder
Green Gold
Girl
G-Rock
Freeze
Foo Foo
Flake
Benzoylethylecgonine
Bazooka
Badrock
Benzoylmethylecgonine
Bump
Burese
C" Carrie
Cocain
Cholly
Chicken Scratch
Charlie
Cecil
Caviar
Carrie
Cabello
Dextrocaine
Depsococaine
Delcaine
Dama Blanca

DATABASE IDS

CAS Number 50-36-2

PROPERTIES

Hydrophobicity(logP) 2.3
Solubility 1800 mg/L

DETAILS

Description (English)
Item Information
Drug Groups illicit; approved
Description 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. [PubChem]
Indication For the introduction of local (topical) anesthesia of accessible mucous membranes of the oral, laryngeal and nasal cavities.
Pharmacology Cocaine is a local anesthetic indicated for the introduction of local (topical) anesthesia of accessible mucous membranes of the oral, laryngeal and nasal cavities.
Toxicity Intense agitation, convulsions, hypertension, rhythm disturbance, coronary insufficiency, hyperthermia, rhabdomyolysis, and renal impairment. Oral mouse LD50 = 96 mg/kg
Affected Organisms
Humans and other mammals
Biotransformation Hepatic. Cocaine is metabolized to benzoylecgonine and ecgonine methyl ester, which are both excreted in the urine. In the presence of alcohol, a further active metabolite, cocaethylene is formed, and is more toxic then cocaine itself.
Absorption Cocaine is absorbed from all sites of application, including mucous membranes and gastrointestinal mucosa. By oral or intra-nasal route, 60 to 80% of cocaine is absorbed.
Half Life 1 hour
References
Siegel RK, Elsohly MA, Plowman T, Rury PM, Jones RT: Cocaine in herbal tea. JAMA. 1986 Jan 3;255(1):40. [Pubmed]
Volkow ND, Wang GJ, Fischman MW, Foltin R, Fowler JS, Franceschi D, Franceschi M, Logan J, Gatley SJ, Wong C, Ding YS, Hitzemann R, Pappas N: Effects of route of administration on cocaine induced dopamine transporter blockade in the human brain. Life Sci. 2000 Aug 11;67(12):1507-15. [Pubmed]
Dimitrijevic N, Dzitoyeva S, Manev H: An automated assay of the behavioral effects of cocaine injections in adult Drosophila. J Neurosci Methods. 2004 Aug 30;137(2):181-4. [Pubmed]
Uz T, Akhisaroglu M, Ahmed R, Manev H: The pineal gland is critical for circadian Period1 expression in the striatum and for circadian cocaine sensitization in mice. Neuropsychopharmacology. 2003 Dec;28(12):2117-23. [Pubmed]
McClung CA, Sidiropoulou K, Vitaterna M, Takahashi JS, White FJ, Cooper DC, Nestler EJ: Regulation of dopaminergic transmission and cocaine reward by the Clock gene. Proc Natl Acad Sci U S A. 2005 Jun 28;102(26):9377-81. Epub 2005 Jun 20. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

  • Siegel RK, Elsohly MA, Plowman T, Rury PM, Jones RT: Cocaine in herbal tea. JAMA. 1986 Jan 3;255(1):40. Pubmed
  • Volkow ND, Wang GJ, Fischman MW, Foltin R, Fowler JS, Franceschi D, Franceschi M, Logan J, Gatley SJ, Wong C, Ding YS, Hitzemann R, Pappas N: Effects of route of administration on cocaine induced dopamine transporter blockade in the human brain. Life Sci. 2000 Aug 11;67(12):1507-15. Pubmed
  • Dimitrijevic N, Dzitoyeva S, Manev H: An automated assay of the behavioral effects of cocaine injections in adult Drosophila. J Neurosci Methods. 2004 Aug 30;137(2):181-4. Pubmed
  • Uz T, Akhisaroglu M, Ahmed R, Manev H: The pineal gland is critical for circadian Period1 expression in the striatum and for circadian cocaine sensitization in mice. Neuropsychopharmacology. 2003 Dec;28(12):2117-23. Pubmed
  • McClung CA, Sidiropoulou K, Vitaterna M, Takahashi JS, White FJ, Cooper DC, Nestler EJ: Regulation of dopaminergic transmission and cocaine reward by the Clock gene. Proc Natl Acad Sci U S A. 2005 Jun 28;102(26):9377-81. Epub 2005 Jun 20. Pubmed