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Namespace Prefixes

PrefixIRI
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Statements

Subject Item
n2:DB00907
rdf:type
n3:Drug
n3: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]
n3:generalReferences
# Siegel RK, Elsohly MA, Plowman T, Rury PM, Jones RT: Cocaine in herbal tea. JAMA. 1986 Jan 3;255(1):40. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/3940302 # 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":http://www.ncbi.nlm.nih.gov/pubmed/10983846 # 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":http://www.ncbi.nlm.nih.gov/pubmed/15262059 # 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":http://www.ncbi.nlm.nih.gov/pubmed/12865893 # 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":http://www.ncbi.nlm.nih.gov/pubmed/15967985
n3:group
approved illicit
n3:halfLife
1 hour
n3:indication
For the introduction of local (topical) anesthesia of accessible mucous membranes of the oral, laryngeal and nasal cavities.
owl:sameAs
n13:DB00907 n15:DB00907
dcterms:title
Cocaine
adms:identifier
n17:2286 n18:27958 n19:DB00907 n20:D00110 n21:PA449072 n22:2286 n23:C01416 n24:50006232 n28:Cocaine
n3:mechanismOfAction
Cocaine produces anesthesia by inhibiting excitation of nerve endings or by blocking conduction in peripheral nerves. This is achieved by reversibly binding to and inactivating sodium channels. Sodium influx through these channels is necessary for the depolarization of nerve cell membranes and subsequent propagation of impulses along the course of the nerve. Cocaine is the only local anesthetic with vasoconstrictive properties. This is a result of its blockade of norepinephrine reuptake in the autonomic nervous system. Cocaine binds differentially to the dopamine, serotonin, and norepinephrine transport proteins and directly prevents the re-uptake of dopamine, serotonin, and norepinephrine into pre-synaptic neurons. Its effect on dopamine levels is most responsible for the addictive property of cocaine.
n3:packager
n14:271B5D4F-363D-11E5-9242-09173F13E4C5 n14:271B5D4D-363D-11E5-9242-09173F13E4C5 n14:271B5D4E-363D-11E5-9242-09173F13E4C5 n14:271B5D4C-363D-11E5-9242-09173F13E4C5
n3:synonym
(−)-cocaine Benzoylmethylecgonine L-Cocaine (-)-Cocaine Cocaine Kokain Methyl benzoylecgonine 2-Methyl-3beta-hydroxy-1alphah,5alphah-tropane-2beta-carboxylate benzoate (ester) beta-Cocain L-Cocain Cocainum Cocain Neurocaine Cocaina [1R-(Exo,exo)]-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid, methyl ester Methyl [1R-(exo,exo)]-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
n3:toxicity
Intense agitation, convulsions, hypertension, rhythm disturbance, coronary insufficiency, hyperthermia, rhabdomyolysis, and renal impairment. Oral mouse LD<sub>50</sub> = 96 mg/kg
n6:hasAHFSCode
n26:52-16-00
n3:synthesisReference
Nobuyuki Shigetoh, Hiroshi Nakayama, Jinsei Miyazaki, Tadayasu Mitsumata, "Labelling colors for detecting cocaine or methamphetamine, method of preparing the same and detector for cocaine or methamphetamine." U.S. Patent US5571727, issued October, 1981.
n8:hasConcept
n9:M0004670
foaf:page
n11:cocaine-hydrochloride-topical.html n27:cocaine.htm
n3:IUPAC-Name
n4:271B5D57-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B5D5D-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B5D5C-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B5D59-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B5D5A-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B5D5B-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B5D55-363D-11E5-9242-09173F13E4C5 n4:271B5D6C-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B5D56-363D-11E5-9242-09173F13E4C5 n4:271B5D53-363D-11E5-9242-09173F13E4C5 n4:271B5D6E-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B5D6F-363D-11E5-9242-09173F13E4C5 n4:271B5D54-363D-11E5-9242-09173F13E4C5
n3:pKa
n4:271B5D70-363D-11E5-9242-09173F13E4C5
n6:hasATCCode
n7:S01HA01 n7:N01BC01 n7:S02DA02 n7:R02AD03
n3:H-Bond-Acceptor-Count
n4:271B5D63-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B5D64-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B5D5E-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B5D5F-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B5D61-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B5D60-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B5D62-363D-11E5-9242-09173F13E4C5
n3: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.
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
50-36-2
n3:category
n3:containedIn
n25:271B5D51-363D-11E5-9242-09173F13E4C5 n25:271B5D52-363D-11E5-9242-09173F13E4C5 n25:271B5D50-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n4:271B5D68-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B5D6A-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B5D6B-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n4:271B5D6D-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B5D67-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B5D66-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B5D69-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B5D58-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n4:271B5D65-363D-11E5-9242-09173F13E4C5