Preferred Name

cocaine

Synonyms

methyl (1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

COCAINE

(1R,2R,3S,5S)-2-(methoxycarbonyl)tropan-3-yl benzoate

Cocaine

l-Cocain

cocainum

2-methyl-3beta-hydroxy-1alphaH,5alphaH-tropane-2beta-carboxylate benzoate (ester)

Cocain

Kokain

l-cocaine

Neurocaine

Cocaina

(-)-cocaine

Benzoylmethylecgonine

methyl benzoylecgonine

[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

beta-Cocain

Isococain

D-pseudococaine

Erytroxylin

Delcaine

Methyl Benzoylecgonine

Benzoylethylecgonine

Beta-Cocain

Cocaine hydrochloride

Depsococaine

Isococaine

Dextrocaine

Cocaine-M

L-Cocain

Eritroxilina

Isocaine

L-Cocaine

Definitions

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) 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. Mechanism of action: 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. Cocaine also produces a number of indirect actions, which alter other neuromodulatory systems (i.e., opioidergic, glutamatergic, and GABAergic systems). Drug type: Approved. Illicit. Small Molecule. Drug category: Anesthetics. Anesthetics, Local. Dopamine Uptake Inhibitors. Local Anesthetics. Vasoconstrictor Agents Street names: Badrock, Bazooka, Bernice, Bernies, Blast, Blizzard, Blow, Bouncing Powder, Bump, Burese, C" Carrie, Cabello, Candy, Carrie, Caviar, Cecil, Charlie, Chicken Scratch, Cholly, Coca, Cocktail, Coke, Cola, Corine, Dama Blanca, Dust, Flake, Flex, Florida Snow, Foo Foo, Freeze, G-Rock, Girl, Gold Dust, Goofball, Green Gold, Happy Dust, Happy Powder, Happy Trails, Heaven, Hell, Jam, Kibbles N' Bits, Kokain, Kokan, Kokayeen, Lady, Leaf, Line, Moonrocks, Pimp's Drug, Prime Time, Sleighride, Snort, Star Dust, Star-Spangled Powder, Sugar, Sweet Stuff, Toke, Toot, Trails, Yeyo, Zip A tropane alkaloid obtained from leaves of the South American shrub Erythroxylon coca.

ID

http://purl.obolibrary.org/obo/CHEBI_27958

comment

Street names: Badrock, Bazooka, Bernice, Bernies, Blast, Blizzard, Blow, Bouncing Powder, Bump, Burese, C" Carrie, Cabello, Candy, Carrie, Caviar, Cecil, Charlie, Chicken Scratch, Cholly, Coca, Cocktail, Coke, Cola, Corine, Dama Blanca, Dust, Flake, Flex, Florida Snow, Foo Foo, Freeze, G-Rock, Girl, Gold Dust, Goofball, Green Gold, Happy Dust, Happy Powder, Happy Trails, Heaven, Hell, Jam, Kibbles N' Bits, Kokain, Kokan, Kokayeen, Lady, Leaf, Line, Moonrocks, Pimp's Drug, Prime Time, Sleighride, Snort, Star Dust, Star-Spangled Powder, Sugar, Sweet Stuff, Toke, Toot, Trails, Yeyo, Zip

charge

0

createdDate

March 5, 2010

database_cross_reference

CAS:50-36-2

PMID:21150772

Beilstein:91034

Beilstein:5291037

Drug_Central:723

DrugBank:DB00907

PMID:17551070

Wikipedia:Cocaine

PMID:11416615

Reaxys:91034

Gmelin:170209

KEGG:C01416

PMID:11853120

PMID:19536276

PDBeChem:COC

PMID:14962054

MetaCyc:CPD-9776

KEGG:D00110

PMID:25303034

Reaxys:5291037

KNApSAcK:C00002285

Beilstein:3621912

definition

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) 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. Mechanism of action: 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. Cocaine also produces a number of indirect actions, which alter other neuromodulatory systems (i.e., opioidergic, glutamatergic, and GABAergic systems). Drug type: Approved. Illicit. Small Molecule. Drug category: Anesthetics. Anesthetics, Local. Dopamine Uptake Inhibitors. Local Anesthetics. Vasoconstrictor Agents

formula

C17H21NO4

has characteristic

http://uri.neuinfo.org/nif/nifstd/nlx_chem_090801

has exact synonym

methyl (1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

COCAINE

(1R,2R,3S,5S)-2-(methoxycarbonyl)tropan-3-yl benzoate

Cocaine

has role

http://purl.obolibrary.org/obo/CHEBI_35337

http://purl.obolibrary.org/obo/CHEBI_76924

http://purl.obolibrary.org/obo/CHEBI_51039

http://purl.obolibrary.org/obo/CHEBI_35524

http://purl.obolibrary.org/obo/CHEBI_50949

http://purl.obolibrary.org/obo/CHEBI_35703

http://purl.obolibrary.org/obo/CHEBI_36333

http://purl.obolibrary.org/obo/CHEBI_75771

http://purl.obolibrary.org/obo/CHEBI_38633

http://purl.obolibrary.org/obo/CHEBI_35640

http://purl.obolibrary.org/obo/CHEBI_78298

http://purl.obolibrary.org/obo/CHEBI_50514

has_alternative_id

CHEBI:23346

CHEBI:41642

CHEBI:3801

has_obo_namespace

chebi_ontology

has_related_synonym

l-Cocain

cocainum

2-methyl-3beta-hydroxy-1alphaH,5alphaH-tropane-2beta-carboxylate benzoate (ester)

Cocain

Kokain

l-cocaine

Neurocaine

Cocaina

(-)-cocaine

Benzoylmethylecgonine

methyl benzoylecgonine

[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

beta-Cocain

hasExternalSource

DB00907

hasStreetName

Blast

Toot

Kibbles N' Bits

Carrie

Happy Dust

G-Rock

Jam

Candy

Blow

Bouncing Powder

Happy Powder

Zip

Sleighride

Badrock

Coke

Chicken Scratch

Snort

C" Carrie

Freeze

Moonrocks

Kokayeen

Lady

Leaf

Goofball

Star Dust

Caviar

Flake

Happy Trails

Star-Spangled Powder

Trails

Line

Pimp's Drug

Cocktail

Coca

Bump

Dust

Yeyo

Girl

Kokan

Cholly

Cecil

Dama Blanca

Heaven

Corine

Sugar

Hell

Sweet Stuff

Foo Foo

Charlie

Prime Time

Cabello

Florida Snow

Cola

Bernies

Toke

Bernice

Green Gold

Gold Dust

Blizzard

Bazooka

Flex

Burese

id

CHEBI:27958

in_subset

http://purl.obolibrary.org/obo/chebi#3_STAR

inchi

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

is conjugate base of

http://purl.obolibrary.org/obo/CHEBI_60056

label

cocaine

mass

303.35290

modifiedDate

June 30, 2010

monoisotopicmass

303.14706

notation

CHEBI:27958

prefLabel

cocaine

smiles

[H][C@]12CC[C@]([H])([C@H]([C@H](C1)OC(=O)c1ccccc1)C(=O)OC)N2C

synonym

Isococain

D-pseudococaine

Erytroxylin

Delcaine

Methyl Benzoylecgonine

Benzoylethylecgonine

Beta-Cocain

Cocaine hydrochloride

Depsococaine

Isococaine

Dextrocaine

Cocaine-M

L-Cocain

Eritroxilina

Isocaine

L-Cocaine

subClassOf

http://purl.obolibrary.org/obo/CHEBI_37332

http://purl.obolibrary.org/obo/CHEBI_36054

http://uri.neuinfo.org/nif/nifstd/nlx_chem_1003011

http://purl.obolibrary.org/obo/CHEBI_25248

http://purl.obolibrary.org/obo/CHEBI_50996

Delete Subject Author Type Created
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Create mapping

Delete Mapping To Ontology Source
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