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 | ||
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 |
|
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 | ||
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 | ||
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 |