CHEBI:27958 - cocaine

Main ChEBI Ontology Automatic Xrefs
ChEBI Name cocaine
ChEBI ID CHEBI:27958
Definition A tropane alkaloid obtained from leaves of the South American shrub Erythroxylon coca.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:41642, CHEBI:3801, CHEBI:23346
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Formula C17H21NO4
Net Charge 0
Average Mass 303.35290
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
SMILES [H][C@]12CC[C@]([H])([C@H]([C@H](C1)OC(=O)c1ccccc1)C(=O)OC)N2C
Metabolite of Species Details
Erythroxylum coca (NCBI:289672) See: PubMed
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Biological Role(s): sodium channel blocker
An agent that inhibits sodium influx through cell membranes.
adrenergic uptake inhibitor
Adrenergic uptake inhibitors are drugs that block the transport of adrenergic transmitters into axon terminals or into storage vesicles within terminals. The tricyclic antidepressants and amphetamines are among the therapeutically important drugs that may act via inhibition of adrenergic transport. Many of these drugs also block transport of serotonin.
dopamine uptake inhibitor
A dopaminergic agent that blocks the transport of dopamine into axon terminals or into storage vesicles within terminals. Most of the adrenergic uptake inhibitors also inhibit dopamine uptake.
serotonin uptake inhibitor
A compound that specifically inhibits the reuptake of serotonin in the brain. This increases the serotonin concentration in the synaptic cleft which then activates serotonin receptors to a greater extent.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
sympathomimetic agent
A drug that mimics the effects of stimulating postganglionic adrenergic sympathetic nerves. Included in this class are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters.
xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): adrenergic uptake inhibitor
Adrenergic uptake inhibitors are drugs that block the transport of adrenergic transmitters into axon terminals or into storage vesicles within terminals. The tricyclic antidepressants and amphetamines are among the therapeutically important drugs that may act via inhibition of adrenergic transport. Many of these drugs also block transport of serotonin.
dopamine uptake inhibitor
A dopaminergic agent that blocks the transport of dopamine into axon terminals or into storage vesicles within terminals. Most of the adrenergic uptake inhibitors also inhibit dopamine uptake.
serotonin uptake inhibitor
A compound that specifically inhibits the reuptake of serotonin in the brain. This increases the serotonin concentration in the synaptic cleft which then activates serotonin receptors to a greater extent.
vasoconstrictor agent
Drug used to cause constriction of the blood vessels.
local anaesthetic
Any member of a group of drugs that reversibly inhibit the propagation of signals along nerves. Wide variations in potency, stability, toxicity, water-solubility and duration of action determine the route used for administration, e.g. topical, intravenous, epidural or spinal block.
central nervous system stimulant
Any drug that enhances the activity of the central nervous system.
sympathomimetic agent
A drug that mimics the effects of stimulating postganglionic adrenergic sympathetic nerves. Included in this class are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing cocaine (CHEBI:27958) has role adrenergic uptake inhibitor (CHEBI:35640)
cocaine (CHEBI:27958) has role central nervous system stimulant (CHEBI:35337)
cocaine (CHEBI:27958) has role dopamine uptake inhibitor (CHEBI:51039)
cocaine (CHEBI:27958) has role environmental contaminant (CHEBI:78298)
cocaine (CHEBI:27958) has role local anaesthetic (CHEBI:36333)
cocaine (CHEBI:27958) has role plant metabolite (CHEBI:76924)
cocaine (CHEBI:27958) has role serotonin uptake inhibitor (CHEBI:50949)
cocaine (CHEBI:27958) has role sodium channel blocker (CHEBI:38633)
cocaine (CHEBI:27958) has role sympathomimetic agent (CHEBI:35524)
cocaine (CHEBI:27958) has role vasoconstrictor agent (CHEBI:50514)
cocaine (CHEBI:27958) has role xenobiotic (CHEBI:35703)
cocaine (CHEBI:27958) is a benzoate ester (CHEBI:36054)
cocaine (CHEBI:27958) is a methyl ester (CHEBI:25248)
cocaine (CHEBI:27958) is a tertiary amino compound (CHEBI:50996)
cocaine (CHEBI:27958) is a tropane alkaloid (CHEBI:37332)
cocaine (CHEBI:27958) is conjugate base of cocaine(1+) (CHEBI:60056)
Incoming cocaine(1+) (CHEBI:60056) is conjugate acid of cocaine (CHEBI:27958)
IUPAC Names
(1R,2R,3S,5S)-2-(methoxycarbonyl)tropan-3-yl benzoate
methyl (1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
Synonyms Sources
(−)-cocaine ChEBI
2-methyl-3β-hydroxy-H,5αH-tropane-2β-carboxylate benzoate (ester) NIST Chemistry WebBook
[1R-(exo,exo)]-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid, methyl ester NIST Chemistry WebBook
Benzoylmethylecgonine ChemIDplus
beta-Cocain KEGG COMPOUND
Cocain DrugBank
Cocaina DrugBank
Cocaine KEGG COMPOUND
COCAINE PDBeChem
cocainum ChEBI
Kokain ChemIDplus
Kokain ChEBI
l-Cocain KEGG COMPOUND
l-cocaine ChemIDplus
methyl [1R-(exo,exo)]-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate ChEBI
methyl benzoylecgonine ChemIDplus
Neurocaine ChemIDplus
Database Links Databases
C00002285 KNApSAcK
C01416 KEGG COMPOUND
COC PDBeChem
Cocaine Wikipedia
CPD-9776 MetaCyc
D00110 KEGG DRUG
DB00907 DrugBank
View more database links
Registry Numbers Types Sources
170209 Gmelin Registry Number Gmelin
3621912 Beilstein Registry Number Beilstein
50-36-2 CAS Registry Number ChemIDplus
50-36-2 CAS Registry Number NIST Chemistry WebBook
5291037 Beilstein Registry Number Beilstein
5291037 Reaxys Registry Number Reaxys
91034 Reaxys Registry Number Reaxys
91034 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
11416615 PubMed citation CiteXplore
11853120 PubMed citation CiteXplore
14962054 PubMed citation CiteXplore
17551070 PubMed citation CiteXplore
19536276 PubMed citation CiteXplore
21150772 PubMed citation CiteXplore
25303034 PubMed citation CiteXplore
Last Modified
16 марта 2015
General Comment
2014-10-29 Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag