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CHEBI:27958 - cocaine
| Formula | C17H21NO4 |
| Net Charge | 0 |
| Average Mass | 303.358 |
| Monoisotopic Mass | 303.14706 |
| SMILES | [H][C@]12CC[C@]([H])([C@@H](C(=O)OC)[C@@H](OC(=O)c3ccccc3)C1)N2C |
| 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 |
| Wikipedia |
|---|
| Species of Metabolite | Component | Source | Comments |
|---|---|---|---|
| Erythroxylum coca (ncbitaxon:289672) | - | PubMed (25303034) | |
| Mus musculus (ncbitaxon:10090) | - | PubMed (19425150) | Source: BioModels - MODEL1507180067 |
| Roles Classification |
|---|
| Chemical Roles: | environmental contaminant Any minor or unwanted substance introduced into the environment that can have undesired effects. Bronsted base A molecular entity capable of accepting a hydron from a donor (Brønsted acid). |
| Biological Roles: | 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. 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. sodium channel blocker An agent that inhibits sodium influx through cell membranes. 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. 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. mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. 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. metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. |
| Applications: | 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. 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. central nervous system stimulant Any drug that enhances the activity of the central nervous system. 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. 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. 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. vasoconstrictor agent Drug used to cause constriction of the blood vessels. |
| ChEBI Ontology |
|---|
| Outgoing Relation(s) |
| 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 mouse metabolite (CHEBI:75771) |
| 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 Relation(s) |
| cocaine(1+) (CHEBI:60056) is conjugate acid of cocaine (CHEBI:27958) |
| IUPAC Names |
|---|
| methyl (1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate |
| (1R,2R,3S,5S)-2-(methoxycarbonyl)tropan-3-yl benzoate |
| Synonyms | Source |
|---|---|
| Cocaine | KEGG COMPOUND |
| l-Cocain | KEGG COMPOUND |
| beta-Cocain | KEGG COMPOUND |
| methyl benzoylecgonine | ChemIDplus |
| l-cocaine | ChemIDplus |
| 2-methyl-3β-hydroxy-1αH,5αH-tropane-2β-carboxylate benzoate (ester) | NIST Chemistry WebBook |
| Citations |
|---|