cocaine (CHEBI:27958)

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CHEBI:27958 - cocaine

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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

Supplier Information	eMolecules:524652, ZINC000003875336

Download	Molfile XML SDF

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Wikipedia	License
Cocaine (from French cocaïne, from Spanish coca, ultimately from Quechua kúka) is a tropane alkaloid that acts as a central nervous system (CNS) stimulant. As an extract, it is mainly used recreationally and often illegally as a euphoriant and as an aphrodisiac. It is also used in medicine by indigenous South Americans for various purposes and rarely, but more formally, as a local anaesthetic or diagnostic tool by medical practitioners in more developed countries. It is primarily obtained from the leaves of two coca species native to South America: Erythroxylum coca and E. novogranatense. After extraction from the plant, and further processing into cocaine hydrochloride (powdered cocaine), the drug is administered by being either snorted, applied topically to the mouth, or dissolved and injected into a vein. It can also then be turned into free base form (typically crack cocaine), in which it can be heated until sublimated and then the vapours can be inhaled. Cocaine stimulates the mesolimbic pathway in the brain. Mental effects may include an intense feeling of happiness, sexual arousal, loss of contact with reality, or agitation. Physical effects may include a fast heart rate, sweating, and dilated pupils. High doses can result in high blood pressure or high body temperature. Onset of effects can begin within seconds to minutes of use, depending on method of delivery, and can last between five and ninety minutes. As cocaine also has numbing and blood vessel constriction properties, it is occasionally used during surgery on the throat or inside of the nose to control pain, bleeding, and vocal cord spasm. Cocaine crosses the blood–brain barrier via a proton-coupled organic cation antiporter and (to a lesser extent) via passive diffusion across cell membranes. Cocaine blocks the dopamine transporter, inhibiting reuptake of dopamine from the synaptic cleft into the pre-synaptic axon terminal; the higher dopamine levels in the synaptic cleft increase dopamine receptor activation in the post-synaptic neuron, causing euphoria and arousal. Cocaine also blocks the serotonin transporter and norepinephrine transporter, inhibiting reuptake of serotonin and norepinephrine from the synaptic cleft into the pre-synaptic axon terminal and increasing activation of serotonin receptors and norepinephrine receptors in the post-synaptic neuron, contributing to the mental and physical effects of cocaine exposure. A single dose of cocaine induces tolerance to the drug's effects. Repeated use is likely to result in addiction. Addicts who abstain from cocaine may experience prolonged craving lasting for many months. Abstaining addicts also experience modest drug withdrawal symptoms lasting up to 24 hours, with sleep disruption, anxiety, irritability, crashing, depression, decreased libido, decreased ability to feel pleasure, and fatigue being common. Use of cocaine increases the overall risk of death, and intravenous use potentially increases the risk of trauma and infectious diseases such as blood infections and HIV through the use of shared paraphernalia. It also increases risk of stroke, heart attack, cardiac arrhythmia, lung injury (when smoked), and sudden cardiac death. Illicitly sold cocaine can be adulterated with fentanyl, local anesthetics, levamisole, cornstarch, quinine, or sugar, which can result in additional toxicity. In 2017, the Global Burden of Disease study found that cocaine use caused around 7,300 deaths annually.
Read full article at Wikipedia

Formula

C17H21NO4

Net Charge

Average Mass

303.35290

Monoisotopic Mass

303.14706

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
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Erythroxylum coca (NCBI:txid289672)	See: PubMed

Roles Classification
Chemical Role(s):	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 (Bronsted acid). (via organic amino compound )

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. 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. 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 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	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-1αH,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

Manual Xrefs	Databases
723	DrugCentral
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	Reaxys Registry Number	Reaxys
91034	Reaxys Registry Number	Reaxys

Citations

Colley VL, Casale JF (2015)
Differentiation of South American crack and domestic (US) crack cocaine via headspace-gas chromatography/mass spectrometry.
Drug testing and analysis 7, 241-246 [PubMed:25303034]
[show Abstract]

Bhargava S, Arora RR (2011)
Cocaine and cardiovascular complications.
American journal of therapeutics 18, e95-e100 [PubMed:21150772]
[show Abstract]

Ward A, Walker VJ, Feng Z, Xu XZ (2009)
Cocaine modulates locomotion behavior in C. elegans.
PloS one 4, e5946 [PubMed:19536276]
[show Abstract]

Treadwell SD, Robinson TG (2007)
Cocaine use and stroke.
Postgraduate medical journal 83, 389-394 [PubMed:17551070]
[show Abstract]

Kollias-Baker C, Maxwell L, Stanley S, Boone T (2003)
Detection and quantification of cocaine metabolites in urine samples from horses administered cocaine.
Journal of veterinary pharmacology and therapeutics 26, 429-434 [PubMed:14962054]
[show Abstract]

Barroso-Moguel R, Mendez-Armenta M, Villeda-Hernandez J, Nava-Ruiz C, Santamaria A (2002)
Brain lesions induced by chronic cocaine administration to rats.
Progress in neuro-psychopharmacology & biological psychiatry 26, 59-63 [PubMed:11853120]
[show Abstract]

Brecklin CS, Bauman JL (1999)
Cardiovascular Effects of Cocaine: Focus on Hypertension.
Journal of clinical hypertension (Greenwich, Conn.) 1, 212-217 [PubMed:11416615]
[show Abstract]

Last Modified

22 February 2017

General Comment
2014-10-29	Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag

CHEBI:27958 - cocaine

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