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Cocaine

This article is about the purified salt form of cocaine. For the vaporized freebase, see Crack cocaine. For the crude coca leaf extract, see Cocaine paste. For the disguised smuggled form, see Black cocaine.
Not to be confused with "Pink cocaine", which typically does not contain cocaine; see Tusi (drug).
For other uses, see Cocaine (disambiguation).

Cocaine
Clinical data
Pronunciationkə(ʊ)ˈkeɪn
Trade namesNeurocaine,[1] Goprelto,[2] Numbrino,[3] others
Other namesBenzoylmethylecogine
AHFS/Drugs.comMicromedex Detailed Consumer Information
License data
Dependence
liability		Physical: Low Psychological: High[4]
Addiction
liability		High[5]
Routes of
administration		Topical, by mouth, insufflation, intravenous, inhalation
Drug class
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability
MetabolismLiver, CYP3A4
MetabolitesNorcocaine, benzoylecgonine, cocaethylene (when consumed with alcohol)
Onset of actionSeconds to minutes[13]
Duration of action20 to 90 minutes[13]
ExcretionKidney
Identifiers
  • Methyl (1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.000.030 Edit this at Wikidata
Chemical and physical data
FormulaC17H21NO4
Molar mass303.358 g·mol−1
3D model (JSmol)
Melting point98 °C (208 °F)
Boiling point187 °C (369 °F)
Solubility in water1.8g/L (22 °C)
  • CN1[C@H]2CC[C@@H]1[C@@H](C(OC)=O)[C@@H](OC(C3=CC=CC=C3)=O)C2
  • 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 checkY
  • Key:ZPUCINDJVBIVPJ-LJISPDSOSA-N checkY
Data page
Cocaine (data page)
 ☒NcheckY (what is this?)  (verify)

Cocaine is a central nervous system stimulant and tropane alkaloid derived primarily from the leaves of two coca species native to South America: Erythroxylum coca and E. novogranatense.[14][15][16][17][18] Coca leaves are processed into cocaine paste, a crude mix of coca alkaloids which cocaine base is isolated and converted to cocaine hydrochloride, commonly known as "cocaine".[18] Cocaine was once a standard topical medication as a local anesthetic with intrinsic vasoconstrictor activity, but its high abuse potential, adverse effects, and cost have limited its use and led to its replacement by other medicines.[19][20][21] "Cocaine and its combinations" are formally excluded from the WHO Model List of Essential Medicines.[22]

Street cocaine is commonly snorted, injected, or smoked as crack cocaine, with effects lasting up to 90 minutes depending on the route.[13][23] Cocaine acts pharmacologically as a serotonin–norepinephrine–dopamine reuptake inhibitor (SNDRI),[7][24][17] producing reinforcing effects such as euphoria, increased alertness, concentration, libido, and reduced fatigue and appetite.[25]

Cocaine has numerous adverse effects. Acute use can cause vasoconstriction, tachycardia, hypertension, hyperthermia, seizures, while overdose may lead to stroke, heart attack, or sudden cardiac death.[17][13][26] Cocaine also produces a spectrum of psychiatric symptoms including agitation, paranoia, anxiety, irritability, stimulant psychosis, hallucinations, delusions, violence, as well as suicidal and homicidal thinking.[27][17] Prenatal exposure poses risks to fetal development.[28][29][30][31] Chronic use may result in cocaine dependence, withdrawal symptoms, neurotoxicity, and nasal damage, including cocaine-induced midline destructive lesions.[32][33][34][35][36][37] No approved medication exists for cocaine dependence, so psychosocial treatment is primary.[38][39] Cocaine is frequently laced with levamisole to increase bulk.[40][41] This is linked to vasculitis (CLIV) and autoimmune conditions (CLAAS).[42][43]

Coca cultivation and its subsequent processes occur primarily Latin America, especially in the Andes of Bolivia, Peru, and Colombia, though cultivation is expanding into Central America, including Honduras, Guatemala, and Belize.[18][44][45][46][47] Violence linked to the cocaine trade continues to affect Latin America and the Caribbean and is expanding into Western Europe, Asia, and Africa as transnational organized crime groups compete globally.[48][49] Cocaine remains the world’s fastest-growing illicit drug market.[50][51] Coca chewing dates back at least 8,000 years in South America.[52] Large-scale cultivation occurred in Taiwan and Java prior to World War II.[53][54] Decades later, the cocaine boom marked a sharp rise in illegal cocaine production and trade, beginning in the late 1970s and peaking in the 1980s.[55] Cocaine is regulated under international drug control conventions, though national laws vary: several countries have decriminalized small quantities.[56][57][58][59]

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