Cocaine

Cocaine
Clinical data
Pronunciationkə(ʊ)ˈkeɪn
Trade namesNeurocaine, Goprelto, Numbrino, others
AHFS/Drugs.comMicromedex Detailed Consumer Information
License data
Dependence
liability
Physical: Low Psychological: High
Addiction
liability
High
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
Duration of action20 to 90 minutes
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
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 Y
  • Key:ZPUCINDJVBIVPJ-LJISPDSOSA-N Y
Data page
Cocaine (data page)
 NY (what is this?)  (verify)

Cocaine is a tropane alkaloid and central nervous system stimulant, derived primarily from the leaves of two South American coca plants, Erythroxylum coca and E. novogranatense, which are cultivated almost exclusively in the Andes.

Indigenous South Americans have traditionally used coca leaves for over a thousand years. Medically, cocaine is rarely employed, mainly as a topical medication under controlled settings, due to its high abuse potential, adverse effects, and expensive cost. Recreational use of cocaine is widespread, driven by its euphoric and aphrodisiac properties.

Street cocaine is typically snorted, injected, or smoked as crack cocaine, with effects beginning within seconds to minutes and lasting up to 90 minutes depending on the route. Pharmacologically, it is a serotonin–norepinephrine–dopamine reuptake inhibitor (SNDRI) that activates the mesolimbic pathway. Intoxication may cause euphoria, psychosis, and physical symptoms like tachycardia and mydriasis. An overdose can lead to stroke, heart attack, or sudden cardiac death. Chronic cocaine use leads to cocaine dependence and can cause nose disorders, commonly referred to as "cocaine nose", including cocaine-induced midline destructive lesions (CIMDL) when insufflated.

Large-scale chemical synthesis of cocaine is unexplored; Instead, 99% of all global cocaine is made by first harvesting coca leaves by cocaleros from their coca plantations in the Andes. These leaves are then extracted into cocaine paste, which is subsequently processed into powdered hydrochloride salt. Both the pharmaceutical supply chain and the illicit supply chain use all these steps, but they operate under very different controls and oversight. In Peru, for example, legal coca cultivation is monopolized by the state company National Coca Company (ENACO), yet approximately 90% of coca leaves produced in the country are diverted to illegal actors for cocaine manufacturing. As a result, these illicit coca crops are a primary target of ongoing government-led coca eradication efforts.

Cocaine is prohibited globally except for restricted medical and scientific uses under treaties like the Single Convention on Narcotic Drugs. Nevertheless, legal penalties vary by country. Some jurisdictions decriminalize possession of small amounts, leading to inconsistency in the legal status of cocaine worldwide.