Cocaine

Cocaine
Clinical data
Pronunciationkə(ʊ)ˈkeɪn
Trade namesNeurocaine, Goprelto, Numbrino, others
Other namesBenzoylmethylecogine
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
  • AU: S8 (Controlled drug)
  • BR: Class F1 (Prohibited narcotics)
  • CA: Schedule I
  • DE: Anlage III (Special prescription form required)
  • NZ: Class A
  • UK: Class A
  • US: Schedule II
  • UN: Narcotic Schedules I and III
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
IUPAC name
  • 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)
SMILES
  • CN1[C@H]2CC[C@@H]1[C@@H](C(OC)=O)[C@@H](OC(C3=CC=CC=C3)=O)C2
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 Y
  • Key:ZPUCINDJVBIVPJ-LJISPDSOSA-N Y
Data page
Cocaine (data page)
 NY (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. 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". In cocaine-producing countries, cocaine paste—an intermediate product from illicit production known as "poor man's cocaine"—is smoked in impoverished communities because it is cheap, but it poses serious health risks from toxic extraction chemicals that remain after processing. Cocaine hydrochloride was once a standard topical medication, but its high abuse potential, adverse effects, and cost have limited its use and led to its replacement by other medicines. "Cocaine and its combinations" are formally excluded from the WHO Model List of Essential Medicines.

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

Cocaine has numerous adverse effects. Acute use can cause vasoconstriction, tachycardia, hypertension, hyperthermia, anxiety, irritability, psychosis, and seizures, while overdose may lead to stroke, heart attack, or sudden cardiac death. Prenatal exposure poses risks to fetal development. Chronic use may result in cocaine dependence, withdrawal symptoms, neurotoxicity, and nasal damage, including cocaine-induced midline destructive lesions. Cocaine is frequently laced with levamisole to increase bulk. This is linked to vasculitis (CLIV) and autoimmune conditions (CLAAS).

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. 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. Cocaine remains the world’s fastest-growing illicit drug market. Coca chewing dates back at least 8,000 years in South America, and prior to World War II, large-scale production occurred in Taiwan and Java. The cocaine boom was a sharp rise in illegal cocaine production and trade, starting in the late 1970s and peaking in the 1980s. Cocaine is regulated under international drug control conventions, though national laws vary: several countries have decriminalized small quantities.