Cocaine

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 tropane alkaloid and central nervous system stimulant derived primarily from the leaves of two coca species native to South America: Erythroxylum coca and E. novogranatense.[14][15][16][17][18] Indigenous South Americans have used coca leaves for over a thousand years. Today, cocaine is rarely used medically, primarily as a topical medication, due to its high abuse potential, adverse effects, and high cost.[19][20] Recreational use is widespread, and cocaine is one of the most consumed stimulants worldwide.[21][22][23]

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.[13][24] Pharmacologically, it is a serotonin–norepinephrine–dopamine reuptake inhibitor (SNDRI) that activates the mesolimbic pathway.[6][7][25][17] Reinforcing effects include euphoria, improved alertness and concentration, increased libido, a general sense of well-being, and reduced fatigue and appetite.[21]

Cocaine has numerous adverse effects. Short-term risks include vasoconstriction, tachycardia, hypertension, hyperthermia, anxiety, irritability, psychosis, and seizures.[13] Overdose may result in stroke, heart attack, or sudden cardiac death.[17][26] Use during pregnancy can lead to prenatal cocaine exposure, affecting fetal development.[27][28][29][30] Chronic use may cause cocaine dependence, withdrawal symptoms, and nasal damage, including cocaine-induced midline destructive lesions when insufflated.[31][32][33][34][35]

Large-scale biosynthesis of cocaine is unexplored;[36] As a result, the coca leaves are processed into cocaine paste and subsequently into powdered cocaine hydrochloride salt. According to a 2006 report by the United Nations Office on Drugs and Crime (UNODC), 99% of all global illicit cocaine is sourced from coca plantations in the Andes of South America—primarily in Colombia, Peru, and Bolivia.[18] While most coca cultivation remains concentrated in South America, recent years have seen rapid expansion into northern Central America, specifically in Honduras, Guatemala, and Belize.[37][38][39][40] Both South America and Central America are subregions of Latin America, which, together with the Caribbean, face increased violence and inequality due to drug war policies. This has prompted calls for rights-based reforms.[41]

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.[42][43][44][45]

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  4. ^ Ghodse H (2010). Ghodse's Drugs and Addictive Behaviour: A Guide to Treatment (4 ed.). Cambridge University Press. p. 91. ISBN 978-1-139-48567-8. Archived from the original on 10 September 2017.
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  7. ^ a b Azizi SA (April 2022). "Monoamines: Dopamine, Norepinephrine, and Serotonin, Beyond Modulation, "Switches" That Alter the State of Target Networks". The Neuroscientist. 28 (2): 121–143. doi:10.1177/1073858420974336. PMID 33292070. S2CID 228080727.
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  18. ^ a b "Coca Cultivation in the Andean Region" (PDF). UNODC. June 2006.
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  20. ^ Armbuster YC, Banas BN, Feickert KD, England SE, Moyer EJ, Christie EL, et al. (December 2021). "Decline and Pronounced Regional Disparities in Medical Cocaine Usage in the United States". The Journal of Pharmacy Technology. 37 (6): 278–285. doi:10.1177/87551225211035563. PMC 8592245. PMID 34790964.
  21. ^ a b Roque Bravo R, Faria AC, Brito-da-Costa AM, Carmo H, Mladěnka P, Dias da Silva D, et al. (April 2022). "Cocaine: An Updated Overview on Chemistry, Detection, Biokinetics, and Pharmacotoxicological Aspects including Abuse Pattern". Toxins. 14 (4): 278. doi:10.3390/toxins14040278. PMC 9032145. PMID 35448887.
  22. ^ "Cocaine & Crack". Erowid.
  23. ^ "Cocaine". DEA.
  24. ^ Cortés E, Metaal P. Smokable cocaine markets in Latin America and the Caribbean (PDF).
  25. ^ Cheng MH, Block E, Hu F, Cobanoglu MC, Sorkin A, Bahar I (2015). "Insights into the Modulation of Dopamine Transporter Function by Amphetamine, Orphenadrine, and Cocaine Binding". Frontiers in Neurology. 6: 134. doi:10.3389/fneur.2015.00134. PMC 4460958. PMID 26106364.
  26. ^ Sordo L, Indave BI, Barrio G, Degenhardt L, de la Fuente L, Bravo MJ (September 2014). "Cocaine use and risk of stroke: a systematic review". Drug Alcohol Depend. 142: 1–13. doi:10.1016/j.drugalcdep.2014.06.041. PMID 25066468.
  27. ^ Cite error: The named reference Buckingham-Howes_2013 was invoked but never defined (see the help page).
  28. ^ Cite error: The named reference Lambert_2012 was invoked but never defined (see the help page).
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  30. ^ Cite error: The named reference Eiden_2009 was invoked but never defined (see the help page).
  31. ^ Cite error: The named reference Gawin_1989 was invoked but never defined (see the help page).
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  34. ^ Cite error: The named reference Nitro_2022 was invoked but never defined (see the help page).
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  37. ^ Murillo-Sandoval PJ, Sesnie SE, Ordoñez Armas ME, Magliocca N, Tellman B, Devine JA, et al. (1 October 2024). "Central America's agro-ecological suitability for cultivating coca, Erythroxylum spp". Environmental Research Letters. 19 (10): 104068. Bibcode:2024ERL....19j4068M. doi:10.1088/1748-9326/ad7276.
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