cocaine

Also known as (-)-cocaine, benzoylmethylecgonine, methyl benzoylecgonine, methyl [1R-(exo,exo)]-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate, [1R-(exo,exo)]-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid, methyl ester, 2-methyl-3beta-hydroxy-1alphah,5alphah-tropane-2beta-carboxylate benzoate (ester), beta-cocaine, cocaina

Cocaine is a stimulant of the central nervous system and tropane alkaloid, derived primarily from the leaves of two coca species native to South America: Erythroxylum coca and E. novogranatense. The leaves are processed into cocaine paste, a crude mixture of coca alkaloids, from which cocaine base is isolated and then converted to cocaine hydrochloride. Although total synthesis is possible, it is complex and not used for production. Historically, cocaine was a standard topical medication used as a local anesthetic with intrinsic vasoconstrictor properties. However, its high abuse potential, ad

AI overview

Cocaine is a powerful stimulant drug derived from coca plant leaves native to South America, historically used in medicine as a local anesthetic but now primarily known for its high potential for abuse and addiction. It matters because of its significant impact on public health and drug policy, given its addictive properties and the widespread illicit drug trade built around it.

AI-generated from the Wikipedia summary — may contain errors.

In the Vinony graph

Vinony's link graph records 6,696 inbound references to cocaine, and connects out to valproic acid, drug liberalization and tryptamines.

It sits within the topics 1855 in science, 1855 in the German Confederation and 1855 introductions.

Vinony links it to 101 Wikipedia language editions.

Key facts

Drug.legal_DE: Anlage III
Drug.image: Kokain - Cocaine.svg
Drug.image_class: skin-invert-image
Drug.image2: Cocaine-from-xtal-1983-3D-balls.png
Drug.image_class2: bg-transparent
Drug.pronounce: kə(ʊ)ˈkeɪn
Drug.tradename: Neurocaine, Goprelto, Numbrino, others
Drug.DailyMedID: Cocaine
Drug.dependency_liability: Physical: Low Psychological: High
Drug.addiction_liability: High
Drug.routes_of_administration: Topical, by mouth, insufflation, intravenous, inhalation
Drug.ATC_prefix: N01
Drug.ATC_suffix: BC01
Drug.ATC_supplemental: , ,
Drug.legal_AU: Schedule 8
Drug.legal_BR: F1
Drug.legal_CA: Schedule I
Drug.legal_NZ: Class A

via Wikipedia infobox

Chemical data

Formula: C17H21NO4
Molecular weight: 303.35 g/mol
IUPAC name: methyl (1R,2R,3S,5S)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
SMILES: CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)C3=CC=CC=C3)C(=O)OC
InChIKey: ZPUCINDJVBIVPJ-LJISPDSOSA-N
XLogP: 2.3
Polar surface area: 55.8 Å²
H-bond donors: 0
H-bond acceptors: 5
Formal charge: 0

via PubChem

Research

50,329 papers

Cocaine: An Updated Overview on Chemistry, Detection, Biokinetics, and Pharmacotoxicological Aspects including Abuse Pattern.ReviewToxins · 2022Roque Bravo R, Faria AC, Brito-da-Costa AM et al.DOI: 10.3390/toxins14040278
Cocaine-Induced Time-Dependent Alterations in Cytochrome P450 and Liver Function.ReviewInternational journal of molecular sciences · 2023Jastrzębska J, Daniel WADOI: 10.3390/ijms24021632
Cocaine abuse and its impact on the thymus and spleen.ReviewHistology and histopathology · 2025Aki T, Unuma KDOI: 10.14670/HH-18-904
Role of Mitochondrial Dynamics in Cocaine's Neurotoxicity.ReviewInternational journal of molecular sciences · 2022Wen S, Aki T, Funakoshi T et al.DOI: 10.3390/ijms23105418
Cocaine's appetite for fat and the consequences on body weight.ReviewThe American journal of drug and alcohol abuse · 2015Billing L, Ersche KDDOI: 10.3109/00952990.2014.966196
Cocaine's effects on neuroendocrine systems: clinical and preclinical studies.ReviewPharmacology, biochemistry, and behavior · 1997Mello NK, Mendelson JHDOI: 10.1016/s0091-3057(96)00433-9
Cocaine use in trauma: the vices-paradox revisited.Surgery · 2023Bhullar A, Nahmias J, Kong A et al.DOI: 10.1016/j.surg.2023.06.024
Cocaine abuse and reproduction.ReviewInternational journal of clinical pharmacology and therapeutics · 1994Das G

via PubMed

Wikidata facts

Mass: 303.147
Image: Amapolaa en polvo (cocaina).jpg

Show 10 more facts

pKa: 8.41
Commons category: Cocaine
chemical formula: C₁₇H₂₁NO₄
melting point: 98
isomeric SMILES: CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)C3=CC=CC=C3)C(=O)OC
canonical SMILES: CN1C2CCC1C(C(C2)OC(=O)C3=CC=CC=C3)C(=O)OC
boiling point: 187
refractive index: 1.5022
density: 1.22
sublimation temperature: 90

Sources (9)

via Wikidata · CC0

~70 min read

Encyclopedic overview

83 sections

Contents

Uses
Traditional medicine
Coca leaves
Coca tea
Ypadu
Medical
Topical
Topical anesthetic
Ophthalmological use
Recreational
Insufflation
Cocaine spoon
Injection
Inhalation
Cocaine paste
Crack cocaine
Contraindications
Pregnancy
Breastfeeding
Adverse effects
Cardiac complications
Levamisole syndromes
Levamisole-induced necrosis syndrome
Cocaine/levamisole-associated syndromes
Cocaine- and levamisole-induced vasculitis
Cocaine/levamisole-associated autoimmune syndrome
Mortality
Neurotoxicity
Psychiatric symptoms
Psychosis
Short-term effects
Long-term effects
Addiction
Dependence and withdrawal
Treatment
Cocaine nose
Cocaine-induced midline destructive lesions
Causes
Treatment
Overdose
Interactions
Alcohol
MAOIs
Opioids
Pharmacology
Pharmacokinetics
Detection in the body
Body fluids
Hair
Pharmacodynamics
Chemistry
Forms
Synthesis
Total synthesis
Biosynthesis
GMO synthesis
Field analysis
Society and culture
Street names
Legal status
Australia
United States
Prevalence and trends
Impact
Impact of illicit cocaine
Impact on impoverished communities
Environmental impact
Impact of illicit cocaine trade
Latin America
West Africa
Impact of enforcement
Impact of coca eradication
Impact of interdiction
Research
Cocaine vaccines
Calixcoca
TA-CD
History
Etymology
See also
References
Further reading
External links

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

Excerpted from Wikipedia’s “cocaine” article, available under the CC BY-SA 4.0 licence.