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cocaine

File:Kokain_-_Cocaine.svg · Wikimedia Commons · See Wikimedia Commons

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cocaine

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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

OverviewAI-generated

Cocaine is a chemical compound with the formula C₁₇H₂₁NO₄. Its IUPAC name is methyl (1R,2R,3S,5S)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate. The substance has a mass of 303.147 and a weight of 303.35. It exhibits a melting point of 98 and a boiling point of 187. Additional physical properties include a density of 1.22, a refractive index of 1.5022, and a sublimation temperature of 90.

The compound has a pKa of 8.41 and an xlogP value of 2.3. It contains zero hydrogen bond donors and five hydrogen bond acceptors, with a topological polar surface area of 55.8. Its isomeric SMILES string is CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)C3=CC=CC=C3)C(=O)OC. In academic literature, there are 50,329 PubMed articles referencing cocaine. It is also referenced by 6,696 other encyclopedia articles.

Synthesized by Vinony from 24 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

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 Ų
H-bond donors
0
H-bond acceptors
5
Formal charge
0

via PubChem

Research

50,329 papers

via PubMed

Wikidata facts

Has part
hydrogen
Mass
303.147
Image
Amapolaa en polvo (cocaina).jpg
Has use
medication
Show 20 more facts
natural product of taxon
Erythroxylum novogranatense
pKa
8.41
Commons category
Cocaine
topic's main category
Category:Cocaine
route of administration
insufflation
significant drug interaction
thioridazine
chemical formula
C₁₇H₂₁NO₄
melting point
98
medical condition treated
cough
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
active ingredient in
crack
subject has role
stimulant
safety classification and labelling
Regulation (EC) No. 1272/2008
found in taxon
Homo sapiens
on focus list of Wikimedia project
Wikipedia:Vital articles/Level/4
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

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, adverse effects, and cost have limited its medical use and led to its replacement by alternative medicines.

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.

Gallery (51)

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via Wikidata sitelinks · CC0