Cocaine

Molecular structure via molpic based on CDK

Conformer []

Conformer structure via JSmol

Physical properties []
Molecular mass	303.35 g/mol ^[1]
Appearance	Colorless to white crystals or white powder ^[1]
Melting point	98 °C ^[1]
Boiling point	187 °C ^[1]
Decomposition	When heated to decomposition it emits highly toxic fumes. ^[1]
Solubility	Crystals; MP 58-63 °C; freely sol in water or alcohol, slightly sol in ether. /Cocaine nitrate dihydrate/ ^[1]
Predicted LogP	2.3 ^[1]

Structural Identifiers []
Molecular formula	C₁₇H₂₁NO₄ ^[1]
IUPAC name	methyl (1R,2R,3S,5S)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate ^[1]
SMILES	CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)C3=CC=CC=C3)C(=O)OC ^[1]
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 ^[1]
InChIKey	ZPUCINDJVBIVPJ-LJISPDSOSA-N ^[1]

Dosing []
Duration of action	20 - 90 minutes

Cocaine

Cocaine (also known as Benzoylmethylecgonine, Neurocaine, Kokain, Cocain, Cocaina, β-Cocain, (-)-Cocaine, cocainum, Methyl Benzoylecgonine or l-Cocain and brand names including Neurocaine) is a stimulant substance of the tropane class.

Chemistry

Salts []

Cocaine is typically found in the form of its hydrochloride, borate, hydrobromide, hydriodide and citrate salts.

Stereochemistry []

Cocaine is a absolute mixture

History and culture

Cocaine was first isolated from coca leaves in 1855 by German chemist Friedrich Gaedcke.

Subjective effects []

Physical effects
Abnormal heartbeat Appetite suppression Dehydration Dry mouth Increased blood pressure Increased heart rate Increased libido Restless legs Shakiness Stamina enhancement Stimulation Teeth grinding Vasoconstriction

Cognitive effects
Analysis enhancement Cognitive euphoria Compulsive redosing Disinhibition Ego inflation Focus enhancement Increased music appreciation Mania Motivation enhancement Suggestibility suppression Thought acceleration Wakefulness

Anodyne Usernotes []
0xea / Cocaine^{[freebase][hydrochloride][citrate]} via Intravenous and Vaporized	Strong Stimulation; Strong Euphoria; Strong Vasoconstriction; Intravenously Very Short Duration(~10 minutes); surprisingly Entactogenic; occasional comfortable full body feeling; Auditory alteration- or suppression; Vaporized Strong Fishy Smell

Experience reports []

There are currently 25+ experience reports involving cocaine on OpenErowid:

Legal status []

Australia: Cocaine is a Schedule 8 substance.
Brazil: Cocaine is a F1 substance.
Canada: Cocaine is a Schedule I substance.
Germany: Cocaine is a Anlage III substance.
New Zealand: Cocaine is a Class A substance.
United Kingdom: Cocaine is a Class A substance.
United States: Cocaine is a Schedule I under the "Controlled Substances Act (CSA)".^[3]
United Nations: Cocaine is a Schedule I and III narcotic under the "Single Convention on Narcotic Drugs 1961".

External links []

References []

National Center for Biotechnology Information. PubChem Compound Summary for CID 446220, Cocaine. Accessed June 26, 2025. https://pubchem.ncbi.nlm.nih.gov/compound/446220
U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. Cocaine. UNII: I5Y540LHVR. Global Substance Registration System. Accessed June 26, 2025. https://gsrs.ncats.nih.gov/ginas/app/beta/substances/I5Y540LHVR
DEA / Drug Scheduling. Accessed June 26, 2025. https://www.dea.gov/druginfo/ds.shtml