Anodyne

Cocaine
Cocaine
Salts
[]
Cocaine hydrochloride
Cocaine hydrochloride
Cocaine borate
Cocaine borate
Cocaine hydrobromide
Cocaine hydrobromide
Cocaine hydriodide
Cocaine hydriodide
Cocaine citrate
Cocaine citrate
Molecular structure via molpic
Conformer structure via 3Dmol.js
Molecular formulaC17H21NO4
Molecular mass303.35 g/mol
AppearanceColorless to white crystals or white powder
Predicted LogP2.3
Melting point98 °C
Boiling point187 °C
DecompositionWhen heated to decomposition it emits highly toxic fumes.
SolubilityCrystals; MP 58-63 °C; freely sol in water or alcohol, slightly sol in ether. /Cocaine nitrate dihydrate/
Chiralityabsolute
Identifiers
[]
IUPAC namemethyl (1R,2R,3S,5S)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
SMILESCN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)C3=CC=CC=C3)C(=O)OC
InChIInChI=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
InChIKeyZPUCINDJVBIVPJ-LJISPDSOSA-N
Dosing
Intravenous
[]
Threshold0.125 - 0.3 mg
Light0.3 - 0.5 mg
Common0.5 - 1 mg
Strong1 - 28.75 mg
Heavy28.75 - 125 mg
Insufflated
[]
Threshold0.125 - 0.5 lines
Light0.5 - 1 lines
Common1 lines
Strong1 - 2.5 lines
Heavy2.5 - 4 lines
Statistically derived dosages by Sernyl

Cocaine

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

History and culture

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

Chemistry

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

Stereochemistry

Cocaine is a absolute mixture

Enzyme activity

Cocaine is a substrate of CYP3A4, coadministration of substances which inhibit CYP3A4 may result in altered drug effects and prolong its elimination half-life.

See also