Cocaine
Cocaine
Systematic (IUPAC) name
methyl (1R,2R,3S,5S)-3- (benzoyloxy)-8-methyl-
-8-azabicyclo[3.2.1] octane-2-carboxylate
Identifiers
CAS number
50-36-2
ATC code
N01BC01 R02AD03, S01HA01,
S02DA02
PubChem
5760
DrugBank
APRD00080
ChemSpider
5557
Chemical data
Formula
C17H21NO4
Mol. mass
303.353 g/mol
SMILES
eMolecules & PubChem
Synonyms
methylbenzoylecgonine,
benzoylmethylecgonine
Physical data
Melt. point
195 °C (383 °F)
Solubility in
water
1800 mg/mL (20 °C)
Pharmacokinetic data
Bioavailability Oral: 33%[1]
Insufflated: 60[2]–80%[3]
Nasal Spray: 25[4]–43%[1]
Metabolism
Hepatic CYP3A4
Half life
1 hour
Excretion
Renal (benzoylecgonine and
ecgonine methyl ester)
Therapeutic considerations
Pregnancy cat. C
Legal status
Controlled (S8)(AU) Schedule
I(CA) Class A(UK) Schedule II(US)
Dependence
Liability
High
Routes
Topical, Oral, Insufflation, IV,
PO
Cocaine (benzoylmethyl ecgonine) is a crystalline tro-
pane alkaloid that is obtained from the leaves of the
coca plant.[5] The name comes from "coca" in addition to
the alkaloid suffix -ine, forming cocaine. It is both a stim-
ulant of the central nervous system and an appetite sup-
pressant. Specifically, it is a dopamine reuptake inhibit-
or, a norepinephrine reuptake inhibitor and a serotonin
reuptake inhibitor which mediates functionality of such
as an exogenous DAT ligand. Because of the way it af-
fects the mesolimbic reward pathway, cocaine is addict-
ive.[6]
Its possession, cultivation, and distribution are illeg-
al for non-medicinal and non-government sanctioned
purposes in virtually all parts of the world. Although its
free commercialization is illegal and has been severely
penalized in virtually all countries, its use worldwide re-
mains widespread in many social, cultural, and personal
settings.
History
Coca leaf
For over a thousand years South American indigenous
peoples have chewed the coca leaf (Erythroxylon coca), a
plant that contains vital nutrients as well as numerous
alkaloids, including cocaine. The leaf was, and is, chewed
almost universally