Cocaine
Medicinal Chemistry
Molecular Weight
303.35
Molecular Formula
C17H21NO4
IUPAC Name
Methyl (1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
Pharmacognosy
Biological Source
Erythroxylum coca
Active Constituents
Cocaine
Pharmacology & Synthesis
Mechanism of Action
Blocks voltage-gated sodium channels (local anesthesia); inhibits reuptake of DA, NE, and 5-HT.
Pharmacokinetics (ADME)
A: Rapid from mucous membranes.
D: Crosses BBB rapidly.
M: Hepatic and plasma esterases.
E: Renal.
Pharmacodynamics
Intense local anesthesia, CNS stimulation, vasoconstriction.
Synthesis Pathway
Biosynthesized from ornithine and phenylalanine.
Safety, Warnings & Interactions
Adverse Effects
Hypertension, arrhythmias, addiction, paranoia.
Contraindications
Cardiovascular disease, concurrent MAOI use.
Drug Interactions
Sympathomimetics, MAOIs.
Pharmaceutics & Compendia
Dosage Forms
Topical solutions
Official Compendia
USP