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Cocaine

Benzoylmethylecgonine

Tropane alkaloid of the coca leaf. Potent inhibitor of dopamine, norepinephrine, and serotonin reuptake, producing intense stimulation, euphoria, and local anaesthesia. Whole-leaf coca, with its many minor alkaloids and nutrients, has a profoundly milder profile than isolated cocaine.

stimulant
Chemical structure of Cocaine
Structure · Wikimedia contributor See Wikimedia
THREE-DIMENSIONAL STRUCTURE

The molecule, in space.

Atoms positioned in their lowest-energy 3D geometry, sourced from PubChem. Drag to rotate · scroll to zoom · switch between stick, sphere, and line representations to feel the shape from different angles.

3D structure · PubChem CID 446220 · drag to rotate · scroll to zoom
SMILES NOTATION
CN1C2CCC1C(C(C2)OC(=O)C3=CC=CC=C3)C(=O)OC
PubChem CID 446220 →
RECEPTOR PROFILE

The pharmacological targets through which this compound exerts its effects.

Dopamine transporter inhibitorNorepinephrine transporter inhibitorSerotonin transporter inhibitorLocal anaesthetic (sodium channel block)
NATURAL SOURCES

Living organisms in which this compound is naturally found.

Erythroxylum coca (Coca)
plant
Andean
Erythroxylum coca
Coca

Andean shrub whose chewed leaves provide one of the world's most enduring stimulant traditions — sustaining high-altitude work, ritual, and medicine for at least 8000 years before its alkaloid cocaine was isolated and globally misused.

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REFERENCES
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  • Plowman 1979
  • Karch 2005
RELATED MOLECULES

Other tropanes

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Chemical structure of Atropine
Tropane
6–24+ hours
Atropine
DL-Hyoscyamine
deliriant

Racemic tropane alkaloid of the deadly nightshade family — a competitive antagonist of muscarinic acetylcholine receptors that produces dilated pupils, dry mouth, racing heart, and (at higher doses) a deliriant state of fully formed, often disturbing hallucinations.

Atropa belladonnaDatura stramoniumHyoscyamus niger +2 more
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Chemical structure of Hyoscyamine
Tropane
6–24+ hours
Hyoscyamine
L-Hyoscyamine
deliriant

Pure L-isomer counterpart to atropine and substantially more potent at muscarinic receptors. The principal active tropane of henbane and a major component of belladonna, datura, and mandrake.

Hyoscyamus nigerAtropa belladonnaDatura stramonium +1 more
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Chemical structure of Scopolamine
Tropane
8–48 hours (including significant after-effects)
Scopolamine
Hyoscine
deliriant

Tropane alkaloid found in Brugmansia, Datura, and other Solanaceae. Acts as a competitive muscarinic acetylcholine receptor antagonist, producing intense deliriant effects qualitatively distinct from classical psychedelics — including realistic hallucinations indistinguishable from reality.

Brugmansia suaveolensDatura stramoniumAtropa belladonna +2 more
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