Ecopipam

Ecopipam

Systematic (IUPAC) name
(–)-trans-6,7,7a,8,9,13b-hexahydro-3-chloro-2-hydroxy-N-methyl-5H-benzo[d]naptho-(2,1-b)azepine
Identifiers
CAS Number	112108-01-7 Y
ATC code	none
PubChem	CID: 107930
IUPHAR/BPS	3304
ChemSpider	97053
UNII	0X748O646K Y
Chemical data
Formula	C19H20ClNO
Molecular mass	313.821 g/mol
SMILES CN1CCc2cc(c(cc2[C@@H]3[C@@H]1CCc4c3cccc4)O)Cl
InChI InChI=1S/C19H20ClNO/c1-21-9-8-13-10-16(20)18(22)11-15(13)19-14-5-3-2-4-12(14)6-7-17(19)21/h2-5,10-11,17,19,22H,6-9H2,1H3/t17-,19+/m0/s1 Key:DMJWENQHWZZWDF-PKOBYXMFSA-N
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Ecopipam (SCH-39166) is a synthetic benzazepine derivative drug that acts as a selective dopamine D₁/D₅ receptor antagonist, with little affinity for either dopamine D₂-like or 5-HT₂ receptors.

Chemical synthesis

Ecopipam can be synthesized from a simple tetralin derivative:

Clinical trials

Based on its profile in animal models, ecopipam was first studied as a treatment for schizophrenia but showed no activity. Side effects including sedation, restlessness, emesis and anxiety were generally rated mild. There were no reports of Parkinsonian-like extrapyramidal symptoms typically seen with D₂ antagonists.

Human clinical studies also showed that ecopipam was an effective antagonist of the acute euphoric effects of cocaine. However, the effect did not persist following repeated administration.

Researchers have postulated that dopamine via D₁ receptors in the mesolimbic system is involved with rewarded behaviors and pleasure. One such behavior is eating, and ecopipam has been shown in a large clinical study to be an effective treatment for obesity. However, reports of mild-to-moderate, reversible anxiety and depression made it unsuitable for commercialization as an anti-obesity drug, and its development was stopped.

Recent (2014) open label studies have shown ecopipam to reduce gambling behaviors in subjects with pathological gambling and to decrease the motor and vocal tics in adults with Tourette’s Syndrome. Ecopipam is currently in clinical trials conducted by the biotechnology company Psyadon Pharmaceuticals for the treatment of Tourette syndrome in children ages 7–17.