Ecopipam hydrochloride

• CAT Number: I026700
• CAS Number: 190133-94-9
• Molecular Formula: C19H21Cl2NO
• Molecular Weight: 350.28
• Purity: ≥95%
• Synonyms: (6aS,13bR)-11-chloro-7-methyl-5,6,6a,8,9,13b-hexahydronaphtho[1,2-a][3]benzazepin-12-ol;hydrochloride
• InChI: InChI=1S/C19H20ClNO.ClH/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;1H/t17-,19+;/m0./s1
• InChIKey: APFMVAHRFWBCDG-JUOYHRLASA-N
• SMILES: CN1CCC2=CC(=C(C=C2C3C1CCC4=CC=CC=C34)O)Cl.Cl

Ecopipam (SCH 39166) hydrochloride is a potent, selective and orally active antagonist of dopamine D1/D5 receptor, with Kis of 1.2 nM and 2.0 nM, respectively. Ecopipam hydrochloride shows more than 40-flod selectivity over D2, D4, 5-HT, and α2a receptor (Ki=0.98, 5.52, 0.08, and 0.73 μM, respectively). Ecopipam hydrochloride can be used for the research of schizophrenia and obesity[1][3].
Ecopipam (2 μM) hydrochloride completely abolishes the proconvulsive effect of Dopamine (10 μM) in isolated corticohippocampal formation[2].
Ecopipam (0.003-0.3 mg/kg, a single s.c.) hydrochloride abolishes Nicotine-induced enhancement of a sensory reinforcer in adult rats[3].
Ecopipam (10, mg/kg, oral administration) hydrochloride antagonizes Apomorphine-induced stereotypy in rats[4].
Ecopipam (5 and 10 μM, perfusion, 1 μL/min) hydrochloride reversibly and dose-dependently decreases acetylcholine release in the rat striatum[5].

Reference

[1]. Wu WL, et, al. Dopamine D1/D5 receptor antagonists with improved pharmacokinetics: design, synthesis, and biological evaluation of phenol bioisosteric analogues of benzazepine D1/D5 antagonists. J Med Chem. 2005 Feb 10;48(3):680-93.
 [Content Brief]

[2]. Sharopov S, et al. Dopaminergic modulation of low-Mg²⁺-induced epileptiform activity in the intact hippocampus of the newborn mouse in vitro. J Neurosci Res. 2012 Oct;90(10):2020-33.
 [Content Brief]

[3]. Satanove DJ, et al. Nicotine-induced enhancement of a sensory reinforcer in adult rats: antagonist pretreatment effects. Psychopharmacology (Berl). 2021 Feb;238(2):475-486.
 [Content Brief]

[4]. R E Chipkin, et al. Pharmacological profile of SCH39166: a dopamine D1 selective benzonaphthazepine with potential antipsychotic activity. J Pharmacol Exp Ther. 1988 Dec;247(3):1093-102.
 [Content Brief]

[5]. E Acquas, et al. Local application of SCH 39166 reversibly and dose-dependently decreases acetylcholine release in the rat striatum. Eur J Pharmacol. 1999 Nov 3;383(3):275-9.
 [Content Brief]