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Sch 39166

Names

[ CAS No. ]:
112108-01-7

[ Name ]:
Sch 39166

[Synonym ]:
SCH 39166
(-)-trans-6,7,7a,8,9,13b-hexahydro-3-chloro-2-hydroxy-N-methyl-5H-benzo-[d]naphtho{2,1-b}azepine
(6aS,13bR)-11-chloro-6,6a,7,8,9,13b-hexahydro-7-methyl-5H-benzo[d]naphth[2,1-b]azepin-12-ol
(-)-Ecopipam
(6aS,13bR)-11-Chloro-7-methyl-5,6a,7,8,9,13b-hexahydro-6H-7-aza-benzo[6,7]cyclohepta[1,2-a]naphthalen-12-ol
trans-(-)-(6aS,13bR)-11-chloro-6,6a,7,8,9,13b-hexahydro-7-methyl-5H-benzo[d]naphth[2,1-b]azepin-12-ol
(-)-trans-6,7,7a,8,9,13b-hexahydro-3-chloro-2-hydroxy-N-methyl-5H-benzo[d]naphtho[2,1-b]azepine

Biological Activity

[Description]:

Ecopipam (SCH 39166) 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 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 can be used for the research of schizophrenia, cocaine addition, and obesity[1][3].

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Dopamine Receptor
Signaling Pathways >> GPCR/G Protein >> Adrenergic Receptor
Signaling Pathways >> Neuronal Signaling >> Dopamine Receptor
Research Areas >> Metabolic Disease
Research Areas >> Neurological Disease
Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor
Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor

[Target]

D1 Receptor:1.2 nM (Ki)

D5 Receptor:2.0 nM (Ki)

D2 Receptor:980 nM (Ki)

D4 Receptor:5520 nM (Ki)

5-HT Receptor:80 nM (Ki)

Alpha-2A adrenergic receptor:731 nM (Ki)


[In Vitro]

Ecopipam (2 μM) completely abolishes the proconvulsive effect of Dopamine (10 μM) in isolated corticohippocampal formation[2].

[In Vivo]

Ecopipam (0.003-0.3 mg/kg; a single s.c.) abolishes Nicotine-induced enhancement of a sensory reinforcer in adult rats[3]. Ecopipam (10, mg/kg, oral administration) antagonizes Apomorphine-induced stereotypy in rats[4]. Ecopipam (5 and 10 μM, perfusion, 1 μL/min) reversibly and dose-dependently decreases acetylcholine release in the rat striatum[5]. Animal Model: Male young adult Long-Evans rats injected with Nicotine[3] Dosage: 0.003, 0.01, 0.03, 0.1, 0.3 mg/kg Administration: A single s.c. 20 min before Nicotine (0.1 mg/kg) Result: Dose-dependently reduced pressing on both active and inactive levers.

[References]

[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.

[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.

[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.

[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.

[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.

Chemical & Physical Properties

[ Molecular Formula ]:
C19H20ClNO

[ Molecular Weight ]:
313.82100

[ Exact Mass ]:
313.12300

[ PSA ]:
23.47000

[ LogP ]:
3.91810

Related Compounds