SKF-83822

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H22ClNO2
Molecular Weight	343.847
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC=CC(=C1)C2CN(CC=C)CCC3=C2C=C(O)C(O)=C3Cl

InChI

InChIKey=HLNOXCRCYMOMLA-UHFFFAOYSA-N

InChI=1S/C20H22ClNO2/c1-3-8-22-9-7-15-16(11-18(23)20(24)19(15)21)17(12-22)14-6-4-5-13(2)10-14/h3-6,10-11,17,23-24H,1,7-9,12H2,2H3

HIDE SMILES / InChI

Molecular Formula	C20H22ClNO2
Molecular Weight	343.847
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11600103
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/7908949 | https://www.ncbi.nlm.nih.gov/pubmed/11600103

SKF-83822 is a D1/D5 receptor agonist, which activates D1-like receptors coupled to stimulation of adenyl cyclase (AC), but not phosphoinositide (PI) hydrolysis. SKF-83822 is used as a tool compound to study the role of AC-coupled D1 receptors.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
D(1A) dopamine receptor 18 Target ID: P21728 Gene ID: 1812.0 Gene Symbol: DRD1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/7908949	Agonist 2678	1.7 nM [Ki]
D(2) dopamine receptor 58 Target ID: P14416 Gene ID: 1813.0 Gene Symbol: DRD2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/1973652	Binding Agent 1064	71.0 nM [Ki]
D(1B) dopamine receptor 6 Target ID: P21918 Gene ID: 1816.0 Gene Symbol: DRD5 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/24552847	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Dopamine receptor agonists: selectivity and dopamine D1 receptor efficacy.	1990 Jun 12	1973652
Aberrant behavioral effects of a dopamine D1 receptor antagonist and agonist in monkeys: evidence of uncharted dopamine D1 receptor actions.	2001 Oct 1	11600103

Patents

Sample Use Guides

In Vivo Use Guide

In preclinical experiments on monkeys, SKF-83822 was administered intravenously at 0.08 mg/kg.

Route of Administration: Intravenous

In Vitro Use Guide

Male rats weighing 225-300 g were decapitated, and the striata were dissected on ice, then gently the tissues were gently homogenized at 0°C in 50 mM Tris-maleate buffer (pH 7.4) containing 2 M EGTA. Aliquots of the homogenate were incubated in medium containing Tris-maleate buffer and SKF-83822. Reaction was started by adding [14C]ATP and shaking at 30°C. After 3 min the reaction was terminated in a boiling water bath, the [14C]cyclic AMP formed was separated from unreacted [14C]ATP using alumina and cation exchange resin columns, and the [14C]cyclic AMP content was measured by liquid scintillation counting.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:03:54 GMT 2023` Edited by `admin` on `Sat Dec 16 08:03:54 GMT 2023`
Record UNII	661JNG0144
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

SKF-83822

Common Name

English

1H-3-BENZAZEPINE-7,8-DIOL, 6-CHLORO-2,3,4,5-TETRAHYDRO-1-(3-METHYLPHENYL)-3-(2-PROPEN-1-YL)-

Systematic Name

English

J2.054.792H

Code

English

SKF 83822

Common Name

English

6-CHLORO-2,3,4,5-TETRAHYDRO-1-(3-METHYLPHENYL)-3-(2-PROPENYL)-1H-3-BENZAZEPINE-7,8-DIOL

Systematic Name

English

1H-3-BENZAZEPINE-7,8-DIOL, 6-CHLORO-2,3,4,5-TETRAHYDRO-1-(3-METHYLPHENYL)-3-(2-PROPENYL)-

Systematic Name

English

Code System Code Type Description

PUBCHEM

10020353