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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H20ClNO2
Molecular Weight 317.81
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SKF-83959, (R)-

SMILES

CN1CCC2=C(C=C(O)C(O)=C2Cl)[C@H](C1)C3=CC(C)=CC=C3

InChI

InChIKey=JXMYTVOBSFOHAF-OAHLLOKOSA-N
InChI=1S/C18H20ClNO2/c1-11-4-3-5-12(8-11)15-10-20(2)7-6-13-14(15)9-16(21)18(22)17(13)19/h3-5,8-9,15,21-22H,6-7,10H2,1-2H3/t15-/m1/s1

HIDE SMILES / InChI

Molecular Formula C18H20ClNO2
Molecular Weight 317.81
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/17207791

(R)-SKF-83959 (MCL 202) is enantiomer of D1 receptor agonist SKF-83959. (R)-SKF-83959 is reported to be a functionally selective dopamine D1 and D5 receptors ligand with much lower affinity to dopamine D2 and D3 receptors. (R)-SKF-83959 like SKF-83959, produced dose related effects on overt behavior (eye blinking) and schedule-controlled performance in squirrel monkeys. (R)-SKF-83959 increases in eye blinking and decreases in rates of fixed-ratio responding. In contrast to the effects of its S-(-) enantiomer, was relatively devoid of behavioral activity up to doses that were approximately 10-fold greater than (R)-SKF-83959. Pretreatment with the selective D1- like receptor antagonist SCH 39166 dose-dependently antagonized increases in eye blinking produced by (R)-SKF-83959, confirming the involvement of D1 mechanisms in its effects.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.49 nM [Ki]
515.0 nM [Ki]
1.53 nM [Ki]
88.6 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed

Sample Use Guides

Rats were treated with (R)-SKF-83959 (0.0003–1.0 mg/kg) as single i.m. injection
Route of Administration: Intramuscular
(R)-SKF-83959 was assayed for affinity at dopamine receptors in rat caudate – putamen tissue from adult male Sprague–Dawley rats. Fresh, rapidly dissected brain tissue was hand-homogenized in 50 mM Tris–HCl buffer pH 7.4, dopamine D1 receptor assays, tissue was incubated with (R)-SKF-83959 or [3H]SCH-23390 (0.30 nM) for 30 min at 30C, using excess cis-flupenthixol (10 mkM) as a blank
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:40:57 GMT 2023
Edited
by admin
on Sat Dec 16 10:40:57 GMT 2023
Record UNII
39YLC3L0ZU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SKF-83959, (R)-
Common Name English
R-(+)-SKF-83959
Common Name English
1H-3-BENZAZEPINE-7,8-DIOL, 6-CHLORO-2,3,4,5-TETRAHYDRO-3-METHYL-1-(3-METHYLPHENYL)-, (1R)-
Systematic Name English
MCL-202
Code English
Code System Code Type Description
FDA UNII
39YLC3L0ZU
Created by admin on Sat Dec 16 10:40:57 GMT 2023 , Edited by admin on Sat Dec 16 10:40:57 GMT 2023
PRIMARY
CAS
652994-63-3
Created by admin on Sat Dec 16 10:40:57 GMT 2023 , Edited by admin on Sat Dec 16 10:40:57 GMT 2023
PRIMARY
PUBCHEM
9995976
Created by admin on Sat Dec 16 10:40:57 GMT 2023 , Edited by admin on Sat Dec 16 10:40:57 GMT 2023
PRIMARY
Related Record Type Details
RACEMATE -> ENANTIOMER