SKF-83,959

SKF-83,959

Identifiers
IUPAC name 6-chloro-7,8-dihydroxy-3-methyl-1-(3-methylphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine
PubChem CID	24278699
ChemSpider	10131933 Y
UNII	8CJ9F3C4Q0
ChEMBL	ChEMBL520992 Y
Chemical and physical data
Formula	C18H20ClNO2
Molar mass	317.81 g·mol−1
3D model (JSmol)	Interactive image
SMILES Br.Clc1c3c(cc(O)c1O)C(c2cccc(c2)C)CN(CC3)C
InChI InChI=1S/C18H20ClNO2.BrH/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;1H Y Key:FHYWNBUFNGHNCP-UHFFFAOYSA-N Y
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SKF-83,959 is a synthetic benzazepine derivative used in scientific research which acts as an agonist at the D₁–D₂ dopamine receptor heteromer. It behaves as a full agonist at the D₁protomer and a high-affinity partial agonist at the D₂ protomer. It was further shown to act as an allosteric modulator of the sigma-1 receptor. SKF-83,959 additionally inhibits sodium channels as well as delayed rectifier potassium channels. SKF-83,959 is a racemate that consists of the R-(+)- and S-(−)-enantiomers MCL-202 and MCL-201, respectively.

SKF-83,959 was described as a SNDRI. The synthesis has been described:

Further reading

• Lee SM, Yang Y, Mailman RB (2014). "Dopamine D1 receptor signaling: Does GαQ-phospholipase C actually play a role?". J. Pharmacol. Exp. Ther. 351 (1): 9–17. doi:10.1124/jpet.114.214411. PMC 4165024. PMID 25052835.
• Lee SM, Kant A, Blake D, et al. (2014). "SKF-83959 is not a highly-biased functionally selective D1 dopamine receptor ligand with activity at phospholipase C". Neuropharmacology. 86: 145–54. doi:10.1016/j.neuropharm.2014.05.042. PMC 4188748. PMID 24929112.