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 ;
ChEMBL	ChEMBL520992 ;
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 ; Key:FHYWNBUFNGHNCP-UHFFFAOYSA-N ;

SKF-83,959 is a synthetic benzazepine derivative used in scientific research which acts as an agonist at the D₁–D₂ dopamine receptor heteromer.^[1] It behaves as a full agonist at the D₁ protomer 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.^[2] SKF-83,959 additionally inhibits sodium channels^[3] as well as delayed rectifier potassium channels.^[4] SKF-83,959 is a racemate that consists of the R-(+)- and S-(−)-enantiomers MCL-202 and MCL-201, respectively.

References[]

^ Rashid AJ, So CH, Kong MM, et al. (2007). "D1-D2 dopamine receptor heterooligomers with unique pharmacology are coupled to rapid activation of Gq/11 in the striatum". Proc. Natl. Acad. Sci. U.S.A. 104 (2): 654–9. Bibcode:2007PNAS..104..654R. doi:10.1073/pnas.0604049104. PMC 1766439. PMID 17194762.
^ Guo L, Zhao J, Jin G, et al. (2013). "SKF83959 is a potent allosteric modulator of sigma-1 receptor". Mol. Pharmacol. 83 (3): 577–86. doi:10.1124/mol.112.083840. PMID 23295385. S2CID 5848058.
^ Chu HY, Wu Q, Zhou S, et al. (2011). "SKF83959 suppresses excitatory synaptic transmission in rat hippocampus via a dopamine receptor-independent mechanism". J. Neurosci. Res. 89 (8): 1259–66. doi:10.1002/jnr.22653. PMID 21538463. S2CID 43869359.
^ Chen XQ, Zhang J, Neumeyer JL, et al. (2009). "Arylbenzazepines are potent modulators for the delayed rectifier K+ channel: a potential mechanism for their neuroprotective effects". PLOS ONE. 4 (6): e5811. Bibcode:2009PLoSO...4.5811C. doi:10.1371/journal.pone.0005811. PMC 2690691. PMID 19503734.

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.

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[1] Rashid AJ, So CH, Kong MM, et al. (2007). "D1-D2 dopamine receptor heterooligomers with unique pharmacology are coupled to rapid activation of Gq/11 in the striatum". Proc. Natl. Acad. Sci. U.S.A. 104 (2): 654–9. Bibcode:2007PNAS..104..654R. doi:10.1073/pnas.0604049104. PMC 1766439. PMID 17194762.

[2] Guo L, Zhao J, Jin G, et al. (2013). "SKF83959 is a potent allosteric modulator of sigma-1 receptor". Mol. Pharmacol. 83 (3): 577–86. doi:10.1124/mol.112.083840. PMID 23295385. S2CID 5848058.

[3] Chu HY, Wu Q, Zhou S, et al. (2011). "SKF83959 suppresses excitatory synaptic transmission in rat hippocampus via a dopamine receptor-independent mechanism". J. Neurosci. Res. 89 (8): 1259–66. doi:10.1002/jnr.22653. PMID 21538463. S2CID 43869359.

[4] Chen XQ, Zhang J, Neumeyer JL, et al. (2009). "Arylbenzazepines are potent modulators for the delayed rectifier K+ channel: a potential mechanism for their neuroprotective effects". PLOS ONE. 4 (6): e5811. Bibcode:2009PLoSO...4.5811C. doi:10.1371/journal.pone.0005811. PMC 2690691. PMID 19503734.

[1]

[2]

[3]

[4]

v t Sigma receptor modulators
σ₁	Agonists: 3-PPP 4-PPBP 5-MeO-DMT Alazocine (SKF-10047) Amantadine Arketamine BD-1052 Blarcamesine Captodiame Citalopram CGRP Cloperastine Cocaine Cutamesine (SA-4503) Cyclazocine Dehydroepiandrosterone (DHEA) (prasterone) Dehydroepiandrosterone sulfate (DHEA-S) (prasterone sulfate) Dextrallorphan Dextromethorphan (DXM) Dextrorphan (DXO) Dimemorfan Dimethyltryptamine (DMT) Ditolylguanidine (DTG) Donepezil Eliprodil Escitalopram Fabomotizole (afobazole) Fluoxetine Fluvoxamine Ifenprodil Igmesine (JO-1784) Ketamine L-687384 MDMA (midomafetamine) Memantine Methamphetamine Methoxetamine Methylphenidate Nepinalone Neuropeptide Y Noscapine Opipramol Pentazocine Pentoxyverine (carbetapentane) PRE-084 Pregnenolone Pregnenolone sulfate Pridopidine Racemethorphan (methorphan) Racemorphan (morphanol) Antagonists: 3-PPP AC-927 BD-1008 BD-1031 BD-1047 BD-1060 BD-1063 BD-1067 BMY-14802 (BMS-181100) CM-156 E-52862 (S1RA) Haloperidol NE-100 Panamesine (EMD-57455) Pentazocine Progesterone Rimcazole (BW-234U) Sertraline Allosteric modulators: Phenytoin; Positive: Methylphenylpiracetam Unknown/unsorted: 3-MeO-PCP 4C-T-2 4-MeO-PCP 5-MeO-DALT 5-MeO-DiPT Amitriptyline Chlorpromazine Clemastine Clomipramine Clorgiline D-Deprenyl DiPT DPT Ibogaine Imipramine Nemonapride Noribogaine RS-67,333 RTI-55 Saffron Safinamide Selegiline Trifluoperazine W-18 YKP10A
σ₂	Agonists: 3-PPP Arketamine BD-1047 BD1063 Ditolylguanidine (DTG) Haloperidol Ifenprodil Ketamine MDMA (midomafetamine) Methamphetamine Opipramol PB-28 Phencyclidine Siramesine (Lu 28-179) Antagonists: AC-927 BD-1008 BD-1067 CM-156 MIN-101 Panamesine (EMD-57455) Unknown/unsorted: 3-MeO-PCE 4-MeO-PCP 5-MeO-DALT 5-MeO-DiPT Clemastine DiPT DPT Ibogaine Nemonapride Nepinalone Noribogaine Pentazocine RS-67,333 Safinamide TMA W-18
Unsorted	Agonists: Berberine Ethylketazocine Fourphit Metaphit Naluzotan Tapentadol Tenocyclidine Antagonists: Lamotrigine Naloxone Allosteric modulators: SKF-83959 Unknown/unsorted: 18-Methoxycoronaridine Butaclamol Caramiphen Chlorphenamine (chlorpheniramine) Chlorpromazine Cinnarizine Clocapramine Dezocine Hypericin (St. John's wort) Fluphenazine Gevotroline (WY-47384) Mepyramine (pyrilamine) Molindone Perphenazine Pimozide Proadifen Promethazine Propranolol Quinidine Remoxipride Tiospirone (BMY-13859) Venlafaxine
See also: Receptor/signaling modulators

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
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