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SKF-83,959

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Chemical compound

Pharmaceutical compound

SKF-83,959
Identifiers

IUPAC name 6-chloro-7,8-dihydroxy-3-methyl-1-(3-methylphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine
CAS Number	67287-95-0^Y
PubChemCID	11957685
ChemSpider	10131933^Y
UNII	8CJ9F3C4Q0
ChEBI	CHEBI:63996
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
(verify)

SKF-83,959, asynthetic benzazepine derivative used inscientific research, acts as anagonist at theD₁–D₂ dopamine receptor heteromer.^[1] It behaves as afull agonist at the D₁protomer and a high-affinity partial agonist at the D₂ protomer. It was further shown to act as anallosteric modulator of thesigma-1 receptor.^[2] SKF-83,959 additionally inhibitssodium channels^[3] as well as delayed rectifierpotassium channels.^[4] SKF-83,959 is aracemate that consists of theR-(+)- andS-(−)-enantiomers MCL-202 and MCL-201, respectively.

SKF-83,959 was described as aSNDRI.^[5] The synthesis has been described.^[6]

See also

Substituted 3-benzazepine

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.
^Fang, X., Guo, L., Jia, J., Jin, G., Zhao, B., Zheng, Y., Li, J., Zhang, A., Zhen, X. (September 2013)."SKF83959 is a novel triple reuptake inhibitor that elicits anti-depressant activity".Acta Pharmacologica Sinica.34 (9):1149–1155.doi:10.1038/aps.2013.66.ISSN 1671-4083.PMC 4003162.PMID 23892272.
^Pfeiffer, F. R., Wilson, J. W., Weinstock, J., Kuo, G. Y., Chambers, P. A., Holden, K. G., Hahn, R. A., Wardell, J. R., Alfonso, J. T. (April 1982). "Dopaminergic activity of substituted 6-chloro-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines".Journal of Medicinal Chemistry.25 (4):352–358.doi:10.1021/jm00346a005.PMID 7069713.

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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Dopamine receptor modulators

Agonists	Benzazepines:6-Br-APB Fenoldopam SKF-38,393 SKF-77,434 SKF-81,297 SKF-82,958 SKF-83,959 Trepipam Zelandopam Ergolines:Cabergoline CY-208,243 Dihydroergocryptine LEK-8829 Lisuride Pergolide Terguride Dihydrexidine derivatives:A-77636 A-86929 Adrogolide (ABT-431, DAS-431) Dihydrexidine Dinapsoline Dinoxyline Doxanthrine Phenethylamines:BCO-001 Deoxyepinephrine (N-methyldopamine, epinine) Dopexamine Etilevodopa Ibopamine L-DOPA (levodopa) Melevodopa L-Phenylalanine L-Tyrosine XP21279 Others:A-68930 Apomorphine Isocorypalmine Nuciferine PF-6649751 PF 6669571 Propylnorapomorphine Rotigotine SKF-89,145 SKF-89,626 Stepholidine Tavapadon Tetrahydropalmatine
PAMs	Tetrahydroisoquinolines:DETQ DPTQ Mevidalen
Antagonists	Typical antipsychotics:Butaclamol Chlorpromazine Chlorprothixene Flupentixol (flupenthixol) (+melitracen) Fluphenazine Loxapine Perphenazine (+amitriptyline) Pifluthixol Thioridazine Thiothixene Trifluoperazine (+tranylcypromine) Zuclopenthixol Atypical antipsychotics:Asenapine Clorotepine Clotiapine Clozapine DHA-clozapine Fluperlapine Iloperidone Norclozapine Norquetiapine Olanzapine (+fluoxetine) Paliperidone Quetiapine Risperidone Tefludazine Zicronapine Ziprasidone Zotepine Others:Berupipam Ecopipam EEDQ Metitepine (methiothepin) Odapipam Perlapine SCH-23390

Agonists

Phenethylamines:Deoxyepinephrine (N-methyldopamine, epinine)
Dopexamine
Etilevodopa
Ibopamine
L-DOPA (levodopa)
L-Phenylalanine
L-Tyrosine
Melevodopa
XP21279

Atypical antipsychotics:Alentemol (U-66444B)
Aripiprazole (+sertraline)
Aripiprazole lauroxil
Bifeprunox
Brexpiprazole
Brilaroxazine
Cariprazine
F-15063
Lumateperone
Norclozapine

Antagonists

Antiemetics/gastroprokinetics/sedatives:Aceprometazine
AS-8112
Alimemazine
Alizapride
Benzquinamide
Bromopride
Clebopride
Deudomperidone
Domperidone
Eticlopride
Hydroxyzine
Itopride
Metoclopramide
Metopimazine
Promethazine
Thiethylperazine
Trazpiroben
Trimethobenzamide

See also:Receptor/signaling modulators
Adrenergics
Serotonergics
Monoamine reuptake inhibitors
Monoamine releasing agents
Monoamine metabolism modulators
Monoamine neurotoxins

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Ion channel modulators

VDCCsTooltip Voltage-dependent calcium channels

R-type-selective:SNX-482

L-type-selective:Bay K8644

VGKCsTooltip Voltage-gated potassium channels

KCNQ (K_v7)-specific:Flupirtine
Retigabine

IRKsTooltip Inwardly rectifying potassium channel

K_ATPTooltip ATP-sensitive potassium channel-specific:Acetohexamide
Carbutamide
Chlorpropamide
Glibenclamide (glyburide)
Glibornuride
Glicaramide
Gliclazide
Glimepiride
Glipizide
Gliquidone
Glisoxepide
Glyclopyramide
Glycyclamide
Metahexamide
Mitiglinide
Nateglinide
Repaglinide
Tolazamide
Tolbutamide

GIRKTooltip G protein-coupled inwardly rectifying potassium channel-specific:Barium
Caramiphen
Cloperastine
Clozapine
Dextromethorphan
Ethosuximide
Ifenprodil
Tertiapin
Tipepidine

K_ATPTooltip ATP-sensitive potassium channel-specific:Aprikalim
Bimakalim
Cromakalim
Diazoxide
Emakalim
Levcromakalim
Mazokalim
Minoxidil
Minoxidil sulfate
Naminidil
Nicorandil
Pinacidil
Rilmakalim
Sarakalim

GIRKTooltip G protein-coupled inwardly rectifying potassium channel-specific:ML-297 (VU0456810)

K_CaTooltip Calcium-activated potassium channel

Blockers	BK_Ca-specific:Ethanol (alcohol) GAL-021
Activators	BK_Ca-specific:Flufenamic acid Meclofenamic acid Niflumic acid Nimesulide Rottlerin (mallotoxin) Tolfenamic acid

K2PsTooltip Tandem pore domain potassium channel

Blockers	12-O-Tetradecanoylphorbol-13-acetate Arachidonic acid Fluoxetine Norfluoxetine
Activators	Riluzole

VGSCsTooltip Voltage-gated sodium channels

Antianginals:Ranolazine

Aconitine
Atracotoxins (ω-Atracotoxin,Robustoxin,Versutoxin)
Batrachotoxin
Ciguatoxins
Grayanotoxins
Poneratoxin

ENaCTooltip Epithelial sodium channel

Blockers	Amiloride Benzamil Triamterene
Activators	Solnatide

ASICsTooltip Acid-sensing ion channel

Blockers	A-317567 Amiloride Aspirin Ibuprofen PcTX1

CaCCsTooltip Calcium-activated chloride channel

Blockers	Crofelemer DIDS Ethacrynic acid Flufenamic acid Fluoxetine Furosemide Glibenclamide Mefloquine Mibefradil Niflumic acid
Activators	Carbachol

CFTRTooltip Cystic fibrosis transmembrane conductance regulator

Blockers	Glibenclamide Lonidamine Piretanide
Activators	1,7-Phenanthroline 1,10-Phenanthroline 4,7-Phenanthroline 7,8-Benzoquinoline Ivacaftor Phenanthridine

Unsorted

Blockers	Bumetanide Flufenamic acid Meclofenamic acid Mefenamic acid Mepacrine Niflumic acid Talniflumate Tolfenamic acid Trifluoperazine

Others

TRPsTooltip Transient receptor potential channels	Seehere instead.
LGICsTooltip Ligand gated ion channels	Seehere instead.

See also:Receptor/signaling modulators •Transient receptor potential channel modulators

v t e Sigma receptor modulators
σ₁	Agonists:3-PPP 4-PPBP 5-MeO-DMT Alazocine (SKF-10047) Amantadine Arketamine BD-737 BD-1052 Blarcamesine Captodiame Citalopram CGRPTooltip Calcitonin gene-related peptide 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) IPAB Ketamine L-687384 MDMA (midomafetamine) Memantine Methamphetamine Methoxetamine Methylphenidate Nepinalone Neuropeptide Y Noscapine OPC-14523 Opipramol Pentazocine Pentoxyverine (carbetapentane) PRE-084 Pregnenolone Pregnenolone sulfate Pridopidine Racemethorphan (methorphan) Racemorphan (morphanol) UMB-23 UMB-82 Antagonists:3-PPP AC-927 BD-1008 BD-1031 BD-1047 BD-1060 BD-1063 BD-1067 BMY-14802 (BMS-181100) CM-156 Dup-734 E-5842 E-52862 (S1RA) Haloperidol LR-132 LR-172 MS-377 NE-100 NPC-16377 Panamesine (EMD-57455) PD-144418 Pentazocine Progesterone Rimcazole (BW-234U) Sertraline SR-31742A Allosteric modulators:Phenytoin;Positive:Methylphenylpiracetam SOMCL-668 Unknown/unsorted:3-Methoxydextrallorphan 3-MeO-PCP 4C-T-2 4-IBP 4-IPBS 4-MeO-PCP 5-MeO-DALT 5-MeO-DiPT Amitriptyline Azidopamil Chlorpromazine Clemastine Clomipramine Clorgiline D-Deprenyl DiPTTooltip N,N-Diisopropyltryptamine DPTTooltip N,N-Dipropyltryptamine Ibogaine Imipramine KCR-12-83.1 Nemonapride Noribogaine RHL-033 RS-67,333 RTI-55 Saffron Safinamide Selegiline Spipethiane Trifluoperazine W-18 YKP10A
σ₂	Agonists:3-PPP Arketamine BD-1047 BD1063 Ditolylguanidine (DTG) DKR-1005 DKR-1051 Haloperidol Ifenprodil Ketamine MDMA (midomafetamine) Methamphetamine OPC-14523 Opipramol PB-28 Phencyclidine Siramesine (Lu 28-179) UKH-1114 Antagonists:AC-927 BD-1008 BD-1067 CM-156 LR-172 MIN-101 Panamesine (EMD-57455) SAS-0132 Zervimesine (CT-1812) Unknown/unsorted:3-Methoxydextrallorphan 3-MeO-PCE 4-MeO-PCP 5-MeO-DALT 5-MeO-DiPT Clemastine DiPTTooltip N,N-Diisopropyltryptamine DPTTooltip N,N-Dipropyltryptamine Ibogaine Lu 29-252 Nemonapride Nepinalone Noribogaine Pentazocine RS-67,333 Safinamide TMATooltip 3,4,5-Trimethoxyamphetamine UMB-23 UMB-82 W-18
Unsorted	Agonists:Berberine Ethylketazocine Fourphit Metaphit Naluzotan Tapentadol Tenocyclidine Antagonists:AHD1 AZ66 Lamotrigine Naloxone SM-21 UMB-100 UMB-101 UMB-103 UMB-116 YZ-011 YZ-069 YZ-185 Allosteric modulators:SKF-83959 Unknown/unsorted:18-Methoxycoronaridine BMY-13980 Butaclamol Caramiphen Carvotroline Chlorphenamine (chlorpheniramine) Chlorpromazine Cinnarizine Cinuperone Clocapramine Dezocine EMD-59983 Hypericin (St. John's wort) Fluphenazine Gevotroline (WY-47384) Mepyramine (pyrilamine) Molindone Perphenazine Pimozide Proadifen Promethazine Propranolol Quinidine Remoxipride SL 82.0715 SR-31747A Tiospirone (BMY-13859) Venlafaxine
See also:Receptor/signaling modulators

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