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S2816

Sigma-Aldrich

SKF-83959 hydrobromide

≥98% (HPLC), solid

Synonyme(s) :

6-Chloro-7,8-dihydroxy-3-methyl-1-(3-methylphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine hydrobromide

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About This Item

Formule empirique (notation de Hill):
C18H20NClO2 · HBr
Numéro CAS:
80751-85-5
Poids moléculaire :
398.72
Numéro MDL:
MFCD03792727
Code UNSPSC :
12352200
ID de substance PubChem :
24278699
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Essai

≥98% (HPLC)

Forme

solid

Couleur

white

Solubilité

DMSO: >20 mg/mL
H2O: insoluble

Chaîne SMILES 

Br[H].CN1CCc2c(Cl)c(O)c(O)cc2C(C1)c3cccc(C)c3

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

Clé InChI

FHYWNBUFNGHNCP-UHFFFAOYSA-N

Informations sur le gène

human ... DRD1(1812)

Application

SKF-83959 was used in dopamine signaling studies on eye blinking in monkeys and on phosphorylation of CaMKIIα in mice.

Actions biochimiques/physiologiques

SKF-83959 is an atypical agonist of D1 dopamine receptor and an allosteric modulator of σ-1 receptor on in brain and liver tissues. It has neuroprotective and anti-parkinsonian effects through selective activation of phosphoinositol-linked D1 receptor and promotes migration of cultures astrocytes by ERK1/2 activation. In in vitro studies SKF-83959 exhibits antagonist activity against dopamine D1 receptors coupled to adenylyl cyclase.
D1 dopamine receptor agonist. Displays antagonist activity in vitro and agonist activity in vivo.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Certificats d'analyse (COA)

Lot/Batch Number
047M4747V
109K4704V
109K47041
109K4704
032K47062

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Consulter la Bibliothèque de documents

Katsunori Tomiyama et al.
Synapse (New York, N.Y.), 64(9), 714-720 (2010-03-27)
Orofacial movements are regulated by D(1)-like dopamine receptors interacting with additional mechanisms. Phospholipase C-related catalytically inactive protein (PRIP) regulates cell surface expression of GABA(A) receptors containing a gamma2 subunit. Mutant mice with double knockout of PRIP-1 and PRIP-2 were used
Jue Liu et al.
Neuropharmacology, 57(2), 164-171 (2009-05-26)
Recent work has demonstrated that a phosphatidylinositol (PI)-linked D(1) dopamine receptor selective agonist, SKF83959, mediates phosphatidylinositol hydrolysis via activation of phospholipase C(beta) in brain. Specific contributions of SKF83959 to synaptic plasticity have not been well elucidated. The aim of the
Hong-Yuan Chu et al.
PloS one, 5(10), doi:10-doi:10 (2010-10-20)
Although the potent anti-parkinsonian action of the atypical D₁-like receptor agonist SKF83959 has been attributed to the selective activation of phosphoinositol(PI)-linked D₁ receptor, whereas the mechanism underlying its potent neuroprotective effect is not fully understood. In the present study, the
Ling Zhang et al.
Neurochemistry international, 58(3), 281-294 (2010-12-08)
Accumulating pathological evidence showing layer-specific neuronal reduction, dendrite deficits and brain volume loss have implicated an apoptotic process in schizophrenia, but the exact mechanism remains elusive. Dopamine hyperactivity at D2 receptor sites was considered as an important mechanism in schizophrenia
Hong-Yuan Chu et al.
Journal of neuroscience research, 89(8), 1259-1266 (2011-05-04)
Dopamine (DA) profoundly modulates excitatory synaptic transmission and synaptic plasticity in the brain. In the present study the effects of SKF83959, the selective agonist of phosphatidylinositol (PI)-linked D(1) -like receptor, on the excitatory synaptic transmission were investigated in rat hippocampus.
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