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S2816

Sigma-Aldrich

SKF-83959 hydrobromide

≥98% (HPLC), solid

Synonym(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

Empirical Formula (Hill Notation):
C18H20NClO2 · HBr
CAS Number:
80751-85-5
Molecular Weight:
398.72
MDL number:
MFCD03792727
UNSPSC Code:
12352200
PubChem Substance ID:
24278699
NACRES:
NA.77

Assay

≥98% (HPLC)

form

solid

color

white

solubility

DMSO: >20 mg/mL
H2O: insoluble

SMILES string

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

InChI key

FHYWNBUFNGHNCP-UHFFFAOYSA-N

Gene Information

human ... DRD1(1812)

Application

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

Biochem/physiol Actions

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Emily M Jutkiewicz et al.
The Journal of pharmacology and experimental therapeutics, 311(3), 1008-1015 (2004-08-05)
Dopamine D1 ligands have been classified and ordered according to efficacy in both in vitro and in vivo studies. In the present experiments, dopamine D1 ligands reported to differ in in vitro efficacy were evaluated for efficacy-related effects on eye
Hong-Yuan Chu et al.
Brain research, 1343, 20-27 (2010-04-28)
Central dopaminergic system exerts profound modulation on spontaneous glutamate release in various brain regions mainly through D(1) receptor/cAMP/PKA pathway. It remains unclear whether the phosphatidylinositol (PI)-linked D(1)-like receptors are also involved in such modulatory actions. The identification of substituted phenylbenzazepine
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
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
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
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