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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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Guang-Yu Li et al.
Molecular vision, 18, 2882-2895 (2012-12-13)
Oxidative stress is widely implicated in the death of retinal ganglion cells associated with various optic neuropathies. Agonists of the dopamine D(1) receptor have recently been found to be potentially neuroprotective against oxidative stress-induced injury. The goal of this study
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.
Chao Huang et al.
PloS one, 7(11), e49954-e49954 (2012-11-28)
Extracellular signal-regulated kinase 1/2 (ERK1/2) is a member of the mitogen-activated protein kinase family. It can mediate cell migration. Classical dopamine receptor-mediated ERK1/2 phosphorylation is widely studied in neurons. Here, we report that ERK1/2 phosphorylation is also modulated by putative
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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