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S179

Sigma-Aldrich

R(+)-SKF-81297 hydrobromide

≥98% (HPLC), solid

Synonym(s):

R-(+)-6-Chloro-7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrobromide

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About This Item

Empirical Formula (Hill Notation):
C16H16ClNO2 · HBr
CAS Number:
253446-15-0
Molecular Weight:
370.67
MDL number:
MFCD00671792
UNSPSC Code:
12352200
PubChem Substance ID:
24899496
NACRES:
NA.77

assay

≥98% (HPLC)

form

solid

optical activity

[α]22/D +15.14°, c = 0.52 in DMF(lit.)

storage condition

desiccated
protect from light

color

white to off-white

solubility

H2O: 6 mg/mL
DMSO: soluble

SMILES string

Br[H].Oc1cc2[C@H](CNCCc2c(Cl)c1O)c3ccccc3

InChI

1S/C16H16ClNO2.BrH/c17-15-11-6-7-18-9-13(10-4-2-1-3-5-10)12(11)8-14(19)16(15)20;/h1-5,8,13,18-20H,6-7,9H2;1H/t13-;/m1./s1

InChI key

RMIJGBMRNYUZRG-BTQNPOSSSA-N

Application

R(+)-SKF-81297 hydrobromide has used as D1-type dopamine receptor agonist:
  • to test it effect on the spike firing in rat retinal ganglion cells
  • in human embryonic kidney (HEK) 293T cells
  • to test its inhibitory effect in microglial cells

Biochem/physiol Actions

SKF-81297 administration in spontaneously hypertensive rats (SHR) induces an increase in expression of proto-oncogene c-fos mRNA leading to biphasic effect on locomotion. It favors the turnover of phosphoinositide and adenylyl cyclase. SKF-81297 is involved in the stimulation of neurons, in particular the postsynaptic striatal neurons.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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R J Vermeulen et al.
European journal of pharmacology, 235(1), 143-147 (1993-04-22)
The alleged selective, high efficacy dopamine D1 receptor agonist, SKF 81297 (0.05-0.3 mg/kg i.m.), induced rotational behaviour away from the lesion and stimulated use of the dominant right hand in unilaterally (left side) 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)-lesioned rhesus monkeys (Macaca mulatta). The
C. Reavill et al.
Behavioural pharmacology, 4(2), 135-146 (1993-04-01)
A range of selective dopamine D1 and D2 receptor agonists and antagonists was used to characterize to the discriminative stimuli produced by d-amphetamine (0.5mg/kg) and the D1 agonists SKF 81297 (0.1mg/kg). In rats trained to discriminate d-amphetamine (0.5mg/kg) from saline
Asim J Rashid et al.
Proceedings of the National Academy of Sciences of the United States of America, 104(2), 654-659 (2006-12-30)
We demonstrate a heteromeric D1-D2 dopamine receptor signaling complex in brain that is coupled to Gq/11 and requires agonist binding to both receptors for G protein activation and intracellular calcium release. The D1 agonist SKF83959 was identified as a specific
J Bergman et al.
The Journal of pharmacology and experimental therapeutics, 273(1), 40-48 (1995-04-01)
The effects of dopamine agonists differing in affinity and selectivity at D1 and D2 types of dopamine receptors were compared in squirrel monkeys responding under two different schedules of reinforcement: a fixed-interval (FI) schedule of stimulus-shock termination and a fixed-ratio
Mauricio Dos-Santos-Pereira et al.
Glia, 66(11), 2353-2365 (2018-11-06)
When activated, microglial cells have the potential not only to secrete typical proinflammatory mediators but also to release the neurotransmitter glutamate in amounts that may promote excitotoxicity. Here, we wished to determine the potential of the Parkinson's disease (PD) protein
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