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S179

Sigma-Aldrich

R(+)-SKF-81297 hydrobromide

≥98% (HPLC), solid

Synonyme(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

Formule empirique (notation de Hill):
C16H16ClNO2 · HBr
Numéro CAS:
253446-15-0
Poids moléculaire :
370.67
Numéro MDL:
MFCD00671792
Code UNSPSC :
12352200
ID de substance PubChem :
24899496
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

solid

Activité optique

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

Conditions de stockage

desiccated
protect from light

Couleur

white to off-white

Solubilité

H2O: 6 mg/mL
DMSO: soluble

Chaîne SMILES 

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

Clé InChI

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

Actions biochimiques/physiologiques

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.

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)

Certificats d'analyse (COA)

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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
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
Rochellys Diaz Heijtz et al.
Behavioral and brain functions : BBF, 2, 18-18 (2006-05-30)
Molecular genetic studies suggest the dopamine D1 receptor (D1R) may be implicated in attention-deficit/hyperactivity disorder (ADHD). As little is known about the potential motor role of D1R in ADHD, animal models may provide important insights into this issue. We investigated
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
Maximilian Stalter et al.
Cell reports, 30(1), 164-172 (2020-01-09)
The neurotransmitter dopamine, which acts via the D1-like receptor (D1R) and D2-like receptor (D2R) family, may play an important role in gating sensory information to the prefrontal cortex (PFC). We tested this hypothesis in awake macaques and recorded visual motion-direction
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