S179

R(+)-SKF-81297 hydrobromide

Name: R(+)-SKF-81297 hydrobromide
Brand: SIGMA
Price: 16959 MXP

≥98% (HPLC), Dopamine receptor agonist, solid

Synonym(s):

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

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5 MG

MXP 16,959.00

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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

Key Documents

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Product Name

R(+)-SKF-81297 hydrobromide, ≥98% (HPLC), solid

Quality Level

100

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

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Show Differences

1 of 4

This Item	S178	S2816	S143
Sigma-Aldrich S179 R(+)-SKF-81297 hydrobromide	Sigma-Aldrich S178 (R)-SKF-82957 hydrobromide	Sigma-Aldrich S2816 SKF-83959 hydrobromide	Sigma-Aldrich S143 (±)-6-Chloro-PB hydrobromide
form solid	form solid	form solid	form solid
assay ≥98% (HPLC)	assay -	assay ≥98% (HPLC)	assay ≥98% (HPLC)
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 100
storage condition desiccated, protect from light	storage condition -	storage condition -	storage condition desiccated
solubility H₂O: 6 mg/mL, DMSO: soluble	solubility H₂O: 7.5 mg/mL, DMSO: soluble	solubility DMSO: >20 mg/mL, H₂O: insoluble	solubility H₂O: 1.7 mg/mL, DMSO: >10 mg/mL, ethanol: 6.3 mg/mL
color white to off-white	color white	color white	color white to light tan

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[1]
in human embryonic kidney (HEK) 293T cells[2]
to test its inhibitory effect in microglial cells[3]

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.[4] It favors the turnover of phosphoinositide and adenylyl cyclase.[5] SKF-81297 is involved in the stimulation of neurons, in particular the postsynaptic striatal neurons.[6]

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

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Certificates of Analysis (COA)

Lot/Batch Number

0000408388

0000192454

060M4635V

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The selective dopamine D1 receptor agonist, SKF 81297, stimulates motor behaviour of MPTP-lesioned monkeys.

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

Pharmacological characterization of the discriminative stimulus properties of the dopamine D1 agonist, SKF 81297.

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

Dopamine Gates Visual Signals in Monkey Prefrontal Cortex Neurons.

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

Differential effects of a selective dopamine D1-like receptor agonist on motor activity and c-fos expression in the frontal-striatal circuitry of SHR and Wistar-Kyoto rats.

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

D1-D2 dopamine receptor heterooligomers with unique pharmacology are coupled to rapid activation of Gq/11 in the striatum.

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

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R(+)-SKF-81297 hydrobromide