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S178

Sigma-Aldrich

(R)-SKF-82957 hydrobromide

solid

Synonym(s):

(1R)-6-Chloro-2,3,4,5-tetrahydro-3-methyl-1-phenyl-1H-3-benzazepine-7,8-diol hydrobromide, 1H-3-Benzazepine-7,8-diol,6-chloro-2,3,4,5-tetrahydro-3-methyl-1-phenyl hydrobromide hydrobromide

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About This Item

Empirical Formula (Hill Notation):
C17H18ClNO2 · HBr
CAS Number:
288262-87-3
Molecular Weight:
384.70
UNSPSC Code:
12352200
PubChem Substance ID:
24899494
NACRES:
NA.77

form

solid

optical activity

[α]22/D +22.46°, c = 0.76 in DMF(lit.)

color

white

solubility

H2O: 7.5 mg/mL
DMSO: soluble

SMILES string

Br[H].CN1CCc2c(Cl)c(O)c(O)cc2[C@H](C1)c3ccccc3

InChI

1S/C17H18ClNO2.BrH/c1-19-8-7-12-13(9-15(20)17(21)16(12)18)14(10-19)11-5-3-2-4-6-11;/h2-6,9,14,20-21H,7-8,10H2,1H3;1H/t14-;/m1./s1

InChI key

BCZHWHQKKPEORG-PFEQFJNWSA-N

Biochem/physiol Actions

Selective D1 dopamine receptor agonist.

Caution

hygroscopic, photosensitive

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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F R Pfeiffer et al.
Journal of medicinal chemistry, 25(4), 352-358 (1982-04-01)
6-Chloro-7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines were synthesized and evaluated as agonists of central and peripheral dopamine receptors. These benzazepines were prepared by cyclization of certain amino alcohols followed by demethylation of the 7,8-dimethoxy groups of the precursors to the 7,8-catecholic moiety. Preliminary evidence of
P H Andersen et al.
European journal of pharmacology, 188(6), 335-347 (1990-06-12)
Dopamine receptor selectivity was investigated for a number of dopamine receptor agonists. In vitro, the benzazepine derivatives, e.g., SKF 38393 and SKF 75670 as well as the isoquinoline derivatives, SKF 89626 and SKF 89615, were D1 receptor-selective. All other compounds

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