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S101

Sigma-Aldrich

(R)-(+)-SKF-38393 hydrochloride

≥98% (HPLC), solid

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About This Item

Empirical Formula (Hill Notation):
C16H17NO2 · HCl
CAS Number:
81702-42-3
Molecular Weight:
291.77
MDL number:
MFCD00055189
UNSPSC Code:
12352200
PubChem Substance ID:
329824192
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

solid

optical activity

[α]22/D +16.1°, c = 1.2 in methanol(lit.)

storage condition

desiccated

color

off-white to light tan

solubility

0.1 M HCl: 1.2 mg/mL
ethanol: 3.4 mg/mL
H2O: 5 mg/mL
aqueous base: unstable

SMILES string

Cl.Oc1cc2CCNC[C@H](c3ccccc3)c2cc1O

InChI

1S/C16H17NO2.ClH/c18-15-8-12-6-7-17-10-14(13(12)9-16(15)19)11-4-2-1-3-5-11;/h1-5,8-9,14,17-19H,6-7,10H2;1H/t14-;/m1./s1

InChI key

YEWHJCLOUYPAOH-PFEQFJNWSA-N

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Application

(R)-(+)-SKF-38393 hydrochloride has been used as a D1 dopamine receptor agonist to study its effect on the sleep-wake pattern of macaques rendered parkinsonian with 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP).

Biochem/physiol Actions

(R)-(+)-SKF-38393 hydrochloride is a D1 dopamine receptor agonist and an active enantiomer of (±)-SKF-38393. It enhances pertussis toxin-insensitive and protein kinase A-mediated glutamate release in the hippocampal neurons. SKF-38393, a benzazepine derivative, exhibits anorectic effects.

Features and Benefits

This compound is featured on the Dopamine Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Caution

Light sensitive

Reconstitution

Solutions may be stored for several days at 4 °C.

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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Carole Hyacinthe et al.
Neurobiology of disease, 63, 20-24 (2013-11-12)
Both excessive daytime sleepiness (EDS) and rapid eye movement (REM) sleep deregulation are part of Parkinson's disease (PD) non-motor symptoms and may complicate dopamine replacement therapy. We report here that dopamine agonists act differentially on sleep architecture in the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine
M R Zarrindast et al.
Pharmacology, 87(1-2), 85-89 (2011-01-19)
Both the dopamine receptor D(1) agonist SKF 38393 and the antagonist SCH 23390 are benzazepine derivatives that have been widely used as pharmacological tools and radioligands. Evidence suggests that behavioral effects of both compounds do not always correspond to their
A Bouron et al.
Neuroscience, 94(4), 1063-1070 (2000-01-07)
The present study was undertaken to better assess the role of dopamine on exocytosis. Since direct activation of adenylate cyclase (e.g., with forskolin) enhances neurotransmitter release it was of interest to see whether the activation of D1-type dopamine receptors, which
E Ongini et al.
Life sciences, 37(24), 2327-2333 (1985-12-16)
The dopamine D-1 receptor agonist SKF 38393 dose-dependently (2.5-10 mg/kg) induced desynchronization of the electroencephalographic (EEG) activity and behavioral arousal in both rabbits and rats. Unlike apomorphine, SKF 38393 elicited no signs of stereotyped behavior in rabbits and minimal effects
C Kaiser et al.
Journal of medicinal chemistry, 25(6), 697-703 (1982-06-01)
Resolution of the unique dopamine receptor agonist 2,3,4,5-tetrahydro-7,8-dihydroxy-1-phenyl-1H-3-benzazepine (1) was achieved by a stereospecific multistep conversion of the readily separated enantiomers of its O,O,N-trimethylated precursor 2. The absolute stereochemistry of the antipodes of 2-MeI was determined by single-crystal X-ray diffractometric
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