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D5297

Sigma-Aldrich

Dehydroisoandrosterone 3-sulfate sodium salt dihydrate

≥93% (TLC), powder

Sinónimos:

5-Androsten-3β-ol-17-one sulfate sodium salt dihydrate, Prasterone sulfate sodium salt dihydrate

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About This Item

Fórmula empírica (notación de Hill):
C19H27NaO5S · 2H2O
Número de CAS:
78590-17-7
Peso molecular:
426.50
EC Number:
214-152-2
MDL number:
MFCD11045975
UNSPSC Code:
12352200
PubChem Substance ID:
24278373
NACRES:
NA.77

Quality Level

200

assay

≥93% (TLC)

form

powder

drug control

Home Office Schedule 4.2; regulated under CDSA - not available from Sigma-Aldrich Canada

color

white to off-white

mp

148-149 °C (dec.) (lit.)

solubility

methanol: soluble, clear to hazy

SMILES string

O.O.[Na+].C[C@]12CC[C@H]3[C@@H](CC=C4C[C@H](CC[C@]34C)OS([O-])(=O)=O)[C@@H]1CCC2=O

InChI

1S/C19H28O5S.Na.2H2O/c1-18-9-7-13(24-25(21,22)23)11-12(18)3-4-14-15-5-6-17(20)19(15,2)10-8-16(14)18;;;/h3,13-16H,4-11H2,1-2H3,(H,21,22,23);;2*1H2/q;+1;;/p-1/t13-,14-,15-,16-,18-,19-;;;/m0.../s1

InChI key

NLNMKDUYGPNWAO-OXNWJOIVSA-M

Gene Information

human ... GABRA1(2554) , GABRA2(2555) , GABRA3(2556) , GABRA4(2557) , GABRA5(2558) , GABRA6(2559) , GABRB1(2560) , GABRB2(2561) , GABRB3(2562)

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Application

Dehydroisoandrosterone 3-sulfate sodium salt dihydrate has been used as a supplement to induce superoxide anion production in human neutrophil granulocytes.

Biochem/physiol Actions

Dehydroisoandrosterone 3-sulfate sodium salt dihydrate is a negative allosteric modulator of GABAA receptors.

Features and Benefits

This compound is a featured product for ADME Tox and Neuroscience research. Discover more featured ADME Tox and Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the GABAA Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

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)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Plasma concentration of myeloperoxidase enzyme in pre-and post-climacterial people: related superoxide anion generation
Bekesi G, et al.
Experimental Gerontology, 37(1), 137-148 (2001)
S L Hansen et al.
Molecular pharmacology, 55(3), 489-496 (1999-03-03)
Dehydroepiandrosterone sulfate (DHEAS) is a neuroactive steroid with antagonist action at gamma-aminobutyric acid type A (GABAA) receptors. Patch-clamp techniques were used to investigate DHEAS actions at GABAA receptors of the rat pituitary gland at two distinct loci: posterior pituitary nerve
K R Nilsson et al.
Journal of medicinal chemistry, 41(14), 2604-2613 (1998-07-03)
The unnatural enantiomers of dehydroepiandrosterone sulfate (1), pregnenolone sulfate (2), and (3alpha,5beta)-3-hydroxypregnan-20-one sulfate (3), compounds 4-6, respectively, were prepared by total steroid synthesis. The enantioselectivity of the compounds as negative modulators of the GABAA receptors present in cultured rat hippocampal
M Park-Chung et al.
Brain research, 830(1), 72-87 (1999-06-03)
Sulfated and unsulfated neurosteroids such as pregnenolone sulfate, dehydroepiandrosterone sulfate (DHEAS), pregnanolone, and allopregnanolone, modulate ionotropic amino acid neurotransmitter receptors, and may function as endogenous neuromodulators. The gamma-aminobutyric acid type A (GABAA) receptor exhibits both negative and positive modulation by
P A Lapchak et al.
Stroke, 31(8), 1953-1956 (2000-08-06)
Dehydroepiandrosterone (DHEA) and DHEA sulfate (DHEAS) may function as neurotrophic or neuroprotective factors to protect central nervous system (CNS) neurons against a variety of insults, including excitotoxicity. The present study evaluated the pharmacological effects of DHEAS in a reversible spinal
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