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D5297

Sigma-Aldrich

Dehydroisoandrosterone 3-sulfate sodium salt dihydrate

≥93% (TLC), powder

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C19H27NaO5S · 2H2O
CAS Number:
78590-17-7
Molecular Weight:
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 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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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)
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
Divya Sachidanandan et al.
Journal of molecular neuroscience : MN, 56(4), 868-877 (2015-03-03)
The γ-aminobutyric acid type A receptor (GABAAR) is negatively modulated by two structurally similar neurosteroids, pregnenolone sulfate (PS) and dehydroepiandrosterone sulfate (DHEAS). This study attempted to ascertain the molecular mechanisms of inhibition of the GABA-ergic current by neurosteroids. We demonstrated
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