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Merck
CN

D5297

Dehydroisoandrosterone 3-sulfate sodium salt dihydrate

≥93% (TLC), GABAA modulator, 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
NACRES:
NA.77
PubChem Substance ID:
24278373
UNSPSC Code:
12352200
EC Number:
214-152-2
MDL number:
MFCD11045975
Assay:
≥93% (TLC)
Form:
powder
Quality level:
200

Key Documents

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Product Name

Dehydroisoandrosterone 3-sulfate sodium salt dihydrate, ≥93% (TLC), powder

InChI key

NLNMKDUYGPNWAO-OXNWJOIVSA-M

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

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

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

Quality Level

200

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW6907
MKCW9430
MKCS5294
MKCS6188
MKCS1710

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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
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
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
Manuel de Jesús Gallegos-Saucedo et al.
Neurotoxicity research, 38(2), 447-460 (2020-05-16)
Several pathophysiological processes involve Hypoxia conditions, where the nervous system is affected as well. We postulate that the GABAergic system is especially sensitive. Furthermore, drugs improving the resistance to hypoxia have been investigated, such as the neurosteroid dehydroepiandrosterone sulfate (DHEAS)
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