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D4000

Sigma-Aldrich

trans-Dehydroandrosterone

≥99%

Synonym(s):

3β-Hydroxy-5-androsten-17-one, 5-Androsten-3β-ol-17-one, DHEA, Dehydroepiandrosterone, Dehydroisoandrosterone, Prasterone

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About This Item

Empirical Formula (Hill Notation):
C19H28O2
CAS Number:
53-43-0
Molecular Weight:
288.42
Beilstein/REAXYS Number:
2058110
EC Number:
200-175-5
MDL number:
MFCD00003613
UNSPSC Code:
51111800
PubChem Substance ID:
24278369
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

200

assay

≥99%

form

crystalline powder

drug control

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

mp

149-151 °C (lit.)

solubility

chloroform: 50 mg/mL, clear, colorless

shipped in

ambient

storage temp.

room temp

SMILES string

C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@]34C)[C@@H]1CCC2=O

InChI

1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-16,20H,4-11H2,1-2H3/t13-,14-,15-,16-,18-,19-/m0/s1

InChI key

FMGSKLZLMKYGDP-USOAJAOKSA-N

Gene Information

human ... GABRA1(2554) , GABRA2(2555) , GABRA3(2556) , GABRA4(2557) , GABRA5(2558) , GABRA6(2559) , GABRB1(2560) , GABRB2(2561) , GABRB3(2562) , SERPINA6(866)
rat ... Ar(24208)

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Biochem/physiol Actions

Dehydroandrosterone (DHEA) is a negative modulator of GABAA receptors. It is a steroid secreted by the adrenal gland with both estrogenic and androgenic properties. DHEAs conversion to 5-androstenediol, a potent estrogen, enhances the growth and survival of estrogen-sensitive breast tumors.
Negative modulator of GABAA receptors. Steroid secreted by the adrenal gland with both estrogenic and androgenic properties. Its conversion to 5-androstenediol, a potent estrogen, enhances the growth and survival of estrogen-sensitive breast tumors. At high but physiologically valid concentrations, DHEA inhibits proliferation of chromaffin progenitor cells and induces dopaminergic differentiation.

pictograms

Health hazard
GHS08

signalword

Warning

hcodes

H361fd

Hazard Classifications

Repr. 2

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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Nikolaos E Koundourakis et al.
Hormones (Athens, Greece), 18(2), 151-172 (2019-07-01)
A constant topic reported in the lay press is the effect of sex hormones on athletic performance and their abuse by athletes in their effort to enhance their performance or to either boost or sidestep their hard, protracted, and demanding
Sarah Whittle et al.
Social cognitive and affective neuroscience, 10(9), 1282-1290 (2015-02-14)
Early timing of adrenarche, associated with relatively high levels of Dehydroepiandrosterone (DHEA) in children, has been associated with mental health and behavioral problems. However, little is known about effects of adreneracheal timing on brain function. The aim of this study
D J Handelsman et al.
Human reproduction (Oxford, England), 32(2), 418-422 (2016-12-22)
How well does multi-analyte steroid mass spectrometry (MS) profiling classify women with and without polycystic ovary syndrome (PCOS)? Our liquid chromatography MS (LC-MS) steroid profiling only minimally improves discrimination of women with and without PCOS compared with a direct testosterone
Thomas Piper et al.
Drug testing and analysis, 9(11-12), 1695-1703 (2017-08-25)
In the course of investigations into the metabolism of testosterone (T) by means of deuterated T and hydrogen isotope ratio mass spectrometry, a pronounced influence of the oral administration of T on sulfoconjugated steroid metabolites was observed. Especially in case
Y Zimmerman et al.
Contraception, 91(2), 134-142 (2014-12-17)
Combined oral contraceptives (COCs) decrease androgen levels, including testosterone (T), which may be associated with sexual dysfunction and mood complaints in some women. We have shown that 'co-administration' of dehydroepiandrosterone (DHEA) to a drospirenone (DRSP)-containing COC restored total T levels
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