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P8129

Sigma-Aldrich

5β-Pregnan-3α-ol-20-one

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Synonym(s):
3α-Hydroxy-5β-pregnan-20-one, 3α-Hydroxy-5β-tetrahydroprogesterone, Pregnanolone
Empirical Formula (Hill Notation):
C21H34O2
CAS Number:
Molecular Weight:
318.49
MDL number:
PubChem Substance ID:
NACRES:
NA.77

biological source

synthetic (organic)

assay

≥98% (TLC)

form

powder

solubility

chloroform: 50 mg/mL, clear, colorless

shipped in

ambient

storage temp.

room temp

SMILES string

[H]C12CCC3C4CCC(C(C)=O)C4(C)CCC3C1(C)CC[C@H](O)C2

InChI

1S/C21H34O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14-19,23H,4-12H2,1-3H3

InChI key

AURFZBICLPNKBZ-UHFFFAOYSA-N

Gene Information

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P8129

5β-Pregnan-3α-ol-20-one

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5-Pregnen-3β-ol-20-one

vibrant-m

D4000

trans-Dehydroandrosterone

vibrant-m

P8629

5β-Pregnane-3α,17α,20α-triol

biological source

synthetic (organic)

biological source

synthetic (organic)

biological source

synthetic (organic)

biological source

-

assay

≥98% (TLC)

assay

≥98%

assay

≥99%

assay

≥98.00% (TLC)

solubility

chloroform: 50 mg/mL, clear, colorless

solubility

ethanol: soluble 10 mg/mL, clear, colorless to faintly yellow

solubility

chloroform: 50 mg/mL, clear, colorless

solubility

chloroform: methanol (1:1): 19.60-20.40 mg/mL, clear, colorless

shipped in

ambient

shipped in

ambient

shipped in

ambient

shipped in

ambient

Gene Information

rat ... Gabra2(29706)

Gene Information

human ... SERPINA6(866)
rat ... Ar(24208)

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)

Gene Information

-

Biochem/physiol Actions

5β-Pregnan-3α-ol-20-one or pregnanolone is a neurosteroid that acts as a positive allosteric modulator (PAMs) of γ-aminobutyric acid A receptors (GABAARs). It mediates anti-convulsive, anxiolytic and sedative effects. Pregnanolone inhibits γ-aminobutyric acid C receptor (GABAC) receptor-based response and favors GABAA receptor-mediated currents.

pictograms

Health hazard

signalword

Warning

hcodes

pcodes

Hazard Classifications

Carc. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges


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P Li et al.
British journal of pharmacology, 171(23), 5446-5457 (2014-08-15)
Neurosteroids potentiate responses of the GABAA receptor to the endogenous agonist GABA. Here, we examined the ability of neurosteroids to potentiate responses to the allosteric activators etomidate, pentobarbital and propofol. Electrophysiological assays were conducted on rat α1β2γ2L GABAA receptors expressed
Selwyn S Jayakar et al.
The Journal of biological chemistry, 295(33), 11495-11512 (2020-06-17)
Allopregnanolone (3α5α-P), pregnanolone, and their synthetic derivatives are potent positive allosteric modulators (PAMs) of GABAA receptors (GABAARs) with in vivo anesthetic, anxiolytic, and anti-convulsant effects. Mutational analysis, photoaffinity labeling, and structural studies have provided evidence for intersubunit and intrasubunit steroid-binding
Jonathan J Hirst et al.
The Journal of steroid biochemistry and molecular biology, 139, 144-153 (2013-05-15)
Neuroactive steroid concentrations are remarkably high in the foetal brain during late gestation. These concentrations are maintained by placental progesterone synthesis and the interaction of enzymes in the placenta and foetal brain. 5α-Pregnane-3α-ol-20-one (allopregnanolone) is a key neuroactive steroid during
Samira Afrazi et al.
The Journal of steroid biochemistry and molecular biology, 139, 98-103 (2013-11-02)
Hyperglycemia plays a critical role in the development of diabetic neuropathy. Hyperglycemia induces oxidative stress in neurons, resulting in neuronal cell apoptosis and dysfunction. Anti-apoptotic properties of neurosteroids have been demonstrated in numerous cellular models of neurodegenerative studies. Here, the
Roberta D Brinton
Nature reviews. Endocrinology, 9(4), 241-250 (2013-02-27)
Regenerative therapeutics hold the promise of self-renewal and repair. Ageing and age-associated neurodegenerative diseases are marked by a decline in self-renewal and repair, but a capacity for regeneration is retained. The challenge faced by researchers developing molecular therapeutics to promote

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