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5β-Pregnan-3α-ol-20-one

Name: 5&#946;-Pregnan-3&#945;-ol-20-one
Brand: SIGMA

synthetic (organic), ≥98% (TLC), γ-aminobutyric acid A receptors modulator, powder

Synonym(s):

3α-Hydroxy-5β-pregnan-20-one, 3α-Hydroxy-5β-tetrahydroprogesterone, Pregnanolone

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About This Item

Empirical Formula (Hill Notation):

C₂₁H₃₄O₂

CAS Number:

128-20-1

Molecular Weight:

318.49

UNSPSC Code:

12352202

PubChem Substance ID:

24898909

NACRES:

NA.77

MDL number:

MFCD00067137

Biological source:

synthetic (organic)

Form:

powder

Assay:

≥98% (TLC)

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Properties

Product Name

5β-Pregnan-3α-ol-20-one,

biological source

synthetic (organic)

Quality Level

100

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

rat ... Gabra2(29706)

Description

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.[1] Pregnanolone inhibits γ-aminobutyric acid C receptor (GABAC) receptor-based response and favors GABAA receptor-mediated currents.[2]

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This Item	M6013	P9129	D4000
Sigma-Aldrich P8129 5β-Pregnan-3α-ol-20-one	Sigma-Aldrich M6013 Medroxyprogesterone	Sigma-Aldrich P9129 5-Pregnen-3β-ol-20-one	Sigma-Aldrich D4000 trans-Dehydroandrosterone
biological source synthetic (organic)	biological source synthetic (organic)	biological source synthetic (organic)	biological source synthetic (organic)
assay ≥98% (TLC)	assay ≥98% (HPLC)	assay ≥98%	assay ≥99%
Quality Level 100	Quality Level 100	Quality Level 200	Quality Level 200
form powder	form powder	form powder	form crystalline powder
Gene Information rat ... Gabra2(29706)	Gene Information rat ... Ar(24208)	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)
shipped in ambient	shipped in ambient	shipped in ambient	shipped in ambient

pictograms

GHS08

signalword

Warning

hcodes

H351

pcodes

P281

Hazard Classifications

Carc. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

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

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The neurosteroid 5β-pregnan-3α-ol-20-one enhances actions of etomidate as a positive allosteric modulator of α1β2γ2L GABAA receptors.

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

Photoaffinity labeling identifies an intersubunit steroid-binding site in heteromeric GABA type A (GABAA) receptors.

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

Allopregnanolone and pregnanolone analogues modified in the C ring: synthesis and activity.

Barbora Slavíková et al.

Journal of medicinal chemistry, 56(6), 2323-2336 (2013-02-21)

(25R)-3β-Hydroxy-5α-spirostan-12-one (hecogenin) and 11α-hydroxypregn-4-ene-3,20-dione (11α-hydroxyprogesterone) were used as starting materials for the synthesis of a series of 11- and 12-substituted derivatives of 5ξ-pregnanolone (3α-hydroxy-5α-pregnan-20-one and 3α-hydroxy-5β-pregnan-20-one), the principal neurosteroid acting via γ-aminobutyric acid (GABA). These analogues were designed to study

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Global Trade Item Number

SKU	GTIN
P8129-25MG	04061832851303

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