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P8129

Sigma-Aldrich

5β-Pregnan-3α-ol-20-one

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
MDL number:
MFCD00067137
UNSPSC Code:
12352202
PubChem Substance ID:
24898909
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

rat ... Gabra2(29706)

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
GHS08

Signal Word

Warning

Hazard Statements

H351

Precautionary Statements

P281

Hazard Classifications

Carc. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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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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
Jane Evans et al.
Neuropharmacology, 63(8), 1315-1326 (2012-09-04)
Chronic stress has been implicated as a causal factor in depression and anxiety, and is associated with neuroendocrine dysfunction and impaired hippocampal neurogenesis. The neurosteroid allopregnanolone (3α,5α-THP; ALLO) has been shown to be reduced in depressed patients. ALLO is "stress
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
Sara K Bengtsson et al.
Current Alzheimer research, 10(1), 38-47 (2012-11-20)
Previously, we have shown that chronic treatment with allopregnanolone (ALLO) for three months impaired learning function in the Swe/PS1 mouse model. ALLO is a neurosteroid, produced in the CNS and a GABAA receptor agonist. ALLO modulates the general inhibitory system
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