Skip to Content
Merck
All Photos(1)

Documents

P8129

Sigma-Aldrich

5β-Pregnan-3α-ol-20-one

Synonym(s):

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

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C21H34O2
CAS Number:
Molecular Weight:
318.49
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

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

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

Signal Word

Warning

Hazard Statements

Precautionary Statements

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

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
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
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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service