P8129
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:
Molecular Weight:
318.49
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.77
biological source:
synthetic (organic)
form:
powder
Assay:
≥98% (TLC)
Recommended Products
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
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.
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
Regulatory Information
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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
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
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
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