P8129
5β-Pregnan-3α-ol-20-one
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:
Molecular Weight:
318.49
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Biological source:
synthetic (organic)
Form:
powder
Assay:
≥98% (TLC)
Product Name
5β-Pregnan-3α-ol-20-one,
SMILES string
[H]C12CCC3C4CCC(C(C)=O)C4(C)CCC3C1(C)CC[C@H](O)C2
InChI key
AURFZBICLPNKBZ-UHFFFAOYSA-N
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
biological source
synthetic (organic)
assay
≥98% (TLC)
form
powder
solubility
chloroform: 50 mg/mL, clear, colorless
shipped in
ambient
storage temp.
room temp
Quality Level
Gene Information
rat ... Gabra2(29706)
Related Categories
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.
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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
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
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
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
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
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