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P8129

Sigma-Aldrich

5β-Pregnan-3α-ol-20-one

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Synonym(s):
3α-Hydroxy-5β-pregnan-20-one, 3α-Hydroxy-5β-tetrahydroprogesterone, Pregnanolone
Empirical Formula (Hill Notation):
C21H34O2
CAS Number:
128-20-1
Molecular Weight:
318.49
MDL number:
MFCD00067137
UNSPSC Code:
12352200
PubChem Substance ID:
24898909
NACRES:
NA.77

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)

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

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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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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