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Merck

P8129

Sigma-Aldrich

5β-Pregnan-3α-ol-20-one

别名:

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

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About This Item

经验公式(希尔记法):
C21H34O2
CAS号:
分子量:
318.49
MDL號碼:
分類程式碼代碼:
12352202
PubChem物質ID:
NACRES:
NA.77

生物源

synthetic (organic)

化驗

≥98% (TLC)

形狀

powder

溶解度

chloroform: 50 mg/mL, clear, colorless

運輸包裝

ambient

儲存溫度

room temp

SMILES 字串

[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 密鑰

AURFZBICLPNKBZ-UHFFFAOYSA-N

基因資訊

生化/生理作用

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.

象形圖

Health hazard

訊號詞

Warning

危險聲明

防範說明

危險分類

Carc. 2

儲存類別代碼

11 - Combustible Solids

水污染物質分類(WGK)

WGK 3

個人防護裝備

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges


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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
Eva Innala et al.
Acta obstetricia et gynecologica Scandinavica, 91(12), 1445-1452 (2012-08-29)
To measure serum concentrations of progesterone, estradiol and 5α- and 5β-reduced progesterone metabolites in the follicular and luteal phases of the menstrual cycle in women with latent acute intermittent porphyria and manifest acute intermittent porphyria in comparison with healthy control
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

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