P2016

3α,21-Dihydroxy-5α-pregnan-20-one

≥95%

• Synonym(s): 21-Hydroxyallopregnanolone, 5α-Pregnane-3α,21-diol-20-one, 5α-THDOC, Allopregnane-3α,21-diol-20-one, Allotetrahydrodeoxycorticosterone
• Empirical Formula (Hill Notation): C₂₁H₃₄O₃
• CAS Number: 567-02-2
• Molecular Weight: 334.49
• EC Number: 209-300-8
• MDL number: MFCD00051144
• UNSPSC Code: 12352200
• PubChem Substance ID: 24278624
• NACRES: NA.77

Properties

• Quality Level: 200
• assay: ≥95%
• form: powder
• SMILES string: [H][C@@]12CC[C@@]3([H])[C@]4([H])CC[C@H](C(=O)CO)[C@@]4(C)CC[C@]3([H])[C@@]1(C)CC[C@@H](O)C2
• InChI: 1S/C21H34O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h13-18,22-23H,3-12H2,1-2H3/t13-,14+,15-,16-,17-,18+,20-,21-/m0/s1
• InChI key: CYKYBWRSLLXBOW-GDYGHMJCSA-N
• Gene Information: human ... GABRA1(2554) , GABRA2(2555) , GABRA3(2556) , GABRA4(2557) , GABRA5(2558) , GABRA6(2559) , GABRB1(2560) , GABRB2(2561) , GABRB3(2562) ; rat ... Gabra2(29706)

Description

General description

3α21-Dihydroxy-5α-pregnan-20-one (THDOC) is a neurosteroid. It is synthesized in a two-step process from deoxycorticosterone (DOC) via 5α-dihydrodeoxycorticosterone (DHDOC) intermediate with enzymes 5α-reductase and 3α-hydroxysteroid oxidoreductase catalyzing these steps respectively.

Application

3α,21-Dihydroxy-5α-pregnan-20-one (THDOC) has been used:

• as an γ-aminobutyric acid type A receptor (γ-GABAA) agonist in voltage-clamp measurements studies in Xenopus oocytes
• to test its effect on the spike-wave discharges (SWD) finasteride-treated rats
• in electrophysiological studies with dentate granule cells (DGCs) post controlled cortical impact (CCI) -induced brain injury

Biochem/physiol Actions

3α,21-Dihydroxy-5α-pregnan-20-one (THDOC) is a positive allosteric modulator of the γ-aminobutyric acid A receptor (GABA_A). By modulating GABA_A receptor, THDOC allows sustained hyperpolarization and an increase in chloride influx and membrane conductance in neurons. THDOC, thus modulates neuronal excitability. It possesses anxiolytic, anticonvulsant and sedative properties. The levels of THDOC show variation in different physiological states. A low THDOC level in the mensural phase is speculated to play a role in the pathogenesis of catamenial epilepsy (CE) in women. However, elevated levels are reported in depression. THDOC may have an indirect role in the hypothalamic-pituitary–adrenal (HPA) axis activation during acute stress.

Features and Benefits

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Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)