P2016

3α,21-Dihydroxy-5α-pregnan-20-one

≥95%

• Synonym(e): 21-Hydroxyallopregnanolone, 5α-Pregnane-3α,21-diol-20-one, 5α-THDOC, Allopregnane-3α,21-diol-20-one, Allotetrahydrodeoxycorticosterone
• Empirische Formel (Hill-System): C₂₁H₃₄O₃
• CAS-Nummer: 567-02-2
• Molekulargewicht: 334.49
• EG-Nummer: 209-300-8
• MDL-Nummer: MFCD00051144
• UNSPSC-Code: 12352200
• PubChem Substanz-ID: 24278624
• NACRES: NA.77

Eigenschaften

• Qualitätsniveau: 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
• InChIKey: CYKYBWRSLLXBOW-GDYGHMJCSA-N
• Angaben zum Gen: human ... GABRA1(2554) , GABRA2(2555) , GABRA3(2556) , GABRA4(2557) , GABRA5(2558) , GABRA6(2559) , GABRB1(2560) , GABRB2(2561) , GABRB3(2562) ; rat ... Gabra2(29706)

Beschreibung

Allgemeine Beschreibung

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.[1]

Anwendung

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[2]
• to test its effect on the spike-wave discharges (SWD) finasteride-treated rats[3]
• in electrophysiological studies with dentate granule cells (DGCs) post controlled cortical impact (CCI) -induced brain injury[4]

Biochem./physiol. Wirkung

3α,21-Dihydroxy-5α-pregnan-20-one (THDOC) is a positive allosteric modulator of the γ-aminobutyric acid A receptor (GABA_A).[1] By modulating GABA_A receptor, THDOC allows sustained hyperpolarization and an increase in chloride influx and membrane conductance in neurons.[5] THDOC, thus modulates neuronal excitability.[6] It possesses anxiolytic, anticonvulsant and sedative properties.[1] 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.[7] However, elevated levels are reported in depression.[6] THDOC may have an indirect role in the hypothalamic-pituitary–adrenal (HPA) axis activation during acute stress.[5]

Leistungsmerkmale und Vorteile

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Sicherheitshinweise

• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: Eyeshields, Gloves, type N95 (US)