P2016

3α,21-Dihydroxy-5α-pregnan-20-one

≥95%

• Synonyme(s) : 21-Hydroxyallopregnanolone, 5α-Pregnane-3α,21-diol-20-one, 5α-THDOC, Allopregnane-3α,21-diol-20-one, Allotetrahydrodeoxycorticosterone
• Formule empirique (notation de Hill) : C₂₁H₃₄O₃
• Numéro CAS: 567-02-2
• Poids moléculaire : 334.49
• Numéro CE : 209-300-8
• Numéro MDL: MFCD00051144
• Code UNSPSC : 12352200
• ID de substance PubChem : 24278624
• Nomenclature NACRES : NA.77

Propriétés

• Niveau de qualité: 200
• Essai: ≥95%
• Forme: powder
• Chaîne SMILES: [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
• Clé InChI: CYKYBWRSLLXBOW-GDYGHMJCSA-N
• Informations sur le gène: human ... GABRA1(2554) , GABRA2(2555) , GABRA3(2556) , GABRA4(2557) , GABRA5(2558) , GABRA6(2559) , GABRB1(2560) , GABRB2(2561) , GABRB3(2562) ; rat ... Gabra2(29706)

Description

Description générale

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]

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[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]

Actions biochimiques/physiologiques

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]

Caractéristiques et avantages

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Informations sur la sécurité

• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: Eyeshields, Gloves, type N95 (US)