P2016

3α,21-Dihydroxy-5α-pregnan-20-one

≥95%

• Szinonimák: 21-Hydroxyallopregnanolone, 5α-Pregnane-3α,21-diol-20-one, 5α-THDOC, Allopregnane-3α,21-diol-20-one, Allotetrahydrodeoxycorticosterone
• Tapasztalati képlet (Hill-képlet): C₂₁H₃₄O₃
• CAS-szám: 567-02-2
• Molekulatömeg: 334.49
• EC-szám: 209-300-8
• MDL-szám: MFCD00051144
• UNSPSC kód: 12352200
• PubChem Substance ID: 24278624
• NACRES: NA.77

Tulajdonságok

• Minőségi szint: 200
• Teszt: ≥95%
• Forma: 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
• Nemzetközi kémiai azonosító kulcs: CYKYBWRSLLXBOW-GDYGHMJCSA-N
• Géninformáció: human ... GABRA1(2554) , GABRA2(2555) , GABRA3(2556) , GABRA4(2557) , GABRA5(2558) , GABRA6(2559) , GABRB1(2560) , GABRB2(2561) , GABRB3(2562) ; rat ... Gabra2(29706)

Leírás

Általános leírás

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.

Alkalmazás

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

Biokémiai/fiziológiai hatások

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.

Tulajdonságok és előnyök

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Biztonsági adatok

• Tárolási osztály kódja: 11 - Combustible Solids
• WGK: WGK 3
• Lobbanási pont (F): Not applicable
• Lobbanási pont (C): Not applicable
• Egyéni védőeszköz: Eyeshields, Gloves, type N95 (US)