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3α,21-Dihydroxy-5α-pregnan-20-on

21-HYDROXYALLOPREGNANOLONE Struktur
567-02-2
CAS-Nr.
567-02-2
Bezeichnung:
3α,21-Dihydroxy-5α-pregnan-20-on
Englisch Name:
21-HYDROXYALLOPREGNANOLONE
Synonyma:
3α,21-Dihydroxy-5α-pregnan-20-one;3α,21-dihydroxy-5α-pregnan-20-one;TDOC;5α-THDOC;ALLO TH DOC;3α,5α-THDOC;5alpha-THDOC;ALLOTETRAHYDRO DOC;ALLOTETRAHYDROCORTEXONE;1-HYDROXYALLOPREGNANOLONE
CBNumber:
CB5265066
Summenformel:
C21H34O3
Molgewicht:
334.49
MOL-Datei:
567-02-2.mol

3α,21-Dihydroxy-5α-pregnan-20-on Eigenschaften

Schmelzpunkt:
>150oC (dec.)
storage temp. 
Refrigerator
L?slichkeit
Chloroform (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly)
Aggregatzustand
Solid
Farbe
White to Off-White
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
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

Sicherheit

WGK Germany  3
Speicherklasse 11 - Combustible Solids

3α,21-Dihydroxy-5α-pregnan-20-on Chemische Eigenschaften,Einsatz,Produktion Methoden

Verwenden

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

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.

Biochem/physiol Actions

3α,21-Dihydroxy-5α-pregnan-20-one (THDOC) is a positive allosteric modulator of the γ-aminobutyric acid A receptor (GABAA). By modulating GABAA 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.

3α,21-Dihydroxy-5α-pregnan-20-on Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


3α,21-Dihydroxy-5α-pregnan-20-on Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

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Sigma-Aldrich 021-61415566 800-8193336
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567-02-2(3α,21-Dihydroxy-5α-pregnan-20-on)Verwandte Suche:


  • ALLOPREGNANE-3ALPHA,21-DIOL-20-ONE
  • ALLOTETRADEOXYCORTICOSTERONE
  • ALLOTETRAHYDROCORTEXONE
  • ALLOTETRAHYDRODEOXYCORTICOSTERONE
  • ALLOTETRAHYDRODESOXYCORTICOSTERONE
  • ALLOTETRAHYDRO DOC
  • ALLOTETRAHYDRO SUBSTANCE 'Q'
  • ALLO TH DOC
  • 5-ALPHA-PREGNAN-3-ALPHA, 21-DIOL-20-ONE
  • 5ALPHA-PREGNANE-3ALPHA,21-DIOL-20-ONE
  • 3ALPHA,21-DIHYDROXY-5ALPHA-PREGNAN-20-ONE
  • 21-HYDROXYALLOPREGNANOLONE
  • 5A-pregnane-3A,21-diol-20-one
  • 5alpha-Pregnan-3alpha,21-diol-20-one-17,21,21-D3
  • 5α-Pregnane-3α,21-diol-20-one
  • 5α-Pregnan-3α,21-diol-20-one-17,21,21-D3
  • 21-Hydroxyallopregnanolone, 5α-Pregnane-3α,21-diol-20-one, 5α-THDOC, Allopregnane-3α,21-diol-20-one, Allotetrahydrodeoxycorticosterone
  • 3β,5α-Tetrahydrodeoxycorticosterone
  • TDOC
  • 5α-THDOC
  • Allopregnane-3α,21-diol-20-one
  • Allotetrahydrodeoxycorticosterone (Solution)
  • 1-HYDROXYALLOPREGNANOLONE
  • Pregnan-20-one, 3,21-dihydroxy-, (3α,5α)-
  • "3α,21-Dihydroxy-5a-pregnan-20-one"
  • 5alpha-THDOC
  • 3α,21Dihydroxy5αpregnan20one,3α,21 Dihydroxy 5α pregnan 20 one
  • 3α,5α-THDOC
  • 5α-PREGNAN-3α, 21-DIOL-20-ONE
  • 3α,21-Dihydroxy-5α-pregnan-20-one, CAS 567-02-2
  • 3α,21-Dihydroxy-5α-pregnan-20-one (Standard)
  • 3α,21-Dihydroxy-5α-pregnan-20-one
  • 3α,21-dihydroxy-5α-pregnan-20-one
  • 567-02-2
  • C21H31D3O3
  • BioChemical
  • Cell Biology
  • Cell Signaling and Neuroscience
  • Ligand-Gated Ion Channels
  • Ion Channels
  • GABA and Glycine Receptor Modulators
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