21-HYDROXYALLOPREGNANOLONE Chemical Properties

Melting point:

>150oC (dec.)

storage temp. 

Refrigerator

solubility 

Chloroform (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly)

form 

Solid

color 

White to Off-White

Safety Information

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

21-HYDROXYALLOPREGNANOLONE Usage And Synthesis

Uses

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

Definition

ChEBI: 5-alpha-THDOC is a 21-hydroxy steroid.

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.

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.

storage

Store at RT

21-HYDROXYALLOPREGNANOLONE(567-02-2)Related Product Information

• Alphadolone
• ALLOTETRAHYDRO S
• 3alpha,21-dihydroxy-5alpha-pregnane-11,20-dione 21-acetate
• 21-HYDROXYALLOPREGNANOLONE
• 5-ALPHA-PREGNAN-3-BETA, 17,21-TRIOL-11,20-DIONE
• ALLOTETRAHYDROCORTICOSTERONE
• ALLOTETRAHYDROCORTISOL
• 5-ALPHA-PREGNAN-3-ALPHA, 11-BETA, 17,21-TETROL-20-ONE 3,21-DIACETATE
• TETRAHYDRODEOXYCORTICOSTERONE
• 5-ALPHA-PREGNAN-3-ALPHA, 21-DIOL-20-ONE 3-ACETATE
• 5-ALPHA-PREGNAN-3-ALPHA, 17,21-TRIOL-11,20-DIONE 21-ACETATE
• 5-ALPHA-PREGNAN-3-ALPHA, 21-DIOL-20-ONE DIACETATE
• 5ALPHA-PREGNANE-3ALPHA,21-DIOL-20-ONE (17,21,21-D3)
• 5-ALPHA-PREGNAN-3-ALPHA, 11-BETA, 21-TRIOL-20-ONE 3,21-DIACETATE
• 5-ALPHA-PREGNAN-3-ALPHA, 21-DIOL-20-ONE 21-STEARATE
• 5-ALPHA-PREGNAN-3-ALPHA, 17,21-TRIOL-11,20-DIONE 3,21-DIACETATE
• 5-ALPHA-PREGNAN-3-ALPHA, 21-DIOL-20-ONE 21-ACETATE
• 5-ALPHA-PREGNAN-3-ALPHA, 21-DIOL-20-ONE 3-STEARATE