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21-HYDROXYALLOPREGNANOLONE

Product Name
21-HYDROXYALLOPREGNANOLONE
CAS No.
567-02-2
Chemical Name
21-HYDROXYALLOPREGNANOLONE
Synonyms
TDOC;5α-THDOC;ALLO TH DOC;3α,5α-THDOC;5alpha-THDOC;ALLOTETRAHYDRO DOC;ALLOTETRAHYDROCORTEXONE;1-HYDROXYALLOPREGNANOLONE;21-HYDROXYALLOPREGNANOLONE;ALLOTETRAHYDRO SUBSTANCE 'Q'
CBNumber
CB5265066
Molecular Formula
C21H34O3
Formula Weight
334.49
MOL File
567-02-2.mol
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21-HYDROXYALLOPREGNANOLONE Property

Melting point:
>150oC (dec.)
storage temp. 
Refrigerator
solubility 
Chloroform (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly)
form 
Solid
color 
White to Off-White
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Safety

WGK Germany 
3
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
P2016
Product name
3α,21-Dihydroxy-5α-pregnan-20-one
Purity
≥95%
Packaging
5mg
Price
$116
Updated
2024/03/01
Sigma-Aldrich
Product number
P2016
Product name
3α,21-Dihydroxy-5α-pregnan-20-one
Purity
≥95%
Packaging
10mg
Price
$198.8
Updated
2024/03/01
Cayman Chemical
Product number
28364
Product name
THDOC
Packaging
500μg
Price
$41
Updated
2024/03/01
Cayman Chemical
Product number
28364
Product name
THDOC
Packaging
1mg
Price
$78
Updated
2024/03/01
Cayman Chemical
Product number
28364
Product name
THDOC
Packaging
5mg
Price
$263
Updated
2024/03/01
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21-HYDROXYALLOPREGNANOLONE Chemical Properties,Usage,Production

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 Preparation Products And Raw materials

Raw materials

Preparation Products

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567-02-2, 21-HYDROXYALLOPREGNANOLONERelated Search:

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

  • 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
  • 3α,21-dihydroxy-5α-pregnan-20-one
  • 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,21-Dihydroxy-5α-pregnan-20-one
  • 3α,21Dihydroxy5αpregnan20one,3α,21 Dihydroxy 5α pregnan 20 one
  • 3α,5α-THDOC
  • 5α-PREGNAN-3α, 21-DIOL-20-ONE
  • 567-02-2
  • C21H31D3O3
  • BioChemical
  • Cell Biology
  • Cell Signaling and Neuroscience
  • Ligand-Gated Ion Channels
  • Ion Channels
  • GABA and Glycine Receptor Modulators