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Sigma-Aldrich

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

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About This Item

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

Niveau de qualité

200

Pureté

≥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 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.

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
  • 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

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

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)

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Junn-Liang Chang et al.
American journal of physiology. Renal physiology, 299(1), F43-F48 (2010-04-02)
Recently, we demonstrated a chronic neurosteroid-dependent inhibition of activity-dependent spinal reflex potentiation (SRP), but it remains unclear whether neurosteroids acutely modulate SRP induction. This study shows progesterone as well as two of its 3alpha,5alpha-derivatives, allopregnalonone and 3alpha,5alpha-tetrahydrodeoxycorticosterone (THDOC), to be
Antonella Tuveri et al.
Epilepsia, 49(7), 1221-1229 (2008-03-08)
Seizure exacerbation in catamenial epilepsy (CE) is associated with the decrease in progesterone secretion and increase in estradiol secretion during the premenstrual period. Moreover, experimental evidence suggests that tetrahydrodeoxycorticosterone (THDOC), a positive modulator of the type A receptor for gamma-aminobutyric
Roland Baur et al.
Journal of neurochemistry, 111(5), 1172-1181 (2009-09-22)
Delta (delta) subunit containing GABA(A) receptors are expressed extra-synaptically and mediate tonic inhibition. In cerebellar granule cells, they often form a receptor together with alpha(6) subunits. We were interested to determine the architecture of these receptors. We predefined the subunit
Doodipala S Reddy et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 22(9), 3795-3805 (2002-04-30)
Stress affects seizure susceptibility in animals and humans, but the underlying mechanisms are obscure. Here, we provide evidence that GABA(A) receptor-modulating neurosteroids derived from deoxycorticosterone (DOC) play a role in stress-related changes in seizure control. DOC, an adrenal steroid whose
Jhimly Sarkar et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 31(50), 18198-18210 (2011-12-16)
The hypothalamic-pituitary-adrenal (HPA) axis, which mediates the body's response to stress, is largely under GABAergic control. Here we demonstrate that corticotropin-releasing hormone (CRH) neurons are modulated by the stress-derived neurosteroid, tetrahydrodeoxycorticosterone (THDOC), acting on δ subunit-containing GABA(A) receptors (GABA(A)Rs). Under
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