3α,21-Dihydroxy-5α-pregnan-20-one

SIGMA/P2016 - ≥95%

Synonym: 21-Hydroxyallopregnanolone; 5α-Pregnane-3α,21-diol-20-one; 5α-THDOC; Allopregnane-3α,21-diol-20-one; Allotetrahydrodeoxycorticosterone

CAS Number: 567-02-2
Empirical Formula (Hill Notation): C₂₁H₃₄O₃
Molecular Weight: 334.49
EC Number: 209-300-8
MDL Number: MFCD00051144
Linear Formula: C₂₁H₃₄O₃
Product Type: Chemical

Catalog Number	PKG Qty.	Price


45-P2016-5MG	5 mg	$319.00 1/EA	Add To Favorites
45-P2016-10MG	10 mg	$547.00 1/EA	Add To Favorites

Properties
Descriptions
Safety Info.
Basic Data

assay	≥95%
form	powder
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
InChI key	CYKYBWRSLLXBOW-GDYGHMJCSA-N
Quality Level	200
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

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
Biochem/physiol Actions:	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.
Features and Benefits:	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 .
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.
Packaging:	10 mg in poly bottle
Packaging:	5 mg in glass bottle

RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable

Purity	≥95%
UNSPSC	12352200

To Order From a Quote