P2016
3α,21-Dihydroxy-5α-pregnan-20-one
≥95%
Synonim(y):
21-Hydroxyallopregnanolone, 5α-Pregnane-3α,21-diol-20-one, 5α-THDOC, Allopregnane-3α,21-diol-20-one, Allotetrahydrodeoxycorticosterone
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Informacje o tej pozycji
Wzór empiryczny (zapis Hilla):
C21H34O3
Numer CAS:
Masa cząsteczkowa:
334.49
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
EC Number:
209-300-8
MDL number:
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Pozwól nam pomócNazwa produktu
3α,21-Dihydroxy-5α-pregnan-20-one, ≥95%
InChI key
CYKYBWRSLLXBOW-GDYGHMJCSA-N
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
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
assay
≥95%
form
powder
Quality Level
Gene Information
human ... GABRA1(2554), GABRA2(2555), GABRA3(2556), GABRA4(2557), GABRA5(2558), GABRA6(2559), GABRB1(2560), GABRB2(2561), GABRB3(2562)
rat ... Gabra2(29706)
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 (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.
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.
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Klasa składowania
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Dokumenty związane z niedawno zakupionymi produktami zostały zamieszczone w Bibliotece dokumentów.
D Eser et al.
Neuroscience, 138(3), 1041-1048 (2005-11-29)
Certain neuroactive steroids modulate ligand-gated ion channels via non-genomic mechanisms. Especially 3alpha-reduced pregnane steroids are potent positive allosteric modulators of the GABA type A-receptor. During major depression there is a dysequilibrium of 3alpha-reduced neuroactive steroids, which is corrected by clinically
Patrizia Porcu et al.
Alcoholism, clinical and experimental research, 34(3), 432-442 (2009-12-24)
Acute ethanol administration increases plasma and brain levels of progesterone and deoxycorticosterone-derived neuroactive steroids (3alpha,5alpha)-3-hydroxypregnan-20-one (3alpha,5alpha-THP) and (3alpha,5alpha)-3,21-dihydroxypregnan-20-one (3alpha,5alpha-THDOC) in rats. However, little is known about ethanol effects on GABAergic neuroactive steroids in mice, nonhuman primates, or humans. We investigated
Doodipala S Reddy
Trends in pharmacological sciences, 24(3), 103-106 (2003-03-12)
Endogenous neurosteroids affect brain excitability during physiological states such as pregnancy and the menstrual cycle, and during conditions of acute and chronic stress. The neurosteroid allotetrahydrodeoxycorticosterone (THDOC) is an allosteric modulator of the GABA(A) receptor. Although the role of THDOC
Kuldeep H Kaur et al.
The Journal of biological chemistry, 284(12), 7889-7896 (2009-01-15)
GABA(A) receptors mediate inhibitory neurotransmission in the mammalian brain via synaptic and extrasynaptic receptors. The delta (delta)-subunit-containing receptors are expressed exclusively extra-synaptically and mediate tonic inhibition. In the present study, we were interested in determining the architecture of receptors containing
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
Produkty
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