P2016
3α,21-Dihydroxy-5α-pregnan-20-one
≥95%
别名:
21-Hydroxyallopregnanolone, 5α-Pregnane-3α,21-diol-20-one, 5α-THDOC, Allopregnane-3α,21-diol-20-one, Allotetrahydrodeoxycorticosterone
登录查看公司和协议定价
所有图片(1)
选择尺寸
变更视图
5 MG
$327.00
10 MG
$562.00
About This Item
经验公式（希尔记法）:
C21H34O3
CAS号:
分子量:
334.49
EC 号:
MDL编号:
UNSPSC代码:
12352200
PubChem化学物质编号:
NACRES:
NA.77
推荐产品
质量水平
方案
≥95%
表单
powder
SMILES字符串
[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
InChI key
CYKYBWRSLLXBOW-GDYGHMJCSA-N
基因信息
human ... GABRA1(2554) , GABRA2(2555) , GABRA3(2556) , GABRA4(2557) , GABRA5(2558) , GABRA6(2559) , GABRB1(2560) , GABRB2(2561) , GABRB3(2562)
rat ... Gabra2(29706)
一般描述
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.[1]
应用
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[2]
- to test its effect on the spike-wave discharges (SWD) finasteride-treated rats[3]
- in electrophysiological studies with dentate granule cells (DGCs) post controlled cortical impact (CCI) -induced brain injury[4]
生化/生理作用
3α,21-Dihydroxy-5α-pregnan-20-one (THDOC) is a positive allosteric modulator of the γ-aminobutyric acid A receptor (GABAA).[1] By modulating GABAA receptor, THDOC allows sustained hyperpolarization and an increase in chloride influx and membrane conductance in neurons.[5] THDOC, thus modulates neuronal excitability.[6] It possesses anxiolytic, anticonvulsant and sedative properties.[1] 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.[7] However, elevated levels are reported in depression.[6] THDOC may have an indirect role in the hypothalamic-pituitary–adrenal (HPA) axis activation during acute stress.[5]
特点和优势
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.
储存分类代码
11 - Combustible Solids
WGK
WGK 3
闪点(°F)
Not applicable
闪点(°C)
Not applicable
个人防护装备
Eyeshields, Gloves, type N95 (US)
历史批次信息供参考:
分析证书(COA)
Lot/Batch Number
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
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
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
商品
DISCOVER Bioactive Small Molecules for Neuroscience
Active Filters
我们的科学家团队拥有各种研究领域经验，包括生命科学、材料科学、化学合成、色谱、分析及许多其他领域.
联系技术服务部门
