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Merck
CN

P8887

Sigma-Aldrich

5α-Pregnan-3α-ol-20-one

solid

别名:

3α-Hydroxy-5α-pregnan-20-one, 3α-OH-DHP, Allopregnan-3α-ol-20-one, Allopregnanolone, Brexanolone

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关于此项目

经验公式（希尔记法）:
C21H34O2
CAS Number:
516-54-1
分子量:
318.49
Beilstein:
3211363
MDL编号:
MFCD00003677
UNSPSC代码:
12352200
PubChem化学物质编号:
24278659
NACRES:
NA.77

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表单

solid

质量水平

200

颜色

white

溶解性

DMSO: 5 mg/mL
methanol: soluble

SMILES字符串

[H][C@@]12CC[C@@]3([H])[C@]4([H])CC[C@H](C(C)=O)[C@@]4(C)CC[C@]3([H])[C@@]1(C)CC[C@@H](O)C2

InChI

1S/C21H34O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14-19,23H,4-12H2,1-3H3/t14-,15+,16-,17+,18-,19-,20-,21+/m0/s1

InChI key

AURFZBICLPNKBZ-SYBPFIFISA-N

基因信息

human ... GABRA1(2554), GABRA2(2555), GABRA3(2556), GABRA4(2557), GABRA5(2558), GABRA6(2559), GABRB1(2560), GABRB2(2561), GABRB3(2562), GABRD(2563), GABRE(2564), GABRG1(2565), GABRG2(2566), GABRG3(2567), GABRP(2568), GABRQ(55879)
mouse ... Gabrg2(14406)
rat ... Gabra1(29705), Gabra2(29706), Gabrg2(29709)

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应用

5α-Pregnan-3α-ol-20-one has been used:
  • as an allosteric modulator of GABAA receptors in mice
  • a neuroprotective steroid in transgenic mice
  • a neurosteroid

生化/生理作用

5α-Pregnan-3α-ol-20-one is a positive allosteric modulator of γ-aminobutyric acid (GABA) A receptor (GABAA). It is also called pregnan and during pregnancy it modulates the atrial volume receptors transducer properties. During estrus cycle, 5α-Pregnan-3α-ol-20-one or allopregnanolone levels changes in hypothalamus. It is present in high levels post adrenalectomy and gonadectomy.

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.
This compound is featured on the GABAA Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

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)

法规信息

新产品

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
0000337914
0000285593
0000223917
0000223917
0000285593

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访问文档库

The neurosteroid 5beta-pregnan-3 alpha-ol-20-one enhances actions of etomidate as a positive allosteric modulator of alpha beta gamma L GABAA receptors
Li P, et al.
British Journal of Pharmacology, 171(23), 5446-5457 (2014)
Genetic variations and treatments that affect the lifespan of the NPC1 mouse
Liu B, et al.
Journal of Lipid Research, 49(3), 663-669 (2008)
Neurosteroids and GABA-A receptor function
Wang M
Frontiers in Endocrinology, 2, 44-44 (2011)
Ibuki Ueoka et al.
International journal of molecular sciences, 20(17) (2019-08-24)
Whole exome analyses have identified a number of genes associated with autism spectrum disorder (ASD) and ASD-related syndromes. These genes encode key regulators of synaptogenesis, synaptic plasticity, cytoskeleton dynamics, protein synthesis and degradation, chromatin remodeling, transcription, and lipid homeostasis. Furthermore
Neurosteroid modulation of GABA IPSCs is phosphorylation dependent
Fancsik A, et al.
The Journal of Neuroscience, 20(9), 3067-3075 (2000)
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