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Merck
CN

P8887

5α-Pregnan-3α-ol-20-one

GABAA modulator, 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
化学文摘社编号:
516-54-1
分子量:
318.49
NACRES:
NA.77
PubChem Substance ID:
24278659
UNSPSC Code:
12352200
MDL number:
MFCD00003677
Beilstein/REAXYS Number:
3211363

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产品名称

5α-Pregnan-3α-ol-20-one, solid

SMILES string

[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 key

AURFZBICLPNKBZ-SYBPFIFISA-N

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

form

solid

color

white

solubility

DMSO: 5 mg/mL, methanol: soluble

Quality Level

200

Gene Information

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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相关类别

Application

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

Biochem/physiol Actions

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.

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.
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.

存储类别

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

法规信息

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历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
0000223917
0000285593
0000337914
0000337914
0000285593

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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)
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
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)
Neurosteroids and GABA-A receptor function
Wang M
Frontiers in Endocrinology, 2, 44-44 (2011)
5alpha-reduced progestogens ameliorate mood-related behavioral pathology, neurotoxicity, and microgliosis associated with exposure to HIV-1 Tat
Paris, Jason J and Zou, ShiPing and Hahn, Yun K and Knapp, Pamela E and Hauser, Kurt F
Brain, behavior, and immunity, 55, 202-214 (2016)
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