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P8887

5α-Pregnan-3α-ol-20-one

Name: 5&#945;-Pregnan-3&#945;-ol-20-one
Brand: SIGMA

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

Form:

solid

Quality level:

200

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产品名称

5α-Pregnan-3α-ol-20-one, solid

form

solid

Quality Level

200

color

white

solubility

DMSO: 5 mg/mL, methanol: soluble

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

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

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)

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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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)

Autism Spectrum Disorder-Related Syndromes: Modeling with Drosophila and Rodents.

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

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)

Effect of pregnancy and 5 alpha-pregnan-3 alpha-ol-20-one on atrial receptor afferent discharge in rats

Storey E and Kaufman S

American Journal of Physiology. Regulatory, Integrative and Comparative Physiology, 287(6), R1427-R1433 (2004)

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商品

DISCOVER Bioactive Small Molecules for Neuroscience

全球贸易项目编号

货号	GTIN
P8887-5MG	04061834402022
P8887-10MG	04061834402015

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