P8887

5α-Pregnan-3α-ol-20-one

Name: 5α-Pregnan-3α-ol-20-one
Brand: SIGMA

GABAA modulator, solid

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):

C₂₁H₃₄O₂

CAS Number:

516-54-1

Molecular Weight:

318.49

NACRES:

NA.77

PubChem Substance ID:

24278659

UNSPSC Code:

12352200

MDL number:

MFCD00003677

Beilstein/REAXYS Number:

3211363

Product Name

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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Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

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.

Storage Class

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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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

Neurosteroids and GABA-A receptor function

Wang M

Frontiers in Endocrinology, 2, 44-44 (2011)

Genetic variations and treatments that affect the lifespan of the NPC1 mouse.

Benny Liu et al.

Journal of lipid research, 49(3), 663-669 (2007-12-14)

Niemann-Pick type C (NPC) disease is a multisystem disorder caused primarily by a mutation in the npc1 gene. These studies evaluated the effect of genetic background, deletion of additional genes, and administration of several agents on the age at death

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