Skip to Content
Merck
All Photos(1)

Documents

P8887

Sigma-Aldrich

5α-Pregnan-3α-ol-20-one

solid

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C21H34O2
CAS Number:
516-54-1
Molecular Weight:
318.49
Beilstein:
3211363
MDL number:
MFCD00003677
UNSPSC Code:
12352200
PubChem Substance ID:
24278659
NACRES:
NA.77

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)

Looking for similar products? Visit Product Comparison Guide

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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
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)
Neurosteroid modulation of GABA IPSCs is phosphorylation dependent
Fancsik A, et al.
The Journal of Neuroscience, 20(9), 3067-3075 (2000)
Angela L Cumberland et al.
International journal of developmental neuroscience : the official journal of the International Society for Developmental Neuroscience, 58, 50-58 (2017-02-14)
Neurosteroids are essential for aiding proper fetal neurodevelopment. Pregnancy compromises such as preterm birth, prenatal stress and intrauterine growth restriction are associated with an increased risk of developing behavioural and mood disorders, particularly during adolescence. These pathologies involve the premature
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service