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P8887 Sigma-Aldrich

5α-Pregnan-3α-ol-20-one

solid

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

  • CAS Number 516-54-1

  • Empirical Formula (Hill Notation) C21H34O2

  • Molecular Weight 318.49

  •  Beilstein/REAXYS Number 3211363

  •  MDL number MFCD00003677

  •  PubChem Substance ID 24278659

  •  NACRES NA.77

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Properties

Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience, GABA and Glycine Receptor Modulators,
Quality Level   200
form   solid
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)

Description

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

Packaging

10 mg in poly bottle

5 mg in glass bottle

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 also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

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.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. P8887.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
TU4383000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Discover Bioactive Small Molecules for Neuroscience

The nervous system, comprised of the brain and spinal cord (central nervous system, or CNS) and network of nerves that connects the CNS to the rest of the body (peripheral nervous system, or PNS) is ...
Keywords: Bioactive small molecules, Central Nervous System, Diseases, Metabolism, Neurodegenerative Diseases, Neuroscience, Neurotransmission, Neurotransmitters

Peer-Reviewed Papers
15

References

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