P8887

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

Properties

• 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)

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

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.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)