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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

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About This Item

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

form

solid

Quality Level

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

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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

Regulatory Information

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Certificates of Analysis (COA)

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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)
Neurosteroid modulation of GABA IPSCs is phosphorylation dependent
Fancsik A, et al.
The Journal of Neuroscience, 20(9), 3067-3075 (2000)
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)
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
Liu B, et al.
Journal of Lipid Research, 49(3), 663-669 (2008)

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