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Key Documents

P8887

Sigma-Aldrich

5α-Pregnan-3α-ol-20-one

solid

Sinônimo(s):

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

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About This Item

Fórmula empírica (Notação de Hill):
C21H34O2
Número CAS:
Peso molecular:
318.49
Beilstein:
3211363
Número MDL:
Código UNSPSC:
12352200
ID de substância PubChem:
NACRES:
NA.77

forma

solid

Nível de qualidade

cor

white

solubilidade

DMSO: 5 mg/mL
methanol: soluble

cadeia de caracteres SMILES

[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

chave InChI

AURFZBICLPNKBZ-SYBPFIFISA-N

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Aplicação

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

Ações bioquímicas/fisiológicas

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.

Características e benefícios

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.

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)


Certificados de análise (COA)

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Visite a Biblioteca de Documentos

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)
Neurosteroid modulation of GABA IPSCs is phosphorylation dependent
Fancsik A, et al.
The Journal of Neuroscience, 20(9), 3067-3075 (2000)
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)
Neurosteroids and GABA-A receptor function
Wang M
Frontiers in Endocrinology, 2, 44-44 (2011)
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

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