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81572

Sigma-Aldrich

5α-Pregnan-3α-ol-20-one

≥98.0% (TLC)

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:
516-54-1
Molecular Weight:
318.49
Beilstein:
3211363
MDL number:
MFCD00003677
UNSPSC Code:
12352200

Assay

≥98.0% (TLC)

solubility

chloroform: 20 mg/mL, clear, colorless

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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Storage Class Code

13 - Non 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

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Cristina Suñol et al.
Journal of medicinal chemistry, 49(11), 3225-3234 (2006-05-26)
A GABA(A) receptor study of several B-nor analogues of allopregnanolone and pregnanolone has been carried out. B-norallopregnanolone (i.e., 3alpha-hydroxy-7-nor-5alpha-pregnan-20-one) was found comparable to allopregnanolone when measured with labeled TBPS. Analogous results were obtained from their effect on neurons in culture:
Samira Afrazi et al.
The Journal of steroid biochemistry and molecular biology, 139, 98-103 (2013-11-02)
Hyperglycemia plays a critical role in the development of diabetic neuropathy. Hyperglycemia induces oxidative stress in neurons, resulting in neuronal cell apoptosis and dysfunction. Anti-apoptotic properties of neurosteroids have been demonstrated in numerous cellular models of neurodegenerative studies. Here, the
Jonathan J Hirst et al.
The Journal of steroid biochemistry and molecular biology, 139, 144-153 (2013-05-15)
Neuroactive steroid concentrations are remarkably high in the foetal brain during late gestation. These concentrations are maintained by placental progesterone synthesis and the interaction of enzymes in the placenta and foetal brain. 5α-Pregnane-3α-ol-20-one (allopregnanolone) is a key neuroactive steroid during
Eva Innala et al.
Acta obstetricia et gynecologica Scandinavica, 91(12), 1445-1452 (2012-08-29)
To measure serum concentrations of progesterone, estradiol and 5α- and 5β-reduced progesterone metabolites in the follicular and luteal phases of the menstrual cycle in women with latent acute intermittent porphyria and manifest acute intermittent porphyria in comparison with healthy control
Samuel O Adeosun et al.
PloS one, 7(11), e50040-e50040 (2012-12-05)
Restorative/protective therapies to restore dopamine neurons in the substantia nigra pars compacta (SNpc) are greatly needed to effectively change the debilitating course of Parkinson's disease. In this study, we tested the therapeutic potential of a neurogenic neurosteroid, allopregnanolone, in the
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