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P5052

Sigma-Aldrich

5α-Pregnan-3α-ol-11,20-dione

powder, ≥98% (TLC)

Synonym(s):

3-Hydroxy-5α-pregnane-11,20-dione, Alfaxalone

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About This Item

CAS Number:
23930-19-0
MDL number:
MFCD00083468
UNSPSC Code:
12352200
PubChem Substance ID:
24278637
NACRES:
NA.77

Quality Level

200

Assay

≥98% (TLC)

form

powder

drug control

USDEA Schedule IV

color

white

solubility

chloroform: ≥5 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(=O)[C@]3([H])[C@@]1(C)CC[C@@H](O)C2

InChI

1S/C21H32O3/c1-12(22)16-6-7-17-15-5-4-13-10-14(23)8-9-20(13,2)19(15)18(24)11-21(16,17)3/h13-17,19,23H,4-11H2,1-3H3/t13-,14+,15-,16+,17-,19+,20-,21+/m0/s1

InChI key

DUHUCHOQIDJXAT-OLVMNOGESA-N

Gene Information

human ... GABRA1(2554) , GABRA2(2555) , GABRA3(2556) , GABRA4(2557) , GABRA5(2558) , GABRA6(2559) , GABRB1(2560) , GABRB2(2561) , GABRB3(2562) , GABRG2(2566)

Biochem/physiol Actions

Synthetic steroid compound alphaxalone (AFX) - 5α-Pregnan-3α-ol-11,20-dione- is a neurosteroid that directly activates and potentiates GABAA receptor-activated membrane current (IGABA). It acts as a positive allosteric modulator of the GABAA receptor; anesthetic. The alpha subunit subtype of GABAA determines the efficacy, but not the potency, of AFX neuroactive steroid to potentiate IGABA.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Precautionary Statements

P301 + P310

Hazard Classifications

Acute Tox. 3 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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R Maitra et al.
Brain research, 819(1-2), 75-82 (1999-03-20)
Neurosteroids are potent, endogenous modulators of GABAA receptor function in the central nervous system. The endogenous progesterone metabolite allopregnanolone (ALP) and the synthetic steroid compound alphaxalone (AFX) have been shown to both directly activate and potentiate GABAA receptor-activated membrane current
T Sooksawate et al.
Neuropharmacology, 37(9), 1103-1110 (1998-12-02)
The effects of increased membrane cholesterol on the potentiation of GABA(A) currents by pregnanolone (5beta-pregnan-3alpha-ol-20-one), allopregnanolone (5alpha-pregnan-3alpha-ol-20-one), alphaxalone (5alpha-pregnan-3alpha-ol-11,20-dione) and propofol were investigated in acutely dissociated rat hippocampal neurones using the whole-cell patch clamp technique. Cholesterol enrichment of the neurones

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