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P5052

Sigma-Aldrich

5α-Pregnan-3α-ol-11,20-dione

powder, ≥98% (TLC)

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Synonym(s):
3-Hydroxy-5α-pregnane-11,20-dione, Alfaxalone
CAS Number:
MDL number:
PubChem Substance ID:

Quality Level

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

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This Item
P8887A3009A7755
vibrant-m

P5052

5α-Pregnan-3α-ol-11,20-dione

vibrant-m

P8887

5α-Pregnan-3α-ol-20-one

vibrant-m

A3009

4-Androsten-11β-ol-3,17-dione

vibrant-m

A7755

5α-Androstane-3α,17β-diol

drug control

USDEA Schedule IV

drug control

-

drug control

-

drug control

USDEA Schedule III; Home Office Schedule 4.2; regulated under CDSA - not available from Sigma-Aldrich Canada

form

powder

form

solid

form

powder

form

powder

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

color

white

color

white

color

-

color

-

solubility

chloroform: ≥5 mg/mL, clear, colorless

solubility

DMSO: 5 mg/mL, methanol: soluble

solubility

chloroform: 49-51 mg/mL, clear, colorless to faintly yellow

solubility

methanol: 19.60-20.40 mg/mL, clear, colorless

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

signalword

Danger

hcodes

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves


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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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