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Merck
CN

P162

Pregnenolone sulfate sodium salt

sigma-1 receptor agonist, powder

Synonym(s):

3β-Hydroxy-5-pregnen-20-one 3-sulfate, 3-Hydroxypregn-5-en-20-one sulfate, 5-Pregnen-3β-ol-20-one sulfate

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About This Item

Empirical Formula (Hill Notation):
C21H31NaO5S
Molecular Weight:
418.52
UNSPSC Code:
12352200
PubChem Substance ID:
24278112
NACRES:
NA.77
MDL number:
MFCD00056177

Key Documents

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Product Name

Pregnenolone sulfate sodium salt,

form

powder

SMILES string

[Na].[H][C@@]12CC=C3C[C@H](CC[C@]3(C)[C@@]1([H])CC[C@]4(C)[C@H](CC[C@@]24[H])C(C)=O)OS(O)(=O)=O

InChI

1S/C21H32O5S.Na.H/c1-13(22)17-6-7-18-16-5-4-14-12-15(26-27(23,24)25)8-10-20(14,2)19(16)9-11-21(17,18)3;;/h4,15-19H,5-12H2,1-3H3,(H,23,24,25);;/t15-,16-,17+,18-,19-,20-,21+;;/m0../s1

InChI key

ABFNHVDDMHKJKK-WRHGONFGSA-N

mp

192 °C (lit.)

solubility

methanol and water: 1.93 mg/mL, 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 2 mg/mL

Quality Level

100

Gene Information

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

Related Categories

Application

Pregnenolone sulfate sodium salt has been used as sigma-1 receptor (σ1R) agonist. It has also been used in the stimulation and as a ligand for transient receptor potential melastatin-3 (TRPM3).

Biochem/physiol Actions

Pregnenolone sulfate is a neurosteroid and a neuromodulator. It is involved in the stimulation of N-methyl-D-aspartate receptor (NMDA), γ-Aminobutyric acid type A (GABAA ) and α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA-kainate). It activates transient receptor potential melastatin (TRPM3) which is a calcium-permeable ion channel. It improves schizophrenia and behavioral anomalies by modulating NMDA mediated Ser/Thr kinase - glycogen synthase kinase 3 β (AKT/GSK3β) signaling pathway.

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCS6777
MKCQ8813
MKCQ6499
MKCN5558
MKCM0225

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Activation of gene transcription via CIM0216, a synthetic ligand of transient receptor potential melastatin-3 (TRPM3) channels
Rubil S and Thiel G
Channels (Austin, Tex.), 11(1), 79-83 (2017)
Pregnenolone sulphate-independent inhibition of TRPM3 channels by progesterone
Majeed Y, et al.
Cell Calcium, 51(1), 1-11 (2012)
CREB, AP-1, ternary complex factors and MAP kinases connect transient receptor potential melastatin-3 (TRPM3) channel stimulation with increased c-Fos expression
Rubil S, et al.
British Journal of Pharmacology, 173(2), 305-318 (2016)
J M Mienville et al.
Brain research, 489(1), 190-194 (1989-06-05)
Our previous study showed antagonism of GABAA receptor-mediated whole-cell currents by pregnenolone sulfate (PS). Here, the effects of PS, picrotoxin (PTX) and pentobarbital (PB) were tested on GABA-activated single Cl- channels recorded from membrane patches of rat cortical neurons in
Marie Mulier et al.
eLife, 9 (2020-09-04)
Genetic ablation or pharmacological inhibition of the heat-activated cation channel TRPM3 alleviates inflammatory heat hyperalgesia, but the underlying mechanisms are unknown. We induced unilateral inflammation of the hind paw in mice, and directly compared expression and function of TRPM3 and
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