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Merck

P162

Sigma-Aldrich

Pregnenolone sulfate sodium salt

Sinónimos:

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

Fórmula empírica (notación de Hill):
C21H31NaO5S
Peso molecular:
418.52
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

form

powder

mp

192 °C (lit.)

solubility

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

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

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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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Visite la Librería de documentos

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)
Ligands exert Biased Activity to regulate Sigma 1 Receptor interactions with cationic TRPA1, TRPV1 and TRPM8 channels
Cortes-Montero E, et al.
Frontiers in Pharmacology, 10(3), 634-634 (2019)
Pregnenolone sulfate normalizes schizophrenia-like behaviors in dopamine transporter knockout mice through the AKT/GSK3beta pathway
Wong P, et al.
Translational Psychiatry, 5(3), e528-e528 (2015)
Pregnenolone sulfate as a modulator of synaptic plasticity
Smith CC, et al.
Psychopharmacology, 231(17), 3537-3556 (2014)
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)

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