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T6031

DL-Thiorphan

Name: <SC>DL</SC>-Thiorphan
Brand: SIGMA

≥98% (TLC), Enkephalinase inhibitor., powder

Synonym(s):

(±)-N-(3-Mercapto-2-benzylpropionyl)glycine, DL-3-Mercapto-2-benzylpropanoylglycine

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About This Item

Empirical Formula (Hill Notation):

C₁₂H₁₅NO₃S

CAS Number:

76721-89-6

Molecular Weight:

253.32

NACRES:

NA.77

PubChem Substance ID:

24278747

UNSPSC Code:

12352200

MDL number:

MFCD00058435

Beilstein/REAXYS Number:

4872101

Assay:

≥98% (TLC)

Form:

powder

Quality level:

200

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Product Name

DL-Thiorphan, ≥98% (TLC)

Quality Level

200

assay

≥98% (TLC)

form

powder

mp

138 °C

solubility

ethanol: soluble 49.00-51.00 mg/mL, clear, colorless

SMILES string

OC(=O)CNC(=O)C(CS)Cc1ccccc1

InChI

1S/C12H15NO3S/c14-11(15)7-13-12(16)10(8-17)6-9-4-2-1-3-5-9/h1-5,10,17H,6-8H2,(H,13,16)(H,14,15)

InChI key

LJJKNPQAGWVLDQ-UHFFFAOYSA-N

Gene Information

human ... ACE(1636), ECE1(1889)
rat ... Ace(24310), Mme(24590)

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Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

General description

Thiorphan, also called DL-mercapto-2-benzylpropanoyl-glycine is a specific and potent inhibitor of enkephalinase in nanomolar concentrations. It is an inhibitor of neutral endopeptidase. It interacts with cluster of differentiation 10 (CD10) in bone marrow cells and may modulate hematopoiesis. Thiorphan is a safe drugprescribed for diarrhea. It prevents cortical damage in newborn mice and is a potent agent for treating cerebral palsy.(CP)

Application

DL-Thiorphan has been used to evaluate the activity of NEP-dependent neutral endopeptidase. DL-Thiorphan has also been used for determining NEP enzymatic activity using fluorimetric assays.

Biochem/physiol Actions

Enkephalinase inhibitor.

Features and Benefits

This compound is featured on the Neuropeptidases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Preparation Note

DL-Thiorphan is soluble in ethanol at 49.00 - 51.00 mg/ml and yields a clear, colorless solution.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number

0000483764

0000423820

0000358457

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Global brain delivery of neprilysin gene by intravascular administration of AAV vector in mice

Iwate N, et al.

Scientific Reports (2013)

Thiorphan, a neutral endopeptidase inhibitor used for diarrhoea, is neuroprotective in newborn mice

Medja F, et al.

Brain, 129(12), 3209-3223 (2006)

Methionine enkephalin suppresses metabolic activity of a leukemic cell line (NALM-1) and enhances CD10 expression

Martin-Kleiner I, et al.

International Immunopharmacology, 3, 707-711 (2003)

The enkephalinase inhibitor thiorphan shows antinociceptive activity in mice

Roques BP, et al.

Nature, 288(5788), 286-288 (1980)

Plasma kallikrein-kinin system contributes to peripheral inflammation in temporal lobe epilepsy.

Priscila S R Simões et al.

Journal of neurochemistry, 150(3), 296-311 (2019-06-18)

Temporal lobe epilepsy (TLE) is a chronic disease, characterized by severe and refractory seizures, triggered in the hippocampus and/or amygdala, disrupting the blood-brain barrier. This disruption can sustain, or aggravate, the epileptic condition. The aim of this study was to

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Global Trade Item Number

SKU	GTIN
T6031-5MG	04061832949963
T6031-25MG	04061832949956

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