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Merck
CN

T6031

DL-Thiorphan

≥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
Beilstein:
4872101
MDL number:
MFCD00058435
UNSPSC Code:
12352200
PubChem Substance ID:
24278747
NACRES:
NA.77

Key Documents

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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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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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000483764
0000483764
0000423820
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)
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)
Thiorphan, a neutral endopeptidase inhibitor used for diarrhoea, is neuroprotective in newborn mice
Medja F, et al.
Brain, 129(12), 3209-3223 (2006)
The enkephalinase inhibitor thiorphan shows antinociceptive activity in mice
Roques BP, et al.
Nature, 288(5788), 286-288 (1980)
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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