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T6031

Sigma-Aldrich

DL-Thiorphan

≥98% (TLC)

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

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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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