An internal standard for the quantification of thiorphan
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Unlabeled Version(s)
15600Thiorphan
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Thiorphan-d5

Item No. 28692

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3-mercapto-2-((phenyl-d5)methyl)propanoyl)glycine
CAS Number
2183240-70-0
Molecular Formula
C12H10D5NO3S
Formula Weight
258.3
Purity
≥99% deuterated forms (d1-d5)
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: solubleMethanol: soluble
SMILES
O=C(NCC(O)=O)C(CS)CC1=C([2H])C([2H])=C([2H])C([2H])=C1[2H]
InChi Code
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)/i1D,2D,3D,4D,5D
InChi Key
LJJKNPQAGWVLDQ-RALIUCGRSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $464

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    Product Description

    Thiorphan-d5 is intended for use as an internal standard for the quantification of thiorphan (Item No. 15600) by GC- or LC-MS. Thiorphan is an inhibitor of neprilysin (NEP; IC50 = 0.007 µM).1 It selectivity inhibits NEP over NEP2 (IC50 = 22 µM), as well as angiotensin-converting enzyme (ACE) and endothelin-converting enzyme 1 (ECE1; Kis = >0.1 and >10 µM, respectively, in cell-free assays).1,2 Thiorphan (10 µM) increases bradykinin-induced relaxation of isolated porcine coronary artery rings precontracted with potassium chloride under hypoxic, but not normoxic, conditions.3 Thiorphan reduces increases in gastric acid output induced by pentagastrin (Item No. 28546) by 64% in rats when administered intracerebroventricularly at a dose of 50 µg, but not when administered intravenously at doses of 1.7 and 17 mg/kg.4 Thiorphan (2 mg/ml, i.c.v.) increases cortical levels of insoluble amyloid-β (1-40) (Aβ40) and decreases time spent in the platform quadrant in the Morris water maze, indicating impaired reference memory, in rats.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Whyteside, A.R., and Turner, A.J. Human neprilysin-2 (NEP2) and NEP display distinct subcellular localisations and substrate preferences. FEBS Lett. 582(16), 2382-2386 (2008).

    2. Inguimbert, N., Coric, P., Poras, H., et al. Toward an optimal joint recognition of the S1' subsites of endothelin converting enzyme-1 (ECE-1), angiotensin converting enzyme (ACE), and neutral endopeptidase (NEP). J. Med. Chem. 45(7), 1477-1486 (2002).

    3. Krassói, I., Pataricza, J., and Papp, J.G. Thiorphan enhances bradykinin-induced vascular relaxation in hypoxic/hyperkalaemic porcine coronary artery. J. Pharm. Pharmacol. 55(3), 339-345 (2003).

    4. Chicau-Chover, M., Dubrasquet, M., Chariot, J., et al. Thiorphan and acetorphan inhibit gastric secretion by a central, non-opioid mechanism in the rat. Eur. J. Pharmacol. 154(3), 247-254 (1998).

    5. Mouri, A., Zou, L.B., Iwata, N., et al. Inhibition of neprilysin by thiorphan (i.c.v.) causes an accumulation of amyloid β and impairment of learning and memory. Behav. Brain Res. 168(1), 83-91 (2006).