Identification of a Bioactive Impurity in a Commercial Sample of 6‐Methyl‐2‐ p ‐Tolylaminobenzo[ d ][1,3]Oxazin‐4‐One (URB754) | Zendy

Tarzia Giorgio | Zendy; Antonietti Francesca | Zendy; Duranti Andrea | Zendy; Tontini Andrea | Zendy; Mor Marco | Zendy; Rivara Silvia | Zendy; Traldi Pietro | Zendy; Astarita Giuseppe | Zendy; King Alvin | Zendy; Clapper Jason R. | Zendy; Piomelli Daniele | Zendy

Open Access

Identification of a Bioactive Impurity in a Commercial Sample of 6‐Methyl‐2‐ p ‐Tolylaminobenzo[ d ][1,3]Oxazin‐4‐One (URB754)

Author(s) -

Tarzia Giorgio,

Antonietti Francesca,

Duranti Andrea,

Tontini Andrea,

Mor Marco,

Rivara Silvia,

Traldi Pietro,

Astarita Giuseppe,

King Alvin,

Clapper Jason R.,

Piomelli Daniele

Publication year - 2007

Publication title -

annali di chimica

Language(s) - English

Resource type - Journals

eISSN - 1612-8877

pISSN - 0003-4592

DOI - 10.1002/adic.200790073

Subject(s) - monoacylglycerol lipase , chemistry , enzyme , impurity , high performance liquid chromatography , endocannabinoid system , stereochemistry , chromatography , combinatorial chemistry , biochemistry , organic chemistry , receptor

The compound URB754 was recently identified as a potent inhibitor of the endocannabinoid‐deactivating enzyme monoacylglycerol lipase (MGL) by screening of a commercial chemical library. Based on HPLC/MS, NMR and EI/MS analyses, the present paper shows that the MGL‐inhibitory activity attributed to URB754 is in fact due to a chemical impurity present in the commercial sample, identified as bis(methylthio)mercurane. Although this organomercurial compound is highly potent at inhibiting MGL (IC 50 = 11.9±1.1 nM), its biological use is prohibited by its toxicity and target promiscuity.

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