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±threo-Ritalinic acid-D10 Hydrochloride an internal standard for quantitation of Ritalinic acid by LCMSMS: Synthesis determination of isotopic distribution by qNMR and LCMS

Authors: Elizabeth B. Marek, Joshua Cooper, Huahua Jian, Uma Sreenivasan, Isil Dilek
Presented at Mass Spectrometry Application to the Clinical Lab (MSACL), San Diego, CA, January 2012

Abstract
As a major metabolite of methylphenidate (1, Ritalin), -threo-Ritalinicacid (2) is of clinical relevance. To this end -threo-ritalinicacid-D10HCl(3) was synthesized in seven steps with a purity of 99% and an isotopic purity ratio of D0/D10= 0% and a significant amount of the D9-D7isomers. Because practical ion monitoring is based on the ratio of D0/D10, the standard was found to be suitable for use as an internal standard in LC-MS/MS analysis of ritalinicacid and related compounds. The presence of significant amounts of the D9isomer prompted extensive structure elucidation work using LC-MS/MS scrambling and 1D, 2D, and qNMRtechniques.

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