Rac- and R-(+)-[4,4′,5,5′-2H4]-2- (1′-[2″,6″-dichlorophenoxy]-ethyl)-Δ2- imidazoline (lofexidine)

Ashish P. Vartak, Vijayakumar Sonar, Peter A. Crooks

Research output: Contribution to journalArticlepeer-review


The synthesis of the d4-forms of rac- and R-lofexidine was accomplished. Two methods are described; one method is a two-step synthesis of rac-d4-lofexidine from 2-chloropropionitrile, the second method is a three-step preparation of R-d4-lofexidine in absolute enantiomeric purity from S-methyl lactate. The commercial availability of R-methyl lactate makes this latter enantioselective synthesis applicable also to the synthesis of S-d4- lofexidine. These procedures also conserve the utilization of the relatively expensive [1,1′,2,2′-2H 4]ethylene diamine precursor. The availability of S- and R-d 4-lofexidines will enable pharmacokinetic studies to be carried out to determine if differential in vivo metabolism of the two enantiomers of lofexidine occurs.

Original languageEnglish (US)
Pages (from-to)431-434
Number of pages4
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Issue number10
StatePublished - Aug 2009


  • Deuterated
  • Enantioselective
  • Lofexidine


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