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Radiosynthesis of a photoaffinity probe for the cocaine receptor of the dopamine transporter: 3β‐( p ‐chlorophenyl)tropan‐2β‐carboxylic acid m ‐([ 125 I]‐iodo)‐ p ‐azidophenethyl ester ([ 125 I]‐RTI‐82)
Author(s) -
Lever John R.,
Carroll F. Ivy,
Patel Amrat,
Abraham Philip,
Boja John,
Lewin Anita,
Lew Robert
Publication year - 1993
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580331207
Subject(s) - chemistry , radiosynthesis , tropane , sodium azide , dopamine transporter , azide , electrophile , aniline , sodium , high performance liquid chromatography , transporter , stereochemistry , chromatography , organic chemistry , biochemistry , microbiology and biotechnology , in vivo , gene , biology , catalysis
The tropane alkaloid RTI‐82, an iodoarylazide, has been labeled with iodine‐125 for use as a photoaffinity probe for the cocaine binding site of the dopamine transporter. The one‐flask radiosynthesis involves nocarrier‐added electrophilic radioiodination of the corresponding aniline followed by diazotization and treatment with sodium azide. Isolation by reverse phase HPLC and solid phase extraction gives [ 125 I]‐RTI‐82 in good yield (76 ± 7%, n=6), high radiochemical purity (>99.8%), and high specific radioactivity (1490 ‐ 1880 mCi/μmol).