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Synthesis of 123 I‐labelled 4‐iodo‐2, 5‐dimethoxyphenylisopropylamine
Author(s) -
Braun Gisela,
Shulgin Alexander T.,
Sargent Thornton
Publication year - 1978
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.2580140515
Subject(s) - chemistry , phthalimide , iodine monochloride , moiety , yield (engineering) , hydrazine (antidepressant) , amine gas treating , hydrochloride , medicinal chemistry , iodine , chemical synthesis , organic chemistry , radiochemistry , chromatography , materials science , metallurgy , biochemistry , in vitro
A rapid and convenient synthesis of the psychotomimetic agent 4‐iodo‐2, 5‐dimethoxyphenylisopropylamine is described, incorporating the radioisotope 123 I (T 1/2 13 hr). With the amine function of 2, 5‐dimethoxyphenylisopropylamine blocked as the phthalimide, it was found that the aromatic 4‐position could be directly iodinated with iodine monochloride. The phthalic acid moiety was rapidly removed with hydrazine in butanol to provide the title compound, as the hydrochloride salt, in an overall yield of 10% and in a reaction time of less than one half‐life.