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Synthesis of racemic [α‐ 11 C]amphetamine and [α‐ 11 C]phenethylamine from [ 11 C]nitroalkanes
Author(s) -
Schoeps KarlOlof,
Halldin Christer
Publication year - 1992
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.2580311108
Subject(s) - phenethylamine , chemistry , nitromethane , nitroethane , benzaldehyde , racemic mixture , enantiomer , medicinal chemistry , organic chemistry , stereochemistry , catalysis
The synthesis of racemic [α‐ 11 C]amphetamine and [α‐ 11 C]‐phenethylamine from on‐line produced [ 11 C]nitroethane and [ 11 C]nitromethane, respectively, is described. The condensations of nocarrier‐added [ 11 C]nitroalkanes with benzaldehyde to form [β‐ 11 C]β‐nitrostyrenes were investigated under basic and acidic conditions. The [β‐ 11 C]β‐nitrostyrenes were reduced with lithium aluminium hydride to produce the corresponding saturated amines. Purification was performed with semi‐preparative reversed‐phase HPLC using a Suplex pKb‐100 column. The total radiochemical yields were 7‐20% (from EOB and decaycorrected) and 24‐35% (based on [ 11 C]nitroalkanes and decay‐corrected) with a total synthesis time of 40‐55 min. The specific radioactivity of [α‐ 11 C]amphetamine and [α‐ 11 C]phenethylamine at EOS was 200‐1000 Ci/mmol (7.4‐37 GBq/μmol) with a radiochemical purity >99%.