Synthesis and affinity of a possible byproduct of electrophilic radiolabeling of [123I]IBZM.
The iodobenzamide neuroleptic analogue (S)-N-(1-ethylpyrrolidin-2-ylmethyl)-2-hydroxy-5-iodo-6-methoxybenzamide (5-IBZM) was synthesized stereospecifically and its pharmacological properties were compared with the 3-iodo isomer (IBZM) used for imaging D(2) receptors in vivo. The isomer 5-IBZM had 100-fold lower affinity than IBZM and migrated with similar retention time as the byproduct formed during electrophilic iodination of BZM.
Baldwin
Ronald M
RM
Department of Psychiatry, Yale University and VA CT/HCS, West Haven, CT 06516, USA.
Fu
Xing
X
Kula
Nora S
NS
Baldessarini
Ross J
RJ
Amici
Louis
L
Innis
Robert B
RB
Tamagnan
Gilles D
GD
D001549:Benzamides / Q000138:chemical synthesis* / Q000493:pharmacokinetics; D007202:Indicators and Reagents; D007457:Iodine Radioisotopes; D007553:Isotope Labeling / Q000379:methods; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000493:pharmacokinetics; D013329:Structure-Activity Relationship
D001549:Benzamides; D007202:Indicators and Reagents; D007457:Iodine Radioisotopes; D011759:Pyrrolidines; C055743:3-iodo-2-hydroxy-6-methoxy-N-((1-ethyl-2-pyrrolidinyl)methyl)benzamide