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11 C‐radiolabeling of hallucinogenic psilocin, a potential radioligand for studying the role of serotonin receptors in psychotic symptom formation
Author(s) -
Ametamey S.,
Vollenweider F. X.,
Patt J.,
Bourquin D.,
Hasler F.,
Beer H.F.,
Schubiger P. A.
Publication year - 1998
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/(sici)1099-1344(199807)41:7<585::aid-jlcr115>3.0.co;2-u
Subject(s) - chemistry , radiosynthesis , hallucinogen , radioligand , desmethyl , serotonin , tryptamine , stereochemistry , radiochemistry , receptor , pharmacology , biochemistry , psychology , metabolite , positron emission tomography , neuroscience , medicine
The desmethyl compound, 4‐hydroxy‐N‐methyltryptamine ( 4 ), was synthesized via a four‐step reaction sequence starting from 4‐benzyloxyindole ( 1 ). Psilocin (4‐hydroxy‐N,N‐dimethyltryptamine), an indole hallucinogen, was labeled by N‐monomethylation of the side chain using the classical methylating agent [ 11 C]CH 3 I in 20±5% (decay corrected from [ 11 C]CH 3 I) radiochemical yield. Specific activities obtained ranged from 900‐2300Ci/mmol at EOS (end of synthesis). The radiosynthesis, semi‐preparative HPLC and formulation were completed in an average time of 45 minutes. © 1998 John Wiley & Sons, Ltd.