Radiosynthesis and PET studies of [11C]RJR-2403, a nicotinic agonist

(E)‐N‐methyl‐4‐(3‐pyridinyl)‐3‐butene‐1‐amine (RJR‐2403, or metanicotine), a nicotinic agonist developed as a cognitive‐enhancing drug for Alzheimer's disease, was labeled with carbon‐11 using [11C]methyl iodide via a simple and efficient one‐step procedure. Regioselectivity of [11C]methylation...

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Bibliographic Details
Published in:Journal of labelled compounds & radiopharmaceuticals 2001-05, Vol.44 (6), p.425-436
Main Authors: Studenov, Andrei R., Wegner, Adam M., Ding, Yu-Shin
Format: Article
Language:English
Subjects:
[11C]metanicotine
[11C]RJR-2403
Alzheimer's disease
Biological and medical sciences
Contrast media. Radiopharmaceuticals
Medical sciences
nAChR
Pharmacology. Drug treatments
position emission tomography
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Summary:(E)‐N‐methyl‐4‐(3‐pyridinyl)‐3‐butene‐1‐amine (RJR‐2403, or metanicotine), a nicotinic agonist developed as a cognitive‐enhancing drug for Alzheimer's disease, was labeled with carbon‐11 using [11C]methyl iodide via a simple and efficient one‐step procedure. Regioselectivity of [11C]methylation on the aliphatic nitrogen versus pyridine nitrogen is strongly dependent on the reaction solvent. The reaction in acetonitrile exclusively yields aliphatic N‐[11C‐methyl]alkylation ([11C]RJR‐2403), while only a byproduct is formed when DMF is used as a solvent. Positron emission tomographic (PET) studies in baboon showed a homogeneous distribution of radioactivity within baboon brain with a slow clearance. [11C]RJR‐2403 was metabolized very rapidly as evidenced by the fact that at 2 min after intravenous injection only 50% of the total carbon‐11 in plasma is parent compound. Copyright © 2001 John Wiley & Sons, Ltd.
ISSN:0362-4803
1099-1344
DOI:10.1002/jlcr.472