Synthesis of 3-(C-11-methyl)-nifedipine, a potent Ca/sup ++/ channel antagonist, for positron emission tomography

Conference · Sun Jan 01 04:00:00 EST 1984 · J. Nucl. Med.; (United States)

OSTI ID:6842988

Wilson, A A; Burns, H D; Dannals, R F; Ravert, H T; Zemyan, S E; Snyder, S H; Wagner, Jr, H N

Nifedipine is a potent calcium channel blocker with therapeutic utility in cardiac disease. The authors report here the synthesis of C-11 nifedipine labeled at the methyl ester position. Model reactions showed that 5-methoxycarbonyl-2, 6-dimethyl-4-(o-nitrophenyl)-1,4-dihydropyrideine-3-carboxylic acid (1) could be methylated with CH/sub 3/I in DMF containing tetrabutylammonium hydroxide (TBAH) to produce nifedipine. Yields were essentially quantitative after 7 mins at 25/sup 0/C. C-11 CO/sub 2/, produced by a biomedical cyclotron, was chemically transformed into C-11 CH/sub 3/I and reacted with (1) in DMF containing TBAH. C-11 labeled nifedipine was isolated by preparative HPLC and the chemical and radiochemical purities were determined by analytical HPLC. Two hundred mCi of C-11 nifedipine (99% radiochemically pure) with specific activity (at end-of-synthesis) of up to 1400 mCi/..mu..mole could be obtained in 25 mins from end-of-bombardment. Radiochemical yields (from C-11 Ch/sub 3/I) were 70-80%. Large quantities of C-11 labeled nifedipine, of high specific activity, can routinely be prepared from C-11 CO/sub 2/. The authors are currently conducting biodistribution studies of this material to evaluate its usefulness as an imaging/diagnostic tool.

• Research Organization: The Johns Hopkins Medical Institutions, Baltimore, MD
• OSTI ID: 6842988
• Report Number(s): CONF-840619-
• Conference Information: Journal Name: J. Nucl. Med.; (United States) Journal Volume: 25:5
• Country of Publication: United States
• Language: English

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62 RADIOLOGY AND NUCLEAR MEDICINE
ACCELERATORS
ALKALINE EARTH METALS
ALKYL RADICALS
AMMONIUM COMPOUNDS
AMMONIUM HYDROXIDES
AZINES
BETA DECAY RADIOISOTOPES
BETA-PLUS DECAY RADIOISOTOPES
BODY
CALCIUM
CARBON 11
CARBON COMPOUNDS
CARBON DIOXIDE
CARBON ISOTOPES
CARBON OXIDES
CARBOXYLIC ACIDS
CARDIOVASCULAR DISEASES
CARDIOVASCULAR SYSTEM
CHALCOGENIDES
CHEMICAL PREPARATION
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CHROMATOGRAPHY
COMPUTERIZED TOMOGRAPHY
CYCLIC ACCELERATORS
CYCLOTRONS
DIAGNOSIS
DIAGNOSTIC TECHNIQUES
DIAGNOSTIC USES
DISEASES
ELEMENTS
EMISSION COMPUTED TOMOGRAPHY
ESTERS
EVEN-ODD NUCLEI
HALOGENATED ALIPHATIC HYDROCARBONS
HEART
HETEROCYCLIC COMPOUNDS
HYDROGEN COMPOUNDS
HYDROXIDES
IMAGE PROCESSING
IODINATED ALIPHATIC HYDROCARBONS
ISOTOPES
LABELLING
LIGHT NUCLEI
LIQUID COLUMN CHROMATOGRAPHY
METALS
METHYL IODIDE
METHYL RADICALS
METHYLATION
MINUTES LIVING RADIOISOTOPES
NUCLEI
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC IODINE COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANS
OXIDES
OXYGEN COMPOUNDS
POSITRON COMPUTED TOMOGRAPHY
PROCESSING
PYRIDINES
QUANTITY RATIO
RADICALS
RADIOISOTOPES
RADIONUCLIDE KINETICS
SEPARATION PROCESSES
SYNTHESIS
THERAPEUTIC USES
TOMOGRAPHY
USES
YIELDS