A simple synthesis of [11C]methyl triflate

Jewett, Douglas M.

doi:10.1016/0883-2889(92)90012-4

Cited by 331 publications

(139 citation statements)

References 9 publications

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“…[ 11 C]Methyl triflate was produced by passing [ 11 C]methyl iodide through a silver triflate furnace according to Jewett's procedure (Jewett, 1992). Briefly, [ 11 C]CO 2 was bubbled into a tetrahydrofuran solution of lithium aluminum hydride.…”

Section: Radiochemistrymentioning

confidence: 99%

Modulation of Amphetamine-Induced Dopamine Release by Group II Metabotropic Glutamate Receptor Agonist LY354740 in Non-Human Primates Studied with Positron Emission Tomography

Berckel

Kegeles

Waterhouse

et al. 2005

Neuropsychopharmacol

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Pharmacological evidence suggests that schizophrenia is associated with increased stimulation of dopamine (DA) D 2 receptors. Recently, several groups have demonstrated that amphetamine-induced DA release is increased in schizophrenia, providing direct evidence for dysregulation of DA systems in this condition. In healthy volunteers, pretreatment with the noncompetitive N-methyl-D-aspartate (NMDA) antagonist ketamine increases amphetamine-induced DA release to levels similar to those observed in patients with schizophrenia. Therefore, the dysregulation of DA function observed in schizophrenia might be secondary to NMDA hypofunction. In this study, the regulation of this response by glutamate (GLU) transmission was further characterized by using a metabotropic glutamate (mGlu) receptor group II agonist to inhibit GLU transmission. The amphetamine-(0.5 mg/kg intravenously (i.v.)) induced decrease in [ 11 C]raclopride equilibrium-specific binding (V 3 00 ) was measured under control conditions and following pretreatment with the mGlu2/3 receptor agonist LY354740 (20 mg/kg i.v.) in four baboons. Amphetamine reduced [ 11 C]raclopride V 3 00 by 2877% under control conditions. Following LY354740 pretreatment, amphetamine-induced reduction in [ 11 C]raclopride V 3 00 was significantly enhanced (3577%, p ¼ 0.002). The enhancement of the amphetamine-induced reduction in [ 11 C]raclopride V 3 00 by LY354740 was not a simple additive effect, as LY354740 alone did not reduce [ 11 C]raclopride V 3 00 . In conclusion, the results of this study further document the involvement of GLU transmission in regulating the effect of amphetamine-induced DA release, and provide additional support to the hypothesis that the dysregulation of DA function revealed by the amphetamine challenge in schizophrenia might stem from a deficit in GLU transmission. Neuropsychopharmacology (2006) 31, 967-977.

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Section: Radiochemistrymentioning

confidence: 99%

Modulation of Amphetamine-Induced Dopamine Release by Group II Metabotropic Glutamate Receptor Agonist LY354740 in Non-Human Primates Studied with Positron Emission Tomography

Berckel

Kegeles

Waterhouse

et al. 2005

Neuropsychopharmacol

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“…The reaction mechanism for synthesis of compound 5 is the substitution reaction of amide; in addition, Boc is a bulky group, thus compound 5 was formed through a preferential reaction direction, and no epimers were seen in its 1 H NMR spectra. 27,28 in acetonitrile at 80 °C under basic conditions (NaH) The product was isolated by semipreparative reverse-phase (RP) high performance liquid chromatography (HPLC) with a C-18 column, and then concentrated by solid-phase extraction (SPE) with a disposable C-18 Plus Sep-Pak cartridge [29][30][31] to produce the corresponding pure radiolabeled compound […”

Section: 19mentioning

confidence: 99%

Synthesis of [11C]GSK1482160 as a new PET agent for targeting P2X7 receptor

Gao

Wang

Green

et al. 2015

Bioorganic & Medicinal Chemistry Letters

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Abstract-The authentic standards GSK1482160 and its isomer, as well as the radiolabeling precursors desmethyl-GSK1482160 and Boc-protected desmethyl-GSK1482160 were synthesized from L-pyroglutamic acid, methyl L-pyroglutamate and 2-chloro-3-(trifluoromethyl)benzylamine with overall chemical yield 27-28% in 3 steps, 58% in 4 steps, 76% in 1 step and 33% in 2 steps, respectively. [11 C]GSK1482160 was prepared from either desmethyl-GSK1482160 or Boc-protected desmethyl-GSK1482160 with [11 C]CH 3 OTf through N-[ 11 C]methylation and isolated by HPLC combined with SPE in 40-50% and 30-40% radiochemical yield, respectively, based on [ 11 C]CO 2 and decay corrected to end of bombardment (EOB). The radiochemical purity was >99%, and the specific activity at EOB was 370-1110 GBq/mol with a total synthesis time of ~40-minutes from EOB.

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“…11 C-methyl iodide was synthesized from 11 C-methane and iodine in a gas phase reaction at 720°C (12). 11 C-methyl triflate was prepared online from 11 C-methyl iodide by passing 11 C-methyl iodide through a silver triflate/graphitized carbon column, using argon gas as a carrier at 200°C (13).…”

Section: Radiosynthesis Of 11 C-orm-13070mentioning

confidence: 99%

A PET Tracer for Brain α_2C Adrenoceptors, ¹¹C-ORM-13070: Radiosynthesis and Preclinical Evaluation in Rats and Knockout Mice

et al. 2014

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We report the development of a PET tracer for α 2C adrenoceptor imaging and its preliminary preclinical evaluation. α 2C adrenoceptors in the human brain may be involved in various neuropsychiatric disorders, such as depression, schizophrenia, and neurodegenerative diseases. PET tracers are needed for imaging of this receptor system in vivo. Methods: High-specific-activity 11 C-ORM-13070 (1--(3-11 C-methoxymethylpyridin-2-yl)-piperazine) was synthesized by 11 C-methylation of O-desmethyl-ORM-13070 with 11 C-methyl triflate, which was prepared from cyclotron-produced 11 C-methane via 11 C-methyl iodide. Rats and mice were investigated in vivo with PET and ex vivo with autoradiography. The specificity of 11 C-ORM-13070 binding to α 2 adrenoceptors was demonstrated in rats pretreated with atipamezole, an α 2 adrenoceptor antagonist. The α 2C adrenoceptor selectivity of the tracer was determined by comparing tracer binding in wild-type and α 2A -and α 2AC adrenoceptor knockout (KO) mice. 11 C-ORM-13070 and its radioactive metabolites in rat plasma and brain tissue were analyzed with radio-high-performance liquid chromatography and mass spectroscopy. Human radiation dose estimates were extrapolated from rat biodistribution data. Results: The radiochemical yield, calculated from initial cyclotron-produced 11 C-methane, was 9.6% ± 2.7% (decaycorrected to end of bombardment). The specific activity of the product was 640 ± 390 GBq/μmol (decay-corrected to end of synthesis). The radiochemical purity exceeded 99% in all syntheses. The highest levels of tracer binding were observed in the striatum and olfactory tubercle of rats and control and α 2A KO mice-that is, in the brain regions known to contain the highest densities of α 2C adrenoceptors. In rats pretreated with atipamezole and in α 2AC KO mice, 11 C tracer binding in the striatum and olfactory tubercle was low, similar to that of the frontal cortex and thalamus, regions with low densities of α 2C adrenoceptors. Two radioactive metabolites were found in rat plasma, but only one of them was found in the brain; their identity was not revealed. The estimated effective radiation dose was comparable with the average exposure level in PET studies with 11 C tracers. Conclusion: An efficient method for the radiosynthesis of 11 C-ORM-13070 was developed. 11 C-ORM-13070 emerged as a potential novel radiotracer for in vivo imaging of brain α 2C adrenoceptors.

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A simple synthesis of [11C]methyl triflate

Abstract: [11C]Methyl triflate ([11C]methyl trifluoromethanesulfonate) was formed in high yield when [11C]methyl iodide in a nitrogen carrier was passed at 200 degrees C through a column containing graphitized carbon impregnated with 50% by weight of silver triflate.

Cited by 331 publications

References 9 publications

Modulation of Amphetamine-Induced Dopamine Release by Group II Metabotropic Glutamate Receptor Agonist LY354740 in Non-Human Primates Studied with Positron Emission Tomography

Modulation of Amphetamine-Induced Dopamine Release by Group II Metabotropic Glutamate Receptor Agonist LY354740 in Non-Human Primates Studied with Positron Emission Tomography

Synthesis of [11C]GSK1482160 as a new PET agent for targeting P2X7 receptor

A PET Tracer for Brain α_2C Adrenoceptors, ¹¹C-ORM-13070: Radiosynthesis and Preclinical Evaluation in Rats and Knockout Mice

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A simple synthesis of [11C]methyl triflate

Abstract: [11C]Methyl triflate ([11C]methyl trifluoromethanesulfonate) was formed in high yield when [11C]methyl iodide in a nitrogen carrier was passed at 200 degrees C through a column containing graphitized carbon impregnated with 50% by weight of silver triflate.

Cited by 331 publications

References 9 publications

Modulation of Amphetamine-Induced Dopamine Release by Group II Metabotropic Glutamate Receptor Agonist LY354740 in Non-Human Primates Studied with Positron Emission Tomography

Modulation of Amphetamine-Induced Dopamine Release by Group II Metabotropic Glutamate Receptor Agonist LY354740 in Non-Human Primates Studied with Positron Emission Tomography

Synthesis of [11C]GSK1482160 as a new PET agent for targeting P2X7 receptor

A PET Tracer for Brain α2C Adrenoceptors, 11C-ORM-13070: Radiosynthesis and Preclinical Evaluation in Rats and Knockout Mice

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A PET Tracer for Brain α_2C Adrenoceptors, ¹¹C-ORM-13070: Radiosynthesis and Preclinical Evaluation in Rats and Knockout Mice