Literature DB >> 18468904

High specific activity tritium-labeled N-(2-methoxybenzyl)-2,5-dimethoxy-4-iodophenethylamine (INBMeO): a high-affinity 5-HT2A receptor-selective agonist radioligand.

David E Nichols1, Stewart P Frescas, Benjamin R Chemel, Kenneth S Rehder, Desong Zhong, Anita H Lewin.   

Abstract

The title compound ([3H]INBMeO) was prepared by an O,O-dimethylation reaction of a t-BOC protected diphenolic precursor using no carrier added tritiated iodomethane in DMF with K(2)CO(3). Removal of the t-BOC protecting group and purification by HPLC afforded an overall yield of 43%, with a radiochemical purity of 99% and specific activity of 164Ci/mmol. The new radioligand was suitable for labeling human 5-HT(2A) receptors in two heterologous cell lines and had about 20-fold higher affinity than [(3)H]ketanserin.

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Year:  2008        PMID： 18468904      PMCID： PMC2719953          DOI： 10.1016/j.bmc.2008.04.050

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN： 0968-0896            Impact factor:   3.641


  18 in total

1.  The physiological role of 5-HT2A receptors in working memory.

Authors:  Graham V Williams; Srinivas G Rao; Patricia S Goldman-Rakic
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2.  Chiral Ru-based complexes for asymmetric olefin metathesis: enhancement of catalyst activity through steric and electronic modifications.

Authors:  Joshua J Van Veldhuizen; Dennis G Gillingham; Steven B Garber; Osamu Kataoka; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2003-10-15       Impact factor: 15.419

3.  Molecular interaction of serotonin 5-HT2A receptor residues Phe339(6.51) and Phe340(6.52) with superpotent N-benzyl phenethylamine agonists.

Authors:  Michael R Braden; Jason C Parrish; John C Naylor; David E Nichols
Journal:  Mol Pharmacol       Date:  2006-09-25       Impact factor: 4.436

4.  Localization of 5-HT2A receptor in rat cerebral cortex and olfactory system revealed by immunohistochemistry using two antibodies raised in rabbit and chicken.

Authors:  S Hamada; K Senzaki; K Hamaguchi-Hamada; K Tabuchi; H Yamamoto; T Yamamoto; S Yoshikawa; H Okano; N Okado
Journal:  Brain Res Mol Brain Res       Date:  1998-03-01

5.  Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, -HT(2B) and 5-HT2C receptors.

Authors:  D L Nelson; V L Lucaites; D B Wainscott; R A Glennon
Journal:  Naunyn Schmiedebergs Arch Pharmacol       Date:  1999-01       Impact factor: 3.000

6.  Binding to the serotonin 5-HT2 receptor by the enantiomers of 125I-DOI.

Authors:  M P Johnson; A J Hoffman; D E Nichols; C A Mathis
Journal:  Neuropharmacology       Date:  1987-12       Impact factor: 5.250

7.  Differential phospholipase C activation by phenylalkylamine serotonin 5-HT 2A receptor agonists.

Authors:  Jason C Parrish; Michael R Braden; Emily Gundy; David E Nichols
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8.  Physiological antagonism between 5-hydroxytryptamine(2A) and group II metabotropic glutamate receptors in prefrontal cortex.

Authors:  G J Marek; R A Wright; D D Schoepp; J A Monn; G K Aghajanian
Journal:  J Pharmacol Exp Ther       Date:  2000-01       Impact factor: 4.030

9.  Synthesis and pharmacological characterization of a series of geometrically constrained 5-HT(2A/2C) receptor ligands.

Authors:  James J Chambers; Jason C Parrish; Niels H Jensen; Deborah M Kurrasch-Orbaugh; Danuta Marona-Lewicka; David E Nichols
Journal:  J Med Chem       Date:  2003-07-31       Impact factor: 7.446

10.  Establishment of a cellular assay system for G protein-linked receptors: coupling of human NK2 and 5-HT2 receptors to phospholipase C activates a luciferase reporter gene.

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  16 in total

Review 1.  PET tracers for serotonin receptors and their applications.

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2.  Effects of the hallucinogen 2,5-dimethoxy-4-iodophenethylamine (2C-I) and superpotent N-benzyl derivatives on the head twitch response.

Authors:  Adam L Halberstadt; Mark A Geyer
Journal:  Neuropharmacology       Date:  2013-09-04       Impact factor: 5.250

3.  Determination of 4-bromo-2,5-dimethoxy-N-[(2-methoxyphenyl)methyl]-benzeneethanamine (25B-NBOMe) in serum and urine by high performance liquid chromatography with tandem mass spectrometry in a case of severe intoxication.

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4.  Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT (2A) agonist PET tracers.

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Journal:  Eur J Nucl Med Mol Imaging       Date:  2010-12-21       Impact factor: 9.236

5.  Serotonergic Psychedelics: Experimental Approaches for Assessing Mechanisms of Action.

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Journal:  Handb Exp Pharmacol       Date:  2018

6.  Evolution of the NBOMes: 25C- and 25B- Sold as 25I-NBOMe.

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Journal:  J Med Toxicol       Date:  2015-06

7.  Postmortem detection of 25I-NBOMe [2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine] in fluids and tissues determined by high performance liquid chromatography with tandem mass spectrometry from a traumatic death.

Authors:  Justin L Poklis; Kelly G Devers; Elise F Arbefeville; Julia M Pearson; Eric Houston; Alphonse Poklis
Journal:  Forensic Sci Int       Date:  2013-10-18       Impact factor: 2.395

8.  Synthesis and in vitro evaluation of [18F]FECIMBI-36: A potential agonist PET ligand for 5-HT2A/2C receptors.

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9.  A case of 25I-NBOMe (25-I) intoxication: a new potent 5-HT2A agonist designer drug.

Authors:  S Rutherfoord Rose; Justin L Poklis; Alphonse Poklis
Journal:  Clin Toxicol (Phila)       Date:  2013-03       Impact factor: 4.467

10.  2-(4-Iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine (25I-NBOMe): clinical case with unique confirmatory testing.

Authors:  Samuel J Stellpflug; Samantha E Kealey; Cullen B Hegarty; Gregory C Janis
Journal:  J Med Toxicol       Date:  2014-03
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