919797-20-9Relevant academic research and scientific papers
Synthesis of 25X-BOMes and 25X-NBOHs (X = H, I, Br) for pharmacological studies and as reference standards for forensic purposes
Alves de Barros, Wellington,Queiroz, Marcelo Pereira,da Silva Neto, Leonardo,Borges, Graziele Martins,Martins, Felipe Terra,de Fátima, ?ngelo
, (2021/01/28)
An expeditious method is reported for the synthesis of three NBOHs (25H-, 25I- and 25B-NBOH; 9–38% overall yield) and three NBOMes (25H-, 25I- and 25B-NBOMe; 7–33% overall yield) from salicylaldehyde and 2-methoxyaldehyde, respectively. The X-ray structures of 25H-, 25I- and 25B-NBOH.HCl were also determined. Our approach should provide a general entry for preparing such a class of substances for pharmacological and forensic purposes.
Synthesis and identification of metabolite biomarkers of 25C-NBOMe and 25I-NBOMe
Wu, Xiongyu,Eriksson, Caroline,Wohlfarth, Ariane,Wallgren, Jakob,Kronstrand, Robert,Josefsson, Martin,Dahlén, Johan,Konradsson, Peter
, p. 6393 - 6400 (2017/10/16)
Synthetic routes have been developed for synthesis of potential metabolites of 25C-NBOMe and 25I-NBOMe. Nine potential metabolites have been synthesized, among which compounds 8 and 20a could be used as metabolite biomarkers of 25C-NBOMe and 20b of 25I-NB
Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists
Hansen, Martin,Phonekeo, Karina,Paine, James S.,Leth-Petersen, Sebastian,Begtrup, Mikael,Br?uner-Osborne, Hans,Kristensen, Jesper L.
, p. 243 - 249 (2014/04/03)
N-Benzyl substitution of 5-HT2A receptor agonists of the phenethylamine structural class of psychedelics (such as 4-bromo-2,5- dimethoxyphenethylamine, often referred to as 2C-B) confer a significant increase in binding affinity as well as functional activity of the receptor. We have prepared a series of 48 compounds with structural variations in both the phenethylamine and N-benzyl part of the molecule to determine the effects on receptor binding affinity and functional activity at 5-HT2A and 5-HT2C receptors. The compounds generally had high affinity for the 5-HT2A receptor with 8b having the highest affinity at 0.29 nM but with several other compounds also exhibiting subnanomolar binding affinities. The functional activity of the compounds was distributed over a wider range with 1b being the most potent at 0.074 nM. Most of the compounds exhibited low to moderate selectivity (1- to 40-fold) for the 5-HT2A receptor in the binding assays, although one compound 6b showed an impressive 100-fold selectivity for the 5-HT2A receptor. In the functional assay, selectivity was generally higher with 1b being more than 400-fold selective for the 5-HT2A receptor.
High specific activity tritium-labeled N-(2-methoxybenzyl)-2,5-dimethoxy-4-iodophenethylamine (INBMeO): A high-affinity 5-HT2A receptor-selective agonist radioligand
Nichols, David E.,Frescas, Stewart P.,Chemel, Benjamin R.,Rehder, Kenneth S.,Zhong, Desong,Lewin, Anita H.
, p. 6116 - 6123 (2008/12/21)
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 K2CO3. 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 164 Ci/mmol. The new radioligand was suitable for labeling human 5-HT2A receptors in two heterologous cell lines and had about 20-fold higher affinity than [3H]ketanserin.
