Synthesis of 25X-BOMes and 25X-NBOHs (X = H, I, Br) for pharmacological studies and as reference standards for forensic purposes
Wellington Alves de Barros, Marcelo P. Queiroz, L. D. da Silva, Graziele Martins Borges, F. Martins, Ângelo de Fátima
January 11, 2021 DOI: 10.1016/j.tetlet.2020.152804 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Theoretical or philosophical paper |
|---|---|
| Key points | Reports a rapid synthesis of three NBOH compounds (9–38% overall yield) from salicylaldehyde and three NBOMe compounds (7–33% overall yield) from 2-methoxyaldehyde, with X-ray structures determined for 25H-, 25I- and 25B-NBOH hydrochloride salts. The authors propose the route as a general entry for preparing such substances for pharmacological and forensic purposes. |
Abstract
Abstract 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.
Citations in the library
Cited by 7
- Discovery of β-Arrestin-Biased 25CN-NBOH-Derived 5-HT2A Receptor Agonists. Journal of Medicinal Chemistry September 22, 2022
- Psychoactive substances 25H-NBOMe and 25H-NBOH induce antidepressant-like behavior in male rats. European Journal of Pharmacology September 15, 2023
- Neurotoxic effects of hallucinogenic drugs 25H-NBOMe and 25H-NBOH in organotypic hippocampal cultures Heliyon June 27, 2023
- Locomotor and discriminative stimulus effects of NBOH hallucinogens in rodents. Behavioural Pharmacology December 6, 2024
- Does Conformation Affect the Analytical Response? A Structural and Infrared Spectral Evaluation of Phenethylamines (2C-H, 25H-NBOH, and 25I-NBOMe) Using In Silico Methodology Psychoactives February 25, 2024
and 2 more in the library
Cites 8
- 25C-NBOMe--new potent hallucinogenic substance identified on the drug market. Forensic Science International April 10, 2013
- Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists. ACS Chemical Neuroscience March 19, 2014
- 25C-NBOMe: preliminary data on pharmacology, psychoactive effects, and toxicity of a new potent and dangerous hallucinogenic drug BioMed Research International 2014
- “My Friend Said it was Good LSD”: A Suicide Attempt Following Analytically Confirmed 25I-NBOMe Ingestion Journal of Psychoactive Drugs October 20, 2014
- A Case Review of the First Analytically Confirmed 25I-NBOMe-Related Death in Washington State. Journal of Analytical Toxicology October 1, 2015
and 3 more in the library