^abcdefghTrachsel D, Lehmann D, Enzensperger C (2013).Phenethylamine Von der Struktur zur Funktion. Nachtschatten Verlag AG. pp. 705,708–710,716–718, 723,736–737.ISBN978-3-03788-700-4.
^abcdefghTrachsel D (2012). "Fluorine in psychedelic phenethylamines".Drug Testing and Analysis.4 (7–8):577–590.doi:10.1002/dta.413.PMID22374819.Difluoromescaline (72) and trifluoromescaline (73) increasingly surpassed human potency and duration of mescaline (22) effects. [...] Among numerous modifications of the 4-position,[3,86] 4-fluoroalkoxy derivatives have been prepared and investigated (Figure 5).[86] The smallest investigated fluoro analogs of mescaline (22: 180–360 mg, 10–12 h), namely difluoromescaline (72: 50–100 mg, 12–18 h) and trifluoromescaline (73: 15–40 mg, 14– 24 h) proved to show psychedelic properties, with 73 being one of the most potent mescaline derivatives so far discovered. At least for 72 (Ki= 5949nM) the affinity at the antagonistic [3 H]ketanserinlabelled serotonin h5-HT2A receptor was determined, which was not significantly different from mescaline (22. Ki= 5500nM[85]). As observed with escaline (70),[85] affinity alone cannot explain increased in vivo activity. The long lasting effects of 72 and 73 could also result from enhanced metabolic stabilities as a consequence of fluorination. [...] A total number of 14 fluorinated mescaline analogs/homologs have been described (72, 73, 75–78, 80–82, 84, 86–89; 3,4,5-series). The simplest analogs, difluoromescaline (72: 50–100 mg, 12–18 h) as well as trifluoromescaline (73: 15–40 mg, 14–24 h) have proven to be more potent and showed distinctly longer duration of action in humans when compared to mescaline (22: 180–360 mg, 10–12 h).
^abcdefghiKolaczynska KE, Luethi D, Trachsel D, Hoener MC, Liechti ME (2021)."Receptor Interaction Profiles of 4-Alkoxy-3,5-Dimethoxy-Phenethylamines (Mescaline Derivatives) and Related Amphetamines".Frontiers in Pharmacology.12 794254.doi:10.3389/fphar.2021.794254.PMC8865417.PMID35222010.Introduction of fluorinated alkyloxy groups onto the 4-position of mescaline (5) has also led to derivatives with increased human potency when compared to 5 (Figure 2). These derivatives include difluoromescaline (DFM; 12) and trifluromescaline (TFM; 13), which have a 4-fold and > 9-fold increase in human potency, respectively. Both substances induce strong psychedelic effects and have significantly longer lasting effects than mescaline, with 13 being among the most potent mescaline-based derivatives synthesized to date (Trachsel 2012).
Notes: (1) TAAR1 activity of ligands varies significantly between species. Some agents that are TAAR1 ligands in some species are not in other species. This navbox includes all TAAR1 ligands regardless of species. (2) See the individual pages for references, as well as theList of trace amines,TAAR, andTAAR1 pages. See also:Receptor/signaling modulators
