Daniel Trachsel
Daniel Trachsel is a Swiss medicinal chemist who studied at the Burgdorf University of Applied Sciences and is head of chemistry at ReseaChem GmbH in Burgdorf. From 2002 onward he published a series of papers in Helvetica Chimica Acta and Chemistry & Biodiversity describing new 4-substituted mescaline analogues (the "scalines"), 4-thio-substituted 2C-T compounds, and fluorinated phenethylamines; fluorine chemistry is the thread running through most of his work. He is the author of Psychedelische Chemie (2000) and, with David Lehmann and Christoph Enzensperger, of Phenethylamine: von der Struktur zur Funktion (2013), a reference work that also records dose and effect data supplied to him by others. Unlike Alexander Shulgin, to whom he is often compared, he has publicly distanced himself from self-experimentation, and much of his later output is collaborative pharmacology with Matthias Liechti's group in Basel rather than solo synthesis.
Compounds
37 credited across 2 classes · 34 with a page here
- Methylenedioxyphenethylamines
- DFMDA C10H11F2NO2 first synthesis, 2006 source
3,4-(difluoromethylenedioxy)amphetamine, from Trachsel, Hadorn & Baumberger, Chem. Biodivers. 3:326 (2006). The fluorines were intended to block the metabolic route thought to generate MDMA's neurotoxic metabolites. He found it inactive in humans up to 250 mg orally.
- DFMDMA (F2-MDMA) first synthesis, 2006 source
The N-methyl counterpart of DFMDA, same 2006 paper. Reported inactive up to 120 mg orally.
- Psychedelic Phenethylamines
- 3C-AL C14H21NO3 first synthesis, 2002 source
Named by Shulgin in PiHKAL (1991) but never synthesised or tested by him; Trachsel made it in 2002 and reported its human properties in the 2013 book. Included in the 2021 Basel receptor-profiling series.
- 3C-DFE C13H19F2NO3 first synthesis, 2002 source
Alpha-methyl homologue of difluoroescaline; Helvetica Chimica Acta 85:3019 (2002).
- 3C-FE C13H20FNO3 first synthesis, 2002 source
The amphetamine (alpha-methyl) homologue of fluoroescaline; Helvetica Chimica Acta 85:3019 (2002). Reported inactive up to 24 mg orally.
- 3C-FP C14H22FNO3 first synthesis, 2002 source
Alpha-methyl homologue of fluoroproscaline; Helvetica Chimica Acta 85:3019 (2002). Pharmacology re-examined by Trachsel and colleagues in 2021.
- 3C-MAL C15H23NO3 first synthesis, 2002 source
Alpha-methyl homologue of methallylescaline; first described by Trachsel in 2002. Never tested in humans, so this is a synthesis-and-characterisation claim only.
- 3C-TFE C13H18F3NO3 first synthesis, 2002 source
Alpha-methyl homologue of trifluoroescaline; first described by Trachsel in the 2002 Helvetica paper. Not part of the 2021 receptor-profiling set, so the attribution rests on that paper plus his 2013 book.
- Difluoroescaline C12H17F2NO3 first synthesis, 2002 source
4-(2,2-difluoroethoxy)-3,5-dimethoxyphenethylamine; Helvetica Chimica Acta 85:3019 (2002).
- Fluoroescaline C12H18FNO3 first synthesis, 2002 source
4-(2-fluoroethoxy)-3,5-dimethoxyphenethylamine, from his first Helvetica Chimica Acta paper on 4-substituted mescaline derivatives (85:3019, 2002). The 2021 Frontiers pharmacology paper states the compound was 'synthesized as previously described (… Trachsel 2002 …)' and supplied by ReseaChem.
- Fluoroproscaline C13H20FNO3 first synthesis, 2002 source
4-(3-fluoropropoxy)-3,5-dimethoxyphenethylamine; Helvetica Chimica Acta 85:3019 (2002).
- Isobuscaline C14H23NO3 first synthesis, 2002 source
4-isobutoxy-3,5-dimethoxyphenethylamine. Described by Trachsel in the 2002 Helvetica paper; sources say 'described', not explicitly 'first synthesised', so the first-synthesis role is inferred from the paper being the first report.
- Trifluoroescaline C12H16F3NO3 first synthesis, 2002 source
4-(2,2,2-trifluoroethoxy)-3,5-dimethoxyphenethylamine; Helvetica Chimica Acta 85:3019 (2002).
- 2C-T-16 C13H19NO2S first synthesis, 2003 source
Shulgin named 2C-T-16 in PiHKAL (1991) and got as far as the nitrostyrene intermediate but never completed the synthesis; Trachsel completed it and reported human data (10–25 mg, 4–6 h). From Helvetica Chimica Acta 86:2610 (2003), the paper of twelve novel 4-thio-substituted 2,5-dimethoxyphenethylamines.
- 2C-T-22 C12H16F3NO2S first synthesis, 2003 source
4-(2,2,2-trifluoroethylthio) analogue. Mentioned by Shulgin inside the 2C-T-21 entry of PiHKAL (1991), but he only partially completed the synthesis and never tested it; Trachsel completed the synthesis in 2003 and he and colleagues defined its human properties in 2013.
- 2C-T-25 C14H23NO2S first synthesis, 2003 source
4-isobutylthio analogue; first described by Trachsel in 2003, reported inactive up to 30 mg orally. Receptor profile published with the Basel group in 2018.
- 2C-T-27 C17H21NO2S first synthesis, 2003 source
4-benzylthio analogue; first synthesised and described by Trachsel in 2003. Later found to have the highest 5-HT2A affinity of any 2C drug measured (Ki 1.6 nM) but low efficacy.
- 2C-T-30 C14H22FNO2S first synthesis, 2003 source
Also called 2C-T-FB, the 4-(4-fluorobutylthio) analogue; first described by Trachsel in 2003. Not clearly active at the doses he tried.
- 2C-T-31 C18H20F3NO2S first synthesis, 2003 source
4-(4-trifluoromethylbenzylthio) analogue; first described by Trachsel in 2003. No human data.
- 2C-T-33 C18H23NO3S first synthesis, 2003 source
4-(3-methoxybenzylthio) analogue; first synthesised and described by Trachsel in 2003. Never tested in humans; later shown to be a low-efficacy 5-HT2A partial agonist that does not produce the head-twitch response.
- 2C-YN C12H15NO2 first synthesis, 2003 source
4-ethynyl-2,5-dimethoxyphenethylamine. The third paper in his Helvetica structure–activity series is titled after this compound (Helv. Chim. Acta 86:2754, 2003). He reports ~50 mg orally, ~2 h, mild effects.
- DOYN C13H17NO2 first synthesis, 2003 source
4-ethynyl-2,5-dimethoxyamphetamine, the alpha-methyl homologue of 2C-YN. First mentioned by Trachsel in 2003 alongside the 2C-YN paper and described in depth by him in 2013 (2–6 mg, 10–15 h).
- 2C-V C12H17NO2 first synthesis, 2006 source
4-ethenyl-2,5-dimethoxyphenethylamine, reported at 25 mg / ~5 h. Described as 'first synthesised by Daniel Trachsel and colleagues in 2006', but the only source given is his 2013 book — the 2006 date is not independently confirmed and his 2006 journal paper is about fluorinated MDA analogues, not this compound.
- 2C-BI-8 first synthesis, 2009 source
The 4'-methoxy derivative of 2C-Ph, from the same 2009 paper; among the most potent and efficacious of the 2C-BI series at 5-HT2A (Ki 19 nM).
- 2C-Ph C16H19NO2 first synthesis, 2009 source
2,5-dimethoxy-4-phenylphenethylamine, from Trachsel, Nichols, Kidd, Hadorn & Baumberger, Chem. Biodivers. 6:692 (2009) — the Suzuki-coupling 4-aryl series, designated 2C-BI-1 to 2C-BI-12. This is the paper David Nichols refers to when he says he and Trachsel published together.
- 2C-T-21.5 C12H17F2NO2S first synthesis, 2012 source
4-(2,2-difluoroethylthio) analogue, also called 2C-T-DFE. Named and discussed by Shulgin in PiHKAL but not synthesised then; Trachsel synthesised and tested it (12–30 mg). Sources cite his 2012 fluorine review and 2013 book, so 2012 is the first-publication year rather than a confirmed synthesis year.
- 2C-TFE C12H16F3NO2 first synthesis, 2012 source
4-(2,2,2-trifluoroethyl)-2,5-dimethoxyphenethylamine. Sources say it was first synthesised by Trachsel but give no year; the citations are his 2012 fluorine review and 2013 book, so 2012 is the first-publication year, not a verified synthesis year.
- Difluoromescaline C11H15F2NO3 first synthesis, 2012 source
4-difluoromethoxy-3,5-dimethoxyphenethylamine; first described by Trachsel in his 2012 Drug Testing and Analysis review, pharmacology detailed with the Basel group in 2021. 50–100 mg, 12–18 h.
- DOTFE C13H18F3NO2 discovered its activity, 2012 source
The compound itself was in the literature by at least 1999; Trachsel is credited with evaluating it in humans, reported in 2012 and 2013. He found it inactive up to 3 mg. Explicitly NOT a first synthesis.
- Metadifluoromescaline (MDFM) first synthesis, 2012 source
3-(difluoromethoxy)-4,5-dimethoxyphenethylamine; first described by Trachsel in 2012.
- Trifluoromescaline C11H14F3NO3 first synthesis, 2012 source
4-(trifluoromethoxy)-3,5-dimethoxyphenethylamine, one of the most potent scalines (15–40 mg, 14–24 h; ~34x mescaline's 5-HT2A affinity). Sources say 'first described … by 2012' — his fluorine review — while also citing the 2002 Helvetica paper, so the exact first-report year is 2002 or 2012 and I could not resolve which.
- Trifluoroproscaline C13H18F3NO3 first synthesis, 2012 source
4-(3,3,3-trifluoropropoxy)-3,5-dimethoxyphenethylamine; first described by Trachsel in 2012, only limited human trials.
- 2C-CN C11H14N2O2 discovered its activity, 2013 source
4-cyano-2,5-dimethoxyphenethylamine. In the literature by 1984 and mentioned by Shulgin; Trachsel was the first to describe preliminary properties and effects in humans, in 2013. Not his synthesis.
- 2C-tBu C14H23NO2 first synthesis, 2013 source
4-tert-butyl-2,5-dimethoxyphenethylamine; first described by Trachsel and colleagues in 2013. In his trials it produced pronounced tiredness rather than psychedelic effects at 7–10 mg; he hypothesised 5-HT2A antagonism, later disproved.
- 4C-B C12H18BrNO2 discovered its activity, 2013 source
Briefly mentioned in Shulgin's PiHKAL (1991) but never tested by him; Trachsel and colleagues tested it and reported 50–80 mg over ~8 h, milder than 2C-B or DOB. Credited with the human characterisation, not the first synthesis.
- Cycloproscaline C13H19NO3 first synthesis, 2013 source
4-cyclopropoxy-3,5-dimethoxyphenethylamine; first described by Trachsel and colleagues in the 2013 book, pharmacology studied in 2021. 60 mg or more, ~6 h, not fully evaluated.
- 2C-T-28 C13H20FNO2S first synthesis source
Also called 2C-T-FP. Named by Shulgin but never made or tested by him; sources say Trachsel first synthesised it 'some years later' without giving a year. Most likely the 2003 Helvetica thio series or the 2012–2013 fluorine work, but I could not pin it down, so the year is left null rather than guessed.
Books
- Phenethylamine: von der Struktur zur Funktion 2013 · by them
Co-authored with David Lehmann and Christoph Enzensperger; Nachtschatten-Verlag, Solothurn (Nachtschatten-Science series), ISBN 978-3-03788-700-4. German. A reference work on phenethylamines; an English translation has been reported as in progress by the Alexander Shulgin Research Institute. Much of the human dose/effect data in it comes from Trachsel's own work, but some is relayed from other chemists via personal communication.
- Psychedelische Chemie: Aspekte psychoaktiver Moleküle 2000 · by them
First edition co-authored with N. Richard; Nachtschatten-Verlag. Several later editions, the fifth in 2016.
Reading
- Author page, Nachtschatten Verlag · article
- Researcher profile, Frontiers Loop (ReseaChem GmbH, Burgdorf) · archive
- Passie & Brandt, "Self-Experiments with Psychoactive Substances: A Historical Perspective" (2018) — places Trachsel in context and notes he distanced himself from self-experiments · paper
- Trachsel, "Fluorine in psychedelic phenethylamines", Drug Testing and Analysis 4:577–590 (2012) · paper
- Kolaczynska et al., "Receptor Interaction Profiles of 4-Alkoxy-3,5-Dimethoxy-Phenethylamines (Mescaline Derivatives) and Related Amphetamines", Front. Pharmacol. 12:794254 (2021) · paper
- Halberstadt, Luethi, Hoener, Trachsel, Brandt & Liechti, head-twitch SAR of 4-thio-substituted 2,5-dimethoxyphenylalkylamines, Psychopharmacology 240:115–126 (2023) · paper
- Trachsel, Nichols, Kidd, Hadorn & Baumberger, "4-Aryl-substituted 2,5-dimethoxyphenethylamines", Chem. Biodivers. 6:692–704 (2009) · paper