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Health New molecular structure for psychedelic drugs : ZC-B and LPH-5

ascinating, what's the logic on the SAR with a structure like this? I imagine that the idea would be the creation of a dimer that gets lysed via metabolism into something expected to be active, but do we have an understanding on how adjacent halogens like the two bromines in there would metabolize? Triisopropylsilyl groups are also something I've never seen on a medication expected to be consumed, do you think that would be safe? Genuinely curious here.

Must've been fascinating working in Trachsel's lab as well!!! Any experiences or learnings from there that you wish made it into his book Phenethylamines or his other papers?
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No, the molecule is an intermediate of synthesis, TIPS are protecting groups for indole because next reaction was reacting it with 1 eq. of BuLi and forming the aldehyde. Final molecule will be NCCC1=C2C=CNC2=C(Br)C2=C1NC=C2 , you can generate from this SMILES the molecule on https://www.rcsb.org/chemical-sketch . I choose this work but it is not finished and only appear on the book as idea. The book is the most complete collection of psychedelic phenethylamine chemistry and pharmacology I've ever seen. Congratulation M. Traschel. If I could finished the molecule its activity was determined by him and his team. I live in the same country and we studied at the same time but not in the same university. I wish I couls have more time to make my molecule tested and probably published. There is another team that make isofly structures that are apparently more potent than simple fly or butterfly, it didn't appear on the book but Im pretty sure they designed for the Traschel's team, it have been published somewhere but I don't remember here. Structure is here NCCC1=C2COCC2=C(Br)C2=C1COC2 . This is the full 2c-B-Isofly but I think the most active was hemi-isofly, don't remember whether it's 2- or 5- isomer.
 
Dr.Methyl said:
No, the molecule is an intermediate of synthesis, TIPS are protecting groups for indole because next reaction was reacting it with 1 eq. of BuLi and forming the aldehyde. Final molecule will be NCCC1=C2C=CNC2=C(Br)C2=C1NC=C2 , you can generate from this SMILES the molecule on https://www.rcsb.org/chemical-sketch . I choose this work but it is not finished and only appear on the book as idea. The book is the most complete collection of psychedelic phenethylamine chemistry and pharmacology I've ever seen. Congratulation M. Traschel. If I could finished the molecule its activity was determined by him and his team. I live in the same country and we studied at the same time but not in the same university. I wish I couls have more time to make my molecule tested and probably published. There is another team that make isofly structures that are apparently more potent than simple fly or butterfly, it didn't appear on the book but Im pretty sure they designed for the Traschel's team, it have been published somewhere but I don't remember here. Structure is here NCCC1=C2COCC2=C(Br)C2=C1COC2 . This is the full 2c-B-Isofly but I think the most active was hemi-isofly, don't remember whether it's 2- or 5- isomer.
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This is fascinating! Are you aware of any connections between the extended duration of the 5-Ethoxy variants of Shulgin's 2,4,5-trisubstituted phenethylamines, and the various fly compounds? I've been intrigued by 2C-E-5EtO, which Shulgin claimed was deemed "Eternity" by some members of the initial testing group due to how long the effects lasted. Could this quirk in the phenethylamine SAR be extended to the fly compounds somehow, perhaps a bulkier "wing" where the 5-Ethoxy would be could increase duration, I'm not sure, but it seems like an element of the SAR worth probing into.

2-Ethoxy-5-Methoxy variants of 2,4,5-trisubstituted phenethylamines also play into this, as 2C-B-2EtO was found to have a shorter duration than 2C-B. It seems as if the extra carbon being on the 5 is the longest lasting, both the 2 and the 5 positions being balanced is in the middle, and the 2 position having the extra carbon is the shortest lasting. This characteristic of psychedelic phenethylamines' SAR is what I'm asking about here, my apologies for the verbose description, I'm not a formally trained chemist.
 
Esperighanto said:
I'm interested in synthesizing some of the tetrahydroisoquinolines (THIQs) that give peyote a unique experience, to combine with non-mescaline phenethylamines
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This is just one of many THIQs to be investigated...I'm also curious what the rest do...
Pellotine (1), a Lophophora alkaloid... Furthermore, radioligand-displacement assays showed that 1 is selective for the serotonergic system and in particular the 5-HT1D, 5-HT6, and 5-HT7 receptors, where it binds with affinities in the nanomolar range. Additionally, 1 was functionally characterized at 5-HT6 and 5-HT7, where it was found to be an agonist at the former and an inverse agonist at the latter (source)
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Recently, pellotine (1a), a Lophophora alkaloid, was unexpectedly shown to be an inverse agonist of the 5-HT7R. Therefore, we evaluated close analogs of compound 1a, both naturally occurring and synthetic analogs, as inverse agonists of the 5-HT7R. (source)
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username_required said:
If only I could speak german…
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get the book and you can use google lens. snap a pic translate and screenshot everything. I am doing it with one of his other books that I bought as a kindle book. Psychedelische Chemie. Its a little annoying but so worth it, I just do a few pages every day. It's got a lot of the same compounds of Pihkal and Tihkal, but now there's so many new experience reports and psychedelic anecdotes that I would have never been able to read. I can't afford Phenethylamine - Structure to Funcion yet as it's only available in hardback but someday. I think cost is around $200.

Was just looking through this patent https://patents.google.com/patent/WO2022221774A1/en and what excites me the most is that these azetedine or piperine analogues allow even more places for substitutions. I hadn't realized that Nichols and company wrote the patent on ZC-B. I figured Nichols being retired, wasn't doing so much work in the field any more but i was very wrong about that.

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