4-fluoropsilocin

[Opie]

4-fluoropsilocin, DMT with a fluorine atom at the 4 position. Does such drug exist? Does anyone have any information on it? From what I know, adding halogen atoms can change a lot of things in the drug's action.

 

[Jamshyd]

It would be called 4-fuoro-DMT, not psilocin.

I don't know about this one but I believe shulgin mentions seaweed that contains 4-bromo-DMT.

I have no idea why this doesn't seem to interest anyone...

 

[nuke]

The 4-halogen indoles are cheap and readily available.. 4-fluoro is the best bet to try first as it is probably the safest, though I'm not sure it'd matter as the primary method of metabolism for psilocin is the deamination to the 3-acetic acid.

 

[haribo1]

I'm not certain it would retain activity. So far, only 4-H or 4-OH have proved active. I know fluorine is often described as 'hard hydrogen' in metabolic roles but that 4 position is pretty damned important. I would LOVE it to be a goer, but if it worked, you would think that someone would have spotted it by now.

 

[kidamnesiac]

it doesnt accept or donate H-bonds, I doubt it would be overly similar to Psilocin

 

[haribo1]

Throwing a F somewhere else on the ring (6 or 7), maybe that would work?

 

[mad_scientist]

4-fluoro-DMT is a known compound, one of Nichol's:

J. Med. Chem. (2000), 43, pp4701

Hallucinogen-like activity, evaluated in the two-lever drug discrimination paradigm using LSD-trained rats, was attenuated or abolished for all of the fluorinated analogues.

4-fluoro-5-MeO-DMT is a potent and selective 5HT1A agonist though. So looks like the effect of fluorinating the 4-position is to reduce 5HT2A affinity and increase 5HT1A affinity.

Effects would probably be most comparable to those of pFPP, para-fluorophenylpiperazine, seeing as thats the only compound that comes to mind which is a weak 5HT2A agonist but a more potent 5HT1A agonist. So probably mildly hallucinogenic but lacking that special magic.

I'd be more interested in the 5-position myself, there hasn't been enough research done on 5-X-DMT analogues in my opinion. 5-MeO-DMT is active of course, and so is 5-Me-DMT, Shulgin reported 5-MeS-DMT as being inactive, but thats about all the analogues i've seen trial results for. Theres syntheses available for 5-CN-DMT and 5-Br-DMT but i've never heard of anyone actually taking them.

 

[fastandbulbous]

Throwing a F somewhere else on the ring (6 or 7), maybe that would work?

Well 6-hydroxylation is a metabolic route for DET so 6-fluoro DET might or might not be a good thing. I know it's been synthesized & evaluated, but I can't remember what the final verdict was

 

[haribo1]

So it would 'harden it' but may have unwanted side-effects?

 

[mad_scientist]

No luck...

A series of fluorinated tryptamine analogs of the hallucinogenic compounds DMT, DET, Psilocin, and 5-methoxy-DMT was synthesized to investigate why 6-fluoro-DET is inactive as a hallucinogen....

from that Nichols paper. Fluorinating tryptamines just doesn't seem to be a useful strategy (well not on the aromatic ring anyway) although perhaps N,N-bis(beta-fluoroethyl)tryptamine or N,N-bis(gamma-fluoro-n-propyl)tryptamine might be a different story...

If hydroxylation at the 6-position is a route of metabolic degradation though, what would happen if you replaced that carbon with a nitrogen to make say 6-aza-3-(beta-dimethylamino)ethyl-indole? Would that like totally screw up the binding or cause heinous toxicity having another heterocyclic nitrogen in the indole rings or could it potentially be active?

 

[fastandbulbous]

although perhaps N,N-bis(beta-fluoroethyl)tryptamine

Isn't there a thread that considered these w.r.t. the metabolism by N-dealkylation would produce 2-fluoroacetic acid which is extremely toxic (and is in fact used as a rodenticide under the name 1080 in Australia)?

 

[MattPsy]

Yah, not a good look at all.
Those carbons get stripped off the ethylamine nitrogen during metabolism, and so yeah 2-fluoroacetic acid would likely be made.

I've thought the -7 position might be interesting to tack a halogen on to though, seeing that position (when the analogy is carried over to PEA's, where we consider the indole nitrogen to be analogous to the -5 methoxy) increases activity with the psychedelic PEA's.

 

[egor]

I have heard of 5-fluoro-amt being used as a psychedelic, but none of the info was good and the source was very questionable. Does anyone have any info on 5-fluoro-dmt, which I have also seen offered?

 

[fastandbulbous]

^ you're been very charitable about 'Legal Highs' - I consider it as bodering on a work of fiction in places

 

[egor]

^ you're been very charitable about 'Legal Highs' - I consider it as bodering on a work of fiction in places

Is there any particular reason you feel that way?
Feel free to pm me if you dont want to discuss it in the forum.
Dont worry about offending me, I am an adult

To be honest, I have been very interested in so called "legal highs", though most are truly not, for a very long time, I feel that if i have come across these things, it is unlikely that others have not. If I am stepping out of bounds here, let me know.

 

[djfriendly]

Not legal highs - Legal Highs - the book. As stated, it is full of bullshit.

 

[haribo1]

Isn't there a thread that considered these w.r.t. the metabolism by N-dealkylation would produce 2-fluoroacetic acid which is extremely toxic (and is in fact used as a rodenticide under the name 1080 in Australia)?

What about the anasthetic gases Sevoflurane & Enflurane? I thought they were hydrolized to something along those lines? Not THAT toxic...

 

[mad_scientist]

Isn't there a thread that considered these w.r.t. the metabolism by N-dealkylation would produce 2-fluoroacetic acid which is extremely toxic (and is in fact used as a rodenticide under the name 1080 in Australia)?

Haha yeah i should have thought of that, sticking a beta-fluoroethyl group onto an amine will certainly produce some 2-fluoroacetic acid as a metabolite, which as stated is pretty deadly to mammals...

However i would imagine toxicity will depend on dose. Certainly one of the routes of metabolism for 2CTxx analogues is known to be S-dealkylation, so dealkylation of 2CT21 will presumably then produce 2-fluoroacetic acid as a metabolite...and symptoms of 1080 poisoning are not generally reported as adverse side effects of 2CT21, so the extent of toxicity will depend on what dose of drug is taken, and how much of it is metabolised by dealkylation vs excreted unchanged or metabolised by a different pathway...

 

[Vanadium]

Here are two precursors for N,N-dialkylfluorotryptamines i've found on a swiss RC seller.

5-Fluoro-T [CAS = 2711-58-2]
4-Fluoro-(DL)-Tryptophan [CAS = 25631-05-4]
5-Fluoroindole-3-carboxaldehyde [CAS = 2338-71-8]

They sell lots of tryptamines and also strange ones such as 5-BzO-DMT [CAS = 101832-88-6]

 

[egor]

Not legal highs - Legal Highs - the book. As stated, it is full of bullshit.

Took it out of context. I was not exactly on top of my game if you know what I mean