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Phenethylamines Has anyone heard of 4-perchloryl-2,5-dimethoxyphenethylamine (2C-ClO3)?

Huh, I have no idea. I would be very curious to know, though. I have no idea if 3 oxygens on a chlorine would have any chance of causing the chlorine to be freed when metabolized, that would be my worry. But again, no idea if it would. I mean obviously just a plain chlorine is fine, and a great drug (2C-C).
 
Yeah, that’s exactly what I worry about too, but my knowledge on that matter is limited.
 
Just reading this gave me the heebie jeebies. Perchlorate salts are extremely energetic oxidizers, and fairly toxic (as they get mistaken for iodine and damage thyroid cells).

I looked on wiki to see if organic perchlorates are possible, and methyl perchlorate (methyl group attached to one of the oxygens; I am unsure if it is possible to have a carbon chlorine bond on a chlorine that oxidized) is an alkylating agent. If 2C-perchlorate still retained receptor affinity, it could be a serotonergic neurotoxin, attaching a 2C group to the receptors it binds to (now introducing 2C-5HT2a). This might not happen because the compound could be unstable enough to hydrolyze or just randomly attack proteins in your gut or blood before it reaches the brain.

Yikes though.
 
Thank you very much for your answer. Doesn’t seem like a good idea to ingest then.
 
Just reading this gave me the heebie jeebies. Perchlorate salts are extremely energetic oxidizers, and fairly toxic (as they get mistaken for iodine and damage thyroid cells).
However perchlorate (O3Cl-O-R) is not the same thing as a perchloryl-group (O3Cl-R), just like a nitro-group is not the same as a nitrate. The nitro-group being pretty stable and still used in organic chemistry, although less frequently than it used to be due to toxicological concerns.
Probably still a good idea to avoid though, there’s probably a reason why you never see this substitution.
 
Thank you very much for your answer. Doesn’t seem like a good idea to ingest then.
Alexander Shulgin talks about a theoretical 2C-X with similar properties in his section for the selenium analog of 2C-T. It would be made with polonium and emit radiation, destroying the receptors. I left in his commentary about the tellurium analog, which would smell horrorendous too (i think he is such a wonderful writer about chemistry).
EXTENSIONS AND COMMENTARY: With an entirely new hetero atom in the molecule (the selenium), and with clear indications that large dosages would be needed (100 milligrams. or more), some discretion was felt desirable. There was certainly an odd taste and an odd smell. I remember some early biochemical work where selenium replaced sulfur in some amino acid chemistry, and things got pretty toxic. It might be appropriate to get some general animal toxicity data before exploring those dosages that might get to a +++.
What doors are opened by the observation that the selenium analog of
2C-T
is an active compound? The potency appears to be in the same ball park, whether there is a sulfur atom or a selenium atom there.
From the point of view of the thing that is hung onto the hetero-atom, the selenium, the most active (and as first approximation the most safe) analogue would be the same ones that are the most potent with sulfur. These would probably be the Se-ethyl, the Se-propyl, or the Se-isopropyl, the analogs of S-ethyl, S-propyl, and S-isopropyl. If one were to be systematic, these would be called
2C-SE-2
,
2C-SE-4
, and
2C-SE-7
. And a very special place might be held for
2C-SE-21
, the analogue of
2C-T-21
. Not only is this of high potential potency, but it would certainly be the first time that both fluorine and selenium are in the same centrally active drug. In fact, might not this compound, 2C-SE, be the first compound active within the human CNS with a selenium atom in it? It is certainly the first psychedelic with this atom in it!
From the point of view of the hetero-atom itself, there are two more known below selenium in the Periodic Table. Each deserves some special comment. The next atom, directly below selenium, is tellurium. It is more metallic, and its compounds have a worse smell yet. I heard a story about a German chemist, many years ago, who was carrying a vial of dibutyl telluride in his pocket in a passenger coach from here to there in Germany, back at about the turn of the century. It fell to the floor and broke. No one could remain in the car, and no amount of decontamination could effectively make the smell tolerable. Scratch one railway coach. But the compound,
2C-TE
, would be readily makeable. Dimethyl ditelluride is a known thing.
However, the atom below tellurium (and at the bottom of that particular column of the Periodic Table) is the element polonium. Here one must deal in terms of theory, as far as human activity goes, since there are no non-radioactive isotopes of polonium. The only readily available isotope is that with mass 210, which is also called Radium F, and is an alpha-particle emitter. If this were ever to be put into a living organism, and if it were to seek out and hang around some particular site of action, that area would be thoroughly and completely cooked by alpha-particle emission. It would be a fun academic exercise to make 2C-PO (2,5-dimethoxy-4-methylpoloneophenethylamine), but in no way could it ever go into anyone. I knew an eminent physiologist named Dr. Hardin Jones (now dead) who always argued that the continuing use of drugs would burn out the pleasure center of the brain. It is a certainty that 2C-PO would, quite literally, do this. If I ever made it, I would call it HARDINAMINE in his honor.
 
However perchlorate (O3Cl-O-R) is not the same thing as a perchloryl-group (O3Cl-R), just like a nitro-group is not the same as a nitrate. The nitro-group being pretty stable and still used in organic chemistry, although less frequently than it used to be due to toxicological concerns.
Probably still a good idea to avoid though, there’s probably a reason why you never see this substitution.
You are totally right about this. I was searching for -perchlorates, but perchloryl benzene is a compound that is studied and seems stable in HCL (but hydrolyzes in bases).

It still causes my hairs to stand on in, but this compound wouldn't be a potent alkylating agent. Id really want to see studies on it showing it is metabolized/excreted with the perchloryl group bound to the phenyl ring before ever putting it near my body.
 
Think about it, the Cl is in a +1 oxidation state, not the -1 it's usually observed in. Chlorates tend to be energetic (explosive) and fairly toxic. I guess that their prediction is based on it's in-silico predicted affinity but I do not believe it would ever be tested in vitro.
 
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