Phenethylamines Shulgins missing ETs

[Leprechaun]

For anyone who’s interested in the nitty gritty of the psychedelic amohetamines, there’s a world of desoxy analogues of some key psychedelic phenethylamines.

From what I have read, they aren’t even listed in the Shulgin Index…

You may know of a strange discrepancy between the compound names, such as 3C-E and 2C-E. These are very different compounds. 3C-E is in fact 3c-Escaline. As in the 4-ethoxy homologou.

Now, DOEt was a very interesting compound that was active at a low dose, this was 2,5 dimethoxy 4 ethyl amphetamine…

But no such thing in the realm of the 3,4,5 compounds. There are no ethyl homologues on the 4 position of any 3,4,5 psychedelic phenethylamines/amphetamines…

So there’s a whole new compound with no known record of any synth or taste test, 3,5 dimethoxy, 4 ethyl amphetamine and phenethylamine.

The closest is “Desoxy”: 3,5 dimethoxy, 4 methyl phenethylamine.

Erowid Online Books : "PIHKAL" - #52 DESOXY

Entry #52 DESOXY from PiHKAL by Alexander & Ann Shulgin.

www.erowid.org

 

[tuppingtoncity]

Based on desoxy's complete inactivity, I don't know how promising these would be. Still some interesting analogues that could be made, definitely surprising that the 3,4,5 substituted amphetamines seem to be relatively unexplored.

 

[Skorpio]

It looks like it was made by Daniel Treschel in his thesis, Phenethylamine: Von der Struktur zur Funktion, under the name DE. Not a lot beyond that entry, and I’m not sure that thesis has been translated to English yet.

I found it using the search tool on isomer design, which allows you to draw molecules to search them. Very impressive, and a good way to spend a lot of time.

search | PiHKAL·info

 

[xdrc]

I think it was also patented by Trachsel in 2023.

There is a report of a HyperLab user. During one of the first trials at a low dosage, there was a weird incident with what felt like a sharp drop in blood pressure (not measured). Further bioassays were mixed with low doses of other psychedelics and did not induce any medical concerns or off-normal bp, but other than hinting at long duration of action, no comments regarding the qualitative nature were made, other than the dose still being within "microdosing" range. This was at the highest dose of 7.3 mg Desoxyescaline and 4.8 mg 2C-T-2.

Desoxymescaline itself is active:

(with 40 mg) Initially I felt very chilled, so I lay down under a blanket. Eyes-closed imagery became very dream-like and my general state was felt as having lost my center. Also, not much in touch with feelings, sense of strangeness, almost alien view of the world. Not through recog-nizable eyes. Neither pleasant nor unpleasant, just strange. Was able to drift into sleep very easily, or sleep-like trance state, with disconnected, far-out imagery. After 3 hours the nausea was gone, I was able to get up and explore. A little food went down well. No drive, no strong focus in any direction. Feel this was a quite fascinating experience. Completely down by six hours. Would go a bit slowly because of slight hints of neurological sensitivity--the instant chilling and a tendency to dart on going to sleep. The nervous system does not feel over-exposed, but all of a sudden there will be a millisecond of auditory hallucination, or an out-of-the-blue startle. So take it easy going up. [Some 24 hours after this experiment had been completed, and a normal baseline re-established, a complex and psycho-logically disruptive syndrome occurred, that lasted for the better part of a week. The temporal juxtaposition between the use of desoxy and the subsequent "spiritual crisis" initially suggested some possible connection, but in retrospect the events seem to be unrelated].

(with 40 mg) I have offered to be a control on an experiment where there had been a close relationship between a trial with desoxy and what might have been a psychotic break, or some kind of so-called spiritual emergency. These two events lay within a day of one another. I was aware of my 40 milligram dosage at about three-quarters of an hour into the experiment, and felt that there was no more in-tensification at the two-hour point. At that time I felt distinctly spaced but with a very good feeling, and I could see no reason not to increase the dosage at some future time. There was a good and mellow mood, and enjoyment in escapist reading. The only physical oddity that I noted was that there had been no urge to urinate, and only a small amount of quite concentrated urine was passed rather late in the experiment. I was at baseline at the fifth hour, and there was nothing unusual at any time during the following week.

(with 100 mg) The stuff has a sweet taste! There was a slightheart-push in the early awareness period, with a pulse up to 100 and afeeling of pressure in the chest. There were no apparent visualenhancements, but the eyes-closed imagery to music was noteworthy.Thinking skills and conversation seemed to be fully under control, ifnot enhanced. There was none of the colorful psychedelic world ofmescaline, but this might be just around the corner; perhaps with alarger dose. This is a comfortable in-between level. Sleep was notpossible at the sixth hour, but two hours later, it was easy and veryrestful. There was no negative price to pay the next day.

 

[realgar]

There is a report of a HyperLab user. During one of the first trials at a low dosage, there was a weird incident with what felt like a sharp drop in blood pressure (not measured). Further bioassays were mixed with low doses of other psychedelics and did not induce any medical concerns or off-normal bp, but other than hinting at long duration of action, no comments regarding the qualitative nature were made, other than the dose still being within "microdosing" range. This was at the highest dose of 7.3 mg Desoxyescaline and 4.8 mg 2C-T-2.

(Originally posted in Russian)

4-Et-3,5-DMPEA (7.3 mg) orally + 2C-T-2 (4.8 mg) + loratadine (10 mg); onset about an hour later, intensity slowly increases till T+2:30; tapers off around T+5 (apparently the 2C-T-2 is wearing off), sleep for 6 hours, after which it's still off-baseline; now is T+13, and something's still noticeable. It seems to be long-acting. Feeling OK; blood pressure and heart rate are normal. But this is still microdosing; be more careful going forward.

After T+18:30, the effects slowly began to subside; T+22 still noticeable. What a duration...

 

[tuppingtoncity]

4-Et-3,5-DMPEA (7.3 mg) orally + 2C-T-2 (4.8 mg) + loratadine (10 mg); onset about an hour later, intensity slowly increases till T+2:30; tapers off around T+5 (apparently the 2C-T-2 is wearing off), sleep for 6 hours, after which it's still off-baseline; now is T+13, and something's still noticeable. It seems to be long-acting. Feeling OK; blood pressure and heart rate are normal. But this is still microdosing; be more careful going forward.

After T+18:30, the effects slowly began to subside; T+22 still noticeable. What a duration...

Is this really the only report that exists? Unfortunate that they dosed 2C-T-2 as well, duration seems unbelievably long for a phenethylamine - would rival some of the 2C-Gs if accurate.

 

[Leprechaun]

Based on desoxy's complete inactivity, I don't know how promising these would be. Still some interesting analogues that could be made, definitely surprising that the 3,4,5 substituted amphetamines seem to be relatively unexplored.

DESOXY wasn’t inactive. It’s actually quite active but not as active as something like DOM.

But more active than mescaline… pihkal states around 120mg for full effects.

 

[Didgital]

Is this really the only report that exists? Unfortunate that they dosed 2C-T-2 as well, duration seems unbelievably long for a phenethylamine - would rival some of the 2C-Gs if accurate.

Agreed. However, what surprises me more than the unbelievably long duration is the
the potency. I cant think of any scaline (3,4,5 sub pattern) that is active at 7mg. The T2 is arguably active at 5mg, but for me i wouldnt feel it for more than 8 hrs at that dose.

 

[Esperighanto]

This has always stood out to me too, as well as the underinvestigation of 2/6 substitutions involving fluoroalkyl groups, the 2,3,5-trisubstitution pattern, and trying to take these substitution patterns into the world of cathinones/pyros known to be active. Strapping a 2,5-dimethoxy-4-bromo substitution onto NEP for example would be neat.

On the topic of the post though, there is some clandestine literature surrounding people exploring a ton of desoxy analogs with different 4-substitutions, and iirc 3,5-dimethoxy-4-bromophenethylamine was notably a sedative with no psychedelic properties, which has stuck in my mind for a long time.

 

[tuppingtoncity]

On the topic of the post though, there is some clandestine literature surrounding people exploring a ton of desoxy analogs with different 4-substitutions, and iirc 3,5-dimethoxy-4-bromophenethylamine was notably a sedative with no psychedelic properties, which has stuck in my mind for a long time.

Where would one find these reports? sounds very interesting

 

[Esperighanto]

Where would one find these reports? sounds very interesting

No reports in it, but the chem literature is on Rhodium. The 3,5-dimethoxy-4-bromophenethylamine report was in PiHKAL iirc.

 

[Allylbenzene]

The 3,5-dibr-4-MeO seems to work, it makes PMA useful... see hive archive. The dichloro and diiodo should be interesting. Also the regular phenethylamine versions.

 

[xdrc]

It does not make PMA useful, as it is not amendable to the kind of substitution you are implying - but I'm afraid any further remark would get too close to synthesis talk. Also I wonder if there are any dangers to these compounds given their close relation to thyroid hormones. I know someone who refrained from exploring 3-halo-4-alkoxy-5-methoxyphenethylamines for these concerns, but I have not researched his theory myself.

 

[Allylbenzene]

It does not make PMA useful, as it is not amendable to the kind of substitution you are implying - but I'm afraid any further remark would get too close to synthesis talk.

There is a synthesis of 3,5-diiodo-4-methoxyphenethylamine from tyramine.

Also I wonder if there are any dangers to these compounds given their close relation to thyroid hormones.

Very good point.

 

[xdrc]

There is a synthesis of 3,5-diiodo-4-methoxyphenethylamine from tyramine.

But is there a synthesis of 3,5-diiodo-4-methoxyphenethylamine from O-methyltyramine (i.e. a-desmethyl-PMA), I do wonder...

 

[Allylbenzene]

But is there a synthesis of 3,5-diiodo-4-methoxyphenethylamine from O-methyltyramine (i.e. a-desmethyl-PMA), I do wonder...

Mescaline might be nearby...but starting with the phenylethanol might be more practical for biosynthesis.

 

[xdrc]

Please do actually take a look at mescaline synthesis. Either biosynthesis or synthesis will do. You may learn something.

EDIT: Actually what you are implying may just work. But there is a reason why literature starts from the phenol to ensure selectivity of the dihalogenation.

 

[Allylbenzene]

But is there a synthesis of 3,5-diiodo-4-methoxyphenethylamine from O-methyltyramine

Mescaline might be nearby...

Please do actually take a look at mescaline synthesis.

I think methoxide is just fine.

...but starting with the phenylethanol might be more practical for biosynthesis.

Please do actually take a look at mescaline synthesis. Either biosynthesis or synthesis will do. You may learn something.

I'm well aware of those. I was referring to in-vivo biosynthesis which seems broadly overlooked by nearly everyone.

 

[Didgital]

As an aside, Shulgin would have made an excellent Isoquinoline-iHKAL.

Well... he did write an entire book called "The simple plant isoquinolines" though it is more of a reference book rather than a collection of experiences/synthesis

 

[Esperighanto]

Well... he did write an entire book called "The simple plant isoquinolines" though it is more of a reference book rather than a collection of experiences/synthesis

A variety of these have been made and bioassayed too, DOM-CR, DOB-CR, METH-CR, Beatrice-CR, TDIQ, etc.

As far as I'm aware, none are psychedelic, some (if not all) are adrenergic agonists I think? They seemed rather uninteresting.