Phenethylamines Self experiments with new series of NXXX-phenylethylamines

[Shamanism]

^^
this

Have you ever microdosed 2C-C or 2C-D during sleep and if so; do they give similar results?
I think i'm going to experiment a bit with this.

 

[Hans Meyer]

microdosed 2C-C-NBOMe as antidepressing agent during sleep

^^
this

Have you ever microdosed 2C-C or 2C-D during sleep and if so; do they give similar results?
I think i'm going to experiment a bit with this.

No, I never microdosed 2C-C/D during sleep. And I wouldn't be at all surprised if the well known 2C-C-NBOMe has microdosed similar effect during sleep, may be at a little bit higher dose.

 

[Hans Meyer]

Thanks!

Thanks for doing this stuff and sharing the results, Hans. You're a true psychonaut.

Thanks jason7! Praise welcomed every time!

 

[Hans Meyer]

2C-C-NB2OEt5Cl or 25Cl-NB2OEt5Cl date 140714

**********************************
2C-C-NB2OEt5Cl or 25Cl-NB2OEt5Cl date
**********************************

IUPAC-Name:
2-(4-chloro-2,5-dimethoxy-phenyl)-N-[(5-chloro-2-ethoxy-phenyl)methyl]ethanamine
or shorter:
2-(4-chloro-2,5-dimethoxy-phenyl-N-(2-ethoxy-5-chloro-benzyl)ethanamine

structure:

Recrystallization of 10 mg of 2C-C-NB2OEt5Cl•HCl from 4 mL water yealded long thinn needles:

Trial 1:
Salt: Chloride
Dose of free base [nMol/kg]; (M=384 g/Mol): 0.79
Dose [mg] of free base related to a 75 kg body: 0.023 mg
Route of Administration: s.l. 30´ at 12:25 h
Duration: ≥ 5h
Notes: Substantially more than threshold; more sensitive and optical details; seems to have the potential of powerful effects, but far too strenuous for soul and body: sometimes „hammer hard“; physical weakness, lack of concentration. Later better, 15:15h nordic walking very beautiful, back 17:00h still slight effects - unsure about the quality; afterglow also not so convincing to me; next two days bad cold, muscle ache (nordic walking), but no depression. Even more powerful than 2C-C-NB2OMe5Cl, but psychodelic effects too small compared with the occasional hammer-hard-effects of body and soul.

Trial 2:
Salt: Chloride
Dose of free base [nMol/kg]; (M=384 g/Mol): 1.1
Dose [mg] of free base related to a 75 kg body: 0.031 mg
Route of Administration: s.l. 25´ at 21:00 h
Duration: ≥ 6 h
Notes: 22:00h feel my stomach, but not uncomfortable; stimulated: breathing, erotic, shift in meaning and sight; during the next course throughout inspiring; weakly stunning ~like GHB, only little micro-view or psychodelic; 23:45h to bed, next day 3:00h material still acting, pleasant, fall asleep again. ~8:00h all ok; wonderful breakfast, communicative, fresh impacts, no depressions, depth of sleep was perhaps not as deep as usual; psychodelic potential specially in the afterglow. Two days later: good mood, communicative, no depressions. Three days later: still quite good mood. Four days later: not so good, slight depressions.

Trial 3:
Salt: Chloride
Dose of free base [nMol/kg]; (M=384 g/Mol): 0.71
Dose [mg] of free base related to a 75 kg body: 0.020 mg
Route of Administration: s.l. 40´ at 19:00 h
Duration: ≥ 4 h
Notes: 20:30h first response; 20:50h bad concentration, strong effect; dull-pressing but not serious ache in stomac disappeared quickly; 22:25h being in a good mood, perhaps more aggressive/irritable than normally. 23:00h to bed, sleep well, but not as deep as usual, material worked all night. 7:00h next day rised, feeling somewhat broken, unstable and strained, comparable to alcoholic hang-over (but without headaches etc.), in so far: psychodelic. Two days later still little aftereffects, no depressions. This was, I think, the last test with this material for me. Other people may like it!

Trial 4:
Salt: Chloride
Dose of free base [nMol/kg]; (M=384 g/Mol): 0.85
Dose [mg] of free base related to a 75 kg body: 0.024 mg
Route of Administration: s.l. 25´ at 15:45 h
Duration: ≥ 6 h
Notes: 16:30h brisk walking for 1½ h, very beautiful, windy, cloudy, sunny, cool weather. 19:30h even more power: clear thoughts and quick formulations of them, of good spirits, lively, enjoying life, witty. 20:20h still going on. 22:00h still little but significant power. 22:30h calm coming down. 23:00h going to bed, sleep was o.k. Very slight antipepression effects even two days later. Suppose toxic region at very low doses. Long lasting.

____________________________

Comments at date 140714:

Uncertainties of all doses were ~ ± 25%
Duration: undefined end
Very potent material, but too long-lasting and strenuous for me. Other quality and more active than the analogue 2C-C-NB2OMe5Cl. I myself found a remarkable body load. May be a potent antidepressiv at very low doses of let say <20µg s.l. However, what is striking is the fact that the following two or even three days I could feel a significant antipepression-effect. For these tests introduced here, this resulted in my following working hypotheses which needs to be verified : the mental shock during the tripp seems to loosen the psyche even in those case, where the trip itself was not so positive.
Now (14.07.2014) I must say, that the term „toxic“ should be bette replaced by „body-load“; that is to be say to all of my "Comments".

During preparation of 2C-C-NB2OEt5Cl one of the reactand´s vapour caused allergic irritation to my face, so one way gloves are recommended and inhalation should be avoided. Do not breath vapours, wash contaminations vigorously with soap and water.

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[adder]

I've recently got a similar idea about combining LSD and psychedelic phenethylamines structures, and I'm wondering if you happened to test an N,N-diethylpropanamide derivative of any 4-halogenated 2C-X? It would be the very first thing that I'd check in the NDEPA series if I had a lab and necessary chemicals around. Just like someone has already suggested in this thread, the quickiest way you'd find the best substituent on the nitrogen would be if you took a, say, 2C-B backbone and then substituted its nitrogen with various groups.

I suppose that amide part of a molecule binds to the same site as methoxybenzyl of 2C-X-NBOMe's. At least it's very probable considering how well both overlap and how esters and amides are often bioisosteric with a phenyl group (e.g. pipradrol vs. methylphenidate in a different way, but I'm still hopeful). If it turned out true, I suppose that propanamide substitution would work well only for 2C-X's increasing their potencies drastically and not doing much for DOX's just like NBOMe doesn't. So before someone can confirm that, I wouldn't substitute DOX series, calculated affinities may be misleading. Seeing how even small changes to LSD structure produce inactive compounds and that not all 5-HT2A agonists are psychedelics, I wouldn't be surprised if 2C-X-NDEPA analogues were qualitatively superior to 2C-X-NBOMe's if only NBOMe happened to target the same spot as the amide in LSD. Certainly alpha-methyl in the phenethylamine skeleton is not necessary for a compound to be psychedelic, so I'd treat it as optional.

If I may propose something, if you are to use highly electrophilic substituents on the N-benzyl, then I think the most intuitive substitution would be N-(3-halo-2-alkoxybenzyl) and if it works out, then I think 3-trifluoromethyl would substitute best for an amide. Another interesting thing would be to see how well N-[2-(alkylamino)benzyl] and N-[2-(dialkylamino)benzyl] substitute for NBOMe. Often amino groups substitute for hydroxyls, but usually one is better, if perhaps an amide makes LSD so great, then I'd go for substituted amines.

What do you all think?

 

[Hans Meyer]

General questions to potent structures

I've recently got a similar idea about combining LSD and psychedelic phenethylamines structures, and I'm wondering if you happened to test an N,N-diethylpropanamide derivative of any 4-halogenated 2C-X? It would be the very first thing that I'd check in the NDEPA series if I had a lab and necessary chemicals around. Just like someone has already suggested in this thread, the quickiest way you'd find the best substituent on the nitrogen would be if you took a, say, 2C-B backbone and then substituted its nitrogen with various groups.

I have only a very little hobby-lab, and are very restricted with my experiments. Nowadays I can not buy new chemicals and are restricted to what I have. So I only can prepare NDEPAs (and no other NDEPA-structur-variations) from some restricted substituted Amphetamines (and even PEAs). The same can be said of the variations of NBXs. Never the less in future I will prepare in any case the 2C-C-NBX (including the quasi standard 2C-C-NBOMe, to compare it with others) with still other NBX I tried already. Also of great interes of mine is DOC-NDEPA, which is in pipeline. I also will make in future, as I did in the past, NDEPA- and NBX-derivatives of 3,4- and 3,4,5 substituted PEAs, for I look not only to the most active- but also to qualitatively optimised ones (the last will be generally not the most active one – in toto).

I suppose that amide part of a molecule binds to the same site as 2-methoxybenzyl of 2C-X-NBOMe's. At least it's very probable considering how well both overlap and how esters and amides are often bioisosteric with a phenyl group (e.g. pipradrol vs. methylphenidate in a different way, but I'm still hopeful).

Having in minde that the geometrical dimensions of a center to binde to a appropriate ceter of a receptor must be comparable, then we must say, that the -CH2-CO-N(et)2 group simulate the (o-OMe)ph-group and vice versa. Also the electronical properties of these molecular segments resemble each other with regard to their structure. However, whether these similarities in the electronical structures and in the chemical structural formulas cause a similar binding affinity? May be, there is something to suggest that.

If it turned out true, I suppose that propanamide substitution would work well only for 2C-X's increasing their potencies drastically and not doing much for DOX's just like NBOMe doesn't.

That would support my efforts for preparing PEA-NDEPAs too, despite the QSAR of Mike Alexandru et.al. predicted an effect specially with the DOX-NDEPA (but, as You say also, the binding affinity to the 5-HT2A is not the only important characteristic feature of having hallcinogenic effects.) Some PEA- and Amph-NDEPA I prepared already, and I found more (though not even much more) activity compared to the PEAs and Amphs itself. But the test with DOC-NDEPA (the only one I can make, the most promising DOI-NDEPA I can not make) is still pending.

So before someone can confirm that, I wouldn't substitute DOX series, calculated affinities may be misleading.

...may be misleading! I agree.

Seeing how even small changes to LSD structure produce inactive compounds and that not all 5-HT2A agonists are psychedelics,

I would like to prepare such compounds, but did not have the resources.

I wouldn't be surprised if 2C-X-NDEPA analogues were qualitatively superior to 2C-X-NBOMe's if only NBOMe happened to target the same spot as the amide in LSD. Certainly alpha-methyl in the phenethylamine skeleton is not necessary for a compound to be psychedelic, so I'd treat it as optional.

Yes, therefore I also will prepare and test 2C-X-NDEPAs. Alpha-methyl in PEA is not necessarily necessary , there are examples of deminishing activity of that PEA. But what´s about LSD (and the NDEPA-skeleton?). N-ethyl-LSD is more potent, than LSD itself. And what´s about De-methyl-LSD (LSD without the N-methyl)? I will recherche it.
Your impressions give me hope, I already tested Mescaline-NDEPA and fond it (76 mg oral, empty stomach) like this: „Realy terrible taste like burnt rubber. Morale high; funny talks; easily find formulations; sociable; visual enhanced clarity; recreated; more (or less ?) power compared to Mescaline.“ (see post this issue)

If I may propose something, if you are to use highly electrophilic substituents on the N-benzyl, then I think the most intuitive substitution would be N-(3-halo-2-alkoxybenzyl)

I think the electron donating power of the alk-O with its free electron-pair is important in this case. Second substituent I would place in 3- and/or 5-position, they could have a (quasi) mesomeric support of the nucleophilicity of the 2-substituent (similar to the et2N-group influencing the C=O within NDEPA or LSD).

and if it works out, then I think 3-trifluoromethyl would substitute best for an amide. Another interesting thing would be to see how well N-[2-(alkylamino)benzyl] and N-[2-(dialkylamino)benzyl] substitute for NBOMe. Often amino groups substitute for hydroxyls, but usually one is better, if perhaps an amide makes LSD so great, then I'd go for substituted amines.

I think CF3 has a to big electron withdrawing effect to the necessary nucleophilicity of the 2-OR group. 2-NR2 groups I also proposed in my introduction (first post) to this issue.
It is really a pity, but I can not get new chemicals, I depend on that, what I have for now.
You wrote "... then I think 3-trifluoromethyl would substitute best for an amide..." Oh, yes, may be! But: I can not make it. What a shame!
So long, Hans

 

[Hans Meyer]

M-NB2OEt5Cl or 345-NB2OEt5Cl date 140726

**********************************
M-NB2OEt5Cl or 345-NB2OEt5Cl date 140726
**********************************
IUPAC-Name:
N-[(5-chloro-2-ethoxy-phenyl)methyl]-2-(3,4,5-trimethoxyphenyl)ethanamine

structure:

Crystallized Chloride:

(not all trials are listed)

Trial 2:
Salt: Chloride
Dose of free base [nMol/kg]; (M=380 g/Mol): 22
Dose [mg] of free base related to a 75 kg body: 0.63 mg
Route of Administration: s.l. 20´at 16:00 h
Duration: >6 h
Notes: Suddenly after some minutes seems to me disappearing a grey bloom from the world. A very pleasant soft feeling of cleanliness. 22:30 to bed, sleep was not as deep as usual (but affected by longlasting crosscountry before). However next day fresh mood, efficient in crosscountry skiing.

Trial 3:
Salt: Chloride
Dose of free base [nMol/kg]; (M=380 g/Mol): 55
Dose [mg] of free base related to a 75 kg body: 1.6 mg
Route of Administration: s.l 20´at 8:30
Duration: >6 h
Notes: 9:00h: 1h walking extremely smoothly. Weather 0°C, foggy; communicative with my wife, deep nature appreciation, slightly euphoric. 13:20h: Good trip. 15:00h: after short sleep still good feeling, outside snowing, pleasant afterglow.

Trial 4:
Salt: Chloride
Dose of free base [nMol/kg]; (M=380 g/Mol): 88
Dose [mg] of free base related to a 75 kg body: 2.5 mg
Route of Administration: s.l. 18´at 8:45
Duration: >7 h
Notes: 10:00h: nordic walking, 0°C, 1¾ h; effects hardly surpass 1,6mg; 16:00h: finish, but some hours still very comfortable pleasant afterglow. 23:30h: to bed, good sleep; rised 6:30h next day. Spent a nice day without depressions, communicative, without nap after lunch, sitting in the sun: first sunny day after weeks; felt still very little positive afterglow. Second day without any depressions, communicative, vivid. Think still very little after-effects.

Trial 6:
Salt: Chloride
Dose of free base [nMol/kg]; (M=380 g/Mol): 166
Dose [mg] of free base related to a 75 kg body: 4.7 mg
Route of Administration: s.l. 25´ at 11:10 h
Duration: na
Notes: 12:00h: 1½ h nordic walking, coming up was not so a comfi couch; eyes were irritated in somewhat way, not good feelings, but setting were not at optimum. 12:45h: suddenly good feeling, nearly euphoric. ~15:00h: 2h deep sleep, recreated; after-effects not so comfortable, nevertheless quite good right. ~24:00h: to bed and good sleep (deep of sleep not disturbed!). Next day 8:00h: wakeup. No depression at wakeup, nevertheless some hours feelings of senselessness of my life; that was gone during the morning. tv-film: I acoustically understood nearly all! Normally I don´t understand speaking so good, minor hearing defects may be sometimes caused by depressions, so I have been told. Better with this substance? 24:00h: Deep erotic feeling, sleep very good, deep. Second day 8:00h: wakeup. No depression at wakeup, with profound empathy, communication full of vitality.

________________________________________
Comments:
Optics, euphoria and psychodelia don´t reach that of Mescaline or LSD, may be (quite likely) at higher doses (if one can tolerate it). Higher doses than let say 3mg let increase to me the uncomfortable side effects. Therapeutical index seems to be to small to me. But there is some potential in the feeld of beeing antidepressiv and entactogenic at very low doses of let say 0.1 to 1mg s.l. In so far may be helpful in psycholysis. On the whole I guess ten times or more potent than Mescaline.
Uncertainty of dose ≃ ±30%
The HCl-salt is sparingly soluble in water, but it does in ethanol !

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[jason7]

This line of research doesn't seem to be leading anywhere productive. Maybe try combining syringaldehyde with the PEAs

 

[Hans Meyer]

This line of research doesn't seem to be leading anywhere productive. Maybe try combining syringaldehyde with the PEAs

All literature shows the benzylic part having an electron donating function (-Hal, -OH, -O-alkyl etc...) in ortho position for great potency. So my experience too. But for going into a direction of other quality of action (e.g. not so "agressiv", "smoother") may be syringaldehyde or 3,4,5-Trimethoxybenzaldehyde etc....useful. So I had nice experiences with 3-thenylmethyl as the benzylic component.

 

[Hans Meyer]

Perhaps you don't understand - Chemists that actually make and characterize compounds nowadays don't do so on the basis of their qualitative observations alone. If you don't have any means of checking your reaction products, even a melting point, then it's impossible to tell... just because you get something that is psychoactive and think it works, doesn't mean it worked. If you can't provide any evidence you have made the product in question, what's to say you didn't make some different isomer, or just recovered your starting material unreacted? If you have access to reagents and apparatus for doing reactions why don't you have access to TLC plates and a UV light, or some ninhydrin or something?

Only one analysis (GC-MS of 34-DMPEA-NDEPA) I could execute you may found (attachment!) here: https://www.hyperlab.info/inv/index.php?act=ST&f=52&t=30996&hl= (the url is sure, despite of the browser warnings.)

 

[jason7]

That was a good forum. I got a couple good PDFs from it on morning glory seeds and Hawaiian woodrose seeds. Interestingly, Summer Skies and Wedding Bells had a lot more alkaloids than Heavenly Blues and Pearly Gates.

 

[Hans Meyer]

5-Ethoxy-2-methoxy-4-methylamphetamine, IRIS (nach Shulgin) date 140881

************************************************
5-Ethoxy-2-methoxy-4-methylamphetamine
IRIS (nach Shulgin) date of trials 810808, date of publishing 140903
************************************************
IUPAC-Name:
1-(5-ethoxy-2-methoxy-4-methyl-phenyl)propan-2-amine

structure:

Alexander Shulging synthesized IRIS first and made two tests (PIHKAL p. 695:, Transform Press):

1.) „With 7.5 mg: At about three hours I felt that I was at threshold, but an houre later there was nothing.“
2.) „With 9 mg: Maybe a little light headed? Maybe not. Little effect if any.“

My trials:
Trial 1:
Salt: Hydrogentartrate
Dose of free base [nMol/kg]; (M=223 g/Mol): 47
Dose [mg] of free base related to a 75 kg body: 0.79 mg
Route of Administration: o.e.s.
Duration: na
Notes: nearly nothing

Trial 2:
Salt: Hydrogentartrate
Dose of free base [nMol/kg]; (M= 223 g/Mol): 79
Dose [mg] of free base related to a 75 kg body: 1.3 mg
Route of Administration: o.e.s.
Duration: na
Notes: With 2.5mg Hydrogentartrate: weak but significant response: my stomach starting to churn, a little bit feel dizzy, fantasy, illusions, dreamings, lack of concentration (date 08.08.1981)

Trial 3:
Salt: Hydrogentartrate
Dose of free base [nMol/kg]; (M= 223 g/Mol): 126
Dose [mg] of free base related to a 75 kg body: 4 mg
Route of Administration: o.e.s.
Duration: to about < 15 h
Notes: 1...4h: high attenuation (central nervous system ?) and calming but without tiredness. Lack of concentration. Tingling in arms. 4h: calming suddenly disappeared (within ½ an hour!). To about 15h: weak stimulation, I slept less deeply with much dreaming. Tingling in arms continued, feeling like weak muscle weakness. Weak upper stomach cramps (no nausea!). Weak diarrhea. Little bit panic because of the muscle weakness of the arms. Think it were psychosomatic complaints in psycholytic situation, deep clear organic facts, ready to process analytical treatment, working out and/or redesign. In so far: psychodelic (+...++). (date 07.04.1982)
_____________________________________
Comment: Wondering about the great difference (quali- and quantitative) in power between Shulgin´s tests-results and that of mine.
My only explanation is "set and setting" differs. With the years I found more and more that set and setting are the most powerful influences.
It seems to me that I was in deep physical intervention corresponding to my character traits. For character is not only part of the psyche, but has its part also in the physical condition. In so far IRIS seems to me as a possibility to learn more on ones physical character organisation, in so far: psychodelic.

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[Hans Meyer]

That was a good forum. I got a couple good PDFs from it on morning glory seeds and Hawaiian woodrose seeds. Interestingly, Summer Skies and Wedding Bells had a lot more alkaloids than Heavenly Blues and Pearly Gates.

Why You say "was" and "got". Is it now no longer?

 

[jason7]

Why You say "was" and "got". Is it now no longer?

Why are you screwing around with 4 mg when you already knew that 9 mg had very little effect? Take a good 30 mg and get back to us. Also, the Hyperlab forum won't translate with Google Translator for some reason. It says it can't access page. Maybe because you have to be logged in.

 

[Solipsis]

He said for him the 4 mg resulted in "In so far: psychodelic (+...++)", and careful titration is not a sin, especially with compounds that have nearly no recorded use in humans.. 8)

 

[tacodude]

Jason terrible recommendation... A similar one to eyeball 25i from someone who handled phenanzepam and thought they knew better... What a fool I was not to trust myself that they didn't know better.

 

[Hans Meyer]

research and titration

He said for him the 4 mg resulted in "In so far: psychodelic (+...++)", and careful titration is not a sin, especially with compounds that have nearly no recorded use in humans.. 8)

The reason for my aproache can be read on page 1 of this thread, and also here https://www.hyperlab.info/inv/index.php?s=&act=ST&f=52&t=30996 (under "psychodelic or not ?"). For exactly that reason, that a compound "have nearly no recorded use in humans", makes it a candidate for use in future and for research (when the best substances are all banned by authorities). Shulgin found IRIS having nearly no power, but as You know, set and setting is most influencing. For me it had a remarkable effect on the level of inside into my character-based physical organisation; makes it for that a candidate for Psycholysis (a very important field, and subset or partial quantity of psychodelic use). It is nonetheless worthwhile to pay attention also on such properties.

 

[jason7]

Well, we know Shulgin felt next to nothing from 9 mg so at least 30 would probably be required. Maybe even more like 60-75.

 

[Bagseed]

and how do you know that "at least 30mg" are required?

 

[jason7]

and how do you know that "at least 30mg" are required?

Note the word "probably". If 9 has a barely noticeable effect then it seems reasonable to assume that 20 would have a light effect at best and that 30 would be in a range where significant effects would be a realistic possibility. I'm guessing that 30mg would actually be a threshold dose, if it even has effects, and that 60-75 would be more likely to have noticeable effects. Just my intuition. I think you actually need a methoxy group on the 2 carbon for psych effects though. See this entry in PIHKAL. That's 4,5-DIMETHOXY-2-ETHOXYAMPHETAMINE. 50mg was the highest dose tried.

QUALITATIVE COMMENTS: (with 50 mg) There were no effects.

Apparently an ethoxy on the 5 carbon of a mescaline analogue is still effective, METAESCALINE; 3,4-DIMETHOXY-5-ETHOXYPHENETHYLAMINE

It's about the same potency as mescaline but, interestingly, produces no nausea or other negative physical effects. It does taste very bad though, apparently. Aside from the taste, it might be a good compound, though the low potency would make it impractical for commercial production. However, the question is; would an ethoxy on the 5 carbon of, say, DOM produce a compound with similar effects and potency but less bodyload? I think that's where Hans should concentrate his research, on the 5 ethoxy compounds. The 2 ethoxies are almost certainly going to have little if any activity.