Author Topic: Synthesis of para-fluoro-(4-methylaminorex)  (Read 6972 times)

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Lucid_Dreamer

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Depends on your country, and which isomer of...
« Reply #20 on: November 28, 2003, 11:22:00 AM »
Depends on your country, and which isomer of 4-mar you want, you can make cyanate easily, and you can make different isomers with different precursors, If it isn't already illegal to posess PPA then you can make the trans isomer, if not, then you can use ephedrine as a precursor to get the trans too, I am still pondering the idea of substituting pseudo in the cyanate syth which might result in the N-methyl isomer, but I think the pseudo can't be cleaned enough for the reaction, I say go for it, let us know. Read all of the following first, and I mean all of it.

Post 212038

(Rhodium: "4-Methylaminorex Synth w/o CNBr", Novel Discourse)

Post 354295

(Bandil: "trans-4-MAR synth w/o cyanogenbromide writeup!", Methods Discourse)

Post 458588

(Bandil: "One pot synthesis of 4-methylaminorex", Novel Discourse)

Post 214057

(foxy2: "NaOCN and KOCN Production", Novel Discourse)

Post 442105

(DRIVEN: "NaOCN from urea and sodium carbonate", Methods Discourse)


Try reading all of the threads for best results, I couldn't find the thing that tells you that you can get pulminary hypertension from ice and die with high doses. But you get the idea right?


Bandil

  • Guest
Lucid_Dreamer> I'd think twice about ...
« Reply #21 on: November 28, 2003, 11:43:00 AM »
Lucid_Dreamer>

I'd think twice about playing around with the 3,4-dimethylaminorex(which would be the result from using ephedrine in the reaction).

Read

Post 354971

(Rhodium: "PPA synthetic routes + 3,4-DMAR Note", Methods Discourse)
as a cautionary note!

Now let's keep this thread on-topic again for the fluoro version. I have a feeling a few bioassays will be added soon  8)

Regards
Bandil


Vitus_Verdegast

  • Guest
Be careful with 3,4-dimethylaminorex!
« Reply #22 on: November 28, 2003, 12:07:00 PM »
Pseudoephedrine will not give 3,4-dimethylaminorex, but 3,4-dimethyl-5-phenyl-oxazolid-2-one (the amide). You will need ephedrine for the aminorex analogue. Isomerization from pseudoephedrine to ephedrine and back is possible using conc. HCl.

Post 299256

(SPISSHAK: "isomerization of amino acohols", Novel Discourse)

Post 423903 (missing)

(Rhodium: "Russian articles beyond my reach", Russian HyperLab)
(<- if someone has access to the journal)

Beware of 3,4-dimethylaminorex, it is less active and more toxic than 4-MAR.

Post 462392 (missing)

(Rhodium: "N-Methyl-4-Methylaminorex/3,4-dimethylaminorex", General Discourse)

Post 460413 (missing)

(akdov: "similar study, different article.", General Discourse)

Post 464400

(Rhodium: "Apples & Oranges", Methods Discourse)

Post 450130

(Vibrating_Lights: "Future amphetamines and a little Purple Jewl", Serious Chemistry)

Post 212184

(Rhodium: "Re: 4-Methylaminorex Synth w/o CNBr", Novel Discourse)


This is the 4-MAR pulmonary hypertension post by Megatherium:

Post 456788

(Megatherium: "A word of caution ...  & another KOCN patent", Methods Discourse)

also read:

Post 346726 (missing)

(Dr_Heckyll: "4-Methylaminorex Dangers", General Discourse)



suttleila

  • Guest
4-mar
« Reply #23 on: November 28, 2003, 12:46:00 PM »
lucid which one of those would be the easiest and would less likely kill you lol because most of them release ammonia and everything else i am looking for a method that takes all the danger out and would end up with a decent but not perfect yield keep in mind the only thing i can produce is meth either the e/rp/i2 or ammonia/li method i am trying to learn something better but its a fucking bitch because all the chemist i know or people that showed me how are in prison now!!!!

Lucid_Dreamer

  • Guest
You want the trans or the cis- isomer, but you
« Reply #24 on: November 28, 2003, 12:58:00 PM »
You want the trans or the cis- isomer, but you would have to find a good source of PPA, judging by your southern euphanism, you might just live in a border town, and if you do your a lucky mofo, don't try it with the ephedrine, even if you have a source, and with pseudo all you will get is the amide, although I really like that link to switching to and from ephedrine-pseudo, thanks Vitus. To put your ammonia worries to rest, it just produces nh3 and co2 because that's what urea is made from, and the cyanate also uses carbons and urea, nh3 isn't as bad as some stuff, and it won't be produced rapidly and isn't flammible, it is way better than before ppa was regulated when you had to use cyanogen bromide, now that was danger.


Rhodium

  • Guest
pseudoephedrine isomerization
« Reply #25 on: November 28, 2003, 03:50:00 PM »
Vitus: The pseudoephedrine isomerization article has been retrieved:

Post 425116 (missing)

(Flogiston: "Èçîìåðèçàöèÿ ïñåâäîýôåäðèíà â ýôåäðèí.", Russian HyperLab)


Here is a rough machine tanslation (courtesy of

Promt Online

(http://translation2.paralink.com)) which creates a document readable to me at least, but the experimental part contained too many technical words for the translation to be useful. We'll have to ask one of our Russian friends to edit this translation for clarity, and to translate the experimental part in its entirety.


IZOMERIZATSIJA PSEVDOEFEDRINA IN EFEDRIN
M.I.Gorjaev, E.I.Satdarova

 For last decade efedrin has found wide application in
To medical practice, in particular at treatment of a bronchial asthma and as the agent stimulating blood circulation [1]; diastereoizomer it alkaloida ? psevdoefedrin ? on action it is similar with efedrinom, but is much weaker and consequently in medicine it is not applied.

Efedrin and psevdoefedrin usually accompany each other in plants. These alkaloidy are widely enough distributed; they meet in efedre and in other kinds of plants [2,3,4,5,6]. From them only the few have industrial value. Now in a plenty two kinds are prepared: Åphedra equisetina and Åðhådra intermedia which contain up to 3 % alkaloidov (efedrina and psevdoefedrina). Other kinds contain less alkaloidov and besides are insufficiently investigated in chemical botanical attitudes.
    In prepared efedre on a share psevdoefedrina 80 % and about 20 % on efedrin are necessary on the average.
    Now it is established, that psevdoefedrin and connections of its lines have treo-ksnfiguratsiju, and efedrin ? an eritro-configuration [7,8].

Ability to mutual transformation of these alkaloidov has been established for a long time. In 1906. Schmidt [9] at attempt to prepare ratsemat efedrina kipjacheniem from 25-percents a hydrochloric acid has received psevdoefedrin. From here there was an idea on an opportunity of transformation efedrina in psevdoefedrin and back. Mutual izomerizatsija these alkaloidov long time it was studied by Schmidt and Emde [10,11,12,13].
    It is necessary to note work Kallisa and Schmidt [14] whom as they assert, it was possible to transform completely psevdoefedrin in efedrin, heating up a hydrochloride psevdoefedrina in the sealed - in tubes with baritovoj water at addition of powder Va (IT) 2; within 8 hours sweat pressure at temperature 170-180.
    Now it is necessary to consider established, that transformations of these alkaloidov are connected to inversion of It-group at the carbon atom located about fenilnsgo of a radical as at restoration both alkaloida pass in same dszoksiefedrin
[15,16].

Izomerizatsija, connected to inversion of It-group, can be osushchestvleva various ways. So, at processing N-àöåòèëýôåäðèíà by a hydrochloric acid boiling by 5-percents the mix of hydrochlorides efedrina and psevdoefedrina in a provisional parity 38:62 [18] turns out. Mitchel [19] has received the same results, but only alkaloidy have been submitted in a return parity (2 parts efedrina and 1 part psevdoefedrina).
    This izomerizatsija, touching alpha-carbon atom at efedrina, does not meet at N-àöåòèëïñåâäîýôåäðèíà which at acid and shelochaom hydrolysis gives only psevdoefedrin. It is typical, that similar izomerizatsija it was observed Kanao [20] at heating with concentrated hydrochloric acid N-áåíçîèë-íîð-dl-ýôåäðèíà. As a result of reaction it turned out only Î-áåíçîèë-íîð-dl-ïñåâäîýôåäðèí; Reaction was accompanied by migration benzoilnoj groups from N to About.

At hydrolysis individual chlorine both bromproizvodnyh efedrina and psevdoefedrina, turning out at replacement with haloid gidroksila, also is formed a mix efedrina and psevdoefedrina.
    From works Emde [21, 22] it is visible, that chloride and bromide psevdoefedrina are steadier at hydrolysis, than the same derivatives efedrina.
    However these data demand additional check whereas the parity alkaloidov was defined only on the basis of specific rotation of a mix after hydrolysis chlorine and bromproizvodnyh.
    In some cases izomerizatsija psevdoefedrina and efedrina it is accompanied by formation of by-products which are investigated in an insufficient degree.

So, the cold sulfuric acid forms with both alkaloidami the same ether psevdoefedrina [12, 14, 17] which at hydrolysis in boiling water or with a hydrochloric acid gives a mix efedrina and psevdoefedrina [13]. At more long action of the concentrated sulfuric acid (5 days, at 15 °) turn out some by-products among which, in particular, has been found metilamin and Others.

At a usual, factory method izomerizatsii psevdoefedrina in 50-percents the sulfuric acid manages 10?15 % of pitch and other products of irreversible change which studying can give a material for finding-out of the mechanism izomerizatsii psevdoefedrina in efedrin. It is possible, that izomerizatsija to mineral acids occurs with
obrazevaniem intermediate products, such, as hlorefedringidrohlorid at action of a hydrochloric acid, bromefedringidrobromid with bromistovodorodnoj an acid and a corresponding ether at action of a sulfuric acid. Hlorefedringidrohlorid easily enough it turns out At action of a smoking hydrochloric acid on efedringidrohlorid [22].
     
Similar should be, apparently, and action of alkalis on efedrin and psevdoefedrin, however message Kallisa and Schmidt [14] about full transformation psevdoefedrina in efedrin under action of hydrate okisi barium has not proved to be true our experiences and experiences of others
Authors [23].
    From the patent literature it is known, that efedrin and psevdoefedrin it is easy ratsemizirujutsja at heating with alkaline alkogoljatami. From ratsematov it is possible to receive again initial opticheski active components [24, 25, 26].
    Complex connections of metals and their salts with alkaloidami efedry, probably, influence also on a course of reaction izomerizatsii.
Complex connections of these alkaloidov with ÑuSÎ4 (is more true, with Ñu (IT) 2â presence of alkali) are received and described Grade Tung-fengom [27];
To regret, the author ve results their structure.
    Formation of complex connection, probably, is connected to obligatory presence of two functional groups at these alkaloidov ? it and-NÍÑÍ3; so, according to Hailey [28], dezoksiefedrin this complex does not give.
    The question about izomerizatsii psevdoefedrina in efedrin has got from us great value after works of Item. Ñ. Màññàãåòîâà [29, 30], opened in 30th years in Kazakhstan and Central Asia big promyshlen nye thrickets efedry.
    The method izomerizatsii, used on Chimkent himfarmzavode, developed VNIHFI, leads to to loss up to 50 % psevdoefedrina. With the purpose of improvement of an output efedrina at izomerizatsii psevdoefedrina the given work also has been undertaken.

Experimental part

Work on izomerizatsii psevdoefedrina in efedrin was carried out in three directions.
1. Izomerizatsija psezdoefedrina in efedrin in exact conformity with a factory method with a potion of definition of possible blanks in factory technology and receptions of products of irreversible change,
Which should give a material for construction of a hypothesis about the mechanism izomerizatsii.
2. Izomerizatsija from 50-percents a sulfuric acid, as well as in the previous case, but at entering various additives as additional catalysts. As additives various substances which could give complex connections on metilaminnoj and gidroksilnoj to groups have been tested, creating stericheskie obstacles for connection gidroksila from party SNz-MN-gruppy.
3. Studying influence of other agents promoting izomerizatsii psevdoefedrina in efedrin.

Prometheuz

  • Guest
Latest advances...
« Reply #26 on: December 12, 2003, 11:30:00 PM »
The p-F-4-MAR was bioassayed at 20 mg recently, and no definate effect was noticed. SOME stimulation was almost definately there, but not more than 10 mg of 4-MAR would do. Good mood and energy, but nothing euphoric and "drug-like" could be pinpointed.
SWIM doesn't feel like taking larger amounts of chemicals of unknown purity, so a GC/MS will be done sometime next week. I'll make sure to post the results.
Was the synth a fuck-up, or is the compound rather inactive? Hope to know soon.


Bandil

  • Guest
Activity confirmation
« Reply #27 on: January 11, 2004, 04:54:00 PM »
Well last night this compound was found to be VERY active!

The bioassay was done by Prometheus, and i suspect he will post a report tomorrow or so, but i can give some pointers of the effects he described untill then:

The dose was 40 mg's of the freebase, and was ingested together with a bottle of red wine.

After about one hour, there where observed a fuzzy MDMA-like come on which continued to climb for another two hours. Subjectively he compared the climb comparable to perhaps 80 mg's of MDMA.

At the three hour mark 80% of all motor control was lost within few minutes. Very odd ideed. It was not a problem to make normal conversation with him. No shaking / shivering where observer. From the 3.5 hour mark it seemed to reach a plateau. The effects where described as "valium-MDMA". Quite emphatogenic but perhaps not the ideal dance drug.

Ill look forward to his report within the next few days; i suspect it will be posted in this thread!

I'll try it out at the 40 mg's level on thursday and post my own experiences!

But this stuff definately targets the seretonin system more than regular 4-mar. Perhaps a combination of the fluoro version and the regular one could provide a great party drug :)

Regards
Bandil


Prometheuz

  • Guest
para-Fluoro-4-MAR: Confirmed activity!
« Reply #28 on: January 12, 2004, 11:41:00 AM »
Well, after a long period of being too busy to do any bioassaying, the p-F-4-MAR was subject to trial again. I have been building up from 0,5 mg, doubling the dose each time when nothing distinct effect was felt. At 20 mg there was a subtle SOMETHING, but very weak indeed, and might be just placebo.
Saturday I ingested 40 mg dissolved in vodka. At T=2:00 I started to feel some kind of definate effect, but subtle, and hard to define. A warm, fuzzy feeling, not unlike MDMA, with pleasant chills and all, but no energetic feeling at all, and no increased psychomotor-activity. 20 mg 4-MAR was ingested about this point to add some energy for partying. Under the come-up 1 bottle of red wine, a couple of beers and a bit of gin was ingested.
In the taxi on the way to the party (T~3:00) definate serotonine-related effects were felt. Later, physical coordination was quite impaired, even though there was absolutely no shaking of the hands or clenching of the jaws. Mood was good, but there was no push at all for dancing or too much social interaction.
At T~5:30 I took a cab home, and aborted the experiment with a bit of zopiclone to get some sleep - even though it might not have been neccesary. No hangover or after-effects were noticed the day after.
Konklusion: The compound has no real stimulant effect, but seems to work in a quite unique way on the serotonine-system. The next experiment will NOT be with the double dose. :) .
...And I'll make sure to keep it in a more controlled setting, and for once be a good scientist.
P.S.: The GC/MS-test was rather inconclusive due to poor sample preparation; had to do it rather quick and dirty. A nice peak did seem to confirm that the desired product was produced, though. Can't say anything about purity yet, but another, more careful run will be done sometime within too long, I hope.


Bandil

  • Guest
Final evaluation
« Reply #29 on: January 17, 2004, 06:10:00 PM »
Subjective evaluation the title compound.

Background:
No other drugs was ingested prior to taking the fluoro-methylaminorex. During dinner two glasses of red wine was ingested (i usually drink quite a bit, so it did not interfer). The mindset was very good in all the subjects. No serious(serious as in causing resistance, such as 4-mar and MDMA) drugs had been taken in the week before. My body weigth is approximately 92 kg´s, mostly distributed as muscular tissue.

Dosage:
I ingested 44 mg´s of the freebased compound dissolved in ethylalcohol and Prometheus took 48. His girlfriend took 30 mg´s.

The experience chronologically described:
At 19:30 in the evening the compound was ingested. An hour later it was obvious that something was in the system. The bloodpressure felt quite raised and continued to climb during the next hour. Nothing to alarming, but it was enough to be felt. At the T+2 hrs mark a fuzzy feeling was noted in all the subjects. It felt like the come up on MDMA, but more smooth. A slightly annoying headache was present in the two male subjects at this point. The blood pressure felt quite annoying. This was accompanied by a tight feeling in the chest. The mood was a little giggly, but not nice enough to make up for the body load. At three hours the fuzzy feeling had faded, but the body load(headache, chest pressure and high blood pressure) remained. The pulse was not affected by the drug. I headed home at T+5:00 hours. I went by bike with really nice music on my walkman. To test the "going out" potential i walked through the main street of the capital city and gazed at the night life. Nothing interesting. I was just plainly annoyed by the body load. At T+6:00 hours the body load had faded somewhat, but sleep was still not possible. At T+7:00 i was at baseline again and went to sleep at T+7:30 hrs.

The day after i was not hung over or anything. No afterglow was noted.

Conclusion:
This is the aminorex version of PMA / PMMA. Hardly any nice effects are present, but there sure is body load. I would be hesitant with increasing the dosage further, as the body-effects where quite high.

Unfortunately this compound is not worth a damn thing. It might do as some killer-street-ecstasy substitute, but thats not for me! To look on the brigth side(as you always should try to do), a compound has been tested and although it is not usefull as recreational drug it has limited the large spectrum of aminorex analogues possible with one.

So dont waste your money and time on this compound.

Have a nice weekend!

Regards
Bandil


Prometheuz

  • Guest
Comments on Bandil's report on the bioassay
« Reply #30 on: January 20, 2004, 02:51:00 PM »
The above description of the bioassay fits my experience well.
The 40 mg amount I had ingested a week ago, with apparently better result, is probably because of potentiation of the other compounds taken; alcohol, THC and 4-MAR. It might seem that p-F-4-MAR works like some kind of "catalyst" for other drugs. In itself it isn't interesting at all IMO.
No stimulant effect was experienced; no significant empatogenic effect, and definately no psychedelic effects what so ever.
Due to the bodyload/effect ratio of this compound, probably no further bioassays will be done. Mainly due to the apparent rise in bloodpressure, there will be no tests at higher doses.
Well, this one apparently was a dud. I hope to get a nice analysis done in a month's time, to confirm the purity and identity of the drug produced; it would be a pity if the pure stuff had a useable profile, and everyone just dropped the subject because we fucked up the synth... :P
Anyway, interesting to try out a completely new substance from scratch, without knowing what effects and dosages to expect. IMO we did it in a quite rational and careful way, but always be extremely careful with untested compounds.


Antoncho

  • Guest
Well done!
« Reply #31 on: January 20, 2004, 04:45:00 PM »
Excellent work, guys!

Thank you.



Sincerely,

Antoncho

Rhodium

  • Guest
3,4-Dimethylaminorex Preparation & Analysis
« Reply #32 on: February 10, 2004, 06:31:00 PM »
Re:

Post 473612

(Vitus_Verdegast: "Be careful with 3,4-dimethylaminorex!", Methods Discourse)


Liquid Chromatographic and Spectral Analysis of the Stereoisomers of Dimethylaminorex
F. Taylor Noggle, Jr, C. Randall Clark And Jack Deruiter

Journal of AOAC International 75(3), 423-427 (1992)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/forensic/dimetylaminorex.pdf)

Abstract
The individual enantiomers of cis- and trans-3,4-dimethylaminorex were prepared by treating ephedrines or pseudoephedrines with cyanogen bromide. These compounds represent potential designer drug modifications of aminorex and 4-methylaminorex, which have appeared recently in the clandestine drug market. The UV spectra for these compounds are typical of phenethylamine-type compounds, and FTIR spectra allow for differentiation of cis- and trans-isomers. The mass spectra for the dimethylaminorex stereoisomers show characteristic fragments at m/z 57, 118, and 190. The cis- and trans-Isomers were separated in a reversed-phase liquid chromatographic system on a C18 stationary phase, with the cis-isomer displaying the higher capacity factor.