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All 28 posts Subject: Preliminary DON writeup Please login to post Down

Bandil
(Hive Bee)
06-11-03 10:48
No 439326
      Preliminary DON writeup
(Rated as: excellent)

Hi!

The two last days in the lab has been great. The goal was DON hydrochloride, which almost certanly has been produced. The vacuum pump was at the repair shop so the entire synth was done without it, which proved to be somewhat annoying, but it wasn't impossible.

to the nitropropene:

10 gm's of 2,5-dimethoxybenzaldehyde was processed alá Barium with nitroethane to produce about 10 gm's of nice canary yellow crystals of (2,5-dimethoxy-phenyl)-nitropropene. The nitropropene seems to be somewhat less prone to crystallization than the ethene, so after one hour of reaction, and following addition of the GAA, the 10 mL IPA was evaporated and the resultant mixture was put in the freezer. After 10 mins the mixture was very viscious, but the second it was touched with a glass spatula, the whole mess crystallized nicely. This was washed three times with water to remove the methylammoniumacetate.

reduction:

Standard LAH reduction in THF. No noted problems. Gave a nice yeild of 5,0 grammes of yellow-tinted DMA freebase. As mentioned there was no vacuum available, so it was not possible to distill it. The DMA was tested with marquis, which turned totally green immediately just like good old 2CB.

The DMA was dissolved in 30 mL's GAA and stored in the freezer untill it was to be used.

Nitration:

Half of the DMA was used for the nitration(the other half has quite another fate heh).

10 mL 62% HNO3 which weighted 13,4 g, was mixed with 3,2 mL's of water to produce 13 mL's 50% HNO3 solution. This was placed in a small flask, and submerged in water/ice. A magnet was put into the flask and stirring was started.

16 mL's of the GAA:DMA mixture(30 mL GAA:5 gm's DMA) was dripped into the solution over the course of ten minutes. The GAA was yellowish in color. As the DMA was put into the nitration liquid, it turned more reddish in color(probably some NOx), but no red gas was evolved. When the addition was complete, it was allowed to stand in ice water for an additional 10 min's. This mixture was poured into 100 mL's of ice/water and stirred. The mixture was brownish/orange and resembeled a nice summer cocktail. The mixture was basified(1) and extracted with DCM(2). The DCM was washed with water and then acidified and extracted into water. The water was washed three times with DCM and then evaporated(3). The resultant "not-so-white-and-beautifull-crystals" has not been weigthed yet, but theres between .5-2 gm's(it's hard to estimate). They'll be subjected to recrystallization and following bioassay.

All in all: it's a quite forgiving synthesis(the nitration that is). It's somewhat less hazardous than bromination with elemental bromine. I just cant figure out how the heck the authors from PiHKAL have made nice crystals from one extraction with DCM. The DCM in this case was less than white and nice with the goodies in it...

I'll probably have some more info when the weekend is due :)

1:
The PiHKAL entry was followed, but it seems unlogical to basify at first. Why not simply wash with DCM a couple of times to remove the grud?

2:
This one should almost be in worst lab mistakes. After adding the "DCM" there was no separation. Even no ugly emulsion?? Thought about that one for 15 mins untill it was realized that it was THF and not DCM that was dumped into the soln ;) Had to wait 20 mins for the THF to boil of. Read the labels very carefully after that one.

3:
The water phase should just have been basified and put in some DCM which then could be boiled off. Gives nicer results in 99% of the cases. But again, the PiHKAL autors do it this way. I'm beginning to think it's a prekambrium synthesis writeup :)

Regards
Bandil

Cops are not there to help you, they're there to bust you.

Barium
(Hive Addict)
06-11-03 13:39
No 439353
      Nice

Nice to see someone finally made this compound. A word of caution though. Roumors has it that DON has been avaliable as a RC in EU. The vendor cancelled it quickly because a high percentage of the customers were hospitalized. I believe the dosage was 4-5 mg. All of them recovered though.

Freaky

Bandil
(Hive Bee)
06-11-03 13:44
No 439354
      Perhaps PiHKAL overestimated the dosages?

Perhaps PiHKAL overestimated the dosages? 4-5 mg's of DOB would probably also hospitalize quite a few.

What would be an appropriate start dosage? I was thinking 4,5 mg's originally, but maybe i should reconsider?

Regards
Bandil

Cops are not there to help you, they're there to bust you.

Barium
(Hive Addict)
06-11-03 13:53
No 439358
      I would start with a few hundred micrograms...

I would start with a few hundred micrograms and titrate upwards, slowly and carefully.

Freaky

Prometheuz
(Hive Bee)
06-12-03 11:10
No 439506
      Bioassay proposal

Being a bit adventurous, an experienced psychenaut, and HATING for a new compound to work without getting any decent effects, my first bioassay of the compound will probably be 1 or 1,5 mg.
Would that be totally irresponsible? Strong psychedelic effects I can handle, but would there be any serious risk of extreme, undesireable physiological effects in anyone's opinion?

To fathom Hell or soar angelic
Just take a pinch of psychedelic

Aurelius
(Hive Addict)
06-12-03 13:53
No 439521
      Barium

Is not so unexperienced either, neither am I, nor the many others on this board who recommend taking it slowly. Start just as Barium proposes, it doesn't take nearly as long as you think, and in the long run- IT'S WORTH THE WAIT!

Act quickly or not at all.

Barium
(Hive Addict)
06-12-03 14:49
No 439527
      Why careful titration?

DON is active no question about it. But perhaps just a few percent can tolerate the dosages necessary to get full activity. As this is unknown territory what one really should look for in the beginning is signs of toxicity. This is done by slow titration. The psychedelic effect will not go unnoticed when it hits you. But you might be to busy looking for it that you miss early signs of severy toxicity.

Prometheuz, I'm sure you are a hard headed psychonaut. But why risk a emergency visit to the intesive care with a sky-high blood pressure and heart arrythmia, when it easily can be avoided?

Freaky

Prometheuz
(Hive Bee)
06-13-03 18:47
No 439823
      Marquis test

Marquis test of the cleaned-up product: Instantly to brownish-red, with slight bubbling, switching to pure green after a couple of minutes.
The product is VERY yellow, quite resembling picric acid. Is this caused by impurities? Wasn't it supposed to be nearly colourless? Very soluble in alcohols.

To fathom Hell or soar angelic
Just take a pinch of psychedelic

yellium
(I'm Yust a Typo)
06-13-03 19:29
No 439833
      Nitro-MDA is also yellowish, also in the HCl...

Nitro-MDA is also yellowish, also in the HCl form. Not really intensely yellow, but certainly not pure white as the other phenethylamine and amphetamine salts are.

Bandil
(Hive Bee)
06-13-03 22:13
No 439863
      Bioassay

Currently bioassaying:

Subjects has been administered 2 mg's each. Two individuals got 2,75. That was two hours and thirty minutes ago and we definately have a positive here. Probably still going up effect wise. No signs of physical discomfort what so ever, no signs of toxicity and spirits are high(VERY high).

Regards
Bandil

PS: Damn it took long to write this post! cool

Cops are not there to help you, they're there to bust you.

Bandil
(Hive Bee)
06-14-03 12:21
No 439966
      Final verdict!

It is now sixteen-seventeen hours since ingestion, im sober and i feel grrrrreat!

The drug peaked after two hours. The climb towards the top was very gentle and generally amusing. At t+6 hours it started going down. At eight hours i was almost able to sleep without cheating(but 20 mg diazepam made sure i DID) Woke up after seven hours feeling quite refreshed. Was told i drooled quite a bit while sleeping, but thats probably the DZP.

The compund was very stimulating. At t+4 hrs some fentanyl was ingested to mellow us out, which did the trick quite well, but severe dosages were needed. I'd suspect it would be good in social settings at the dosages we did, as we were in no way impaired and confused. The mindspace was a bit "crazy" and visuals where shimmering everywhere(clear ++). Double up the dosage and i will suspect that patterns will be flowing everywhere. The lenght of the drug was acid like, which in my world is perfect.

Every subject that ingested the materials were happy about the effects and are more than willing to investigate further soon :)

Effect wise i'd place it somewhere as a mixture of 2CB, meth and maybe a tint of MDA... The next bioassay will determine the nature of the drug further.

I really can't figure out why this material has gotten so little attention. The synthesis is quite ease compared to DOB for instance. The duration/come up is better timed. Maybe it's just the "novelty" thats talking, but i'd put it quite high on my favorite drug list!

Kind regards
Bandil

Size doesn't matter, it's the sound you make when hitting the ground after smoking it, that matters!

yellium
(I'm Yust a Typo)
06-14-03 12:44
No 439969
      >I really can't figure out why this ...

>I really can't figure out why this material has gotten so little attention.

From DON's description in PiHKAL you really don't know what to expect from it. Plus, 2C-N seems to be a bit disappointing compared to the other 2C's. So I bet most clandestine chemists take shulgins word as gospel, and guess that DON just doesn't do it as good as DOB/DOM.

Barium
(Hive Addict)
06-14-03 13:48
No 439978
      Why

The compund was very stimulating. At t+4 hrs some fentanyl was ingested to mellow us out, which did the trick quite well, but severe dosages were needed.

Why mask the true effects of DON at this early stage with fentanyl?? Especially if you are planning to go higher dose-wise. Know your territory before changing it.

Freaky

Bandil
(Hive Bee)
06-14-03 16:45
No 440007
      Barium> I guess that would have been the...

Barium> I guess that would have been the prudent thing to do(not do the fentanyl that is), but the mood was a little hyper, and we weren't able to go anywhere to really flip out(like a festival or outside dance event), so we simply sat in my basement, chilled and tried to grasp the mind space of the compound. It was a tiny weeny to stimulating to sit still and just talk among friends, so it really really was nescassary laugh .

Regards
Bandil

PS: the fentanyl wasn't half as "unscientific" as the 10 mg's of 5-meo-dmt that was smoked on the peak... Pretty intense though ;)

Size doesn't matter, it's the sound you make when hitting the ground after smoking it, that matters!

Prometheuz
(Hive Bee)
06-16-03 10:10
No 440273
      A few comments to the bioassay

crazy Well, sorry, I decided to take PIHKaL as a reliable indication of dose, even though Shulgin never tasted the compound himself. Maybe a bit foolhardy, but I don't really have THAT many occations where I can take a compound that might leave me sky-high for 16 hours.
I took 2,75 mg, delivered as a 1 mg/ml in 40% alcohol solution. The solution is bright, clear yellow.
After 1 hour + 30 minutes we all agreed that PEA-typical stimulation had hit us, and that placebo was out of the question.
The two of us getting 2,75 mg instead of 2 mg seemed to get a bit better psychedelic effects (I had definate, beautiful visuals, though not overwhelming!), but we didn't seem to be noticeable more stimulated. I certainly hope that the stimulant-effect doesn't increase too much with dose, so that strong psychedelic trips would be unadvisable/unpleasant due to overstimulation. In our dose-area, nobody noticed any unsetteling cardiovascular effects.
Overall the compound seemed quite benign to the body in these doses. I'm usually rather sensitive to pre-trip-nausea with PEA's, but I felt NO discomfort whatsoever.
blush Sorry for "tainting" the alpha-test by mixing in a bit of fentanyl, but it just seemed like the thing needed for us best to enjoy the trip at the available setting.
We will slowly proceed with the experiments, raising the dose in rather small steps, and with at least a week in-between the trials.

To fathom Hell or soar angelic
Just take a pinch of psychedelic

Barium
(Hive Addict)
06-16-03 11:25
No 440280
      Good

I'm glad it turned out well for you guys. Remember though, there is a reason why Shulgin takes it slowly to get up to effective levels with unknowns. Please be careful in the future. You know I'm not trying to be a asshole saying this. It's just a friendly advice.

Freaky

yellium
(I'm Yust a Typo)
06-16-03 16:38
No 440318
      I think a week inbetween might be too short.

I think a week inbetween might be too short. For long-lasting suckers like DON I would take at least 2 weeks, when you take 'effective' dosages. Otherwise you might have the risk of tolerance, and people flipping out because 5 mg is way over the top for them..

Prometheuz
(Hive Bee)
06-17-03 07:03
No 440473
      Too short?

Yellium> This one seems to be nowhere near the duration of for instance DOB. In our case we agreed we were very near baseline on the 7-hour mark. I doubt that it will go much longer than 12-14 hours, even at high doses. Could that "curse" you with resistance to the drug for an entire week?
BTW, can anyone give me a good explanation to why we are building resistance to psychedelic drugs like this? The 5-HT-2A-receptor has to forget, before it will be fooled by that trick again cool ? It's not like it should deplete receptor-juices, like MDMA and stims.
But that said, there will usually be at least 2 weeks inbetween trials. We do have other things to do. Sadly. wink

To fathom Hell or soar angelic
Just take a pinch of psychedelic

starlight
(Hive Bee)
06-17-03 16:15
No 440559
      tolerance

tolerance does not only occur due to neurotransmitter depletion or neurotoxicity.

the body and brain do a remarkable job of adapting and maintaining the status quo in the face of "adverse conditions".

there are many reasons for tolerance ranging from receptor down-regulation (less receptors - temporarily), changes in metabolism (faster elimination), changes in intracellular messaging (adnenylate cyclase up regulation for example).

if you disturb the equilibrium, the body/brain will attempt to re-establish it.

Rhodium
(Chief Bee)
06-17-03 18:07
No 440577
User Picture       Mechanism of Tolerance Development

I put together a nice little document on this here: Post 440576 (Rhodium: "Trip Tolerance: Neurons Swallowing own Receptors", Serious Chemistry) - Enjoy!

Prometheuz
(Hive Bee)
06-30-03 08:39
No 443465
      Further DON bioassays and more
(Rated as: good read)

The last couple of weeks, a good handful of experienced, wellinformed people have tasted the compound at different levels. It seems like 4,5 mg is about as high as most people like to go. In the area 4-4,5 mg, everyone have had a satisfying and fulfilling psychedelic experience.
I tasted 4,5 mg myself this weekend. It comes on much faster than DOB; a definate ~+1,5 after an hour. I would say the peak is about 3,5 hours after ingestion (when ingested in solution). I think the level of stimulation will prevent us from taking much higher doses than 4,5 mg. Not that it felt uncomfortable or dangerous at all, but a slight hypertension was noticed. Mentally, the trip is quite easy to manage. No real confusion, and if you feel like it, you can bring yourself "back to reality" without much effort.
The visuals are not really that impressive. As expected, much more like 2C-B or mescaline than acid. Beautiful and fun, but not overwhelming. The mind is racing in entertaining directions, and the experience is quite humorous to most test-pilots.
No adverse effects have been noticed the day after the trip. During the trip, some people get a slight bit of nausea, but the it seems like it is rarer (and less uncomfortable) on this compound than on 2C-B.
BTW, the yield from the 2,3 g of DMA was about 1,5 g. We don't know for sure yet, since only half of it has been purified.

To fathom Hell or soar angelic
Just take a pinch of psychedelic

Rhodium
(Chief Bee)
06-30-03 13:20
No 443517
User Picture       DON Duration

What's the approximate duration of the material at that level?

Prometheuz
(Hive Bee)
06-30-03 13:30
No 443520
      Duration

Well... Sorry for being unscientific again... But this weekend we ended up terminating the trip prematurely with diazepam, to get some sleep before a busy saturday. We downed ourselves after about 7 hours, but there were still quite some effects left. Dreaming was spectacularly lucid and weird!
The other people who tried it at this level, had almost reached baseline at 10 hours. At least sleeping doesn't seem to be a problem after 10 hours.
However, it does induce some severe resistance towards psychedelics. 2 weeks ago, after the first test (with 2,75 mg), I tried 22,5 mg 2C-B the day after. I would have had more effects from drinking a large mug of coffee. Nothing at all!

To fathom Hell or soar angelic
Just take a pinch of psychedelic

yellium
(I'm Yust a Typo)
06-30-03 17:37
No 443540
      Hint: then you better be careful with mdma/mda

Hint: then you better be careful with mdma/mda the day after. There is a reasonable chance that you suddenly notice that this mdma is _very_ trippy.

Prometheuz
(Hive Bee)
07-01-03 08:43
No 443728
      MDMA the day after psychedelics

Yellium> Thank you for sharing, at the upcoming festivals that might very well have been done, without us expecting the effects of the MDxx to be altered in any way.
Is it empirical knowledge, or do you have a pharmacological explanation? Will the MDxx be potentiated/have altered effects in a good/nice/exciting way? Are there any physiological dangers in doing this?
Thank you in advance.

To fathom Hell or soar angelic
Just take a pinch of psychedelic

yellium
(I'm Yust a Typo)
07-02-03 18:01
No 444031
      I've done some mdma on the tail end of a 2ct7...

I've done some mdma on the tail end of a 2ct7 trip and was tripping my balls off an hour later. Ditto when I took some 5htp half a week after doing 2C-D. So, I guess that if you want to be safe, don't take anything which ups serotonin levels.

(I don't recommend taking mdma after psychedelics, simply because you don't know where you might end up. You have absolutely no idea how strong your trip is going to be, and what will happen.)

Rhodium
(Chief Bee)
05-04-04 21:23
No 504855
User Picture       Odd DON study, with bold electrochemical claims
(Rated as: good read)

Electrochemical Study of the Hallucinogen (±)-1-(2,5-Dimethoxy-4-nitrophenyl)-2-aminopropane
Pablo Richter, Alfonso Morales and J. Sebastián Gómez-Jeria, Demián Morales-Lagos
The Analyst, 113, 859-863 (1988) (https://www.rhodium.ws/pdf/don.electrostudy.pdf)

Abstract
An electrochemical study of the hallucinogen (±)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane, which differs from similar compounds in that a hydrophilic nitro group replaces hydrophobic substituents on the 4-position of the benzene ring, was carried out using a solvent - buffer system containing pyridine - formic acid and tetramethylammonium chloride solution. Polarographically and voltammetrically the drug behaves as other, structurally related aromatic nitro derivatives, the nitro group being reduced to the hydroxylamine in a single, well defined irreversible, diffusion-controlled and pH-dependent wave. The E_1/2 versus pH and versus pH relationships were examined and cyclic voltammograms were recorded at different pH values and at different scan rates in order to elucidate the reduction mechanism and to identify relatively unstable intermediate species. The results of this study suggest that a significant relationship can be established between the electrochemical behaviour of any compound and its molecular - electronic structure, and between molecular structure and pharmaceutical or biological activity, as confirmed recently by quantitative structure - activity relationship studies.

^{The Hive - Clandestine Chemists Without Borders}

7is
(Hive Bee)
05-09-04 16:07
No 506011
User Picture       DON study with human trials
(Rated as: good read)

A quantum-chemical and experimental study of the hallucinogen (±)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane (DON)
Juan Sebastián Gomez-Jeria, Bruce K. Cassels and Juan Carlos Saavedra-Aguilar
Eur. J. Med. Chem. 22 (1987) 433-437

Abstract
The electronic structure of 1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane (DON) was calculated at the CNDO/2 level, and the racemic compound was synthesized and found to be hallucinogenic at doses of 4 mg. DON differs from its similarly active congeners in that a hydrophilic nitro group replaces lipophilic substituents at C-4 of the benzene ring. The implications for the mechanism of serotonin receptor binding of these drugs are discussed.

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