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All 26 posts Subject: DOM writeup Please login to post Down

Bandil
(Hive Bee)
08-07-03 05:47
No 452246
      DOM writeup
(Rated as: excellent)

About 30 gm's of dimethoxytoluene, where prepared as described in an earlier post, via the TMP route in high yeilds. While the dimethoxytoluene where distilling the Vilsmeyer complex where prepared in the following manner:
An *very* old can of DMF where dried by dumping several grams of dry sodiumsulfate in it and shaking for at few minues. After settling, 45 mL's of DMF where placed in an 500 mL RBF and stirred magnetically. 40 mL's of -not so new- POCl3 where added in one portion to the DMF via an addition funnel. The solution where stirred for 1½ hour at room temperature where it gradually turned deep orange, which indicated a succesfull formation of the Vilsmeyer
complex.

To this mixture there where added 15 gm's of the freshly distilled dimethoxytoluene in one portion. The addition funnel was replaced with a condensor with attached drying tube. The whole lot was stirred at RT for 15 mins, and placed in boiling water afterwards for two hours. It gradually turned darked and at the of the two hour period it was pitch black. The whole mess was dumped into 1½ L of cold tap water with lots of ice in it. This turned nicely orange immediately and smelled like the substituted benzaldehydes tend to do(sweet). This was filtered when the ice had melted. This whole solution was suction filtered to give 4 grammes of 2,5-dimethoxy-4-methyl-benzaldehyde. The yeild was on the low side, but subsequent examination of the filtered water sludge showed that alot more had precitipated. It's always hard to judge how much is floating around in a slurry mess, but it just might be enough to bring the yeild closer to 12 grammes or so, making it quite a feasibe synth. As always patience is a great asset in these types of operations - maybe swim will also learn someday :) The final yeild will be posted once measured properly filtered, measured etc.

The BA was without further purification subjected to condesation alá Barium. 4 gm's BA, 1,9 gm's nitroethane, ½ mL 40% methylamine, 10 mL methanol and workup in the usual manner. Worked like a charm and gave 4,6 g(87% yeild) of quite purified nitropropene.

3,7 g LAH was placed in 64,5 mL's of THF and placed on a mag. stirrer. To this there where added 4,6 gm's of the nitropropene in 64,5 mL's THF. This mixture was left to reflux overnight and will be purified in a few hours. This will -in theory- of course be tested severly during the forthcoming festival. Swim will report the results back.

All in all, DOM was prepared from scratch(almost) in one day's of work. Pretty neat if you ask swim :)

If anyone has some comments of the somewhat modified Vilsmeyer reagent that was prepared, please do post them. It was a combination of the indole vilsmeyer from rh's page and some from pihkal etc... Seems it worked ok though!

edit:
Final yeild was 3,2 grammes of the hydrochloride as -not so white- substance.

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)
08-07-03 11:24
No 452274
      ..and you can use the leftover aldehyde to...

..and you can use the leftover aldehyde to prepare some 2C-D, which is also jummy...

Bandil
(Hive Bee)
08-07-03 11:49
No 452278
      ..nahh... i'll stick to the amphetamines thank

..nahh... i'll stick to the amphetamines thank you very much cool

I like drugs that last more than a few seconds :)

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)
08-07-03 12:11
No 452280
      2C_D is excellent for partying.

2C_D is excellent for partying. Take it at 1 am, you get gently up (arrival at 2'30); plateau lasts about 1 1/2 - 2 hours, then gently tapers down, and when you get home at 6 am you can easily fall asleep.

Xicori
(Hive Bee)
08-08-03 09:41
No 452440
      great work, bandil!! do you have any results...

great work, bandil!!

do you have any results on the reduction yet?

swim also wants to synth DOM, but the worst step is the methylation of the phenole :( the only non toxic methylating agent is dimethyl carbonate - any ideas if it would work on Toluhydroquinone?
lg
xicori

Aurelius
(Active Asperger Archivist)
08-08-03 19:21
No 452497
      Methylating
(Rated as: excellent)

Post 412790 (Lego: "Betaine for O-methylation of Phenols", Novel Discourse)

OTC and non-toxic.

Post 418138 (bottleneck: "Etherification by cat. amounts of a tosylate?", Novel Discourse)

couple of ideas on the topic

Post 417550 (Antoncho: "Methyl tosylate: _finally_ , OTC!!!", Novel Discourse)

Novel reagent for methlation

Post 398206 (GC_MS: "Electrosynthesis of gamma-asarone", Novel Discourse)
Electromethylation

Post 398635 (Mountain_Girl: "Methyl Eugenol synth references", Novel Discourse)
Sodium methylsulfate synthesis (a methylating agent)

Post 218431 (PolytheneSam: "Re: ArOR, Alternatives to dimethyl sulfate", Novel Discourse)
Post 221040 (PolytheneSam: "Re: ArOR, Alternatives to dimethyl sulfate", Novel Discourse)
Post 330874 (Antoncho: "A very (IMHO) curious idea", Chemistry Discourse)
Post 330714 (Antoncho: "A patented improvement", Chemistry Discourse)
Post 348592 (Antoncho: "Methyl iodide methylation of 2-OH-5-MeO-BA.", Chemistry Discourse)
Post 314724 (Rhodium: "I rather methylate with Me2SO4 than MeI", General Discourse)
Post 51160 (obituary: "MeI methods", Chemistry Discourse)
Post 299818 (foxy2: "MeI and alkyl iodide synthesis", Chemistry Discourse)
Post 301629 (Antoncho: "Two tried-and-true ways to make MeI !", Chemistry Discourse)
Post 331620 (Antoncho: "Another trial.", Chemistry Discourse)
Post 216461 (foxy2: "Ethyl hydrogen sulfate", Chemistry Discourse)
Post 190955 (Antoncho: "CH3-C6H5SO2*CH3O - an OTC methylating agent?", Chemistry Discourse)

any way that's more than 90+% of the people here will read, but there's some ideas on methylation. Not all are non-toxic (obviously) but it's still there. There are, however, some very good examples and fairly safe reagents available.

Act quickly or not at all.

Bandil
(Hive Bee)
08-12-03 11:04
No 453099
      Testing the compound

The compound was subjected to marquis and bioassay.

The marquis turned ever so slightly green/yellowish, but the reaction was so slow that it was inconclusive.

The bioassayes however, were quite conclusive. The two subjects that ingested the material reported of way more fractals around the moon/tree's/whatever than usual :)

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

Prometheuz
(Hive Bee)
08-18-03 13:26
No 454346
      Bioassay

SWIM participated in the bioassay with his GF. The testing was done on the last day of a festival - which compromises the results a bit.... The last two days the test-couple had taken "normal party-doses" of LSD and MDMA.
SWIM takes 7 mg, GF takes 5 mg, oral, in solution, about 16:30. After 1½ hour they deicide that there definately is something. And SWIM has been careful to be sure about such statements, since a certain spectacularily inactive DOB-adventure wink .
Virtually no stimulation is noticed, unlike expected. The feeling is actually very relaxing. SWIM takes 3 more mg after the 3-hour point. By here it is definately also visually active, but not in any overwhelming sense at all. SWIM is also much more used to trip after sunset, so maybe that is the main reason that the visual effects are noticed much more 6 hours after ingestion of the first 7 mg, when the sun sets.
SWIM is much more compelled to relaxed talking to friends than to go partying. There is a very distinct empatogenic feeling, but that might be partly because of the past couple of days of drug-use. The female test-subject seems to be at a very nice place as well, mostly walking around the festival and observing. The female is behaving close to sober, while SWIM seems to be a bit spaced out, but very much more relaxed than the average person under psychedelic influence.
And aye, psychedelic it was. The full moon maintained the shape of a perfect, 64-sided polygon all the night. The stars all looked like little perfect 5-stars. The CEV's were very much impressive, with fractals flowing in a hypnotic, ever expanding way. Nitrous gave a HUGE kick, much like on medium-high doses of LSD.
At about 3 a.m. (T+10:30) the trip has definately been falling in intensity for a while. Being a bit worn out from the last couple of days, the test-subjects deicide to get some sleep. Sleeping is not too hard, even though the visuals are flowing impressively as SWIM falls asleep.
Sorry about the VERY flawed science in this experiment crazy ... But it seemed like the occation to try this one out. And they definately found it worth-while. More experiments will be done soon, in a more controlled way. I really can't think this could possibly be placebo, but who knows...... That stupid bastard WIM didn't really have the best brain-chemistry at the time of trial to evaluate with 100% certainity.

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

Prometheuz
(Hive Bee)
09-03-03 12:49
No 457010
      DOM, first semi-scientific trial

The compound was recently tested on 4 subjects; 2 male weighing about 62 and 85 kg, and 2 females about 60 kg. The males ingested 10 mg each(in solution), the females 7 mg each. The trip-timer was started.
By 40 minutes SWIM definately feels something; it is very unlike the first trial (see the post above), as this is a very stimulating effect. Restlessness and jittery eyes; amphetamine-typical. The first canister of nitrous goes down, and it is without doubt much more powerful than from baseline. The two male subjects felt a slight bit of nausea after about 1 hour, but it dissolved rather quickly.
For all the subjects (apparently most powerful for the males), the visual effects started about 1½ hour after ingestion. The quality of the effects was great, resembling something in between 2C-B and mescaline. SWIM had hoped for something closer to acid, but alas, I doubt that can ever be achieved through a PEA. The mindspace was VERY psychedelic. The train of thoughts was totally derailed - in an amusing way. In one way the mind was rather clear, that is, not as intoxicated as SWIM gets on shrooms, though more intoxicated than on acid. Quite a bit of bodyload of different kinds; trembling muscles, different physical feelings like hot/cold. Inhaling N₂O was an experience of extreme dissociation, and often left the subject quite confused for a while after. Great fun, though...
The peak seemed to be reached about 4 hours after ingestion, and the comedown was nice and easy. Everybody seemed to have had an enjoyable trip. The girls would have liked a bit more effect, though. With help from a bit of diazepam, sleep was reached about 10 hours after ingestion of the DOM.
Conclusion: The synth has given the right compound. SWIM had after the first trial hoped this drug was "the holy grail" he'd been looking for, a psychedelic that didn't bring too much disturbing stimulation, but made it easier to relax. Unfortunately it appears to be just as stimulating as most other related compounds. Not that it is a bad psychedelic at all, SWIM just don't think it's all that different from related PEA's. The rather easy come-up and come-down makes it a pleasant choice over many of the other PEAs, and the duration seems to be just right.

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

Barium
(Heavyweight Chempion(eer))
09-03-03 15:57
No 457022
      Great work!

Great work!

The Unworthy

pHarmacist
(pHantasticant)
09-03-03 18:32
No 457036
User Picture       TMA-2?

SWIM had after the first trial hoped this drug was "the holy grail" he'd been looking for, a psychedelic that didn't bring too much disturbing stimulation, but made it easier to relax.

In that case, TMA-2 sounds like a good candidate, but something tells me that you guys have allready tried it, or am I wrong? TMA-2 is currently one of my favorite materials. Insight.HCl, indeed!

Point... Counter Point...

acid_egg
(Hive Addict)
09-03-03 22:30
No 457078
      TMA-2

Reports of high body load and stimulation for TMA-2 have been made Post 280978 (Chromic: "Re: Tma from Tmma", Chemistry Discourse)

pHarmacist
(pHantasticant)
09-04-03 08:16
No 457143
User Picture       I don't understand some people...

Why take 75mg or above 100 mg when the active dose of pure material is 25? Personally I was way up on 25 mg (+++) and so was Bambi. It is at least to us one of the easiest materials to the body we've tried, very relaxing, very easy, extreanly funny, far from stimulating, extreamly insightful, excellent sleep acieved by the eight hour without help from any sopoforics. Certanly a beautiful an A+ material, but of course beauty is in the eye of the beholder...

Point... Counter Point...

hest
(Hive Adickt)
09-04-03 08:56
No 457145
      TMA

I don't agree, the fun part of TMA-2 (and 6) start at 50mg(and yes it's pure). At 80mg the wisuals are wild and at 110 its almost DMT like.
40 mg is (at leas for me) more like a high museum level.

Prometheuz
(Hive Bee)
09-04-03 09:40
No 457151
      TMA-2

Unfortunately our "family" hasn't yet had the chance to taste TMA-2. If some of you think it can induce the desired state of mind without too much stimulation, that one will be moved further up on the "to do" list... wink

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

pHarmacist
(pHantasticant)
09-04-03 10:14
No 457155
User Picture       Re: I don't agree

hest: Well, I've talked to other bees about TMA-2 and some don't find it as profound as I do. It's pointless to try to generalize the psychedelic experience since every individual is unique at any given time. An extream example is myself. For me and in me MDMA is a useless compound that triggers effect of euphoria with an underlying feeling of falsness - almost a plastic existence during the experience, not at all rewarding, easily compared with cocaine.

However one mysterious part of our TMA-2 experience was from visual aspect. Usually I'm not at all focused on visual, but rather thought pattern. But this time, on TMA-2, both me and Bambi were sharing similar visual imagery. When I, after the trip, described what the imagery mainly consisted of, she agreed and confirmed that it was same for her too. Later she showed me a picture of Indian God Ganesh (I was unaware of it prior to that) and that was an excellent match. My wallpaper is a simple white wallpaper, but during those magic hours it was an extraordianry Indian mosaic of Ganesh's eyes and proboscis as main pieces.

Point... Counter Point...

hest
(Hive Adickt)
09-04-03 14:51
No 457166
      MDMA

I have, for some time, sought a description of MDMA, your's is perfect. The wisuals are quote good on TMA-2 (and I love visuals). AMT is greath for visuals also.

I find TMA greath lone, but almost fantastic in combinations with LSD or shrooms.
Guess wee now are off topic with the DON thing *lol*

hest
(Hive Adickt)
09-04-03 14:53
No 457167
      MDMA

pHarmasist:
I have, for some time, sought a description of MDMA, your's is perfect. The wisuals are quite good on TMA-2 (and I love visuals). AMT is greath for visuals also.

I find TMA greath lone, but almost fantastic in combinations with LSD or shrooms.
Guess wee now are off topic with the DON thing *lol*

Prometheuz
Maybee someone will donate 10g of the aldehyde, who knows.

acid_egg
(Hive Addict)
09-04-03 22:58
No 457235
      pHarmacist

I don't understand some people...Why take 75mg or above 100 mg when the active dose of pure material is 25?

I too asked the same question however I think maybe Rhodium summed it up best Post 329531 (Rhodium: "Aha, that's the key! You are supposed to take ...", Methods Discourse)

...but as with all things..it's personal.

psyloxy
(Hive Addict)
09-16-03 08:30
No 459375
      Effects of R isomere of DOM ?

SWIM had after the first trial hoped this drug was "the holy grail" he'd been looking for, a psychedelic that didn't bring too much disturbing stimulation, but made it easier to relax. Unfortunately it appears to be just as stimulating as most other related compounds

Have you thought about isolation of the R-isomere ? The S seems likely to be responsible for most of the body-load. Maybe R-DOM a step closer to the holy grail of psychedelics, see PIHKAL entry.

--psyloxy--

Prometheuz
(Hive Bee)
09-17-03 08:29
No 459572
      Resolution of stereoisomers of DOM

psyloxy> Great suggestion! It does indeed sound like pure R-DOM would be closer to what is searched for... Not that the racemic version is bad at all wink ... Unfortunately SWIM doesn't have the neccesary skill/equipment for seperation of the isomers - yet. Most of the procedures seem to be quite hard - unless you have access to some sort of stereoselective chromatography gear.

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

hest
(Hive Adickt)
09-17-03 10:05
No 459582
      Stereoisomers

Fractional rextalisation with l-tartaric acid (the natural form) or, even better, the benzyl ester of the r form is not that hard. Usual you won’t lose more than 5-10% (of the right isomer). Biggest drawback is that you want to work in the 3-10g scale.

For the more speculative part. I look's like it's the r-isomer who make all the fun it's 2 times as strong as the racemate. In pikhal under DOB ½mg s-isomer have no effect and 1mg only might have an effect. My guess is that whatever the s-isomer is doing (dopamine system?) it's not very strong and might not bee worth the trouble to sweep out

psyloxy
(Hive Addict)
09-19-03 02:01
No 459842
      request for solubility data of R/S-DOM.tartartes

To successfully resolve R/S isomeres of DOM with tartaric acid the specific solubilities of both salts in a given solvent need to be known, right ? Is that data available ?

--psyloxy--

hest
(Hive Adickt)
09-19-03 07:27
No 459907
      R/S

Triel and error works just fine.
You rextalise all kind of stuff every day without knowing this. I have done it with TMA-2 with ethanole as the solvent. Works fine (but the difference was not that big, 2*power and not so much long term amphetamine effect)

Rhodium
(Chief Bee)
09-19-03 19:56
No 459981
User Picture       Synthesis of DOM optical isomers
(Rated as: excellent)

I made a Beilstein Crossfire search for DOM, and retrieved the references about optical resolution or enantioselective synthesis of R-DOM. They can be seen below. You'll also get the full Beilstein outputs, which contains a whole lot of more references to pharmacology and racemic syntheses.

The green text above each citation is my own summaries.

Beilstein Crossfire - DOM (racemat) (https://www.rhodium.ws/chemistry/articles/beilstein/dom/dom.html)
Beilstein Crossfire - DOM (R-isomer) (https://www.rhodium.ws/chemistry/articles/beilstein/dom/r-dom.html)
Beilstein Crossfire - DOM (S-isomer) (https://www.rhodium.ws/chemistry/articles/beilstein/dom/s-dom.html)

As the title below implies, the article contains a SAR study of nearly 40 different psychedelic amphetamines and PEA's, as well as some comparisons between their optical isomers. It contains a lot of synthetic procedures, as well as pharmacological and physical data not seen before here at the Hive. I'm surprised that this hasn't been posted before.

Structure-activity relations in psychotomimetic phenylalkylamines
F. A. B. Aldous, B. C. Barrass, K. Brewster, D. A. Buxton, D. M. Green, R. M. Pinder, P. Rich, M. Skeels, K. J. Tutt
J. Med. Chem. 17(10), 1100-1111 (1974) (https://www.rhodium.ws/pdf/sar.psychotomimetic.phenylalkylamines.pdf)

Very good article, where DOM is synthesized step by step from 2,5-dimethoxytoluene, and resolved using o-nitrotartanilic acid. It also contains a synthesis of 4-Methyl-2,5-Dimethoxyphenyl-2-propanone, as well as of the 4-COOH and 4-CH₂OH analogs of DOM.

Stereochemical aspects and metabolite formation in the in vivo metabolism of the psychotomimetic amine, 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane
S. B. Matin, P. S. Callery, J. S. Zweig, A. O'Brien, R. Rapoport, N. Castagnoli, Jr.
J. Med. Chem. 17(8), 877-882 (1974) (https://www.rhodium.ws/pdf/dom.synthesis.resolution.pdf)

This article contains preparation of the Tartanilic Acids used for resolving DOM in the previous article.

Substituted tartranilic acids. A new series of resolving acids
Thomas A. Montzka, Terry L. Pindell, John D. Matiskella
J. Org. Chem. 33(10), 3993-3995 (1968) (https://www.rhodium.ws/pdf/tartanilic.resolving.acids.pdf)

latest addition (07-07-04): DOM is synthesized step by step from deuterated 2,5-dimethoxytoluene (prepared from p-dimethoxybenzene), and O-demethylated DOM analogs prepared.

In vitro O-demethylation of the psychotomimetic amine, 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane
Jonathan S. Zweig, Neal Castagnoli, Jr.
J. Med. Chem. 20, 414-421 (1977) (https://www.rhodium.ws/pdf/dom.deuterio-synth.pdf)

Synthesis of N-Hydroxy-DOM from DOM, as well as optical resolution of the product.

Studies on chiral interactions of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane and the corresponding n-hydroxy metabolites with cytochrome P-450
N. Peter McGraw, N. Castagnoli, Jr.
J. Med. Chem. 24(3), 299-304 (1968) (https://www.rhodium.ws/pdf/n-hydroxy-dom.isomers.pdf)

Catalytic reductive amination of substituted phenyl-2-propanones with either (+)- or (-)-alpha-phenethylamine, which by in situ hydrogenolysis forms the corresponding enantiomerically pure amphetamine. Among lots of others, DOM is one of the produced amphetamines.

Asymmetric synthesis of psychotomimetic phenylisopropylamines
David E. Nichols, Charles F. Barfknecht, David B. Rusterholz, Frederick Benington, Richard D. Morin
J. Med. Chem. 16(5), 480-483 (1973) (https://www.rhodium.ws/pdf/nichols/nichols-asymmetric-amphetamines.pdf)

This patent (by Dave Nichols) describes essentially the same thing as the above article.

Patent US4000197

Aurelius
(Active Asperger Archivist)
09-19-03 22:15
No 460000
      Rhodium

Hey Rhodium, shouldn't that be a digest? ( wink )

or at least the start of one?

Act quickly or not at all.

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