jesus (Stranger)
06-27-00 18:14
No 22081
      DMAE of any use for DMT synth ??  Bookmark   

Could DiMethylAminoEthanol be used for DMT synthesis ?

With a structure like this : Me2-N-Et-OH you see you only have to replace the OH with an indole.

The question is how would one accomplish this ?

1) this following text is found in Rhodiums AMT-FAQ:
To a stirred 0.5 M benzene solution of indole was added 2 equiv. of 2-nitropropene as a 10% benzene solution. The reaction mixture was heated at reflux under a nitrogen atmosphere until TLC analysis (dichloromethane/silica gel) indicated that all indole was consumed. The dark reaction mixture was cooled to room temperature and quickly passed through a short silica gel column which was washed with 1:1 toluene/hexane until product recovery was complete. Solvent removal under reduced pressure afforded 1-(Indol-3-yl)-2-nitropropane as an amber oil (81% yield), sufficiently pure (by TLC) to be carried on to the next step without further purification.

Maybe one can dehydrate DMAE and use it in a similar matter to get DMT directly

2) Maybe one can change the OH in DMAE to a Br and let this react with an indole-MgBr. I think the N is protected enough by the 2 Me groups.

3) Or maybe one could oxidize DMAE to Me2-N-AcH which would react with indole-MgBr to produce an alcohol that had to be reduced later.

any ideas ??


(Hive Bee)
07-18-00 04:57
No 29877
      Re: DMAE of any use for DMT synth ??  Bookmark   

It appears to bee possible to make DMT from DMAE and indole in the
presence of an alkali or alkaline earth hydroxide (ie. NaOH or Ba(OH)2)
by heating the mixture in an autoclave to about 200-265 degrees C.

Here's some references to check out on making closely related compounds:

JCS (1942) pg 680-682
JACS vol 79 (1957) pg 5248-5250
US patent 3,197,479

The JCS article describes a process where ethanolamine and also
diethylaminoethanol are reacted with indole-2-carboxylic acid (decarboxylizes
when heated) to make tryptamines.  The yield of the product doesn't seem to be too high. 

(Hive Bee)
07-19-00 03:04
No 30259
      Re: DMAE of any use for DMT synth ??  Bookmark   

Another reference that a lot of tryptamine fans might know about is Organic Synthesis col. vol. V pg 654-656 on making indole-3-acetic acid from indole and glycolic acid with KOH as a catalyst.  The mixture is heated in a rocking autoclave at 250 degrees C for 18 hours.  The potassium indole-3-acetate produced in the reaction is dissolved in H2O and the free acid is precipitated with HCl. 

(Hive Bee)
07-30-00 06:07
No 34654
      Re: DMAE of any use for DMT synth ??
(Rated as: excellent)

Examples 1 and 2 copied from US patent 3,197,479 show a similar type of reaction.


A 3-liter, stainless steel, rocker autoclave was charged with 117 grams of indole, 100 ml. of ethylene glycol, and 7.0 grams of potassium hydroxide.  The autoclave was sealed and heated at 250 degrees C. for 19 hours while agitating the reaction mixture by rocking.  The autoclave was then cooled, opened, and the contents were filtered to remove solids.  The filtrate was evaporated under vacuum to a volume of about 400 ml. and then admixed with 1 liter of water.  The aqueous mixture was extracted with ether.  On vacuum distillation of the ether extract there were recovered 21 grams of 3-(2-hydroxyethyl)indole as a fraction boiling at 150-186 degrees C. at 1.0 mm Hg.  A sample of the 3-(2-hydroxyethyl)indole, after  recrystallization from toluene melted at 56-57 degrees C.
[The melting point of 3-(2-hydroxyethyl)indole was reported by Oddo and Camberi, Gazz. Chem. Ital., 69, 19 (1939) to be 57-58 degrees C.]


Employing apparatus and procedures similar to those described in example 1, an autoclave was charged with 234 grams of indole, 1146 grams of ethylene glycol, 126.2 grams of hydrated barium hydroxide (Ba(OH)2.8H2O) and 128 milliliters of water.  The autoclave was flushed with hydrogen, sealed and heated at 250 degrees C. for 19.5 hours.  There were produced 225 grams of 3-(2-hydroxyethyl)indole which were recovered as a fraction boiling at 160 to 174 degrees C. at 1.0 mm Hg.


Notice that example 2 includes the addition of water just as the Organic Synthesis article on indole-3-acetic acid.  There's 18 examples in the patent using diols such as propylene  glycol, butane diol, hexane diol, etc.  Some include flushing with hydrogen.  It says in the specification (column 4 lines 30-35) the following:

In addition, it has been found desirable, especially when a 3-(hydroxycarbyl)indole is the desired product, to conduct the reaction under a hydrogen atmosphere.  The hydrogen pressure can vary from atmospheric pressure to 500 psig or more, with pressures of from 50 psig to 20 psig preferred.
(Hive Bee)
07-30-00 06:38
No 34659
      Re: DMAE of any use for DMT synth ??  Bookmark   

Very interesting, i wonder if it has a chance?

"Vote Libertarian"
(Hive Bee)
07-30-00 22:20
No 34788
      Re: DMAE of any use for DMT synth ??  Bookmark   

Here's a version of Da Bomb that was found to work at 250 degrees C.  Most of you will probably reognize that it is a bomb calorimeter.  It was bought for $25 in an electronic surplus store warehouse.  In the second picture you can see Da Bomb on top of a hot plate with a metal ("candy style") thermometer used to monitor the temperature.  You need to use a lubricant such as silicone grease (applied beforehand) and two big channel lock pliers to take it apart when cooled down.  This 'Da Bomb' works as the autoclave mentioned above.

08-10-00 17:20
No 38986
      Re: DMAE of any use for DMT synth ??  Bookmark   

Good score! What's the capacity of this da Bomb! incarnation?

That second patent example with ethylene glycol sounds like practical yields. This one added a bit of water, and used more glycol. A reaction giving a terminal hydroxide is much preferable to one giving a carboxylic acid, because no reduction step is needed.

Presumably the indole-3-ethan-2-ol would be iodinated, and reacted with dialkylamine. That sounds real good.

The original post of this thread, with dimethylaminoethanol, could undoubtedly use some development work, since U (Mm) have found a ref with success at low yields. I wondered about this mechanism some years back, but thought it was necessary to dehydrate the dimethylaminoethanol to dimethylallylamine first. The reason for low yields in these procedures is undoubtedly from rearrangement, because the adding group is so complex. Still, dimethylamino ethanol is so eminently available, it seems a shame to leave this pathway unexamined, despite the messy isolation at the end. Column chromotagraphy is good for that.

But yo bomb with the glycol, sounds like da biz. Industrial scale sho nuff.


Half a pint's a half a pound, a half the world around, around.
(Hive Bee)
08-13-00 04:37
No 40062
      Re: DMAE of any use for DMT synth ??  Bookmark   

DMAE was tried out by FOAF a while back (with indole-2-COOH made from phenylhydrazine and pyruvic acid).  He smoked it a number of times last summer and found it was definately psychoactive.  No visuals but weird perceptual effects.  He especially liked how it enhanced computer generated movies.  Music also sounded better.  He made his DMAE free base by distilling some DMAE powder from some capsules (containing DMAE tartrate) and Red Devil Lye solution (after trying out some prior experiments with lime and NaOH).  His last batch of DMAE free base didn't seem to smell as "fishy" as the best experiments before but he seemed to get positive results.  This process has been posted a number of times during the year even at DMT World without too much interest (except at DMT World once).

08-13-00 17:24
No 40239
      Re: DMAE of any use for DMT synth ??  Bookmark   

OK, sounds good on adding to the 2-COOH indole with DMAE. But I'll bet there were some rearrangement products which kept your final honey from being as smooth as it ought to bee. Or maybee you diddled with marginal doses, or got stuck in DMT's odd tolerance thingy, until it was all gone. A good clean DMT shouldn't bee described as "psychoactive", it should knock you on your tail.

The tartrate must be an ester, or is it a salt of the tert. amine? If it's just a salt, how about just using lime to free it? Likely it would be pretty easy to trick calcium tartrate into losing its solubility and precipitating out of your DMAE, making its isolation easier.

In a previous post, I said "allylamine" without thinking. The dehydration product of DMAE has just a two-carbon chain, not 3 carbons. The dehydration product of DMAE should bee n,n-dimethylamino ethene, or some such rot meaning (CH3)2N-CH=CH2. Now how do I get some? First banish Markovnikov's rule, so I won't end up with a-methyl gramine, hmm?


Half a pint's a half a pound, a half the world around, around.