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turd
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Dimethylation of tryptamine via formaldehyde/STAB
This should have been posted a long time ago, anyway here it is:
A few years ago a preparation of DMT via aq. formaldehyde solution and STAB (sodiumtriacetoxyborohydride) with excellent yields was posted at erowid:
https://www.erowid.org/experiences/exp.php?ID=61171. Some people doubted the results, since STAB is supposedly very water sensitive and there are
fears of reduction to the indoline, acetylation of the indole-N or the dreaded Pictet-Spenger. The thing is: it definitely works.
Tryptamine was prepared by decarboxylation of tryptophan (cheap!) in tetraline with carvone fractionated out of spearmint oil and purifed by
distilling. Works like a charm. People likewise recommend decarboxylation in neat acetophenone (search the board).
In an ice bath with good stirring 5.93 g finely powdered NaBH4 was suspended in 150 ml THF. <del>9.38</del> 28.59 g AcOH was added slowly,
letting foaming subside after every addition (Practically no more foaming after addition of 2/3rd of the AcOH). The reaction was stirred for another
hour. 5.00 g tryptamine and 3.75 g AcOH in 10 ml THF were added. 13.4 g 36% HCHO (prepared by heating an appropriate paraformaldehyde / water
suspension in an autoclave at 150°C) was slowly dropped in and the reaction stirred for another 2.5 h. All tryptamine was gone on TLC (EtOAc/MeOH 2:1
with NH3), minor amounts of side products (tryptamine: Rf~0.1, DMT~0.2).
The reaction was made basic with 25% NaOH, extracted with toluene, washed with brine, dried over freshly dried and powdered K2CO3 and distilled. 1 g
of a light yellow oil was obtained which crystallized in the freezer to a pale yellow, waxy solid with characteristic tryptamine scent. M.p: not sharp
~60°C. Bioassay: A++++ smashing success, highly recommended (smoke not nearly as bad as the lore says).
The reaction was repeated at a lower scale, this time with column chromatography (EtOAc/MeOH) as work up procedure followed by crystallization from
cyclohexane/pentane - very nice pale yellow crystals, but similar low yields.
Due to the TLC I'm convinced that the reaction is not the problem, but rather the workup. This should be tried with bigger batches. And even if the
yield stays as terrible - the reactants are dirt cheap. Everything is OTC; do this at home, kids.
<hr width="800" />
<b>Attention</b>: megalodon found an error in the original post (thank you!): It must read "28.59 g AcOH" instead of "9.38 g AcOH". The
goal was 1 eq. tryptamine, 5 eq. NaBH4 and 15.25 eq. AcOH.
Would be great if a moderator could fix the original post. Thank you.
[Edited on 6-8-2013 by turd]
<!-- bfesser_edit_tag -->[<a href="u2u.php?action=send&username=bfesser">bfesser</a>:
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[Edited on 9.8.13 by bfesser]
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Nicodem
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Though there are several examples in the literature of STAB being used for the dimethylation of primary amines with formaldehyde, this one is peculiar
in that the substrate is a tryptamine for which NaCNBH3 has been traditionally applied. Its good to have a checker for that procedure as
most people prefer to endlessly speculate on the validity of whats published rather than go and do some real work.
I like the idea of the in situ formation of the reagent - it makes it more amateur friendly (even though STAB become widely available in the
last years).
Now, to the low yield problem.
Was there a TLC spot at the starting point? If there was, the apparent mass balance can not be judged just from the disappearance of the starting
material and minor spots of the side products. Things sometimes polymerize into TLC-immobile crap.
During the vacuum distillation, was there a nonvolatile residue?
Even stranger is the loss during the column chromatography. Did you weight the crude product before the column? Does the product trail on silica when
using EtOAc/MeOH only (without added ammonia)? Some could have stuck on silica.
But seeing that you tried out two very different isolations and both gave you similar results, I'm more keen to believe that the low yield is due to
crap formation rather than the losses during the isolation.
…there is a human touch of the cultist “believer” in every theorist that he must struggle against as being
unworthy of the scientist. Some of the greatest men of science have publicly repudiated a theory which earlier they hotly defended. In this lies their
scientific temper, not in the scientific defense of the theory. - Weston La Barre (Ghost Dance, 1972)
Read the The ScienceMadness Guidelines!
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turd
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Well, all things considered you are probably right. I had conversation via U2U with another person who reports the same isolated yields.
Unfortunately, to find out what really happened, the experiment will have to be repeated since this was performed quite some time ago and my memories
may be tainted by wishful thinking. I will hunt the depths of my freezer for remaining tryptamine, but first I'd like to finish two other projects.
The rest of this posting is from memory with support by my notes, so it may not be 100% accurate.
What I'm sure is that yes, there was lots of residue after distillation. I attributed this to (wishful thinking) scorching - the crude product was an
orange, but not very dark, oil and after distillation it was the typical dark red oil. But we all know that colours don't mean anything.
I believe(!) there was no significant amount of product at the application spot of the TLC.
The problem with chromatography was that it was ineffective - I had to apply a gradient and the resulting pale orange oil did not crystallize,
therefore it had to be crystallized from cyclohexane/pentane. Unfortunately it was not weighed before crystallization. There was a very pale yellow
colouration of the column which coincided with the main fraction but there was no colouration remaining at the start of the column. And yes, of course
ammonia was added.
Even if the dimethyltryptamine is only a side product, I don't think the main product is undefined polymer, but rather a dimer or an
indole-N-alkylated thing. But unless this is repeated all of this is idle speculation...
And hey, it's very unlikely, but maybe I even encouraged someone to do independent experimentation. 
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bananaman
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Amines are known to be rather polar, and would often stick to polar silica gel. Usually, there is a need basify the column with a base such as
triethylamine to minimize losses, else, use a reversed phase packing material.
Additionally, consider salting the amines out using HCl gas or ethereal HCl.
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Meakanesis
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salting spice
GAA would be better for salting HCL would work so would gassing but acetic is often used with great success with this compound, making sure your GAA
is very dry will result in a crash using dilute gaa will result in a tincture that can be used to measure out dose if done correctly, the nexus is
your friend on this subject and i really think they would appreciate you dropping this in there.
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hive3
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Quote: Originally posted by turd  | | All tryptamine was gone on TLC (EtOAc/MeOH 2:1 with NH3), minor amounts of side products (tryptamine: Rf~0.1, DMT~0.2). |
thanks turd, Its nice to see a real confirmation of this process. What was the proportion of Ammonia used in the TLC?
<!-- bfesser_edit_tag -->[<a href="u2u.php?action=send&username=bfesser">bfesser</a>: fixed
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[Edited on 31.7.13 by bfesser]
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turd
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Sorry, it was a long time ago and I don't have that information in my notes. But I'm quite sure it was "a few drops" conc. aq. NH3 from a Pasteur
pipette.
| Quote: | | Believe the sodiumtriacetoxyborohydride is created in situ from NaBH4 and the acidic acid. |
Yes, but if you can use commercial triacetoxyborohydride directly, this is certainly the way to go. The reasons for the low yields are not yet
established and it's a good idea to exclude as many variables as possible.
Edit: grammar.
[Edited on 5-8-2013 by turd]
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Nicodem
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Thread Split
8-8-2013 at 00:56 |
Nicodem
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All the numerous off topic posts in regard to the acquisition of STAB and synthesis of NaBH4 were split into a separate thread. Please continue that discussion there and leave this thread only for discussions about the "Dimethylation of tryptamine via
formaldehyde/STAB" topic.
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megalodon
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Looking at the reaction schema for STAB given at wikipedia:
https://en.wikipedia.org/wiki/Triacetoxyborohydride
it seems that a similar procedure might be able to produce diisopropyl tryptamine, DiPT. This is an interesting compound in that its psychedelic
properties are primarily aural rather than visual. Would it be as simple as replacing the formaldehyde with acetone?
Another interesting possibility is methyl isopropyl tryptamine, MiPT. Perhaps this could be synthesized via STAB and a mixture of formaldehyde and
acetone. Combinatorically, I would expect a half and half mixture of formaldehyde and acetone to produce a quarter DMT, a quarter DiPT, and a half
MiPT. Acetone being more sterically hindered than formaldehyde, the ratios wouldn't be exactly that, probably depleted of DiPT and enriched somewhat
in the other two. The mixture could be separated by chromatography.
Does this sound reasonable?
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lullu
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It could be possible that the reaction time for the in-situ preparation of STAB-H is the problem here.
see below:
| Quote: |
Sodium Triacetoxyborohydride. A 100” Schlenk flask equipped
with a Schlenk filter was charged with 186 mg (4.93 mmol) of sodium
borohydride and 50 mL of anhydrous benzene. The slurry was cooled
to 10 OC and 860 pL (15.0 mmol, 3.04 equiv) of anhydrous acetic acid was added dropwise so as to maintain an internal temperature no higher
than 20 OC. Hydrogen evolution was measured with a gas buret. After
addition of acetic acid was complete the mixture was allowed to warm
to ambient temperature and stirred at that temperature for 8 h. Hy-
drogen evolution had ceased at 330 mL (theoretical for 3.00 equiv is 331
mL) after 5 h. The colorless slurry was filtered and the resultant white
powder washed with three 20-mL portions of freshly distilled, anhydrous
ether. The combined ether filtrates did not liberate hydrogen when
treated with 1 N aqueous hydrochloric acid. The powder was held under vacuum over night to afford 961 mg (92%) of analytically pure sodium
triacetoxyborohydride as a white, hygroscopic solid: IR (Nujol) 2500,
1682, 1375, 1316, 1149, 1023, 962, 845 cm-I; ‘H NMR (250 MHz
CD3CN) 6 1.88 (s, 9 H, CH,CO,B); "C NMR (75.5 MHz, CDJCN)
6 175.25, 23.36; "B NMR (96.3 MHz, CD3CN) 6 -1.47 (d, JBH 122
Hz).
Anal. Calcd for C6HloO6BNa: C, 34.00; H, 4.76. Found: C, 33.87;
H, 4.79. |
Directed Reduction of @-Hydroxy Ketones Employing
Tetramethylammonium Triacetoxyborohydride
D. A. Evans,* K. T. Chapman, and E. M. Carreira
Contribution from the Department of Chemistry, Harvard University, Cambridge, Massachusetts 021 38.
Received July 10, I987
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bfesser
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Thread Pruned
20-2-2014 at 05:13 |
Dr.Q
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Could be the low yields because of the water. I want to the this reaction with only difference using paraformaldhyde.
Since i have limited amount of NaBH4 i wonder will paraformladhyde rise some problems if it is used beside formalin ? any ideas ?
[Edited on 26-2-2014 by Myeou]
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*FWOOSH*
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The problem you're going to run into with paraformaldehyde is that there will likely be no or minimal reaction. Formaldehyde tends to polymerize in
acidic solutions, so with the GAA catalyst around it it's probably going to be very comfortable staying that way.
I've tried using paraformaldehyde as a formalin replacement in a similar reaction and was not happy with the results.
The poor yields are, as stated before I think, most likely due to pictet-spengler cyclization. Which, with tryptamine, occurs under even mildly acidic
conditions in the presence of formaldehyde. It's basically a race between the borohydride and the proton to see who gets to reduce the molecule first
The cyclization product is extremely difficult to remove from methylated tryptamine without using chromatography.
Another possible side reaction is tryptamine being reduced to an indoline.
You can likely repeat this procedure with success, but follow it closely and expect to get diddly if you don't use a column to purify.
Just my two cents.
[Edited on 13-3-2014 by *FWOOSH*]
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Dr.Q
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| Quote: Originally posted by *FWOOSH* | The problem you're going to run into with paraformaldehyde is that there will likely be no or minimal reaction. Formaldehyde tends to polymerize in
acidic solutions, so with the GAA catalyst around it it's probably going to be very comfortable staying that way.
I've tried using paraformaldehyde as a formalin replacement in a similar reaction and was not happy with the results.
The poor yields are, as stated before I think, most likely due to pictet-spengler cyclization. Which, with tryptamine, occurs under even mildly acidic
conditions in the presence of formaldehyde. It's basically a race between the borohydride and the proton to see who gets to reduce the molecule first
The cyclization product is extremely difficult to remove from methylated tryptamine without using chromatography.
Another possible side reaction is tryptamine being reduced to an indoline.
You can likely repeat this procedure with success, but follow it closely and expect to get diddly if you don't use a column to purify.
Just my two cents.
[Edited on 13-3-2014 by *FWOOSH*] |
if it is because of acidic conditions how it is even possible %80 yield with cyanoborohydride and with the STAB-H...
You can easily find succesive reports on scifinder with over %70 yield with cyanoborhydride in acidic conditions.
Also for STAB-H link in first post.
Yes formaldehyde polimerize under acidic conditions but that compare to the our reduction reaction this will take much longer time and i think one of
the reason that to add 30 eq. formaldehyde is this.
As you said it is race between the proton and borohydride. But i think since kinetically borohydride reduction reaction is far more faster that
proton , there will be no time to proton to reduce the imine
[Edited on 20-3-2014 by Myeou]
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madscientist
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I agree that the Pictet-Spengler reaction is probably tanking the yield. There's a lot of misconceptions spread far and wide about it - it
does work with ketones, for example, and a proton source is unnecessary (even Na+ can suffice). Reductive amination routes to N-alkyl
tryptamines are usually problematic for this reason.
I weep at the sight of flaming acetic anhydride.
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lullu
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I stumbled over this and remembered this thread.
So hopefully it resolves the ongoing pictet spengler speculations:
from miamiechin
| Quote: |
5-Methoxy-N,N-dimethyltryptamine, 5-MeO-DMT
5-methoxy-tryptamine freebase (12.5 g, 63 mmol, 95% pure) was dissolved in MeOH (250 mL) and the solution was cooled to 0 °C with a ice/salt bath.
There was then added, while controling the temperature to not go above 5 °C, in six portions espaced by 15 min : 5 g of 36% HCHO solution in MeOH
(39% m/v) followed after 10 sec by NaBH4 (1.2 g, powder). Hence in total during 1h30 there was added 6 x (5 g 36% HCHO in MeOH + 1.2 g NaBH4) = 10.8 g
HCHO (360 mmol, 6 eq) and 7.2 g NaBH4 (189 mmol, 3 eq). After each addition an exothermic reaction occur and the temperature must be controlled to
stay under 5 °C. The conversion of 5-MeO-T to 5-MeO-DMT was complete under these conditions. The solvent was evaporated, water was added followed by
NaOH until pH 12 and the residue was extracted with CH2Cl2. Drying over Na2CO3, filtration, washing with CH2Cl2 and recrystallization from boiling
hexanes yielded pale yellow crystals (8.5 g, 62%), >99% pure by NMR and HPLC.
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| Quote: |
By using neutral conditions and several additions of formaldehyde immediately followed by NaBH4 the pictet reaction has no time to occur and the
procedure is remarkably straightforward. Just be sure to cool efficiently and do not allow the temperature to go higher than 5 °C to not have side
products. There is no need to use NaBH3CN for this reaction anymore now!
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Crowfjord
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Likewise, in my research into reduction of the indolene double bond, I found a paper detailing the synthesis of the migraine medicine rizatriptan
using N,N-dimethyltryptamine as an intermediate. The authors synthesize this intermediate via reductive amination of formaldehyde with tryptamine and
sodium borohydride in methanol/water, similar to the above quotation posted by lullu.
Attachment: Novel rizatriptan synthesis.pdf (607kB)
This file has been downloaded 1044 times
Attachment: Rizatriptan supplementary material.doc (2.8MB)
This file has been downloaded 896 times
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stoichiometric_steve
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| Quote: Originally posted by Crowfjord | | Likewise, in my research into reduction of the indolene double bond, I found a paper detailing the synthesis of the migraine medicine rizatriptan
using N,N-dimethyltryptamine as an intermediate. |
Just how trustworthy is this paper?
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Crowfjord
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I have heard that Tetrahedron's credibility is hit and miss, but the theory seems sound to me as far as the chemistry goes in the above paper. The
reductive amination is at least corroborated by the write-up quoted by lullu above.
[Edited on 29-1-2017 by Crowfjord]
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HollowMan
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Someone tried Tetrahedron´s method?
(Patent of making Rizatriptan)
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chemrox
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I propose an alternate route bypassing the reduction step. Tryptamine, MeI (1.2 eq.) in acetonitrile with 1.5 eq of DPEA. It should take a little time
(monitor with TLC). The DPEA should prevent the quartenary amine formation. Also I've seen writeups using para and ZnCl2 in Ch2Cl2 and 35% formalin
in MeOH both followed by NaBH4 redux.
"When you let the dumbasses vote you end up with populism followed by autocracy and getting back is a bitch." Plato (sort of)
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mackolol
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from miamiechin
| Quote: |
5-Methoxy-N,N-dimethyltryptamine, 5-MeO-DMT
5-methoxy-tryptamine freebase (12.5 g, 63 mmol, 95% pure) was dissolved in MeOH (250 mL) and the solution was cooled to 0 °C with a ice/salt bath.
There was then added, while controling the temperature to not go above 5 °C, in six portions espaced by 15 min : 5 g of 36% HCHO solution in MeOH
(39% m/v) followed after 10 sec by NaBH4 (1.2 g, powder). Hence in total during 1h30 there was added 6 x (5 g 36% HCHO in MeOH + 1.2 g NaBH4) = 10.8 g
HCHO (360 mmol, 6 eq) and 7.2 g NaBH4 (189 mmol, 3 eq). After each addition an exothermic reaction occur and the temperature must be controlled to
stay under 5 °C. The conversion of 5-MeO-T to 5-MeO-DMT was complete under these conditions. The solvent was evaporated, water was added followed by
NaOH until pH 12 and the residue was extracted with CH2Cl2. Drying over Na2CO3, filtration, washing with CH2Cl2 and recrystallization from boiling
hexanes yielded pale yellow crystals (8.5 g, 62%), >99% pure by NMR and HPLC.
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| Quote: |
By using neutral conditions and several additions of formaldehyde immediately followed by NaBH4 the pictet reaction has no time to occur and the
procedure is remarkably straightforward. Just be sure to cool efficiently and do not allow the temperature to go higher than 5 °C to not have side
products. There is no need to use NaBH3CN for this reaction anymore now!
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Hi, I performed the procedure as described, but with this difference, that I used aqueous formaldehyde instead of methanol solution, but I don't think
it should be a problem as borohydride is not very unstable in water conditions and there are similar procedures that use aq solution of nabh4.
After evaporation of methylene chloride I was left with brown oil totally insoluble in naphtha, which means that it is not alkylated tryptamine (DMT
should be soluble in hydrocarbons). What could cause the problem, maybe somebody had successfully performed such synthesis?
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karlos³
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I read that synthesis is regularly performed in amateur labs with yields above 80%.
And they even discuss that on a forum dedicated for this specific kind of amateur chemistry, you can surely find it easily, but you need to register
since said forum is not open to the public.
DMT and soluble in naphtha? It is badly soluble in hot naphtha, yes.
Did you do any test to check the composition of the brown oil?
Because it works.
I think you DMT is just really dirty, maybe distill it first?
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TheMrbunGee
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| Quote: Originally posted by karlos³ | I read that synthesis is regularly performed in amateur labs with yields above 80%.
And they even discuss that on a forum dedicated for this specific kind of amateur chemistry, you can surely find it easily, but you need to register
since said forum is not open to the public.
DMT and soluble in naphtha? It is badly soluble in hot naphtha, yes.
Did you do any test to check the composition of the brown oil?
Because it works.
I think you DMT is just really dirty, maybe distill it first? |
Are You sure those are not extractions, not synthesis. Extraction is easy, materials are available, I do not see a need for synthesis.
@ Few gram scales DMT is soluble enough, and quite selective for purification means. Trying to distill it would be enormous shot in the dark. Also, I
don't think mackolol had more then few grams of final product.
And for what could the product be - Insolubility in naphtha, assuming You know Your naphtha is in fact - naphtha You think it is, confirms that it is
not DMT. Guessing is not my strong side in OC.
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mackolol
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| Quote: Originally posted by TheMrbunGee | | Quote: Originally posted by karlos³ | I read that synthesis is regularly performed in amateur labs with yields above 80%.
And they even discuss that on a forum dedicated for this specific kind of amateur chemistry, you can surely find it easily, but you need to register
since said forum is not open to the public.
DMT and soluble in naphtha? It is badly soluble in hot naphtha, yes.
Did you do any test to check the composition of the brown oil?
Because it works.
I think you DMT is just really dirty, maybe distill it first? |
Are You sure those are not extractions, not synthesis. Extraction is easy, materials are available, I do not see a need for synthesis.
@ Few gram scales DMT is soluble enough, and quite selective for purification means. Trying to distill it would be enormous shot in the dark. Also, I
don't think mackolol had more then few grams of final product.
And for what could the product be - Insolubility in naphtha, assuming You know Your naphtha is in fact - naphtha You think it is, confirms that it is
not DMT. Guessing is not my strong side in OC. |
I just want to explore chemistry behind it. So what does the scale mean if it's less than few grams it is worse to purify? And could my product be so
poor quality that it doesn't behave normally?
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karlos³
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NaBH4 reduction of tryptamine, with formaldehyde.
But yes, it is followed by an extraction afterwards, so... both? 
Reductive amination is much easier and you don't need to deal with obscenely large volumes for tiny bits of product, you can do that very convenient
in a small flask instead.
And not only the dimethylated tryptamine, you can a lot of sorts of alkyl groups via reductive amination, try that with an extraction.
A few grams, are there limits for the amount below which a proper purification is not needed?
I purify everything, a few hundred mg's, or a few dozen grams, I don't understand?
Especially when it is a dirty oil like he described, wouldn't a proper purification be in order especially in such a case?
The sentence with the naphtha, I don't understand what that means.
I know many people who used that reaction successful.
Extractions, I don't see the need for, where would one even get the plant matter, and isn't that stuff expensive and illegal or controlled?
I don't know if someone I knew extracted a tryptamine lately, guess not, at least not from a natural source?
[Edited on 13-5-2020 by karlos³]
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