Tryptamine synthesis DMT

huanf

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Is anyone familiar with the synthesis steps of dmt? Can you help me see where I'm going wrong?
Experiment 1:
1、tryptamine is dissolved in methanol. 2、add formaldehyde solution of 2 molar equivalent. 3、 add methanol solution of sodium cyanoborohydride. 4、 mix and stir, slowly add glacial acetic acid, stir and reaction for 60 hours, and the final reaction liquid is turbid brown, as shown in image
K0XqsAIv4K


Experiment 2:
Dissolve tryptamine in DMSO, microwave heating, add 2 mole equivalent of triethylamine, then add 3 mole equivalent of sodium formaldehyde hyposulfate, stir for 10 minutes, wait for the reaction liquid to cool to room temperature, slowly add dmso solution of sodium triacetoxyborohydride, reaction for 24 hours, and finally no dmt was obtained

Does anyone know the correct steps ?
 

The-Hive

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Tryptamine (1.12g, 7 mmol), Sodium Cyanoborohydride (0.88g, 14 mmol) and Glacial Acetic Acid (2ml, 35 mmol) was dissolved in 110ml Methanol at 0°C, and a solution of 37% Formaldehyde (1.4 mL, 18.5 mmol) in 15ml Methanol was added dropwise over 20 min, and the resulting solution was allowed to stir for 20 min at 0°C and 2.5h at room temp. The methanol was evaporated under reduced pressure, and 80ml 25% aqueous potassium carbonate was added and the solution extracted with 2x125ml EtOAc, the extracts washed with 2x40ml brine, dried over MgSO4and the solvent evaporated under reduced pressure to give an amber oil, which was purified by flash chromatography on 30g silica gel (using a gradient of EtOAc:MeOH) to give an oil, which was crystallized from boiling hexane to give N,N-Dimethyltryptamine as colorless waxy crystals, weighing 0.9g (69%).
Good luck and be safe
 

huanf

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Tryptamine (1.12g, 7 mmol), Sodium Cyanoborohydride (0.88g, 14 mmol) and Glacial Acetic Acid (2ml, 35 mmol) was dissolved in 110ml Methanol at 0°C, and a solution of 37% Formaldehyde (1.4 mL, 18.5 mmol) in 15ml Methanol was added dropwise over 20 min, and the resulting solution was allowed to stir for 20 min at 0°C and 2.5h at room temp. The methanol was evaporated under reduced pressure, and 80ml 25% aqueous potassium carbonate was added and the solution extracted with 2x125ml EtOAc, the extracts washed with 2x40ml brine, dried over MgSO4and the solvent evaporated under reduced pressure to give an amber oil, which was purified by flash chromatography on 30g silica gel (using a gradient of EtOAc:MeOH) to give an oil, which was crystallized from boiling hexane to give N,N-Dimethyltryptamine as colorless waxy crystals, weighing 0.9g (69%).
Good luck and be safe
The-HiveSo the experiment failed because I mixed them at room temperature? I finally extracted it with dcm, and the result after spin steaming is also amber clear glue, but it does not dissolve in boiling hexane, nor does it dissolve in boiling petroleum ether, so it should not be dmt, thank you for your method, I will try
 

archae

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So the experiment failed because I mixed them at room temperature? I finally extracted it with dcm, and the result after spin steaming is also amber clear glue, but it does not dissolve in boiling hexane, nor does it dissolve in boiling petroleum ether, so it should not be dmt, thank you for your method, I will try
huanfYes. You have to get everything as cold as possible, so all solvents in the freezer, put the reaction vessel in an ice bath, or even better: an acetone and ry ice bath, so that it stays nice and cold.
 

LazZzZz

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Please be careful, Hamilton morris discussed in a podcast about the concern that cyanoborohydride may product cyanide containing adducts that present as an issue with use as heat will genarate HCN when smoked. I reccomend if you are looking to do a reaction at higher yeilds than NaBH4 would be STAB, as this is a much more selective reducing agent between carbonyls and primary/secondary amines.
 

huanf

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Please be careful, Hamilton morris discussed in a podcast about the concern that cyanoborohydride may product cyanide containing adducts that present as an issue with use as heat will genarate HCN when smoked. I reccomend if you are looking to do a reaction at higher yeilds than NaBH4 would be STAB, as this is a much more selective reducing agent between carbonyls and primary/secondary amines.
LazZzZzMany thanks, I had the same concern before, but tried Hamilton's method without success: "Microwave heating of tryptamine dce solution, adding triethylamine, sodium formaldehyde hyposulfate, 4A molecular sieve, and drip STAB". So i was tried this way, using sodium cyanoborohydride as a reducing agent... Let me try again what the guys above said, lowering the reaction temperature and see if that works,I'll share the result
 
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LazZzZz

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Many thanks, I had the same concern before, but tried Hamilton's method without success: "Microwave heating of tryptamine dce solution, adding triethylamine, sodium formaldehyde hyposulfate, 4A molecular sieve, and drip STAB". So i was tried this way, using sodium cyanoborohydride as a reducing agent... Let me try again what the guys above said, lowering the reaction temperature and see if that works,I'll share the result
huanfActually, in the same podcast mentioned that the method showed in his video using STAB doesnt actually work, id say its worth listening too. Also a handy tip, any reduction with sodium cyanoborohydride will be most efficant at room temperature, same with phenylethylamines
 

huanf

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Actually, in the same podcast mentioned that the method showed in his video using STAB doesnt actually work, id say its worth listening too. Also a handy tip, any reduction with sodium cyanoborohydride will be most efficant at room temperature, same with phenylethylamines
LazZzZzyou late, STAB was arranged,what this shit like ?😂That doesn't look like it's going to work, “Mixture of tamine methanol solution with SATB and 99% acetic acid at zero degree Celsius, then drop formaldehyde solution for half an hour, stir at zero degree for one hour, and slowly return to room temperature reaction for 24 hours” ⬅️tried ,not work
 

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Chain react

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you late, STAB was arranged,what this shit like ?😂That doesn't look like it's going to work, “Mixture of tamine methanol solution with SATB and 99% acetic acid at zero degree Celsius, then drop formaldehyde solution for half an hour, stir at zero degree for one hour, and slowly return to room temperature reaction for 24 hours” ⬅️tried ,not work
huanfSomeone mentioned in Youtube comment that you should use 3A mole sieve. He said These tend to absorb a whole bunch of stuff including formaldehyde freed up by the acidic conditions that will break down sodium sulfoxylate formaldehyde.

But I have one question that why people using "sodium sulfoxylate formaldehyde" or "sodium formaldehyde hyposulfate" I think correct one is "Formaldehyde-sodium bisulfite adduct" (CAS: 870-72-4)
 

The-Hive

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Say whattt
 

The-Hive

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Oh sorry about that
 

huanf

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Oh sorry about that
The-Hivethat's ok,
just confused about why I keep failing with the dmt experiments, wonder if anyone has actually succeeded in following these steps?I think I should to switch tryptamine to tryptamine hydrochloride and try again,maybe work
 

The-Hive

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One off the chemicals or something mite be Impure could always try the plant extract way from Mimosa hostilis
 

huanf

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One off the chemicals or something mite be Impure could always try the plant extract way from Mimosa hostilis
The-HiveThe reagents are all new and high purity, and I tried several different combinations of reagents, which should not be the reason for the purity of the reagents. In fact, I have tried mimosa root bark powder, it is simple and effective, but still want to try chemical synthesis, just for fun . anyway thanks bro
 

pickledill

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Im looking to do DMT synth what do I use sodium boro or cyanaboro?
 
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