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Author: Subject: What to do with tryptamine?
ParanoidAndroid
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[*] posted on 22-12-2011 at 14:15
What to do with tryptamine?


I have a large amount of pure tryptophan and recently came across an exceedingly simple method of making it into tryptamine: basically just reflux it a mixture of xylene and acetone until CO2 stops evolving. A spearmint oil catalyst can be used to speed the reaction but adds a purification step afterward and reduces yield.

My question is: what can I do with the resulting tryptamine? There are a whole slew of interesting substances that are related to tryptamine, but there's very little information on synthesizing those substances using tryptamine as a starting material. Are there any easy ways to do this?

Of particular interest to me are AMT (an MAOI), serotonin (neurotransmitter), and DMT (which is an interesting precursor to other syntheses). The molecular changes aren't complicated; there just isn't a lot of experimental info out there.
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[*] posted on 22-12-2011 at 15:08


Decarboxylate and post a write up with the procedure, yield, and product identification ( melting point, solubility's, etc) before even worrying about methylation.

[Edited on 22-12-2011 by Bot0nist]




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[*] posted on 22-12-2011 at 15:19


Wow, if you really made it, it is a good news! You can make DMT (if it's legal in your country) or DIPrT - this is known to cause auditory hallucinations only.



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[*] posted on 22-12-2011 at 18:19


Very interesting. Have you successfully thermally decarboxylated tryptophan? Tryptamines fascinate me. I'm going to read TIHKAL one of these days, I hear Shulgin did a serious amount of research on tryptamines.

[Edited on 23-12-2011 by JibbyDee]
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[*] posted on 22-12-2011 at 19:02


PiHKAL and TiHKAL would probably be your best resources.

[Edited on 23-12-2011 by zoombafu]




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[*] posted on 22-12-2011 at 21:02


Doubtful, he mostly obtains his typtamines using other starting materials or hard to get reagents. Google is your friend here.





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[*] posted on 23-12-2011 at 00:14


Actually Shulgin was eager to develop routes from uncontrollable materials and you will find that he published a route for most of his not ring substituted tryptamines starting with tryptamine or at least gave an outline. Shulgin is a good, humble guy who lets his actions speak.

What he missed was the sodium triacetoxy borohydride (made in-situ) reductive methylation of tryptamine with formaldehyde to DMT. I have heard a few success reports. Yields are low in an amateur setting, but given that it's only two steps from (dirt cheap) tryptophan, overall yield is better than for most OTC routes to phenethylamines.

Original poster: Follow Bot0nist's advice and come back once you have geniune tryptamine. Some successful attempts have been posted on this forum.
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[*] posted on 23-12-2011 at 08:46


I dont think alkylation that occurs via an imine will be possible... ever heard of the Pictet-Spengler reaction?
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[*] posted on 23-12-2011 at 08:48


Isn't it possible to methylate tryptamine using simply H2SO4 + methanol?



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[*] posted on 23-12-2011 at 09:40


Quote: Originally posted by DJF90  
I dont think alkylation that occurs via an imine will be possible... ever heard of the Pictet-Spengler reaction?

Maybe it's not possible in theory, but in practice it is.

Quote:
Isn't it possible to methylate tryptamine using simply H2SO4 + methanol?

Doubtful.
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[*] posted on 23-12-2011 at 10:23


A lot of triptan drugs are methylated by reductive alkylations. I think this is a conditions thing. But yes...pictet-spengler can be a competing reaction.

Edit: haha originally unintelligible.


[Edited on 12-23-2011 by smuv]




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[*] posted on 23-12-2011 at 12:52


Thing is, formation of an intermediate imine/iminium cation should react much faster intramolecularly than intermolecularly, although I agree perhaps there are conditions where the Pictet-Spengler cannot occur. I suspect if you can use conditions which would adversely affect the breaking of aromaticity in the intramolecular attack then it may be possible. Perhaps thats why typical Eschweiler-Clarke conditions cannot be employed, as I am sure that reaction proceeds via the P-S pathway.
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[*] posted on 23-12-2011 at 13:03


I was just looking up naturally occuring tryptamines and came across this one:

Norbaeocystin

its psilocybin without the N-methyl groups. The wiki page doesn't say much about it but the wiki page for its mono-N-methylated analogue, baeocystin, states that:
Quote:

Little information exists with regard to human pharmacology, but in the book Magic Mushrooms Around the World, author Jochen Gartz reports being aware of a study in which "10 mg of baeocystin were found to be about as psychoactive as a similar amount of psilocybin."


Heres another interesting one:
5-Bromo-DMT

According to the wiki page, it occurs naturally in some marine invertebrates. I read that in animal studies, there were indications that it had sedative and antidepressant properties. This molecule caught my interest because I remember, in a documentary about LSD, hearing about bromo-LSD which has no psychoactive properties but happens to cure cluster headaches.

Heres a strange one:
Convolutindole A

It also occurs in some marine invertebrates. According to the wiki page, it is an effective anti-nematode (parasitic worm) drug.

[Edited on 23-12-2011 by JibbyDee]
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[*] posted on 23-12-2011 at 16:52


Melatonin powder is pretty easy to find too, making all 5-MeO tryptamines available easily. Assymetrically substituted 5-MeO tryptamines should be easy from melatonin too.





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[*] posted on 23-12-2011 at 20:32


Quote: Originally posted by DJF90  
imine/iminium cation should react much faster


http://www.scribd.com/doc/48650605/Contemporary-Drug-Synthes... Ch12 many examples w. borohydrides/formalin. You can track down primary refs.

Edit:http://pubs.acs.org/doi/pdf/10.1021/jm00018a016
NaBH3CN in acidic MeOH.

[Edited on 12-24-2011 by smuv]




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[*] posted on 25-12-2011 at 06:31


Quote: Originally posted by turd  

What he missed was the sodium triacetoxy borohydride (made in-situ) reductive methylation of tryptamine with formaldehyde to DMT. I have heard a few success reports. Yields are low in an amateur setting, but given that it's only two steps from (dirt cheap) tryptophan, overall yield is better than for most OTC routes to phenethylamines.

Really? I heard only of one success report wich was with comercial triacetoxyborohydride and I think a fake as triacetoxy borohydride is extremly sensetive to water and aqueous formaldehyde was used. NaBH(CH3COO)3 or NaBH4/CH3COOH are also able to reduce the indole (see for example "NaBH4 in carboxylic acid media" on Rhodium archive)! You will get a product but I guess no dialkytryptamines.
Can u link any success reports?

Cold alkaline aquesous NaBH4 solution and aq. formaldehyde should work for formylation by simultaneuos titration (and large excess) into an ice cold alcoholic solution of the substrate. Or build imine first before adding NaBH4.

A little cross quoting about reductive alkylation:
Quote:

Eschweiler-Clarke does not work at all. Picted-Spengler would be the main-reaction.

Also Al/Hg does not work very well/ ~20% yields. Source: Tihkal

NaBH(CH3COO)3 or NaBH4/CH3COOH does also not work/leads to extremly low yields or needs special conditions, because it does reduce indole. Source: Rhodium archive - several documents on triacetoxyborohydride and NabH4 in carboxylic acid media are mentioning reduction of indoles with it and some derivates.There are some other reciepes on the in the internet, where this is used to make DMT from tryptamine and aq. Formaldehyde. I think it's pure a fake. Triacetoxyborohydride is very sensitive to water and does reduce indole - no big chance to work under the mentioned conditions (RT, THF, excess CH3COOH as solvent).

BH3*THF or NaBH4/H2SO4 or NaBH4/I2 does also not work. The indole gets also reduced very fast under normal conditions.

NaBH4/MeOH . Does work (!!!), but does reduce aldehydes faster than imines/enamines form. It has to be very cold and a large excess of NaBH4 and aldehyde are neccessary. Does work better for diethylated than for dimethylated tryptamines Source: The Vespiary

H2+Pd/C. Does also work. But needs high pressure of H2. Does sometimes overdo it's job when the catalyst is too strong. Source: Tihkal

Sodium cyaboborohydride does work well but produces side products, esp. beta carbolines. Good workup necessary. Source: Rhodium archive/Vespiary

Untested but very interesting: Zinc borohydride, potassium borohydride and Zn/NaH2PO4

Zinc borohydride because it's known to perfom very well for dialkylations of amines, potassium borohydride because it less active and smoother than NaBH4 and Zn/NaH2PO4 because it's known to alkylate amino acids and alkylamines in high yields. Zn/NaH2PO4 and formaldehyde does also work for dialkylation of tryptophane.... but dimethyltryptophane is very hard to get ripped of CO2 and is extremely toxic. Try it yourself.



[Edited on 25-12-2011 by Methansaeuretier]

[Edited on 25-12-2011 by Methansaeuretier]

[Edited on 25-12-2011 by Methansaeuretier]
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[*] posted on 26-12-2011 at 09:51


Quote: Originally posted by Methansaeuretier  

Really?

Yes.
Quote:
I heard only of one success report wich was with comercial triacetoxyborohydride and I think a fake as triacetoxy borohydride is extremly sensetive to water and aqueous formaldehyde was used.

I've seen the analytical data and it's unambigous. Though isolated yield was low (~1 g DMT from 5 g tryptamine).

Quote:
NaBH(CH3COO)3 or NaBH4/CH3COOH are also able to reduce the indole (see for example "NaBH4 in carboxylic acid media" on Rhodium archive)!

See Chem. Soc. Rev.,27,395(1998).

Quote:
Can u link any success reports?

No, Private Communication. I will not disclose the author, but post some data in due course.
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[*] posted on 30-12-2011 at 17:17


Here's an interesting Schiff base reduction method.

ReductionSchiffBases.jpg - 94kB
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[*] posted on 6-1-2012 at 11:15


Do an old school DMT synthesis and grow the cool looking crystals DMT forms. Don't vaporize them because its neurotoxic to your 5ht2a and you need those.
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[*] posted on 7-1-2012 at 02:17


Quote: Originally posted by overload  
Do an old school DMT synthesis and grow the cool looking crystals DMT forms. Don't vaporize them because its neurotoxic to your 5ht2a and you need those.


DMT is neurotoxic? Really? It occurs naturally in our brains...




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[*] posted on 7-1-2012 at 11:39


From last I heard, the "spearmint" method of decarboxylation was fake (the "Student").

I attempted myself very crudely with a sticky, nasty mess. My skills by no means constitute incapability of the reaction. However I do believe that a molar ratio of spearmint oil (or molar equivalent of acetophenone) will fully decarboxylate the product... Whether the pictet-spengler occurs, I am again not sure.

I may continue reading up on this in the future.

I'll report anything.

==Making ethyl bromide is quite easy.
==Obtaining diisopropylethylamine is tricky - but some people can get it.

Tryptophan -> DET may be an easy route for a hobbyist.
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[*] posted on 7-1-2012 at 16:10


I don't believe the OP asked anything about ingestion of tryptamine or its methylated variants. I do hope that the original poster has read these threads on decarboxylation of tryptophan right here on SciMad. I also saw some patents on the subject IIRC.

<a href="http://www.sciencemadness.org/talk/viewthread.php?tid=8574#pid97905">L-tryptophan decarboxylation</a>
<a href="http://www.sciencemadness.org/talk/viewthread.php?tid=2255#pid23507">decarboxylation of tryptophan</a>
<a href="http://www.sciencemadness.org/talk/viewthread.php?tid=3544#pid39231">tryptophan decarboxylation</a>
*<a href="http://www.sciencemadness.org/talk/viewthread.php?tid=14147#pid182233">Tryptamine refusing to crystallize</a>


*edit: Sorry turd. I missed that good thread when searching. Thanks.

[Edited on 8-1-2012 by Bot0nist]




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[*] posted on 7-1-2012 at 16:30


I would just use it to enrich cubensis substrate and get some potent-ass shrooms, but that's just me. :D
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[*] posted on 7-1-2012 at 16:50


Quote: Originally posted by Adas  
Quote: Originally posted by overload  
Do an old school DMT synthesis and grow the cool looking crystals DMT forms. Don't vaporize them because its neurotoxic to your 5ht2a and you need those.


DMT is neurotoxic? Really? It occurs naturally in our brains...


yes

Edit: On second thought I feel like I should explain the theory ive formed after researching DMT. DMT is a naturally occurring chemical in the brain as well as plants and possibly other places. It is released during life or death situations or near death experiences and has been thought to be the cause of people hallucinating when they die but are resuscitated. It may exist as natures way of saying you need to not let that happen again because it is not a pleasant experience for most people. However.. It's said to produce some euphoria by agonizing 5ht2b receptors and is considered neurotoxic to these receptors along with others. Its associated with the "I'm going to die" state of mind.


[Edited on 8-1-2012 by overload]
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[*] posted on 7-1-2012 at 17:00


On a similar note, what can be done with phenylethylamine? You can buy tons of pure PEA hydrochloride from some supplement website. Nothing naughty of course.



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