Sciencemadness Discussion Board

Compound from tryptophan?

Hermann-Inclusus - 22-11-2017 at 06:40

Quote:

M.V. Smith ; psychedelic chemistry
tryptophan, if oxidized by H202, and cyclized by HCL gives a psychedelic compound


I can not find any reference as to what compound was supposed to be produced through this reaction, further more, I am uncertain as to whether such a reaction would produce a psychoactive compound at all.

At first glance I assumed that some type of beta-carboline or a compound like oxindolylalanine (2-hydroxy-tryptophan) was being produced, however, for obvious reasons these can not be the compounds produced by the reaction described in the excerpt from Smith's book.

What compound could this excerpt possibly be referring to?

LearnedAmateur - 22-11-2017 at 14:07

The closest psychoactive compounds to tryptophan I can think of are di/methyltryptamine. However, these aren't cyclicised in comparison and are instead produced after decarboxylation..

zed - 22-11-2017 at 16:37

Somebody said it once. Doesn't mean its true.

Sure would like it, if you performed the experiment, and let us know what product is produced.

Me? I gotta go now. I got some "mellow yellow" that needs smokin'.

P.S. Just kidding, but I really would like to know those results.

Assured Fish - 22-11-2017 at 20:28

I would have also assumed a beta carboline at first glance, or another tryptoline derivative of some kind. Im not sure if it is possible to attack the aryl ring with just H2O2 alone however i did manage to find this, which may answer the cyclisation part:
http://orgsyn.org/demo.aspx?prep=cv6p0965

Could you site the page and paragraph, there might me more context to it than what you have written and i just so happen to have the pdf for this book.


Attachment: phychodelic chemistry.pdf (396kB)
This file has been downloaded 1668 times

Please let me know if the file doesn't work.

Hermann-Inclusus - 25-11-2017 at 07:38

Quote: Originally posted by Assured Fish  
I would have also assumed a beta carboline at first glance, or another tryptoline derivative of some kind. Im not sure if it is possible to attack the aryl ring with just H2O2 alone however i did manage to find this, which may answer the cyclisation part:
http://orgsyn.org/demo.aspx?prep=cv6p0965

Could you site the page and paragraph, there might me more context to it than what you have written and i just so happen to have the pdf for this book.




Please let me know if the file doesn't work.


In my printed copy this can be found on page 52-53.

It's in quotations near the end of the "tryptamine from tryptophan JCS 3993 (1965) work-up at the bottom of page 52, if you read through until near the end, now on page 53, you will see this quotation in parentheses


It says:
Quote:

(tryptophan, if oxidized by h202 and cyclized with hcl gives a psychedelic compound) much interest has been generated by the mention of tryptophan oxidation to a psychedelic compound, but the original method gives no details of the method

-psychedelic chemistry:M.V. Smith;tryptamine from tryptophan JCS 3993 (1965) (page 52-53 in the printed copy)

Hermann-Inclusus - 25-11-2017 at 07:52

Quote: Originally posted by LearnedAmateur  
The closest psychoactive compounds to tryptophan I can think of are di/methyltryptamine. However, these aren't cyclicised in comparison and are instead produced after decarboxylation..


Actually, many psychoactive compounds can be produced using tryptophan/tryptamine as a starting material, however, to go into detail would be straying off topic, but I can recommend you browse through TIHKAL by alexander shulgin, it really is fascinating chemistry whether you are interested in psychoactive compounds or not.

These links are vaguely related to the topic at hand, but still fail to answer any of my questions, still, very interesting.

https://www.google.com/url?sa=t&source=web&rct=j&...

https://www.google.com/url?sa=t&source=web&rct=j&...






Crowfjord - 25-11-2017 at 10:59

I've attached the full paper whose abstract is linked above for those interested. It looks like oxidation of tryptophan with hydrogen peroxide is pretty messy, which is to be expected.

The statement by Valentine-Smith is pretty vague, so it's hard to tell what he was talking about. Maybe the compound in question is a pyrroloindole, but from the paper that cyclizes on its own without acid treatment. That would lead me to believe that maybe the mystery compound is indeed a beta carboline derivative. Perhaps there is an unnamed catalyst or reaction condition that favors more of a Strecker degradation to indoleacetaldehyde, which could then be reacted with tryptophan or tryptamine with acid catalysis to form indolemethyl-tryptoline. Hard to say whether it would be psychoactive, though.

Attachment: simat1998.pdf (203kB)
This file has been downloaded 421 times