Hermann-Inclusus
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Compound from tryptophan?
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M.V. Smith ; psychedelic chemistry
tryptophan, if oxidized by H202, and cyclized by HCL gives a psychedelic compound
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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?
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Texium
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Thread Moved
22-11-2017 at 08:36 |
LearnedAmateur
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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..
In chemistry, sometimes the solution is the problem.
It’s been a while, but I’m not dead! Updated 7/1/2020. Shout out to Aga, we got along well.
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zed
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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.
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Assured Fish
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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 1772 times
Please let me know if the file doesn't work.
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Hermann-Inclusus
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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:
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(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)
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Hermann-Inclusus
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| 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&...
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Crowfjord
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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 465 times
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