TheEnlightenedScientist
Harmless
Posts: 1
Registered: 23-2-2015
Member Is Offline
Mood: No Mood
|
|
Dimethylation of Tryptamine with amine N-methyltransferase
Hello members of Science Madness!
I am just starting to educate my self about organic chemistry and the mechanisms that are involved. For some time i have been reading about the indole
family and the different tryptamines that are present in nature.
I noticed that there are already different routes from Tryptophan to Tryptamine. Where tryptamine is a very interesting compound but often very
expensive. My question is if it is possible to Dimethylate Tryptamine using an amine N-methyltransferase. S-adenosyl-L-methionine or (SAM) is often
used in this progress doing the following procedure:
S-adenosyl-L-methionine + an amine <=> S-adenosyl-L-homocysteine + a methylated amine
Since Tryptamine can be made fairly OTC and cheap by the decarboxylation of Tryptophan and S-Adenosyl-L-methionine(SAMe)
(S-Adenosyl-L-MethionineDisulfate p-toluenesulfonate) is easily available as a food supplement. This can be a pretty good route to yield
N,N-dimethyltryptamine.
Can anybody tell me if this way is plausible?
-TheEnlightenedScientist
|
|
|
Chemosynthesis
International Hazard
Posts: 1071
Registered: 26-9-2013
Member Is Offline
Mood: No Mood
|
|
I'm not really sure you posted this here, as it's not really organic chemistry, nor is this forum a drug forum, but if you have to ask how to make
drugs, I doubt you have the requisite sources of tryptamine-N-methyltransferase (which you didn't mention), or could optimize reactor design given the
turnover of whatever homolog/isoform you choose.
|
|
|
Bert
|
Thread Moved
23-2-2015 at 10:35 |
Polverone
Now celebrating 21 years of madness
|
Thread Moved
23-2-2015 at 12:23 |
mayko
International Hazard
Posts: 1218
Registered: 17-1-2013
Location: Carrboro, NC
Member Is Offline
Mood: anomalous (Euclid class)
|
|
Tryptamine is dimethylated in vivo by an indoleethylamine-N-methyl transferase. I'm rather skeptical that you could get it working at all in vitro,
let alone whether this would be an effective means of getting the target molecule in ... useful quantities.
If molecular biology is your interest, engineering E. coli/arabidopsis to overexpress INMT and growing them on tryptophan/SAM-rich feedstock would be
a potentially productive, though likely challenging and felonious, DIY project.
A few papers you might find interesting:
Axelrod, J. (1962). The enzymatic N-methylation of serotonin and other amines. The Journal of Pharmacology and Experimental Therapeutics, 138,
28–33.
Baxter, C., & Michael Slaytor. (EDIT: 1972). Biosynthesis and Turnover of N,N Dimethyltryptamine and 5-Methoxy-N,N-Dimethyltryptamine in Phalaris
Tuberosa. Phytochemistry, 11(1966), 2767–2773.
Mack, J., & Slaytor, M. (1979). Indolethylamine N-methyl transferases of Phalaris Tuberosa, purificantion and properties. Phytochemistry, 18,
1921–1925.
[Edited on 24-2-2015 by mayko]
al-khemie is not a terrorist organization
"Chemicals, chemicals... I need chemicals!" - George Hayduke
"Wubbalubba dub-dub!" - Rick Sanchez
|
|
|
Chemosynthesis
International Hazard
Posts: 1071
Registered: 26-9-2013
Member Is Offline
Mood: No Mood
|
|
same enzyme. It has at
least six names. I wish people could standardize them because sometimes it feels like half my job is finding them all.
|
|
|
mayko
International Hazard
Posts: 1218
Registered: 17-1-2013
Location: Carrboro, NC
Member Is Offline
Mood: anomalous (Euclid class)
|
|
The biosynthetic pathway in Psilocybes has been unraveled; might be of interest. In particular, they found that the methylating enzyme is unrelated to
the mammalian INMT.
| Quote: |
Psilocybin is the psychotropic tryptamine-derived natural product of Psilocybe carpophores, the so-called “magic mushrooms”. Although its
structure has been known for 60 years, the enzymatic basis of its biosynthesis has remained obscure. We characterized four psilocybin biosynthesis
enzymes. These include i) PsiD which represents a new class of fungal L-tryptophan decarboxylases, ii) PsiK, that catalyzes the phosphotransfer step,
iii) the methyl transferase PsiM, catalyzing iterative N-methyltransfer as terminal biosynthetic step, and iv) PsiH, a monooxygenase. In a combined
PsiD/PsiK/PsiM reaction, psilocybin was synthesized enzymatically in a step- economic route from 4-hydroxy-L-tryptophan. Given the renewed
pharmaceutical interest in psilocybin, our results may lay the foundation for its biotechnological production.
|
Fricke, J., Blei, F., & Hoffmeister, D. (2017). Enzymatic Synthesis Of Psilocybin. Angewandte Chemie - International Edition, eingereich. http://doi.org/10.1002/anie.201705489
Attachment: Enzymatic synthesis of psilocybin.pdf (1.7MB)
This file has been downloaded 1373 times
al-khemie is not a terrorist organization
"Chemicals, chemicals... I need chemicals!" - George Hayduke
"Wubbalubba dub-dub!" - Rick Sanchez
|
|
|
zed
International Hazard
Posts: 2283
Registered: 6-9-2008
Location: Great State of Jefferson, City of Portland
Member Is Offline
Mood: Semi-repentant Sith Lord
|
|
Well, some of those pesky little mushrooms that make Psilocybin, are native to my locale.
So, hereabouts, folks usually let the natural world do the work, and they either pick mushrooms wild, or they grow 'em at home in jars.
Now, DMT and some other Indole alkaloids, those materials are less easily acquired, and there is a lot of scientific interest in them. Thanks for the
reference.
|
|
|
![[*]](images/xpblue/default_icon.gif){kind=icon}
