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Opioids Mitragynine (Kratom) Derivatives (Chemistry Help)

K

KitchenChemist

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Joined
Apr 19, 2011
Messages
18
I have long been a fan of Kratom - a tree of the Rubiaceae family of the scientific name Mitragyna speciosa. This tree contains the psychoactive alkaloid Mitragynine and 7-Hydroxymitragynine, which both funtion as powerful mu-Opioid receptor agonists.

Kratom reminds me of high dose hydrocodone or low - moderate dose oxycodone, as it is rather stimulatory, though, this may be due to other adrenergic alkaloids in the tree, rather than the principal opioid alkaloids.

The opioid alkaloids contained in Kratom are as follows:

Mitragynine%20with%20Label.png
7-hydroxy%20with%20Label.png


Another synthetic anaolugue, known as 7-Acetoxymitragynine occurs as follows:

7-Acetoxymitragynine.png


Both 7-Hydroxymitragynine and 7-Acetoxymitragynine seem to be much more potent than Mitragynine itself. However, I have known people who have obtained pure samples of both 7-Hydroxymitragynine and 7-Acetoxymitragynine from chemical suppliers, and state that they do not provide much of an IV rush, and are not much more actively intravenously rather than orally.

What I am wondering is if any of the advanced chemists here can shed any light on which chemical derivatives of these compounds may make it more IV active. I am also wondering if anyone knows of any other chemical substitutions of these compounds that may also be psychoactive, either orall, IM, or IV.

Paging seiko..

Hanks for any help that you can provide!
 
Pinpoint might be able to provide information as well on this topic. He's very well in versed in Kratom.
 
Hah I'm hardly an 'advanced chemist'.

OP wouldn't 7-AcO-Mit just react to form 7-OH-Mit once ingested?

There was a post about one of the metabolites of mitragynine with the removal of the methyl group to form something like o-desmethylmitragynine.

If you truly have the equipment that you say you do (in your other thread) you should work to debunk the UEI/FST debate about what's actually in those extracts. You could become a legend.
 
Actually, most of the extracts that I have analyzed seem to contain only trace amounts of Mitragynine, 7-Hydroxymitragynine, and Mitraphylline, an oxindole derivative of Mitragynine. A lot of the extracts from Kratom suppliers seem to be water extracts, which is pretty useless, as I believe the Mitragynine alkaloids are probably poorly water-soluble, and are probably much more soluble in alcohols (ethanol, isopropyl) or methanol.

I have not had the pleasure of obtaining some of the laboratory-grade 7-Hydroxy or 7-Acetoxy extracts, as they are pretty cost-prohibitive for me, personally.

My background is in pharmacology, but mostly simple Phenethylamine syntheses and clinical trials. The advanced Mitragynine alkaloid chemistry trips me up.

That is why I am asking somebody with a more advanced biochemistry background to help answer my questions. Your input was helpful. The Mitragynine metabolites sure are interesting, however I am looking to see if anybody has any ideas about novel synthetic Mitragynine derivatives.
 
Actually, I found a very interesting article, which seems to describe a novel 7-Hydroxmitragynine derivative that acts as a potent mu-opioid and delta-opioid receptor agonist. They refer to it in the article as MGH-16, but I believe they provide the full Systematic (UPAC) name. The structure is as follows:

MGH-16.png



Referring to the UPAC name, can anybody come up with a suitable chemical name as opposed to just referring to it as MGH-16 ?

The article is available in full PDF format at:

http://jpet.aspetjournals.org/content/348/3/383.full.pdf
 
Nice addition. I've always wondered what exactly could be in the high potency extracts UEI and oxindole enhanced bali. I've tried pure 7-hydroxymitragynine personally and it didn't have much effect (definitely not worth the $$$!), and based on that experience and the other anecdotal reports, I believe that there is an as yet unidentified analog in the UEI/oxindole based extracts. Whatever it is, that's some strong s**t, and I'd very much like to find its structure.
 
KitchenChemist said:
Kratom reminds me of high dose hydrocodone or low - moderate dose oxycodone, as it is rather stimulatory, though, this may be due to other adrenergic alkaloids in the tree, rather than the principal opioid alkaloids.
Click to expand...

This thread is kind of old, but I have a theory that posted in the kratom mega thread:
Mitragynine is the only alkaloid I see in kratom that is listed as adrenergic. Mitragynine is also the most abundant alkaloid found it kratom. Wikipedia states that Mitragynine is metabolized into mitragynine pseudoindoxyl, "an even more potent and selective mu opioid agonist." Im wondering if the analgesia comes from the mitragynine pseudoindoxyl, similar to how codeine is metabolized into morphine, which is a more powerful agonist. Except that Mitragynine is the speedy, stimulating part of the high, and then when it's converted to its secondary metabolite, that's when you get the opiated sedated part of the high.
 
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