7-acetoxymitragynine

[DopaMan]

Edit: I originally posted this is ADD but no one answered so I've moved it into here.

I've been wanting to give 7-hydoxymitragynine a try but it is somewhat cost prohibitive. The 7-acetoxymitragynine analogue, however, is available at a cheaper price.

My question is this: Would the acetoxy group be hydrolyzed in the stomach due to the low pH and aqueous environment leaving behind 7-hydoxymitragynine and acetaldehyde? (Obviously and even more acidic environment could be created if need be but asking about that may violate the board's rule on synthesis discussion).

Im pretty sure this is what is going to happen but I thought Id check in with the proper chemists in here.

Oh and if anyone has experience with either substance feel free to chime in.

 

[mepat1111]

Yeah you're asking a pretty hard question there dude, all I know about mitragynine analogues is that they're Kratom alkyloids. You're gonna have to wait a while for an answer to that one.

 

[lyserg]

Kratom itself contains numerous psychoactive alkaloids, chiefly mitragynine, along with paynanthine, 7-hydroxy mitragynine, speciogynine, mitraphylline, speciofoline, ajmalicine, corynanthedine, mitraversine, rhychophylline, and stipulatine. Its believed that a lot of the effects of kratom are from the other alkaloids, the major one being 7-hydroxy-mitragynine. Here's a list of equivalent doses. The dosage for preparations using the dried leaf is 3 to 5 grams, and less if smoked. The clinical treatment dosages which have been reported are as follows
30% extract (400mg+)
75% extract (30mg-80mg).This extract by weight contains 55% mitragynine.
Mitragynine 97%+ (10-50mg)
7-Acetoxy-Mitragynine (3-12mg)
Im pretty sure that 7-acetoxy mitragynine does not have any metabolites and doesnt trun into 7-hydroxy-mitragynine but someone else is gonna have to chime in cause im not 100% positive.

 

[lyserg]

Im gonna move this back to ADD. ---> Mods, if the other thread is still up there than either merge them or delete that one and keep this one up.

 

[hugo24]

I'm pretty sure that the acetyl will be cleaved metabolically (just a general trend).

And no wonder that the acetoxi compound is a dud/inactive itself on receptor studies but shows in vivo activity --> confirming the prod-drug theory.

 

[DopaMan]

Thanks for the replies. I wish Smyth or F&B would join up and let us know if the the addition of the acetoxy group would alter the chirality of the molecule as raybeez suggested. If so then I wouldn't trust this stuff unless some more reports came out on its use.

 

[Xorkoth]

Unfortunately I cannot answer your main question. However, I can answer one of your other questions...

I'm an extremely experienced user of kratom. I've tried about every preparation there is, resins, extracts, "super" leaf, and both isolated mitragynine and 7-hydroxymitragynine. And I can safely say that none of them come close to the strength of regular, standard-grade kratom leaf from a good supplier (well, 1 gram of 10x extract is stronger than 1 gram of kratom leaf, but a lot, lot weaker than 10 grams of kratom leaf).

As lyserg stated, kratom contains a plethora of alkaloids, several of whcih are known to be active, and the rest of which I'm quite sure are active enough to color the experience when combined together. Even standardized extracts which claim to contain both primary alkaloids (mitragynine and 7-HO-M) seem to be missing a large portion of the buzz, and they simply don't even come close to the potency that they claim.

I've also tried M and 7-HO-M themselves, and neither measured up. 7-HO-M was the stronger of the two and most resembled kratom, but it was definitely lacking. Mitragynine itself was actually quite weak at the doses I am presumably getting on a standard dose of regular leaf.

For reference, with the regular leaf I use, without tolerance 6 grams is plenty for a great, euphoric, unique kratom high complete with dreamy closed-eye imagery (especially with cannabis). Even with addiction in place 10 grams is the limit that I use.

 

[DopaMan]

I am also a very experienced kratom user and I have had very poor results with any sort of extract and prefer the leaf. I was more interested in the 7-oh-mitragynine as a mu opioid agonist than as a more potent kratom subsititution.

Xorkoth, if you could post your dosages and experience with 7-oh-mitragynine and your tolerance to normal opoids/opiates I would appreciate it. Although I dose rather high compared to most people (20-35 grams of whole leaf which I grind to a fine powder) to achieve my desired results, so Im not sure how much I could relate.

 

[Xorkoth]

Damn, man... 20-35 grams powdered? I also finely powder mine. I used to use 12-18 grams back in the day but I think my kratom source kept getting stronger. The effects I get now are not as strong as the ones I used to get, but I'm not sure if it's because my dose is lower or because I've been using it for over 2 years, or both. I do know that I can't handle 12-18 grams anymore because it makes me dizzy and nauseous, which is the downside to kratom, I find. I'd always like to take it higher but the limiting factor is always nausea and/or dizziness.

Anyway, we can't talk about sources of course but I find that the source for your kratom makes a big difference. Also the quality between batches varies somewhat, but not nearly as much as between suppliers. My hunch is that a lot of suppliers get it from wild grown kratom trees, whereas some more reliable sources get it from farms where it is taken very good care of to produce an optimal product.

 

[DopaMan]

Hmm I've tried several different suppliers (the top ones) and I haven't noticed much difference in potency. I must state that I have used pharmaceutical opiates/opioids for years (although I have kept my tolerance low ~40-60mg oxycodone).

 

[Xorkoth]

Ahh, I've never developed a tolerance to any opiates/oids other than kratom, although I enjoy the occasional morphine/oxy/hydro run. However I use kratom daily and have tolerance to the point of withdrawal upon discontinuation.

 

[GeisterxFahrer]

Hmm I've tried several different suppliers (the top ones) and I haven't noticed much difference in potency. I must state that I have used pharmaceutical opiates/opioids for years (although I have kept my tolerance low ~40-60mg oxycodone).

I know the absolute BEST and most trustworthy supplier. Sadly, I cannot say. Always free shipping, free tracking, and they even send you free stuff. and it works, and their customer service is better than most 'high class' businesses. They treat their customers with massive respect. But my main question to you is (since I saw you compare kratom to opiates), I have an extremely high tolerance to opiates/oids. for example, in the ER the other day, they had to IV me with 3mg of Hydromorphone to bring my pain down. But I have noticed that Kratom seems to help a lot more, but I was under the impression that there would be an issue of cross tolerance. Do you know anything about that idea?

 

[sekio]

7-AcO-mitragynine should hydrolize quite neatly to 7-OH-mitragynine.

On Tertiary Alcohol Ester Hydrolysis

The esters of linalyl acetate and alpha-terpineol acetate are hydrolyzed under various in vitro
and in vivo conditions to yield linalool or alpha-terpineol, respectively, and acetic acid. In an in
vitro hydrolysis study, linalyl acetate was easily hydrolyzed in water, simulated gastric juice (pH
1.8), and pancreatic fluids (pH 7.5) [Buck and Renwick, 19991. The mean half-lives for linalyl
acetate hydrolysis in gastric juice with and without added hydrolytic enzymes was less than 2.5
minutes, respectively.

So, same deal as with 4-AcO-DMT being converted to 4-HO-DMT.

 

[GeisterxFahrer]

7-AcO-mitragynine should hydrolize quite neatly to 7-OH-mitragynine.

On Tertiary Alcohol Ester Hydrolysis


So, same deal as with 4-AcO-DMT being converted to 4-HO-DMT.

Thank you for the info! I will be doing more research into this and figuring out what I can come up with thanks again!