Jump to content
The Corroboree
Sign in to follow this  
theobromos

Mitragynine pseudoindoxyl

Recommended Posts

This appears to suggest that badly prepared kratom extracts might be interesting.

"and of mitragynine pseudoindoxyl, whose analgesic activity is more potent than that of morphine"

Yakugaku Zasshi. 2000 Oct;120(10):959-67.[Chemical studies on the analgesic indole alkaloids from the traditional medicine (Mitragyna speciosa) used for opium substitute]

[Article in Japanese]

Takayama H, Aimi N, Sakai S.

Share this post


Link to post
Share on other sites

Merck Index, 13th edition. pg. 1110 entry # 6240

Mitragynine: "9-methoxycorynantheidine...soluble in alcohol, chloroform, acetic acid."

Share this post


Link to post
Share on other sites

Where legal of course :)And when.

Mitragynine scheduled here in Aus yet? My reading of the Schedule suggests 1 May 2004 is the date it goes S9.

The actual plant is up for debate *again* next week in front of the NDPSC- they're seeking to ban even cultivation, and they're trying rather hard in the face of a lack of data from scientific studies. This will be the third or fourth attempt.

Given that we've heard reports of its potential as an anti-addiction substance which may be useful for tobacco addiction, and one report at least for migraine control, wiping it off the table for future medical research seems a bit over the top. :mad:

Thel here has been most proactive in organising ppl to take this up with the appropriate legislative bodies, a search should provide the interested with actions we can take to stop the lunacy

Share this post


Link to post
Share on other sites

Mitragynine pseudoindoxyl is not the same as mitragynine. It is the result of an oxidation process very common in the extraction of ibogoids by indelicate chemists.

I am suggesting here that by ensuring that you boil your ethanol extract while passing oxygen through it, possibly with some mild catalysts, the effects may well be very different from the herb tea with lemon or other antioxidant acid sources.

Share this post


Link to post
Share on other sites

I was merely attempting to indicate the solvents by which mitragynine itself can be concentrated.

Manufacturing any compounds thereof were not the point of my post.

Share this post


Link to post
Share on other sites

Very interesting! Would it be possible performing this oxidation process without making an alcohol extract, for example with an infusion as the raw material?

Share this post


Link to post
Share on other sites

Studies on the Synthesis and Opioid Agonistic Activities of Mitragynine-Related Indole Alkaloids: Discovery of Opioid Agonists

Structurally Different from Other Opioid Ligands

Hiromitsu Takayama,*,† Hayato Ishikawa,† Mika Kurihara,† Mariko Kitajima,† Norio Aimi,† Dhavadee Ponglux,‡

Fumi Koyama,§ Kenjiro Matsumoto,§ Tomoyuki Moriyama,§ Leonard T. Yamamoto,§ Kazuo Watanabe,§

Toshihiko Murayama,§ and Syunji Horie*,§

Received December 21, 2001

Mitragynine (1) is a major alkaloidal component in the Thai traditional medicinal herb,

Mitragyna speciosa, and has been proven to exhibit analgesic activity mediated by opioid

receptors. By utilizing this natural product as a lead compound, synthesis of some derivatives,

evaluations of the structure-activity relationship, and surveys of the intrinsic activities and potencies on opioid receptors were performed with guinea pig ileum. The affinities of some

compounds for Ì-, ‰-, and -receptors were determined in a receptor binding assay. The essential structural moieties in the Corynanthe type indole alkaloids for inducing the opioid agonistic activity were also clarified. The oxidative derivatives of mitragynine, i.e., mitragynine pseudoindoxyl (2) and 7-hydroxymitragynine (12), were found as opioid agonists with higher potency than morphine in the experiment with guinea pig ileum. In addition, 2 induced an analgesic activity in the tail flick test in mice.

1949 J. Med. Chem. 2002, 45, 1949-1956

The prep of mitragynine pseudoindoxyl from mitragynine is relatively simple:

Treatment of 1 with lead tetraacetate gave the 7-acetoxyindolenine derivative (11) in 50% yield. By alkaline hydrolysis of 11, 7-hydroxy-7H-mitragynine (12), which has been found as a minor constituent in the leaves of M. speciosa,17 was obtained in 95% yield. Treatment of 12 with sodium methoxide in methanol gave the pseudoindoxy derivative (2).

You chemists out there better hurry up and get your shit together if you want to play with this stuff!

Share this post


Link to post
Share on other sites

Thanks, Fractalhead.

Hope I can work out a better method than lead salts and sodding methoxide.

Idplugg, the salts are probably much more stable than the free base so it would be difficult to do in a water solution.

Share this post


Link to post
Share on other sites

Well, this is in English and available to anyone with academic journal access, the journal being General Pharmacology:

Yamamoto, L.T., S. Horie, H. Takayama, N. Aimi, S. Sakai, S. Yano, J.J. Shan, P.K.T. Pang, D. Ponglux and K. Watanabe. Opioid receptor agonistic characteristics of mitragynine pseudoindoxyl in comparison with mitragynine derived from Thai medicinal plant Mitragyna speciosa. Gen. Pharmacol. 1999 Jul;33(1): 73--81.

Share this post


Link to post
Share on other sites
Guest electro

any idea if kmno4 could be used on extracts ???

peroxide maybe ?

calcium hypochlorite ?

-------------------------------------------

boils 3 large leaves in water.

strains after 10 mins

transfers liquid to metal bowl to cool

once cool 10 ml 3% peroxide mixed in

placed back on heat, change in smell noted

broth very bitter - must reduce to a resin

waiting for water to evap .. will post result :)

-----------------------------------------------

also has anyone noticed differences in the bitterness of leaves ?

is it a temperature / time of day thing ? stress ...

the first leaves i tried from my plant were lovely, though now only 2 days later (after two days of the plant being in almost full sun in this heat [40c] rather than in a nice cool shaded shipping box) the tea from them is very bitter ...

[ 20. February 2004, 18:11: Message edited by: electro ]

Share this post


Link to post
Share on other sites
Guest electro

also, does anyone know what strain hhh is selling (their "tea")

it tastes vastly different to the rif clone. (unless the taste dif is in preperation ?)

Share this post


Link to post
Share on other sites

HHH probably has kavaman's kratom.

I have a little bit of this too, but it totally puzzles me. A fair bit of study has been done on kratom, so there are a few scientific 'facts' that can be taken as quite reliable. here are some:

* Analyses of leaf shows an alkaloid content of about half a percent. Of this about half is mitragynine.

* Top quality kratom produces stimulation at a dose of about 5 leaves. This changes to sedation at about 10 leaves.

* 5 leaves weigh about 2.5g dry weight.

10 leaves are about 5g dry weight.

* 2.5g of dry leaf at 0.25% (half of 0.5%) mitragynine is presumably 6mg of mitragynine.

* "Smiling Cloud" (forum member), Ray & Liz (HHH) and a few others have tried between 3 and 4g doses and this put them on their asses for several hours (ie, way beyond just the stimulating dose).

Something doesn't add up here. Kavaman says that his kratom comes from 20 year plus trees. The research material that the rifat clone was derived from was also more than 20 years old, yet no comparison. In fact, of all the research samples derived from any single plant, commercial source, or homegrown product, NONE have shown potency that comes even close to the kratom offered by kavaman.

The crossover dose (from stimulation to sedation) for most kratom is about 10-20g, which makes it about 25mg of mitragyine. For the kavaman kratom this dose is probably less than 2g, hence about 5mg of mitragynine. See the problem I am having with this?? Kavaman's kratom is a full 5 times stronger than any other commercial or scientific source.

I am not saying there is anything dodgy about this!!!!! Kavaman has a good product and has shown himself to be totally reliable and generous. The problem is not one of consumer issues!! My problem is from a scientific point of view. The discrepancies above need to be researched.

For example, it was the fact that the previous batch of fake kratom (now marketed as "mellow gold") that made the rounds had 4% alkaloids which first alerted me to the fact that it was probably misidentified. I documented this months before others started querying the authenticity based on botanical markers and then later on the basis of TLC results. The BIG difference between last time and this time is that the effects of kavaman's kratom are in fact the same as for other strains of kratom - just a lot more potent.

So we have to look at why this is so and the obvious questions are:

* Why does it taste different to other kratom?

* What is the alkaloid percentage of kavaman's kratom?

* Does it contain mitragynine?

The first one is the one that got me confused. My kratom from the rifat clone and from other sources tastes foul. It is so bad I can barely finish chewing ONE fresh leaf. Dried leaves are a little easier, but still require training to get over the bitterness. Kavaman's kratom smells sweet and tastes no more bitter than green tea powder.

The alkaloid content is easy enough to work out - if I found the time to do an extraction. Anyone else interested in doing this?

The third is the most timeconsuming step and hence not done yet. I obtained some mitragynine reference samples a little while ago which can be used. Also, the rifat clone was tested by Daniel Siebert and was found to contain mitragynine, so even this can be used as a reference sample.

The world is awash with kratom at the moment and if such vast differences in quality really exist within the one species, then we need to find out why. And obviously quality will also dictate prices, so we don't want to be paying top dollar for low quality product.

For the time being I suggest though that you try kavaman's kratom and post the trip reports here. It is certainly strong stuff.

Share this post


Link to post
Share on other sites

electro, I have been reading up on pseudoindoxyls. I have not come to a conclusion yet but peroxide will only only take it to the first stage of three, and can result in two different pathways of reactions.

Of course the other intermediates may be active but test at your own risk. Remember to make your notes waterproof and stainproof for the coroner :)

The best bet looks like recipes for iboga alkaloids: freebase air oxidation in a solvent like chloroform giving the hydroxyindolenine. This is followed by rearrangement to the pseudoindoxyl in hot methanol saturated with hydrogen chloride for one hour. However some are more resistant and need platinum catalysts.

I have yet to look at yohimbine pseudoindoxyl.

Share this post


Link to post
Share on other sites

This might be one of those cases where the leaves at the top of an old tree don't bother with some of the defences they needed when the leaf was within reach of ground-dwelling herbivores. Like the holly which at the top of the tree doesn't have spines on the leaves.

Share this post


Link to post
Share on other sites
Guest electro

wow a link to me telling kavaman off ! apologies if anyone is friends with him.

also

re peroxide

i didnt get time to evaporate all the liquids, so 1/8th the liquid was placed into a shotglass and drunk.

within 20 mins the effect was beginning to be felt, but was not sure if it was psychosomatic (as 1/8th of the liquid [made from 3 leaves] is still less than 1/2 a leaf)

By the 40 min mark it was undeniable. the effects were similar to hhh's kratom in that the dose was very small, the taste was much less bitter [despite being so concentrated] and there was no stimulation, only a very pleasent stoning effect ... the taste was also alot less bitter than earlier.

It lasted from when i posted last night until i went to bed (was beginning to wear off then) at about midnight.

the rest has been dried (made nice redish brown powder & lumps reminiscant of mexican poppy extract.) this was re wet (a few drops of water) then mixed into 2 teaspoons of flour, then 4 spheres formed with the mix & placed in the oven at 70 to dry- will try again and post back (to confirm findings - as they are very premature atm)

id like to know if hhh really does have a different strain (with higher alkaloid %) or if their leaves have just been treated to oxidise the actives into something "stronger".

[ 21. February 2004, 08:56: Message edited by: electro ]

Share this post


Link to post
Share on other sites
Guest electro

there is nothing wronmg with rifat clone, it just tastes different to whatever it is hhh is selling ....

Does the Rifat Clone still produce a quality product?

yes, it just doesnt taste like green tea :)

Share this post


Link to post
Share on other sites

The rifat clone is equal in effect, taste, quality, and botanical characteristics with ALL kratom plants and herbal products available around the world - EXCEPT kavaman's. The Rifat clone itself is derived from a plant identified by a Thai government botanist and used for several scientific studies.

Kavaman ONLY sells powdered herb, so botanical comparison is not possible. hence we can only work with the other characteristics.

Share this post


Link to post
Share on other sites

Hey,has anyone had any experience with the kratom extract kavaman is selling here?

http://www.ethnobotany-australia.net/forum...opic.php?t=1613

I've been interested in kratom for quite some time and have decided to try it. Would you recommend leaves or an extract.

Torsten,I hear you will have a new batch of kratom plants avaliable soon,if so do you know approximatly when you will have them in stock. Also,will it be from the rifat clone?

Thanks in advance.

Share this post


Link to post
Share on other sites

Create an account or sign in to comment

You need to be a member in order to leave a comment

Create an account

Sign up for a new account in our community. It's easy!

Register a new account

Sign in

Already have an account? Sign in here.

Sign In Now
Sign in to follow this  

×