Hello,
For those that don't know, Kratom is a psychoactive plant that originates from Thailand. The active ingredients in the plant, which is primarily Mitragynine, produces stimulant-type effects at low doses and opiate-like euphoria at higher doses. Mitragynine binds to the delta opiate receptors, and crosses over to the mu opiate receptors as dosage increases.
Anyway, in one study a derivative of Mitragynine was created - Mitragynine Pseudoindoxyl. Testing on this derived compound indicated that its
analgesic properties were stronger than morphine.
I'm interesting doing the same thing - deriving Mitragynine Pseudoindoxyl from Mitragynine, and was hoping one or more of you chemists out there could provide some ideas on how to do so?
Here is a quote from one of the articles:
"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 Ě-, ?-, 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)."
On another message forum, someone indicated that the lead stuff mentioned above wouldn't be good for human consumption. They also mentioned that simple oxidization of Mitragynine should produce some quantity of Pseudoindoxyl.
Anyway, I'm not a chemist, and would appreciate any help in figuring out a simple way to produce this stuff at home. My ultimate purpose here is to create a more cost-effective drug. Kratom, and the resultant extracted Mitragynine, is fairly expensive. If the pseudoindoxyl were several times more potent, then obviously the dosage could be decreased. (Of course, I realize that the derivitive may not produce the same pleasant results as the "parent" drug, and that will need to be determined.)
Thanks,
Mr. Kratom
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