(αE,2S,3S,7aS,12bS)-3-Ethyl-1,2,3,4,6,7,7a,12b-octahydro-7a-hydroxy-8-methoxy-α-(methoxymethylene)indolo[2,3-a]quinolizine-2-acetic acid methyl ester
|Molar mass||414.49 g·mol−1|
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
|what is: / ?)(|
7-Hydroxymitragynine (mitragynine hydroxyindolenine) is a terpenoid indole alkaloid in the plant Mitragyna speciosa, commonly known as Kratom. It has opioid agonistic activity. "The potency, calculated using pD (2) values, was 30-fold higher than that of mitragynine and 17-fold higher than that of morphine, respectively. Antagonism of naloxone on concentration-response curves for 7-hydroxymitragynine confirmed its opioid effect. These results suggest that the opioid effect of M. speciosa is mostly based on the activity of 7-hydroxymitragynine." One notable distinction between 7-hydroxymitragynine and traditional opioids is that 7-hydroxymitragynine does not cause hypoventilation (respiratory depression) and therefore does not carry the primary safety risk associated with traditional opioids.
7-Hydroxymitragynine is orally active in animals as an analgesic, and produces normal opioid side effects including constipation, though significantly less than morphine, development of tolerance and withdrawal syndrome upon abstinence. The O-acetyl ester (Acetoxy), 7-acetoxymitragynine has also been reported and found to be an active μ-opioid agonist.
- β-prodine - molecule which overlays with 7-hydroxymitragynine's opioid QSAR
- Takayama, H. (2004). "Chemistry and Pharmacology of Analgesic Indole Alkaloids from the Rubasceous Plant, Mitragyna speciosa" (PDF). Chem. Pharm. Bull. 52 (8): 916—928. doi:10.1248/cpb.52.916. PMID 15304982. - synthesis of 7-hydroxymitragynine from mitragynine
- Chemical Abstracts Service: Columbus, OH, 2004; RN 174418-82-7 (accessed via SciFinder Scholar, version 2007.3; November 30, 2011)
- Takayama H, Ishikawa H, Kurihara M, Kitajima M, Aimi N, Ponglux D, Koyama F, Matsumoto K, Moriyama T, Yamamoto LT, Watanabe K, Murayama T, Horie S (April 2002). "Studies on the synthesis and opioid agonistic activities of mitragynine-related indole alkaloids: discovery of opioid agonists structurally different from other opioid ligands". J. Med. Chem. 45 (9): 1949–56. doi:10.1021/jm010576e. PMID 11960505.
- Horie S; Koyama F; Takayama H et al. (March 2005). "Indole alkaloids of a Thai medicinal herb, Mitragyna speciosa, that has opioid agonistic effect in guinea-pig ileum". Planta Med. 71 (3): 231–6. doi:10.1055/s-2005-837822. PMID 15770543.
- Matsumoto K; Horie S; Ishikawa H et al. (March 2004). "Antinociceptive effect of 7-hydroxymitragynine in mice: Discovery of an orally active opioid analgesic from the Thai medicinal herb Mitragyna speciosa". Life Sci. 74 (17): 2143–55. doi:10.1016/j.lfs.2003.09.054. PMID 14969718.
- Matsumoto K; Hatori Y; Murayama T et al. (November 2006). "Involvement of mu-opioid receptors in antinociception and inhibition of gastrointestinal transit induced by 7-hydroxymitragynine, isolated from Thai herbal medicine Mitragyna speciosa". Eur. J. Pharmacol. 549 (1–3): 63–70. doi:10.1016/j.ejphar.2006.08.013. PMID 16978601.
- Takayama H; Ishikawa H; Kurihara M et al. (April 2002). "Studies on the synthesis and opioid agonistic activities of mitragynine-related indole alkaloids: discovery of opioid agonists structurally different from other opioid ligands". J. Med. Chem. 45 (9): 1949–56. doi:10.1021/jm010576e. PMID 11960505.