7-Hydroxymitragynine
| 7-Hydroxymitragynine | |
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(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[citation needed] |
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| Identifiers | |
| CAS number | 174418-82-7  |
| PubChem | 44301524 |
| ChemSpider | 23152144  |
| ChEMBL | CHEMBL61630 |
| Jmol-3D images | Image 1 Image 2 |
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| Properties | |
| Molecular formula | C23H30N2O5 |
| Molar mass | 414.49 g mol−1 |
| Exact mass | 414.215472080 g mol−1 |
| log P | 1.266 |
| Acidity (pKa) | 12.203 |
| Basicity (pKb) | 1.794 |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
7-Hydroxymitragynine (mitragynine hydroxyindolenine), an indole, is an active alkaloid in the plant Mitragyna speciosa, commonly known as Kratom. It has opioid agonistic activity.[2] "The potency, calculated using pD (2) values, was 30- and 17-fold higher than that of mitragynine and 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."[3]
7-Hydroxymitragynine is orally active in animals as an analgesic,[4] and produces normal opioid side effects including constipation, though significantly less than morphine,[5] development of tolerance and withdrawal syndrome upon abstinence.[4] The O-acetyl ester (Acetoxy), 7-acetoxymitragynine has also been reported and found to be an active μ-opioid agonist.[6]
[edit] See also
[edit] References
- ^ a b 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.
- ^ a b 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.
