7-Hydroxymitragynine
From Wikipedia, the free encyclopedia
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| Names | |
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| IUPAC name
Methyl (E)-2-[(2S,3S,7aS,12bS)-3-ethyl-7a-hydroxy-8-methoxy-2,3,4,6,7,12b-hexahydro-1H-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate
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| Other names | |
| Identifiers | |
174418-82-7  |
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| ChEMBL | ChEMBL61630  |
| ChemSpider | 23152144 |
| Jmol 3D model | Interactive image Interactive image |
| PubChem | 44301524 |
| UNII | 2T3TWA75R0 |
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| Properties | |
| C23H30N2O5 | |
| Molar mass | 414.50 g·mol−1 |
| log P | 1.266 |
| Acidity (pKa) | 12.203 |
| Basicity (pKb) | 1.794 |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 verify (what is ?) |
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| Infobox references | |
7-Hydroxymitragynine is a terpenoid indole alkaloid from the plant Mitragyna speciosa, commonly known as Kratom. In mice, it is orally active and has analgesic effects.[2]
7-Hydroxymitragynine is a partial agonist at the μ-opioid receptor[3] with a potency, calculated using pD (2) values, that is 30-fold higher than that of mitragynine and 17-fold higher than that of morphine, respectively.[4] As a G protein biased ligand at this receptor[5] it causes significantly less side effects than morphine,[6] like constipation, development of tolerance and withdrawal syndrome upon abstinence.[2] The O-acetyl ester (Acetoxy), 7-acetoxymitragynine has also been reported and found to be an active μ-opioid agonist.[7]
See also[edit]
- Mitragynine
- Mitraphylline
- β-Prodine - molecule which overlays with 7-hydroxymitragynine's opioid QSAR
References[edit]
- ^ a b Chemical Abstracts Service: Columbus, OH, 2004; RN 174418-82-7 (accessed via SciFinder Scholar, version 2007.3; November 30, 2011)
- ^ 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.
- ^ 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.
- ^ Kruegel AC, Gassaway MM, Kapoor A, Váradi A, Majumdar S, Filizola M, Javitch JA, Sames D (2016). "Synthetic and Receptor Signaling Explorations of the Mitragyna Alkaloids: Mitragynine as an Atypical Molecular Framework for Opioid Receptor Modulators". J. Am. Chem. Soc. 138 (21): 6754–64. doi:10.1021/jacs.6b00360. PMID 27192616.
- ^ 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.
External links[edit]
- 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
