- 7-Hydroxymitragynine
Chembox new
Name = 7-Hydroxymitragynine
ImageFile = 7OHMitragynine.png
ImageName = 7-Hydroxymitragynine
IUPACName = 7-Hydroxymitragynine
Section1 = Chembox Identifiers
CASNo =
SMILES =
Section2 = Chembox Properties
Formula = C23H30N2O5
MolarMass = 414.495 g/mol
Density =
MeltingPt =
BoilingPt =7-Hydroxymitragynine, an
indole , is an activealkaloid in the plant "Mitragyna speciosa ", commonly known asKratom . It has opioid agonistic activity.cite journal | author = 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 | title = Studies on the synthesis and opioid agonistic activities of mitragynine-related indole alkaloids: discovery of opioid agonists structurally different from other opioid ligands | journal = J. Med. Chem. | volume = 45 | issue = 9 | pages = 1949–56 | year = 2002 | month = April | pmid = 11960505 | doi = 10.1021/jm010576e] "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."cite journal |author=Horie S, Koyama F, Takayama H, "et al" |title=Indole alkaloids of a Thai medicinal herb, Mitragyna speciosa, that has opioid agonistic effect in guinea-pig ileum |journal=Planta Med. |volume=71 |issue=3 |pages=231–6 |year=2005 |month=March |pmid=15770543 |doi=10.1055/s-2005-837822 |url=]7-Hydroxymitragynine is orally active in animals as an
analgesic , [cite journal |author=Matsumoto K, Horie S, Ishikawa H, "et al" |title=Antinociceptive effect of 7-hydroxymitragynine in mice: Discovery of an orally active opioid analgesic from the Thai medicinal herb Mitragyna speciosa |journal=Life Sci. |volume=74 |issue=17 |pages=2143–55 |year=2004 |month=March |pmid=14969718 |doi=10.1016/j.lfs.2003.09.054 |url=] and produces normal opioid side effects includingconstipation [cite journal |author=Matsumoto K, Hatori Y, Murayama T, "et al" |title=Involvement of mu-opioid receptors in antinociception and inhibition of gastrointestinal transit induced by 7-hydroxymitragynine, isolated from Thai herbal medicine Mitragyna speciosa |journal=Eur. J. Pharmacol. |volume=549 |issue=1-3 |pages=63–70 |year=2006 |month=November |pmid=16978601 |doi=10.1016/j.ejphar.2006.08.013 |url=] development of tolerance and withdrawal syndrome upon abstinence. [cite journal |author=Matsumoto K, Horie S, Ishikawa H, "et al" |title=Antinociceptive effect of 7-hydroxymitragynine in mice: Discovery of an orally active opioid analgesic from the Thai medicinal herb Mitragyna speciosa |journal=Life Sci. |volume=74 |issue=17 |pages=2143–55 |year=2004 |month=March |pmid=14969718 |doi=10.1016/j.lfs.2003.09.054 |url=] The O-acetyl ester ,7-acetoxymitragynine has also been reported and found to be an active μ-opioid agonist. [cite journal |author=Takayama H, Ishikawa H, Kurihara M, "et al" |title=Studies on the synthesis and opioid agonistic activities of mitragynine-related indole alkaloids: discovery of opioid agonists structurally different from other opioid ligands |journal=J. Med. Chem. |volume=45 |issue=9 |pages=1949–56 |year=2002 |month=April |pmid=11960505 |doi=10.1021/jm010576e]ee also
*
Mitragynine
*Mitraphylline
*Kratom
*7-acetoxymitragynine References
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