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7-Hydroxymitragynine
7-Hydroxymitragynine
IUPAC name
Properties
Molecular formula C23H30N2O5
Molar mass 414.495 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

7-Hydroxymitragynine, an indole, is an active alkaloid in the plant Mitragyna speciosa, commonly known as Kratom. It has opioid agonistic activity.[1] "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."[2]

7-Hydroxymitragynine is orally active in animals as an analgesic, [3] and produces normal opioid side effects including constipation[4] development of tolerance and withdrawal syndrome upon abstinence. [3] The O-acetyl ester, 7-acetoxymitragynine has also been reported and found to be an active μ-opioid agonist.[5]

See also

References

  1. ^ 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.  
  2. ^ 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.  
  3. ^ 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.  
  4. ^ 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.  
  5. ^ 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.  
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7-Hydroxymitragynine
Properties
Molecular formula C23H30N2O5
Molar mass 414.49 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

7-Hydroxymitragynine, an indole, is an active alkaloid in the plant Mitragyna speciosa, commonly known as Kratom. It has opioid agonistic activity.[1] "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."[2]

7-Hydroxymitragynine is orally active in animals as an analgesic,[3] and produces normal opioid side effects including constipation[4] development of tolerance and withdrawal syndrome upon abstinence.[3] The O-acetyl ester, 7-acetoxymitragynine has also been reported and found to be an active μ-opioid agonist.[5]

See also

References

  1. ^ 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). [Expression error: Unexpected < operator "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. 
  2. ^ Horie S, Koyama F, Takayama H, et al (March 2005). [Expression error: Unexpected < operator "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. 
  3. ^ a b Matsumoto K, Horie S, Ishikawa H, et al (March 2004). [Expression error: Unexpected < operator "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. 
  4. ^ Matsumoto K, Hatori Y, Murayama T, et al (November 2006). [Expression error: Unexpected < operator "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. 
  5. ^ Takayama H, Ishikawa H, Kurihara M, et al (April 2002). [Expression error: Unexpected < operator "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. 

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