7-Hydroxymitragynine

From The Lycaeum
(Redirected from 7-hydroxymitragynine)
Jump to: navigation, search
7-Hydroxymitragynine
Stereo, Kekulé, skeletal formula of 7-hydroxymitragynine with an explicit hydrogen added
Identifiers
CAS number 174418-82-7 7pxN
PubChem 44301524
ChemSpider 23152144 7pxY
ChEMBL CHEMBL61630 7pxY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C23H30N2O5
Molar mass Script error g mol−1
log P 1.266
Acidity (pKa) 12.203
Basicity (pKb) 1.794
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 14pxN (verify) (what is: 10pxY/10pxN?)
Infobox references

7-Hydroxymitragynine (mitragynine hydroxyindolenine) is a terpenoid indole 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-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.[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]

7-Acetoxymitragynine

See also

External links

References

  1. 1.0 1.1 Chemical Abstracts Service: Columbus, OH, 2004; RN 174418-82-7 (accessed via SciFinder Scholar, version 2007.3; November 30, 2011)
  2. 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. PMID 11960505. doi:10.1021/jm010576e. 
  3. 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. PMID 15770543. doi:10.1055/s-2005-837822. 
  4. 4.0 4.1 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. PMID 14969718. doi:10.1016/j.lfs.2003.09.054. 
  5. 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. PMID 16978601. doi:10.1016/j.ejphar.2006.08.013. 
  6. 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. PMID 11960505. doi:10.1021/jm010576e. 
      
Personal tools
Namespaces

Variants
Actions
Navigation
Forums
Lycaeum IRC Chat
TheAntiDrug Diaspora
Starting Points
Tools