7-Hydroxymitragynine

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7-Hydroxymitragynine
Stereo, Kekulé, skeletal formula of 7-hydroxymitragynine with an explicit hydrogen added
Names
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
Other names
7α-Hydroxy-7H-mitragynine;[1] 9-Methoxycorynantheidine hydroxyindolenine[1]
Identifiers
174418-82-7 N
3D model (Jmol) Interactive image
Interactive image
ChEMBL ChEMBL61630 YesY
ChemSpider 23152144 YesY
PubChem 44301524
UNII 2T3TWA75R0 N
Properties
C23H30N2O5
Molar mass 414.50 g·mol−1
log P 1.266
Acidity (pKa) 12.203
Basicity (pKb) 1.794
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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]

7-Acetoxymitragynine

See also[edit]

References[edit]

  1. ^ a b Chemical Abstracts Service: Columbus, OH, 2004; RN 174418-82-7 (accessed via SciFinder Scholar, version 2007.3; November 30, 2011)
  2. ^ 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. 
  3. ^ 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. 
  4. ^ 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. 
  5. ^ 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. 
  6. ^ 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. 
  7. ^ 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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