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
ChEMBL ChEMBL61630 YesY
ChemSpider 23152144 YesY
Jmol 3D model Interactive image
Interactive image
PubChem 44301524
  • InChI=1S/C23H30N2O5/c1-5-14-12-25-10-9-23(27)20-17(7-6-8-19(20)29-3)24-21(23)18(25)11-15(14)16(13-28-2)22(26)30-4/h6-8,13-15,18,27H,5,9-12H2,1-4H3/b16-13+/t14-,15+,18+,23+/m1/s1 YesY
    Key: RYENLSMHLCNXJT-CYXFISRXSA-N YesY
  • CC[C@@H]1CN2CC[C@@]3(O)C(=Nc4cccc(OC)c34)[C@@H]2C[C@@H]1\C(=C/OC)C(=O)OC
  • CC[C@@H]1CN2CC[C@@]3(O)C(=NC4=CC=CC(OC)=C34)[C@@H]2C[C@@H]1\C(=C/OC)C(=O)OC
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 (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." [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

  • Lua error in package.lua at line 80: module 'strict' not found. - synthesis of 7-hydroxymitragynine from mitragynine

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. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ 4.0 4.1 Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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