7-Hydroxymitragynine
Names | |
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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
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Other names | |
Identifiers | |
174418-82-7 | |
ChEMBL | ChEMBL61630 |
ChemSpider | 23152144 |
Jmol 3D model | Interactive image Interactive image |
PubChem | 44301524 |
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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).
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verify (what is ?) | |
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]
See also
- Mitragynine
- Mitraphylline
- β-prodine - molecule which overlays with 7-hydroxymitragynine's opioid QSAR
External links
- Lua error in package.lua at line 80: module 'strict' not found. - synthesis of 7-hydroxymitragynine from mitragynine
References
- ↑ 1.0 1.1 Chemical Abstracts Service: Columbus, OH, 2004; RN 174418-82-7 (accessed via SciFinder Scholar, version 2007.3; November 30, 2011)
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ 4.0 4.1 Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.