7-Hydroxymitragynine

7-Hydroxymitragynine is a terpenoid indole alkaloid from the plant Mitragyna speciosa, commonly known as Kratom.[2]

7-Acetoxymitragynine

7-Hydroxymitragynine

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
CAS Number	174418-82-7^N
3D model (JSmol)	Interactive image Interactive image
ChEMBL	ChEMBL61630^Y
ChemSpider	23152144^Y
PubChem CID	44301524
UNII	2T3TWA75R0^N
CompTox Dashboard (EPA)	DTXSID20903988
InChI 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^Y Key: RYENLSMHLCNXJT-CYXFISRXSA-N^Y
SMILES 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
Chemical formula	C23H30N2O5
Molar mass	414.502 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 ^YN ?)
Infobox references

See also

• Mitragynine
• Mitragynine pseudoindoxyl
• Mitraphylline
• β-Prodine - molecule which overlays with 7-hydroxymitragynine's opioid QSAR

References

1. Chemical Abstracts Service: Columbus, OH, 2004; RN 174418-82-7 (accessed via SciFinder Scholar, version 2007.3; November 30, 2011)
2. Matsumoto K, Horie S, Ishikawa H, Takayama H, Aimi N, Ponglux D, Watanabe K (March 2004). "Antinociceptive effect of 7-hydroxymitragynine in mice: Discovery of an orally active opioid analgesic from the Thai medicinal herb Mitragyna speciosa". Life Sciences. 74 (17): 2143–55. doi:10.1016/j.lfs.2003.09.054. PMID 14969718.

External links

• Takayama H (August 2004). "Chemistry and pharmacology of analgesic indole alkaloids from the rubiaceous plant, Mitragyna speciosa" (pdf). Chemical & Pharmaceutical Bulletin. 52 (8): 916–28. doi:10.1248/cpb.52.916. PMID 15304982. - synthesis of 7-hydroxymitragynine from mitragynine