7-hydroxymitragynine

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; 9-Methoxycorynantheidine hydroxyindolenine
Identifiers
CAS Number	174418-82-7 N
3D model (Jmol)	Interactive image Interactive image
ChEMBL	ChEMBL61630 Y
ChemSpider	23152144 Y
PubChem	44301524
UNII	2T3TWA75R0 N
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	414.50 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  (what is YN ?)
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.

7-Hydroxymitragynine is a partial agonist at the μ-opioid receptor 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. As a G protein biased ligand at this receptor it causes significantly less side effects than morphine, like constipation, development of tolerance and withdrawal syndrome upon abstinence. The O-acetyl ester (Acetoxy), 7-acetoxymitragynine has also been reported and found to be an active μ-opioid agonist.