7-Acetoxymitragynine

7-Acetoxymitragynine is an opioid drug which is a semi-synthetic derivative of 7-hydroxymitragynine, a natural product derived from the South-East Asian tree kratom. It can be derived by acetylation of the hydroxyl group of 7-hydroxymitragynine, for instance with acetic anhydride, but can also be produced directly from mitragynine by reaction with Lead(IV) acetate, and is a common synthetic intermediate in the production of 7-hydroxymitragynine from crude kratom extracts. Unlike the higher potency seen with acetyl esters of some other opioids such as morphine, 7-acetoxymitragynine is less potent than 7-hydroxymitragynine, but nevertheless retains opioid activity and has been sold as a designer drug since around 2006.^{[1][2][3][4][5]}

7-Acetoxymitragynine

Identifiers
IUPAC name Methyl (E)-2-[(2S,3S,7aS,12bS)-7a-acetyloxy-3-ethyl-8-methoxy-2,3,4,6,7,12b-hexahydro-1H-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate
CAS Number	174418-81-6
PubChem CID	11015924
Chemical and physical data
Formula	C25H32N2O6
Molar mass	456.539 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC[C@@H]1CN2CC[C@]3(C(=NC4=C3C(=CC=C4)OC)[C@@H]2C[C@@H]1/C(=C\OC)/C(=O)OC)OC(=O)C
InChI InChI=1S/C25H32N2O6/c1-6-16-13-27-11-10-25(33-15(2)28)22-19(8-7-9-21(22)31-4)26-23(25)20(27)12-17(16)18(14-30-3)24(29)32-5/h7-9,14,16-17,20H,6,10-13H2,1-5H3/b18-14+/t16-,17+,20+,25+/m1/s1 Key:RJTCCQKAKCMBTR-XBULZMPJSA-N

See also

• MGM-15
• 6-Monoacetylmorphine