7-Acetoxymitragynine

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;

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]

References

^ Takayama H, Ishikawa H, Kurihara M, Kitajima M, Aimi N, Ponglux D, et al. (April 2002). "Studies on the synthesis and opioid agonistic activities of mitragynine-related indole alkaloids: discovery of opioid agonists structurally different from other opioid ligands". Journal of Medicinal Chemistry. 45 (9): 1949–1956. doi:10.1021/jm010576e. PMID 11960505.
^ Takayama H (August 2004). "Chemistry and pharmacology of analgesic indole alkaloids from the rubiaceous plant, Mitragyna speciosa". Chemical & Pharmaceutical Bulletin. 52 (8): 916–928. doi:10.1248/cpb.52.916. PMID 15304982.
^ Raffa RB, Beckett JR, Brahmbhatt VN, Ebinger TM, Fabian CA, Nixon JR, et al. (June 2013). "Orally active opioid compounds from a non-poppy source". Journal of Medicinal Chemistry. 56 (12): 4840–4848. doi:10.1021/jm400143z. PMID 23517479.
^ Raffa RB, ed. (2014). Kratom and Other Mitragynines. doi:10.1201/b17666. ISBN 978-1-4822-2519-8.
^ Sakamoto J, Kitajima M, Ishikawa H (2022). "Asymmetric Total Syntheses of Mitragynine, Speciogynine, and 7-Hydroxymitragynine". Chemical & Pharmaceutical Bulletin. 70 (9) c22-00441: 662–668. doi:10.1248/cpb.c22-00441. PMID 36047237.

[1] Takayama H, Ishikawa H, Kurihara M, Kitajima M, Aimi N, Ponglux D, et al. (April 2002). "Studies on the synthesis and opioid agonistic activities of mitragynine-related indole alkaloids: discovery of opioid agonists structurally different from other opioid ligands". Journal of Medicinal Chemistry. 45 (9): 1949–1956. doi:10.1021/jm010576e. PMID 11960505.

[2] Takayama H (August 2004). "Chemistry and pharmacology of analgesic indole alkaloids from the rubiaceous plant, Mitragyna speciosa". Chemical & Pharmaceutical Bulletin. 52 (8): 916–928. doi:10.1248/cpb.52.916. PMID 15304982.

[3] Raffa RB, Beckett JR, Brahmbhatt VN, Ebinger TM, Fabian CA, Nixon JR, et al. (June 2013). "Orally active opioid compounds from a non-poppy source". Journal of Medicinal Chemistry. 56 (12): 4840–4848. doi:10.1021/jm400143z. PMID 23517479.

[4] Raffa RB, ed. (2014). Kratom and Other Mitragynines. doi:10.1201/b17666. ISBN 978-1-4822-2519-8.

[5] Sakamoto J, Kitajima M, Ishikawa H (2022). "Asymmetric Total Syntheses of Mitragynine, Speciogynine, and 7-Hydroxymitragynine". Chemical & Pharmaceutical Bulletin. 70 (9) c22-00441: 662–668. doi:10.1248/cpb.c22-00441. PMID 36047237.

[1]

[2]

[3]

[4]

[5]

See also

References