7-Acetoxymitragynine

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7-Acetoxymitragynine
7-Acetoxymitragynine structure.png
Identifiers
  • 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
PubChem CID
Chemical and physical data
Formula C25H32N2O6
Molar mass 456.539 g·mol−1
3D model (JSmol)
  • 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=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 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]

See also

References

  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.
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