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7-Acetoxymitragynine

中文

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Chemical compound

Pharmaceutical compound

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
PubChemCID	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 anopioid drug which is a semi-synthetic derivative of7-hydroxymitragynine, anatural product derived from the South-East Asian treekratom. It can be derived by acetylation of the hydroxyl group of 7-hydroxymitragynine, for instance withacetic anhydride, but can also be produced directly frommitragynine by reaction withLead(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 asmorphine, 7-acetoxymitragynine is less potent than 7-hydroxymitragynine, but nevertheless retains opioid activity and has been sold as adesigner drug since around 2006.^[1]^[2]^[3]^[4]^[5]

References

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^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.