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Dihydroetorphine

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Dihydroetorphine
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
  • (5R,6R,7R,9R,13S,14R)-7-[(R)-2-Hydroxypentan-2-yl] -6-methoxy-17-methyl-4,5-epoxy-6,14-ethanomorphinan-3-ol
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.214.784 Edit this at Wikidata
Chemical and physical data
FormulaC25H35NO4
Molar mass413.5497 g/mol g·mol−1
3D model (JSmol)
  • Oc6ccc4c1c6O[C@H]3[C@]5(OC)[C@H](C[C@@]2([C@H](N(CC[C@@]123)C)C4)CC5)[C@@](O)(C)CCC
  • InChI=1S/C25H35NO4/c1-5-8-22(2,28)17-14-23-9-10-25(17,29-4)21-24(23)11-12-26(3)18(23)13-15-6-7-16(27)20(30-21)19(15)24/h6-7,17-18,21,27-28H,5,8-14H2,1-4H3/t17-,18-,21-,22-,23-,24+,25-/m1/s1 checkY
  • Key:BRTSNYPDACNMIP-FAWZKKEFSA-N checkY
  (verify)

Dihydroetorphine was developed by K. W. Bentley at McFarlan-Smith in the 1960s[1] and is a potent opioid analgesic,[2] which is used mainly in China. It is a derivative of the more well-known opioid etorphine, which is used as a very potent veterinary painkiller and anesthetic medication, primarily for the sedation of large animals such as elephants, giraffes and rhinos.

Dihydroetorphine is a semi-synthetic opioid, used mainly as a strong painkiller for humans.[3] It is several thousand times stronger than morphine (between 1000x and 12000x more potent depending what method is used for comparison),[1] although it is poorly absorbed when taken orally. Sublingual forms of dihydroetorphine are used in China at doses ranging from 20 to 40µg repeated every 3-4 hours, and are reported to cause strong analgesia and relatively mild side effects compared to other opioids, although all the usual opioid side effects such as dizziness, sedation, nausea, constipation, and respiratory depression can occur. Transdermal patches of dihydroetorphine have also been developed.[4]

Dihydroetorphine is considered to be somewhat less addictive than many other opioids, and is also sometimes used in China as a substitute maintenance drug for opioid addicts,[5] in a similar way to how the related drug buprenorphine is used in western nations.[6][7] It is presumably controlled as an "ester, ether, salt ..." of etorphine in the United States under the Controlled Substances Act 1970 and/or its pieces of the morphine carbon skeleton put it under the "morphine rule" thereof and/or the 1986 analogues act; it does not have its own ACSCN.[8] Regulation elsewhere may vary but would likely be similar to that for other strong opioid agonists.

See also

References

  1. ^ a b Bentley, K. W.; Hardy, D. G. (1967). "Novel analgesics and molecular rearrangements in the morphine-thebaine group. 3. Alcohols of the 6,14-endo-ethenotetrahydrooripavine series and derived analogs of N-allylnormorphine and -norcodeine". Journal of the American Chemical Society. 89 (13): 3281–3292. doi:10.1021/ja00989a032. PMID 6042764.
  2. ^ Martin, T. J.; Hairston, C. T.; Lutz, P. O.; Harris, L. S.; Porreca, F. (1998). "Anti-allodynic actions of intravenous opioids in the nerve injured rat: Potential utility of heroin and dihydroetorphine against neuropathic pain". European Journal of Pharmacology. 357 (1): 25–32. doi:10.1016/S0014-2999(98)00531-7. PMID 9788770.
  3. ^ Lewis, J. W.; Husbands, S. M. (2004). "The orvinols and related opioids--high affinity ligands with diverse efficacy profiles". Current Pharmaceutical Design. 10 (7): 717–732. doi:10.2174/1381612043453027. PMID 15032698.
  4. ^ Ohmori, S.; Morimoto, Y. (2002). "Dihydroetorphine: a potent analgesic: pharmacology, toxicology, pharmacokinetics, and clinical effects". CNS Drug Reviews. 8 (4): 391–404. doi:10.1111/j.1527-3458.2002.tb00236.x. PMID 12481194.
  5. ^ Bo-Yi, Q. (1996). "Advances in dihydroetorphine: From analgesia to detoxification". Drug Development Research. 39 (2): 131–134. doi:10.1002/(SICI)1098-2299(199610)39:2<131::AID-DDR3>3.0.CO;2-Q.
  6. ^ Gerak, L. R.; Gauthier, C. R.; France, C. R. (2003). "Discriminative stimulus and antinociceptive effects of dihydroetorphine in rhesus monkeys". Psychopharmacology. 166 (4): 351–359. doi:10.1007/s00213-002-1268-y. PMID 12601499.
  7. ^ Husbands, S. M.; Lewis, J. W. (2003). "Opioid ligands having delayed long-term antagonist activity: potential pharmacotherapies for opioid abuse". Mini Reviews in Medicinal Chemistry. 3 (2): 137–144. doi:10.2174/1389557033405395. PMID 12570846.
  8. ^ http://www.deadiversion.usdoj.gov/quotas/conv_factor/index.html



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