Dihydroetorphine

Dihydroetorphine

Systematic (IUPAC) name
(5R,6R,7R,9R,13S,14R)-7-[(R)-2-Hydroxypentan-2-yl] -6-methoxy-17-methyl-4,5-epoxy-6,14-ethanomorphinan-3-ol
Clinical data
Legal status	DE: Anlage I (Controlled) US: Schedule II
Identifiers
CAS Number	14357-76-7 Y
ATC code	none
PubChem	CID: 107765
DrugBank	DB01450 Y
ChemSpider	96924 Y
UNII	QQX8S479YV Y
Chemical data
Formula	C25H35NO4
Molecular mass	413.5497 g/mol
SMILES 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 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 Y Key:BRTSNYPDACNMIP-FAWZKKEFSA-N Y
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Dihydroetorphine was developed by K. W. Bentley at McFarlan-Smith in the 1960s and is a potent opioid analgesic, 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. It is several thousand times stronger than morphine (between 1000x and 12000x more potent depending what method is used for comparison), 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.

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, in a similar way to how the related drug buprenorphine is used in western nations. 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. Regulation elsewhere may vary but would likely be similar to that for other strong opioid agonists.

See also

• Thienorphine