Dextromoramide

Dextromoramide

Clinical data
Trade names	Palfium
AHFS/Drugs.com	International Drug Names
Pregnancy category	AU: C
Routes of administration	Oral, Rectal, Intravenous, Insufflation
ATC code	N02AC01 (WHO)
Legal status
Legal status	AU: S8 (Controlled) CA: Schedule I DE: Anlage II (Prohibited) US: Schedule I
Pharmacokinetic data
Bioavailability	>75%
Protein binding	High
Metabolism	Liver, partly mediated by CYP3A4
Biological half-life	3.5 hours
Excretion	Urine, faeces
Identifiers
IUPAC name (3S)-3-methyl-4-morpholin-4-yl-2,2-diphenyl-1-pyrrolidin-1-yl-butan-1-one
CAS Number	357-56-2 N
PubChem (CID)	92943
DrugBank	DB01529 Y
ChemSpider	83901 Y
UNII	9S4S6CIY83 Y
KEGG	D07287 Y
ChEBI	CHEBI:74274 N
ChEMBL	CHEMBL431928 N
ECHA InfoCard	100.006.013
Chemical and physical data
Formula	C25H32N2O2
Molar mass	392.534
3D model (Jmol)	Interactive image
SMILES C[C@@H](C(C1=CC=CC=C1)(C(N2CCCC2)=O)C3=CC=CC=C3)CN4CCOCC4
InChI InChI=1S/C25H32N2O2/c1-21(20-26-16-18-29-19-17-26)25(22-10-4-2-5-11-22,23-12-6-3-7-13-23)24(28)27-14-8-9-15-27/h2-7,10-13,21H,8-9,14-20H2,1H3/t21-/m1/s1 Y Key:INUNXTSAACVKJS-OAQYLSRUSA-N Y
NY (what is this?)

Dextromoramide (Palfium, Palphium, Jetrium, Dimorlin) is a powerful opioid analgesic approximately three times more potent than morphine but shorter acting. It is subject to drug prohibition regimes, both internationally through UN treaties and by the criminal law of individual states. It is still marketed solely in the Netherlands.

Dextromoramide was discovered and patented in 1956 by Dr Paul Janssen at Janssen Pharmaceutica, who also discovered fentanyl, another important synthetic opioid, widely used to treat pain and in combination with other drugs as an anaesthetic, as well as haloperidol, piritramide, the loperamide-diphenoxylate series and other important drugs

Dextromoramide was singled out along with ketobemidone and several other synthetics by the United Nations and European Union as being "extra-dangerous" in the early 1960s, with dextromoramide being alleged to be three times more euphoric than heroin at equianalgesic doses, though this did little to stem production in the first half of the decade. The development of the moramides and the coming to fruition of work on piritramide were two of the events that precipitated the 1961 update to the Single Convention On Narcotic Drugs, as cited by Dr Shulgin in Controlled Substances and various monographs.

Dextromoramide was much favoured by drug users in Australia in the 1970s and the United Kingdom. It has the main proprietary name of Palfium amongst others, though as of mid-2004 the drug was discontinued in the UK due to limited supplies of precursor chemicals. Although this is true, it is believed there was an approximate one year shortage of Dextromoramide and the real reason that Palfium was not put back into production for the UK market is because of how addictive and potent it is as an oral painkiller. Dependence liability is similar to morphine, but with a less severe withdrawal syndrome.