Dextromoramide

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Image:Dextromoramide.png
Dextromoramide
Systematic (IUPAC) name
?
Identifiers
CAS number	?
ATC code	N02AC01
PubChem	92943
Chemical data
Formula	C25H32N2O2
Mol. weight	392.534
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status	Schedule I(US)
Routes	?

Dextromoramide (Palfium®, Palphium®, Jetrium®, Dimorlin®) is the right-handed isomer of the moramide molecule. The left handed molecule is called levomoramide, and a mixture of the two is called racemoramide. Its full chemical name is (+)-1-(3-Methyl-4-morpholino-2,2-diphenylbutyryl)pyrrolidine, and its molecular formula: C₂₅H₃₂N₂O₂, with an atomic weight of ~392.5. It is one of a group of molecules known as substituted α,α-Diphenyl-γ-Amino-Butyramides.

It is a powerful opioid analgesic, and as such is subject to drug prohibition regimes, both internationally through UN treaties, and by the criminal law of individual states.

It 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. It has the proprietary name Palfium, though as of mid 2004 the drug was dicontinued in the UK due to limited supplies of precursor chemicals.

In many countries dextromoramide is unused, for example the USA, where it is considered a Schedule 1 drug, alongside cannabis and LSD, as having no medicinal uses.

As is the case with so many drug discoveries, dextromoramide was discovered by accident during research into almost identical compounds, namely α,α-Diphenyl-γ-Dialkyamino-Butyramides, which show no analgesic activity, but are extremely active physiologically as inhibitors of gastric secretions in man.

The typical dose was 5mg four hourly for cancer pain - the drug has a short half life comparable with pethidine.

Dextromoramide was much favoured by drug abusers in Australia in the 1970s. A single case report and a review of the subject appears in the Australian Journal of Pharmacy 1980;61:641-644

[edit] References

• Den Otter G, Pain control with dextromoramide (pyrrolamidolum, R 875, palfium), Ned Tijdschr Geneeskd. 1958 Aug 23;102(34):1637-41.
• Lasagna L, De Kornfeld T, Safar P, A clinical trial of dextromoramide, (R 875, SKF D-5137), J Chronic Dis. 1958 Dec;8(6):689-93.