Dextromoramide

Title: Dextromoramide
CAS Registry Number: 357-56-2
CAS Name: 1-[(3S)-3-Methyl-4-(4-morpholinyl)-1-oxo-2,2-diphenylbutyl]pyrrolidine
Additional Names: (+)-1-(3-methyl-4-morpholino-2,2-diphenylbutyryl)pyrrolidine; 4-[2-methyl-4-oxo-3,3-diphenyl-4-(1-pyrrolidinyl)butyl]morpholine; d-2,2-diphenyl-3-methyl-4-morpholinobutyrylpyrrolidine; pyrrolamidol
Manufacturers' Codes: R-875; SKF-5137
Trademarks: d-Moramid(e); Palfium (Purdue Frederick); Palphium; Jetrium (Hek); Dimorlin
Molecular Formula: C25H32N2O2
Molecular Weight: 392.53
Percent Composition: C 76.50%, H 8.22%, N 7.14%, O 8.15%
Literature References: Synthesis: Janssen, J. Am. Chem. Soc. 78, 3862 (1956); GB 822055 (1959 to Janssen).
Properties: Crystals, mp 180-184°. [a]D20 +25.5° (c = 5 in benzene). uv max (0.01N isopropanol-HCl): 254, 260, 264 nm. Practically insol in water. Soly in 0.1N HCl: 1:25 (w/v). Soly (g/100 ml) in ethanol 50; in methanol 40; in acetone 50; in ethyl acetate 40; in benzene 5; in chloroform 5. Sol in ether.
Melting point: mp 180-184°
Optical Rotation: [a]D20 +25.5° (c = 5 in benzene)
Absorption maximum: uv max (0.01N isopropanol-HCl): 254, 260, 264 nm
Derivative Type: Bitartrate
Molecular Formula: C25H32N2O2.C4H6O6
Molecular Weight: 542.62
Percent Composition: C 64.19%, H 7.06%, N 5.16%, O 23.59%
Properties: Minute crystals, bitter taste. Dec 189-192°. Soly (w/v) at 25°: Water 20%, chloroform 30%, methanol 40%, ethanol 100%, acetone 100%.
NOTE: This is a controlled substance (opiate): 21 CFR, 1308.11.
Therap-Cat: Analgesic (narcotic).
Keywords: Analgesic (Narcotic).
Dezocine DFDD DFDT d-Fenchone D-Fucose

Dextromoramide
Dextromoramide-2D-skeletal.png
Systematic (IUPAC) name
(3S)-3-methyl-4-morpholin-4-yl-2,2-diphenyl-1-pyrrolidin-1-yl-butan-1-one
Clinical data
AHFS/Drugs.com International Drug Names
Legal status Controlled (S8) (AU) Schedule I (US)
Routes Oral, Intravenous, Insufflation
Pharmacokinetic data
Bioavailability "High"
Half-life 1.5 - 4.7 hours
Identifiers
CAS number 357-56-2 N
ATC code N02AC01
PubChem CID 92943
DrugBank DB01529
ChemSpider 83901 YesY
UNII 9S4S6CIY83 YesY
KEGG D07287 YesY
ChEBI CHEBI:74274 N
ChEMBL CHEMBL431928 N
Chemical data
Formula C25H32N2O2 
Mol. mass 392.534
 N (what is this?)  (verify)

Dextromoramide (Palfium, Palphium, Jetrium, Dimorlin)[1] is a powerful opioid analgesic approximately three times more potent than morphine but shorter acting.[2] It is subject to drug prohibition regimes, both internationally through UN treaties, and by the criminal law of individual states. It is still rarely used in Australia and some European countries, but prescription is avoided due to its abuse potential and so use of dextromoramide is now mainly limited to terminal care. It is believed to have the least degree of cross tolerance to morphine of all known opioids, which may be of use in long term opioid therapy.