CHEBI:74274 - dextromoramide

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ChEBI Name dextromoramide
ChEBI ID CHEBI:74274
Definition An N-acylpyrrolidine arising by formal condensation of pyrrolidine with (3S)-3-methyl-4-(morpholin-4-yl)-2,2-diphenylbutanoic acid. An opioid analgesic that is structurally related to methadone, it is more poweful than morphine but shorter acting. It has been used (particularly as the hydrogen tartrate salt) for the treatment of severe pain, but was discontinued in the UK in 2004.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C25H32N2O2
Net Charge 0
Average Mass 392.53380
Monoisotopic Mass 392.246
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
InChIKey INUNXTSAACVKJS-OAQYLSRUSA-N
SMILES C[C@H](CN1CCOCC1)C(C(=O)N1CCCC1)(c1ccccc1)c1ccccc1
Roles Classification
Biological Role(s): opioid analgesic
A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
Application(s): opioid analgesic
A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing dextromoramide (CHEBI:74274) has role opioid analgesic (CHEBI:35482)
dextromoramide (CHEBI:74274) is a N-acylpyrrolidine (CHEBI:46766)
dextromoramide (CHEBI:74274) is a morpholines (CHEBI:38785)
IUPAC Name
(3S)-3-methyl-4-(morpholin-4-yl)-2,2-diphenyl-1-(pyrrolidin-1-yl)butan-1-one
INNs Sources
dextromoramida ChemIDplus
dextromoramide ChemIDplus
dextromoramide WHO MedNet
dextromoramidum ChemIDplus
Synonyms Sources
(+)-2,2-diphenyl-3-methyl-4-morpholinobutyrylpyrrolidine ChemIDplus
(+)-3-methyl-4-morpholino-2,2-diphenyl-1-(pyrrolidin-1-yl)butanone ChEBI
palfium ChEBI
palphium ChEBI
pyrrolamidolum ChemIDplus
R 875 ChemIDplus
SKF 5137 ChemIDplus
SKF-5137 ChEBI
Manual Xrefs Databases
843 DrugCentral
D07287 KEGG DRUG
DB01529 DrugBank
GB822055 Patent
View more database links
Registry Numbers Types Sources
357-56-2 CAS Registry Number NIST Chemistry WebBook
357-56-2 CAS Registry Number ChemIDplus
96553 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
13757828 PubMed citation Europe PMC
2295688 PubMed citation Europe PMC
7632606 PubMed citation Europe PMC
8931067 PubMed citation Europe PMC
89885 PubMed citation Europe PMC
9584342 PubMed citation Europe PMC
Last Modified
22 February 2017