U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C25H32N2O2
Molecular Weight 392.5338
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEXTROMORAMIDE

SMILES

C[C@H](CN1CCOCC1)C(C(=O)N2CCCC2)(C3=CC=CC=C3)C4=CC=CC=C4

InChI

InChIKey=INUNXTSAACVKJS-OAQYLSRUSA-N
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

HIDE SMILES / InChI
Molecular Formula C25H32N2O2
Molecular Weight 392.5338
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including https://books.google.ru/books?id=G7As-qawdzMC&printsec=frontcover&hl=ru#v=onepage&q&f=false | https://www.cbg-meb.nl/documenten/rapporten/2015/09/14/par-dextromoramide | https://medikamio.com/nl-nl/geneesmiddelen/palfium-tablet-5-mg/pil

Dextromoramide is a synthetic strong-acting opioid and full mu-opioid receptor agonist. Dextromoramide is a Schedule I drug illegal to possess. The current indication for Palfium® (dextromoramide) is severe acute or chronic pain requiring opioids, such as post-operative pain, and pain associated with bone fractures, malignancies and acute renal/biliary colic attacks in adults.

CNS Activity

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2752
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
PALFIUM

Approved Use

Palfium® (dextromoramide) is a synthetic strong-acting opioid and full mu-opioid receptor agonist that has been registered in the Netherlands since 1974. The current indication is severe acute or chronic pain requiring opioids, such as post-operative pain, and pain associated with bone fractures, malignancies and acute renal/biliary colic attacks in adults.

Launch Date

1973
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2000 μg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8931067/
5 mg single, intravenous
dose: 5 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
DEXTROMORAMIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
40 μg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8931067/
5 mg single, sublingual
dose: 5 mg
route of administration: Sublingual
experiment type: SINGLE
co-administered:
DEXTROMORAMIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
106 μg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/2714730/
7.5 mg single, oral
dose: 7.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DEXTROMORAMIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1775.4 μg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8931067/
5 mg single, intravenous
dose: 5 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
DEXTROMORAMIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
526 μg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8931067/
5 mg single, sublingual
dose: 5 mg
route of administration: Sublingual
experiment type: SINGLE
co-administered:
DEXTROMORAMIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.81 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/2714730/
7.5 mg single, oral
dose: 7.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DEXTROMORAMIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
9.02 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8931067/
5 mg single, intravenous
dose: 5 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
DEXTROMORAMIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
12.37 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8931067/
5 mg single, sublingual
dose: 5 mg
route of administration: Sublingual
experiment type: SINGLE
co-administered:
DEXTROMORAMIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
12.3 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/2714730/
7.5 mg single, oral
dose: 7.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DEXTROMORAMIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
100 mg single, intravenous
Accidental dose
Dose: 100 mg
Route: intravenous
Route: single
Dose: 100 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/2628587/
unknown, ADULT
Health Status: unknown
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/2628587/
Other AEs: Death...
Other AEs:
Death
Sources:
https://pubmed.ncbi.nlm.nih.gov/2628587/
40 mg 1 times / hour multiple, oral
Highest recorded dose
Dose: 40 mg, 1 times / hour
Route: oral
Route: multiple
Dose: 40 mg, 1 times / hour
Sources:
https://pubmed.ncbi.nlm.nih.gov/6017168/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/6017168/
Disc. AE: Drug abuse...
AEs leading to
discontinuation/dose reduction:
Drug abuse
Sources:
https://pubmed.ncbi.nlm.nih.gov/6017168/
20 mg single, rectal
Highest studied dose
Dose: 20 mg
Route: rectal
Route: single
Dose: 20 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/13539148/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/13539148/
Sources:
https://pubmed.ncbi.nlm.nih.gov/13539148/
AEs

AEs

AESignificanceDosePopulation
Death
100 mg single, intravenous
Accidental dose
Dose: 100 mg
Route: intravenous
Route: single
Dose: 100 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/2628587/
unknown, ADULT
Health Status: unknown
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/2628587/
Drug abuse Disc. AE
40 mg 1 times / hour multiple, oral
Highest recorded dose
Dose: 40 mg, 1 times / hour
Route: oral
Route: multiple
Dose: 40 mg, 1 times / hour
Sources:
https://pubmed.ncbi.nlm.nih.gov/6017168/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/6017168/
PubMed

PubMed

TitleDatePubMed
Effect of methadone and dextromoramide on dopamine metabolism: comparison with haloperidol and amphetamine.
1975-12
Properties and analysis of dextromoramide and its dosage forms.
1961-01
Patents

Patents

GB822055
3

Sample Use Guides

In Vivo Use Guide
IM: 15 mg Intra Rectal: 20 mg PO: 0.071 to 0.285 mg/kg SC: 15 mg
Route of Administration: Other
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:21:21 GMT 2025
Edited
by admin
on Mon Mar 31 18:21:21 GMT 2025
Record UNII
9S4S6CIY83
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LINFADOL
Preferred Name English
DEXTROMORAMIDE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
(+)-4-(2-METHYL-4-OXO-3,3-DIPHENYL-4-(1-PYRROLIDINYL)BUTYL)MORPHOLINE
Systematic Name English
Dextromoramide [WHO-DD]
Common Name English
DEXTROMORAMIDE [MI]
Common Name English
4-(2-METHYL-4-OXO-3,3-DIPHENYL-4-(1-PYRROLIDINYL)BUTYL)MORPHOLINE
Systematic Name English
SKF-5137
Code English
dextromoramide [INN]
Common Name English
TROXILAN
Common Name English
ALCOID
Common Name English
RACEMORAMIDE, (S)-
Common Name English
PYRROLAMIDOL
Systematic Name English
JETRIUM
Common Name English
1-((3S)-3-METHYL-4-(4-MORPHOLINYL)-1-OXO-2,2-DIPHENYLBUTYL)PYRROLIDINE
Systematic Name English
1-BUTANONE, 3-METHYL-4-(4-MORPHOLINYL)-2,2-DIPHENYL-1-(1-PYRROLIDINYL)-, (3S)-
Systematic Name English
MCP-875
Code English
YETRIUM
Common Name English
NARCOLO
Brand Name English
R-875
Code English
DEXTROMORAMIDE [MART.]
Common Name English
MORAMIDE
Brand Name English
D-2,2-DIPHENYL-3-METHYL-4-MORPHOLINOBUTYRYLPYRROLIDINE
Common Name English
(+)-1-(3-METHYL-4-MORPHOLINO-2,2-DIPHENYLBUTYRYL)PYRROLIDINE
Systematic Name English
PALFADONNA
Common Name English
ACSCN-9613
Common Name English
IDS-ND-003
Code English
Classification Tree Code System Code
WHO-VATC QN02AC01
Created by admin on Mon Mar 31 18:21:21 GMT 2025 , Edited by admin on Mon Mar 31 18:21:21 GMT 2025
WHO-ATC N02AC01
Created by admin on Mon Mar 31 18:21:21 GMT 2025 , Edited by admin on Mon Mar 31 18:21:21 GMT 2025
DEA NO. 9613
Created by admin on Mon Mar 31 18:21:21 GMT 2025 , Edited by admin on Mon Mar 31 18:21:21 GMT 2025
NCI_THESAURUS C67413
Created by admin on Mon Mar 31 18:21:21 GMT 2025 , Edited by admin on Mon Mar 31 18:21:21 GMT 2025
Code System Code Type Description
CAS
357-56-2
Created by admin on Mon Mar 31 18:21:21 GMT 2025 , Edited by admin on Mon Mar 31 18:21:21 GMT 2025
PRIMARY
NCI_THESAURUS
C87357
Created by admin on Mon Mar 31 18:21:21 GMT 2025 , Edited by admin on Mon Mar 31 18:21:21 GMT 2025
PRIMARY
EPA CompTox
DTXSID8022909
Created by admin on Mon Mar 31 18:21:21 GMT 2025 , Edited by admin on Mon Mar 31 18:21:21 GMT 2025
PRIMARY
MERCK INDEX
m4228
Created by admin on Mon Mar 31 18:21:21 GMT 2025 , Edited by admin on Mon Mar 31 18:21:21 GMT 2025
PRIMARY Merck Index
RXCUI
3290
Created by admin on Mon Mar 31 18:21:21 GMT 2025 , Edited by admin on Mon Mar 31 18:21:21 GMT 2025
PRIMARY RxNorm
DRUG CENTRAL
843
Created by admin on Mon Mar 31 18:21:21 GMT 2025 , Edited by admin on Mon Mar 31 18:21:21 GMT 2025
PRIMARY
CHEBI
74274
Created by admin on Mon Mar 31 18:21:21 GMT 2025 , Edited by admin on Mon Mar 31 18:21:21 GMT 2025
PRIMARY
FDA UNII
9S4S6CIY83
Created by admin on Mon Mar 31 18:21:21 GMT 2025 , Edited by admin on Mon Mar 31 18:21:21 GMT 2025
PRIMARY
ECHA (EC/EINECS)
206-613-1
Created by admin on Mon Mar 31 18:21:21 GMT 2025 , Edited by admin on Mon Mar 31 18:21:21 GMT 2025
PRIMARY
PUBCHEM
92943
Created by admin on Mon Mar 31 18:21:21 GMT 2025 , Edited by admin on Mon Mar 31 18:21:21 GMT 2025
PRIMARY
MESH
D003916
Created by admin on Mon Mar 31 18:21:21 GMT 2025 , Edited by admin on Mon Mar 31 18:21:21 GMT 2025
PRIMARY
SMS_ID
100000082898
Created by admin on Mon Mar 31 18:21:21 GMT 2025 , Edited by admin on Mon Mar 31 18:21:21 GMT 2025
PRIMARY
EVMPD
SUB07052MIG
Created by admin on Mon Mar 31 18:21:21 GMT 2025 , Edited by admin on Mon Mar 31 18:21:21 GMT 2025
PRIMARY
WIKIPEDIA
DEXTROMORAMIDE
Created by admin on Mon Mar 31 18:21:21 GMT 2025 , Edited by admin on Mon Mar 31 18:21:21 GMT 2025
PRIMARY
INN
733
Created by admin on Mon Mar 31 18:21:21 GMT 2025 , Edited by admin on Mon Mar 31 18:21:21 GMT 2025
PRIMARY
DRUG BANK
DB01529
Created by admin on Mon Mar 31 18:21:21 GMT 2025 , Edited by admin on Mon Mar 31 18:21:21 GMT 2025
PRIMARY
Related Record Type Details
Structure of RACEMORAMIDE
RACEMATE -> ENANTIOMER
Structure of DEXTROMORAMIDE TARTRATE
SALT/SOLVATE -> PARENT
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
Related Record Type Details
Structure of DEXTROMORAMIDE
ACTIVE MOIETY
(+)-4-[2-methyl-4-oxo-3,3-diphenyl-4-(1-pyrrolidinyl)butyl]morpholine (A dextro-rotatory isomer of moramide). as per INCB
NIH
NCATS
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