Dextromoramide

Identification

Generic Name
Dextromoramide
DrugBank Accession Number
DB01529
Background

An opioid analgesic structurally related to methadone and used in the treatment of severe pain. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1070)

Type
Small Molecule
Groups
Experimental, Illicit
Structure
Weight
Average: 392.543
Monoisotopic: 392.246378278
Chemical Formula
C25H32N2O2
Synonyms
  • (+)-1-(3-methyl-4-morpholino-2,2-diphenylbutyryl)pyrrolidine
  • (+)-4-(2-methyl-4-oxo-3,3-diphenyl-4-(1-pyrrolidinyl)butyl)morpholine
  • 1-((3S)-3-methyl-4-(4-morpholinyl)-1-oxo-2,2-diphenylbutyl)pyrrolidine
  • 4-(2-methyl-4-oxo-3,3-diphenyl-4-(1-pyrrolidinyl)butyl)morpholine
  • D-2,2-diphenyl-3-methyl-4-morpholinobutyrylpyrrolidine
  • dextromoramida
  • Dextromoramide
  • dextromoramidum
  • palphium
  • Pyrrolamidol
External IDs
  • ACSCN-9613
  • IDS-ND-003
  • MCP-875
  • R-875
  • SKF-5137

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Dextromoramide is combined with 1,2-Benzodiazepine.
AcetazolamideThe risk or severity of CNS depression can be increased when Acetazolamide is combined with Dextromoramide.
AcetophenazineThe risk or severity of hypotension and CNS depression can be increased when Acetophenazine is combined with Dextromoramide.
AclidiniumThe risk or severity of adverse effects can be increased when Aclidinium is combined with Dextromoramide.
AgomelatineThe risk or severity of CNS depression can be increased when Dextromoramide is combined with Agomelatine.
Food Interactions
Not Available

Products

Drug product information from 10+ global regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
International/Other Brands
palfium

Categories

ATC Codes
N02AC01 — Dextromoramide
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Diphenylmethanes
Direct Parent
Diphenylmethanes
Alternative Parents
Phenylacetamides / Phenylpropanes / N-acylpyrrolidines / Aralkylamines / Morpholines / Tertiary carboxylic acid amides / Trialkylamines / Amino acids and derivatives / Oxacyclic compounds / Dialkyl ethers
show 5 more
Substituents
Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Dialkyl ether / Diphenylmethane
show 19 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
N-acylpyrrolidine, morpholines (CHEBI:74274)
Affected organisms
Not Available

Chemical Identifiers

UNII
9S4S6CIY83
CAS number
357-56-2
InChI Key
INUNXTSAACVKJS-OAQYLSRUSA-N
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
IUPAC Name
(3S)-3-methyl-4-(morpholin-4-yl)-2,2-diphenyl-1-(pyrrolidin-1-yl)butan-1-one
SMILES
C[C@H](CN1CCOCC1)C(C(=O)N1CCCC1)(C1=CC=CC=C1)C1=CC=CC=C1

References

General References
Not Available
KEGG Drug
D07287
PubChem Compound
92943
PubChem Substance
46507896
ChemSpider
83901
RxNav
3290
ChEBI
74274
ChEMBL
CHEMBL2365707
ZINC
ZINC000029402224
Wikipedia
Dextromoramide

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)182 °CPhysProp
logP3.61SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.0175 mg/mLALOGPS
logP4.17ALOGPS
logP3.75Chemaxon
logS-4.4ALOGPS
pKa (Strongest Basic)7.77Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area32.78 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity117.37 m3·mol-1Chemaxon
Polarizability44.36 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9941
Blood Brain Barrier+0.986
Caco-2 permeable+0.5628
P-glycoprotein substrateSubstrate0.6229
P-glycoprotein inhibitor IInhibitor0.6781
P-glycoprotein inhibitor IINon-inhibitor0.573
Renal organic cation transporterInhibitor0.525
CYP450 2C9 substrateNon-substrate0.8056
CYP450 2D6 substrateNon-substrate0.7581
CYP450 3A4 substrateSubstrate0.6149
CYP450 1A2 substrateNon-inhibitor0.9177
CYP450 2C9 inhibitorNon-inhibitor0.9297
CYP450 2D6 inhibitorInhibitor0.5
CYP450 2C19 inhibitorNon-inhibitor0.6691
CYP450 3A4 inhibitorNon-inhibitor0.6655
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7777
Ames testNon AMES toxic0.801
CarcinogenicityNon-carcinogens0.919
BiodegradationNot ready biodegradable0.9549
Rat acute toxicity3.7072 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8914
hERG inhibition (predictor II)Non-inhibitor0.6829
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0159000000-32af6dc12a5d6e0065fd
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0005-9103000000-390368a46a27ddf2c624
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0596-9346000000-1640fd48a548d611eb13
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0005-9000000000-c6c74910677024144675
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fr2-2911000000-fffc1340e10621afff4d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01ox-6947000000-f95257e3485afaf83b8c
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-191.9246
predicted
DeepCCS 1.0 (2019)
[M+H]+194.28262
predicted
DeepCCS 1.0 (2019)
[M+Na]+200.8191
predicted
DeepCCS 1.0 (2019)

Drug created at July 31, 2007 13:10 / Updated at February 21, 2021 18:51