NAV

Desmethylprodine

Identification

Generic Name
Desmethylprodine
DrugBank Accession Number
DB01478
Background

Desmethylprodine, a derivative of meperidine, is an opioid analgesic with the potency of morphine. It has been listed as a Schedule I controlled drug in the United States, and thus is not used clinically. It is known to be a designer drug, synthesized in 1977, for the purpose of recreational use. Illicit manufacturing has occurred.

Type
Small Molecule
Groups
Experimental, Illicit
Structure
3D
Similar Structures
Weight
Average: 247.3327
Monoisotopic: 247.157228921
Chemical Formula
C15H21NO2
Synonyms
  • 1-Methyl-4-phenyl-4-piperidinol propionate
  • 1-Methyl-4-phenyl-4-propionoxypiperidine
  • 3-Demethylprodine
  • MPPP
External IDs
  • IDS-NM-018
  • IDS-NM-018(SECT.3)
  • IK 13
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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
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Toxicity

A toxic impurity which may be encountered in desmethylprodine synthesis, MPTP, is implicated in the destruction of brain tissue in the substantia nigra, and has lead to permanent Parkinsonian symptoms. [1]

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.
Not Available
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Desmethylprodine hydrochlorideNot AvailableNot AvailableWQANBUZBKNCRKH-UHFFFAOYSA-N

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylpiperidines. These are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Piperidines
Sub Class
Phenylpiperidines
Direct Parent
Phenylpiperidines
Alternative Parents
Benzyloxycarbonyls / Aralkylamines / Trialkylamines / Carboxylic acid esters / Amino acids and derivatives / Monocarboxylic acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Benzyloxycarbonyl / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester
show 12 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
07SGC963IR
CAS number
13147-09-6
InChI Key
BCQMRZRAWHNSBF-UHFFFAOYSA-N
InChI
InChI=1S/C15H21NO2/c1-3-14(17)18-15(9-11-16(2)12-10-15)13-7-5-4-6-8-13/h4-8H,3,9-12H2,1-2H3
IUPAC Name
1-methyl-4-phenylpiperidin-4-yl propanoate
SMILES
CCC(=O)OC1(CCN(C)CC1)C1=CC=CC=C1

References

General References
  1. Schmidt N, Ferger B: Neurochemical findings in the MPTP model of Parkinson's disease. J Neural Transm (Vienna). 2001;108(11):1263-82. [Article]
PubChem Compound
61583
PubChem Substance
46504635
ChemSpider
55493
ChEMBL
CHEMBL279865
ZINC
ZINC000001850715
Wikipedia
Desmethylprodine

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
Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.22 mg/mLALOGPS
logP2.91ALOGPS
logP2.3Chemaxon
logS-2.3ALOGPS
pKa (Strongest Basic)8.58Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area29.54 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity71.99 m3·mol-1Chemaxon
Polarizability28.04 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9955
Blood Brain Barrier+0.9852
Caco-2 permeable+0.7325
P-glycoprotein substrateSubstrate0.7813
P-glycoprotein inhibitor IInhibitor0.7959
P-glycoprotein inhibitor IINon-inhibitor0.7171
Renal organic cation transporterInhibitor0.6725
CYP450 2C9 substrateNon-substrate0.8427
CYP450 2D6 substrateSubstrate0.5253
CYP450 3A4 substrateSubstrate0.6336
CYP450 1A2 substrateNon-inhibitor0.8044
CYP450 2C9 inhibitorNon-inhibitor0.8235
CYP450 2D6 inhibitorInhibitor0.5236
CYP450 2C19 inhibitorNon-inhibitor0.9348
CYP450 3A4 inhibitorNon-inhibitor0.7762
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.834
Ames testNon AMES toxic0.9024
CarcinogenicityNon-carcinogens0.8458
BiodegradationNot ready biodegradable0.9631
Rat acute toxicity2.8288 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6864
hERG inhibition (predictor II)Inhibitor0.6207
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 GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-00di-3900000000-8952c44c7fe482061edd
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-006t-1890000000-5d8d423091e536250883
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-9000000000-3515accf88ed0f5c0b8e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-2900000000-bb751081a81d9125b007
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-9420000000-ab0c8a0df24a47c6d51b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00dl-3900000000-36908fa42c2f220f6a9d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01vo-8900000000-7511194512b24bbb2a77
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]-155.84435
predicted
DeepCCS 1.0 (2019)
[M+H]+158.20235
predicted
DeepCCS 1.0 (2019)
[M+Na]+164.2955
predicted
DeepCCS 1.0 (2019)

Drug created at July 31, 2007 13:09 / Updated at June 12, 2020 16:51