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Identification
Namedesmethylprodine
Accession NumberDB01478
TypeSmall Molecule
GroupsExperimental, Illicit
Description

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.

Structure
Thumb
Synonyms
SynonymLanguageCode
1-Methyl-4-phenyl-4-piperidinol propionateNot AvailableNot Available
1-Methyl-4-phenyl-4-propionoxypiperidineNot AvailableNot Available
3-DemethylprodineNot AvailableNot Available
MPPPNot AvailableNot Available
PPMPNot AvailableNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number13147-09-6
WeightAverage: 247.3327
Monoisotopic: 247.157228921
Chemical FormulaC15H21NO2
InChI KeyBCQMRZRAWHNSBF-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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassPiperidines
SubclassPhenylpiperidines
Direct parentPhenylpiperidines
Alternative parentsBenzyloxycarbonyls; Benzylethers; Tertiary Amines; Carboxylic Acid Esters; Enolates; Polyamines; Dialkyl Ethers
Substituentsbenzyloxycarbonyl; benzylether; benzene; tertiary amine; carboxylic acid ester; polyamine; enolate; ether; carboxylic acid derivative; dialkyl ether; amine; organonitrogen compound
Classification descriptionThis compound belongs to the phenylpiperidines. These are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityA 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]
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9955
Blood Brain Barrier + 0.9852
Caco-2 permeable + 0.7325
P-glycoprotein substrate Substrate 0.7813
P-glycoprotein inhibitor I Inhibitor 0.7959
P-glycoprotein inhibitor II Non-inhibitor 0.7171
Renal organic cation transporter Inhibitor 0.6725
CYP450 2C9 substrate Non-substrate 0.8427
CYP450 2D6 substrate Substrate 0.5253
CYP450 3A4 substrate Substrate 0.6336
CYP450 1A2 substrate Non-inhibitor 0.8044
CYP450 2C9 substrate Non-inhibitor 0.8235
CYP450 2D6 substrate Inhibitor 0.5236
CYP450 2C19 substrate Non-inhibitor 0.9348
CYP450 3A4 substrate Non-inhibitor 0.7762
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.834
Ames test Non AMES toxic 0.9024
Carcinogenicity Non-carcinogens 0.8458
Biodegradation Not ready biodegradable 0.9631
Rat acute toxicity 2.8288 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.6864
hERG inhibition (predictor II) Inhibitor 0.6207
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.22ALOGPS
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
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General Reference

1. Schmidt, N., and B. Ferger. “Neurochemical findings in the MPTP model of Parkinson’s disease.” Journal of neural transmission 108.11 (2001): 1263-1282.

External Links
ResourceLink
PubChem Compound61583
PubChem Substance46504635
ChemSpider55493
WikipediaDesmethylprodine
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
Comments
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Drug created on July 31, 2007 07:09 / Updated on January 02, 2014 13:49