Explore a selection of our essential drug information below, or:
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
Structure for Desmethylprodine (DB01478)
- 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
Pharmacology
- Indication
Not Available
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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 outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Desmethylprodine hydrochloride Not Available Not Available WQANBUZBKNCRKH-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
- Schmidt N, Ferger B: Neurochemical findings in the MPTP model of Parkinson's disease. J Neural Transm (Vienna). 2001;108(11):1263-82. [Article]
- External Links
- PubChem Compound
- 61583
- PubChem Substance
- 46504635
- ChemSpider
- 55493
- ChEMBL
- CHEMBL279865
- ZINC
- ZINC000001850715
- Wikipedia
- Desmethylprodine
Clinical Trials
- Clinical Trials
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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
Property Value Source Water Solubility 1.22 mg/mL ALOGPS logP 2.91 ALOGPS logP 2.3 Chemaxon logS -2.3 ALOGPS pKa (Strongest Basic) 8.58 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 29.54 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 71.99 m3·mol-1 Chemaxon Polarizability 28.04 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - 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 inhibitor Non-inhibitor 0.8235 CYP450 2D6 inhibitor Inhibitor 0.5236 CYP450 2C19 inhibitor Non-inhibitor 0.9348 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-00di-3900000000-8952c44c7fe482061edd Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-006t-1890000000-5d8d423091e536250883 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-00di-9000000000-3515accf88ed0f5c0b8e Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-2900000000-bb751081a81d9125b007 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-00di-9420000000-ab0c8a0df24a47c6d51b Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00dl-3900000000-36908fa42c2f220f6a9d Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-01vo-8900000000-7511194512b24bbb2a77 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 155.84435 predictedDeepCCS 1.0 (2019) [M+H]+ 158.20235 predictedDeepCCS 1.0 (2019) [M+Na]+ 164.2955 predictedDeepCCS 1.0 (2019)
Drug created at July 31, 2007 13:09 / Updated at June 12, 2020 16:51