Identification

Generic Name
Alphameprodine
DrugBank Accession Number
DB01499
Background

Alphameprodine is an opioid analgesic classified by the United States Drug Enforcement Administration under Schedule I of illegal substances. The stereoisomer betameprodine is similarly classified, however alphameprodine is more widely used (both are referred to as Meprodine). Alphameprodine is a structural analogue of meperidine. It exerts physiological effects characteristic of opioids, such as analgesia, euphoria and sedation, as well as itching, nausea, and respiratory depression.

Type
Small Molecule
Groups
Experimental, Illicit
Structure
Thumb
Weight
Average: 275.3859
Monoisotopic: 275.188529049
Chemical Formula
C17H25NO2
Synonyms
  • 3alpha-Ethyl-1-methyl-4-phenyl-4alpha-piperidyl propionat
  • Alfameprodina
  • alpha-3-ethyl-1-methyl-4-phenyl-4-propionoxypiperidine
  • alpha-3-Ethyl-1-methyl-4-phenyl-4-propionyloxypiperidine
  • Alphameprodine
  • Alphameprodinum
External IDs
  • ACSCN-9608
  • DEA No. 9604
  • IDS-NA-009

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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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
Adverseeffects
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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.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
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
1177I648L1
CAS number
468-51-9
InChI Key
ODEGQXRCQDVXSJ-WMLDXEAASA-N
InChI
InChI=1S/C17H25NO2/c1-4-14-13-18(3)12-11-17(14,20-16(19)5-2)15-9-7-6-8-10-15/h6-10,14H,4-5,11-13H2,1-3H3/t14-,17+/m0/s1
IUPAC Name
(3S,4R)-3-ethyl-1-methyl-4-phenylpiperidin-4-yl propanoate
SMILES
CC[C@H]1CN(C)CC[C@]1(OC(=O)CC)C1=CC=CC=C1

References

General References
Not Available
PubChem Compound
61119
PubChem Substance
46507922
ChemSpider
55067
ChEMBL
CHEMBL2104027
Wikipedia
Meprodine

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 Solubility0.211 mg/mLALOGPS
logP3.46ALOGPS
logP3.22ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)9.1ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.54 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity81.01 m3·mol-1ChemAxon
Polarizability31.7 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9942
Blood Brain Barrier+0.9778
Caco-2 permeable+0.7392
P-glycoprotein substrateSubstrate0.768
P-glycoprotein inhibitor IInhibitor0.9203
P-glycoprotein inhibitor IIInhibitor0.6555
Renal organic cation transporterInhibitor0.6195
CYP450 2C9 substrateNon-substrate0.8428
CYP450 2D6 substrateNon-substrate0.6067
CYP450 3A4 substrateSubstrate0.7028
CYP450 1A2 substrateNon-inhibitor0.8298
CYP450 2C9 inhibitorNon-inhibitor0.897
CYP450 2D6 inhibitorInhibitor0.6364
CYP450 2C19 inhibitorNon-inhibitor0.9007
CYP450 3A4 inhibitorInhibitor0.5
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8595
Ames testNon AMES toxic0.8872
CarcinogenicityNon-carcinogens0.8008
BiodegradationNot ready biodegradable0.9764
Rat acute toxicity2.8945 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6126
hERG inhibition (predictor II)Inhibitor0.6841
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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Drug created at July 31, 2007 13:09 / Updated at February 21, 2021 18:51