Betameprodine

Identification

Name
Betameprodine
Accession Number
DB01552
Type
Small Molecule
Groups
Experimental, Illicit
Description

Betameprodine is an opioid analgesic classified by the United States Drug Enforcement Administration under Schedule I of illegal substances. The stereoisomer alphameprodine is similarly classified, and was more widely used (both are referred to as Meprodine). Betameprodine 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.

Structure
Thumb
Synonyms
  • beta-1-Methyl-3-ethyl-4-phenyl-4-propionoxy-piperidin
  • beta-3-Ethyl-1-methyl-4-phenyl-4-propionoxypiperidine
  • beta-meprodine
  • Betameprodina
  • Betameprodinum
External IDs
207-407-4 / DEA No. 9608 / IDS-NB-004 / NU 1732 / NU 1932 / NU-1732 / NU-1932
Categories
Not Available
UNII
4XS533X38C
CAS number
468-50-8
Weight
Average: 275.392
Monoisotopic: 275.188529049
Chemical Formula
C17H25NO2
InChI Key
ODEGQXRCQDVXSJ-RHSMWYFYSA-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-/m1/s1
IUPAC Name
(3R,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

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
12218309
PubChem Substance
46505637
ChemSpider
28293685
ChEMBL
CHEMBL2104168
Wikipedia
Betameprodine

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
boiling point (°C)354.295 °C at 760 mmHg Chemspider, http://www.chemspider.com/Chemical-Structure.55066.html
water solubility1.43 mg/L at 25°CChemIDplus, http://chem.sis.nlm.nih.gov/chemidplus/jsp/common/PhysicalProperties.jsp
logP3.61CRAIG,PN (1990)
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
Polarizability31.63 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

Taxonomy

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 / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Phenylpiperidine / Benzyloxycarbonyl / Aralkylamine / Monocyclic benzene moiety / Benzenoid / Amino acid or derivatives / Tertiary aliphatic amine / Tertiary amine / Carboxylic acid ester / Carboxylic acid derivative
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Drug created on July 31, 2007 07:10 / Updated on November 02, 2018 05:03