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Betameprodine

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Overview

Structure
DrugBank ID
DB01552
Type
Small Molecule
US Approved
NO
Other Approved
NO
Patents
0
Indicated Conditions
0
Clinical Trials
Phase 0
0
Phase 1
0
Phase 2
0
Phase 3
0
Phase 4
0

Identification

Generic Name
Betameprodine
DrugBank Accession Number
DB01552
Background

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.

Type
Small Molecule
Groups
Experimental, Illicit
Structure
3D
Similar Structures
Weight
Average: 275.392
Monoisotopic: 275.188529049
Chemical Formula
C17H25NO2
Synonyms
  • beta-1-Methyl-3-ethyl-4-phenyl-4-propionoxy-piperidin
  • beta-3-Ethyl-1-methyl-4-phenyl-4-propionoxypiperidine
  • beta-meprodine
  • Betameprodina
  • Betameprodine
  • Betameprodinum
External IDs
  • 207-407-4
  • DEA No. 9608
  • IDS-NB-004
  • NU 1732
  • NU 1932
  • NU-1732
  • NU-1932
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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

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available
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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 / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Benzyloxycarbonyl / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
4XS533X38C
CAS number
468-50-8
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

References

General References
Not Available
PubChem Compound
12218309
PubChem Substance
46505637
ChemSpider
28293685
ChEMBL
CHEMBL2104168
ZINC
ZINC000004215000
Wikipedia
Betameprodine

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
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-MSsplash10-0udi-3090000000-4bf9e580e79f1322ac05
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fi0-0090000000-3ce91d701c7e1820dac9
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-5090000000-aba5c2248a28302e1a13
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fk9-0390000000-22fd8c165153e049fe11
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-3290000000-57f274e0b0e91c5f8979
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00g0-6960000000-2d118a93435080f8de2a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-000f-0900000000-6b8978266c118091f97a
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]-163.20335
predicted
DeepCCS 1.0 (2019)
[M+H]+165.56136
predicted
DeepCCS 1.0 (2019)
[M+Na]+171.8147
predicted
DeepCCS 1.0 (2019)

Drug created at July 31, 2007 13:10 / Updated at February 21, 2021 18:51