NAV

Benzylfentanyl

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Benzylfentanyl
DrugBank Accession Number
DB09182
Background

Benzylfentanyl (R-4129) is a fentanyl analog opioid that was on the list of Schedule I drugs in America in 1985 due to its structural similarity to fentanyl. In 2010 it was removed from the list after it was found to have minimal opioid activity. Benzylfentanyl has a Ki of 213nM at the mu opioid receptor, binding around 200x less strongly than fentanyl itself.

Type
Small Molecule
Groups
Illicit
Structure
3D
Similar Structures
Weight
Average: 322.452
Monoisotopic: 322.204513465
Chemical Formula
C21H26N2O
Synonyms
Not Available
External IDs
  • NSC-73402
  • R-4129
Poor quality drug data slowing you down?
Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.
Download eBook
Poor quality drug data slowing you down?
Download eBook

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
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
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
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
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as n-benzylpiperidines. These are heterocyclic Compounds containing a piperidine ring conjugated to a benzyl group through one nitrogen ring atom.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Piperidines
Sub Class
Benzylpiperidines
Direct Parent
N-benzylpiperidines
Alternative Parents
Anilides / Phenylmethylamines / Benzylamines / Aralkylamines / Tertiary carboxylic acid amides / Trialkylamines / Amino acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organic oxides
show 2 more
Substituents
Amine / Amino acid or derivatives / Anilide / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Benzylamine / Carbonyl group / Carboxamide group
show 14 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
9BV2D1A57H
CAS number
1474-02-8
InChI Key
POQDXIFVWVZVML-UHFFFAOYSA-N
InChI
InChI=1S/C21H26N2O/c1-2-21(24)23(19-11-7-4-8-12-19)20-13-15-22(16-14-20)17-18-9-5-3-6-10-18/h3-12,20H,2,13-17H2,1H3
IUPAC Name
N-(1-benzylpiperidin-4-yl)-N-phenylpropanamide
SMILES
CCC(=O)N(C1CCN(CC2=CC=CC=C2)CC1)C1=CC=CC=C1

References

General References
Not Available
PubChem Compound
252141
PubChem Substance
310265090
ChemSpider
220920
ChEMBL
CHEMBL172155
ZINC
ZINC000004808161
Wikipedia
Benzylfentanyl

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 Solubility0.0534 mg/mLALOGPS
logP3.64ALOGPS
logP3.53Chemaxon
logS-3.8ALOGPS
pKa (Strongest Basic)8.18Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area23.55 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity98.73 m3·mol-1Chemaxon
Polarizability36.4 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0093000000-ac1e543813cabb3df15b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0009000000-003a41dd8f383055dc65
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0aor-9262000000-7c9df6a228de28db7614
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01b9-3297000000-71ea4d7598aa888e700c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-2901000000-e3517429eee44a303880
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-006x-5941000000-6d4fe113cb3e3df348b0
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]-197.3738633
predicted
DarkChem Lite v0.1.0
[M-H]-173.11003
predicted
DeepCCS 1.0 (2019)
[M+H]+197.6624633
predicted
DarkChem Lite v0.1.0
[M+H]+175.46803
predicted
DeepCCS 1.0 (2019)
[M+Na]+197.4011633
predicted
DarkChem Lite v0.1.0
[M+Na]+181.95401
predicted
DeepCCS 1.0 (2019)

Drug created at October 14, 2015 21:24 / Updated at June 12, 2020 16:52