NAV

Ohmefentanyl

Identification

Generic Name
Ohmefentanyl
DrugBank Accession Number
DB01570
Background

Ohmefentanyl is an extremely potent opioid analgesic drug which selectively binds to the µ-opioid receptor. The Chinese have recorded ohmefentanyl as having a potency that is 6,300 times morphine. Ohmefentanyl is one of the most potent μ -receptor agonists known, comparable to super-potent opioids such as carfentanil and etorphine which are used for tranquilizing large animals such as elephants in veterinary medicine. In mice, ohmefentanyl was 28 times more powerful than fentanyl and 6300 times more effective than morphine. Ohmefentanyl has three stereogenic centers and hence, it can derive into eight stereoisomers, currently named F9201–F9208. Researchers are studying the different pharmaceutical properties of these isomers.

Type
Small Molecule
Groups
Illicit
Structure
3D
Similar Structures
Weight
Average: 366.4965
Monoisotopic: 366.230728214
Chemical Formula
C23H30N2O2
Synonyms
  • Beta-hydroxy-3-methylfentanyl
  • OMF
  • β-hydroxy-3-methylfentanyl
External IDs
  • RTI-4614-4
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 fentanyls. These are compounds containing the fentanyl moiety or a derivative, which is based on a N-(1-(2-phenylethyl)-4-piperidinyl)-N-phenylpropanamide skeleton.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Piperidines
Sub Class
Fentanyls
Direct Parent
Fentanyls
Alternative Parents
Anilides / Aralkylamines / Tertiary carboxylic acid amides / Trialkylamines / Secondary alcohols / Amino acids and derivatives / 1,2-aminoalcohols / Azacyclic compounds / Organopnictogen compounds / Organic oxides
show 3 more
Substituents
1,2-aminoalcohol / Alcohol / Amine / Amino acid or derivatives / Anilide / Aralkylamine / Aromatic alcohol / Aromatic heteromonocyclic compound / Azacycle / Benzenoid
show 16 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Y8263089ZX
CAS number
78995-14-9
InChI Key
FRPRNNRJTCONEC-UHFFFAOYSA-N
InChI
InChI=1S/C23H30N2O2/c1-3-23(27)25(20-12-8-5-9-13-20)21-14-15-24(16-18(21)2)17-22(26)19-10-6-4-7-11-19/h4-13,18,21-22,26H,3,14-17H2,1-2H3
IUPAC Name
N-[1-(2-hydroxy-2-phenylethyl)-3-methylpiperidin-4-yl]-N-phenylpropanamide
SMILES
CCC(=O)N(C1CCN(CC(O)C2=CC=CC=C2)CC1C)C1=CC=CC=C1

References

General References
Not Available
PubChem Compound
62279
PubChem Substance
46507925
ChemSpider
56080
BindingDB
50033531
ChEMBL
CHEMBL333410
Wikipedia
Ohmefentanyl

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 Solubility0.0871 mg/mLALOGPS
logP3.12ALOGPS
logP3.38Chemaxon
logS-3.6ALOGPS
pKa (Strongest Acidic)14.11Chemaxon
pKa (Strongest Basic)8.59Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area43.78 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity109.11 m3·mol-1Chemaxon
Polarizability42.37 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9859
Blood Brain Barrier+0.8166
Caco-2 permeable+0.6217
P-glycoprotein substrateSubstrate0.7502
P-glycoprotein inhibitor IInhibitor0.8878
P-glycoprotein inhibitor IIInhibitor0.667
Renal organic cation transporterNon-inhibitor0.6416
CYP450 2C9 substrateNon-substrate0.7609
CYP450 2D6 substrateNon-substrate0.6912
CYP450 3A4 substrateSubstrate0.6818
CYP450 1A2 substrateNon-inhibitor0.858
CYP450 2C9 inhibitorNon-inhibitor0.8491
CYP450 2D6 inhibitorNon-inhibitor0.589
CYP450 2C19 inhibitorNon-inhibitor0.8011
CYP450 3A4 inhibitorNon-inhibitor0.6046
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7374
Ames testNon AMES toxic0.8161
CarcinogenicityNon-carcinogens0.8433
BiodegradationNot ready biodegradable0.7959
Rat acute toxicity2.7242 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8868
hERG inhibition (predictor II)Inhibitor0.5691
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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014l-0049000000-54d6e48a9d9de5f26d21
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0019000000-d5238689ebf980679455
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0093000000-1ee331e32dafd749f8b0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-6193000000-436684a14d47063f1c0a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-1291000000-de86b27b832543d1d787
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-2493000000-ecff37185a077c7f33a1
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]-183.5296
predicted
DeepCCS 1.0 (2019)
[M+H]+185.88759
predicted
DeepCCS 1.0 (2019)
[M+Na]+193.02559
predicted
DeepCCS 1.0 (2019)

Drug created at July 31, 2007 13:10 / Updated at June 12, 2020 16:51