Ohmefentanyl

Identification

Name
Ohmefentanyl
Accession Number
DB01570
Type
Small Molecule
Groups
Illicit
Description

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 mouse studies, the most active isomer 3R,4S,βS-ohmefentanyl was 28 times more powerful as a painkiller than fentanyl, the chemical from which it is derived, and 6300 times more effective than morphine. Ohmefentanyl has three stereogenic centers and so has eight stereoisomers, which are named F9201–F9208. Researchers are studying the different pharmaceutical properties of these isomers.

Structure
Thumb
Synonyms
  • Beta-hydroxy-3-methylfentanyl
  • OMF
  • β-hydroxy-3-methylfentanyl
External IDs
RTI-4614-4
Categories
UNII
Y8263089ZX
CAS number
78995-14-9
Weight
Average: 366.4965
Monoisotopic: 366.230728214
Chemical Formula
C23H30N2O2
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

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
62279
PubChem Substance
46507925
ChemSpider
56080
BindingDB
50033531
ChEMBL
CHEMBL333410
Wikipedia
Ohmefentanyl

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
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0865 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
Polarizability41.14 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/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 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
Fentanyl / Anilide / Aralkylamine / Monocyclic benzene moiety / Benzenoid / Tertiary carboxylic acid amide / 1,2-aminoalcohol / Amino acid or derivatives / Carboxamide group / Secondary alcohol
show 16 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Drug created on July 31, 2007 07:10 / Updated on October 01, 2018 13:06