α-Methylacetylfentanyl

Identification

Name
α-Methylacetylfentanyl
Accession Number
DB01532
Type
Small Molecule
Groups
Illicit
Description

α-Methylacetylfentanyl (or alphamethylacetylfentanyl) is an opioid analgesic that is an analog of fentanyl. It is a Schedule I controlled substance in the United States, with a DEA ACSCN of 9815. It was sold briefly on the black market in the early 1980s, before the introduction of the Federal Analog Act which for the first time attempted to control entire families of drugs based on their structural similarity rather than scheduling each drug individually as they appeared. α-Methylacetylfentanyl is made with the same synthetic route as α-methylfentanyl, but by substituting the relatively common acetic anhydride for the more difficult to obtain chemical propionic anhydride in the synthesis.

Structure
Thumb
Synonyms
  • Acetyl-alpha-methylfentanyl
  • alphamethylacetylfentanyl
Categories
Not Available
UNII
0O1GKW2BQO
CAS number
101860-00-8
Weight
Average: 336.4705
Monoisotopic: 336.220163528
Chemical Formula
C22H28N2O
InChI Key
OKTLVZBUKMRPLL-UHFFFAOYSA-N
InChI
InChI=1S/C22H28N2O/c1-18(17-20-9-5-3-6-10-20)23-15-13-22(14-16-23)24(19(2)25)21-11-7-4-8-12-21/h3-12,18,22H,13-17H2,1-2H3
IUPAC Name
N-phenyl-N-[1-(1-phenylpropan-2-yl)piperidin-4-yl]acetamide
SMILES
CC(CC1=CC=CC=C1)N1CCC(CC1)N(C(C)=O)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
62307
PubChem Substance
46507041
ChemSpider
56102
Wikipedia
%CE%91-Methylacetylfentanyl

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 Solubility0.022 mg/mLALOGPS
logP4.09ALOGPS
logP3.53ChemAxon
logS-4.2ALOGPS
pKa (Strongest Basic)9.01ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.55 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity103.27 m3·mol-1ChemAxon
Polarizability39.94 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.955
Blood Brain Barrier+0.9908
Caco-2 permeable+0.6875
P-glycoprotein substrateSubstrate0.6579
P-glycoprotein inhibitor IInhibitor0.6235
P-glycoprotein inhibitor IINon-inhibitor0.6464
Renal organic cation transporterInhibitor0.6297
CYP450 2C9 substrateNon-substrate0.7868
CYP450 2D6 substrateNon-substrate0.5211
CYP450 3A4 substrateSubstrate0.6368
CYP450 1A2 substrateNon-inhibitor0.8659
CYP450 2C9 inhibitorNon-inhibitor0.9177
CYP450 2D6 inhibitorInhibitor0.5098
CYP450 2C19 inhibitorNon-inhibitor0.7252
CYP450 3A4 inhibitorNon-inhibitor0.861
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7654
Ames testNon AMES toxic0.8844
CarcinogenicityNon-carcinogens0.8876
BiodegradationNot ready biodegradable0.8682
Rat acute toxicity2.7430 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8834
hERG inhibition (predictor II)Inhibitor0.6335
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 amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenethylamines
Direct Parent
Amphetamines and derivatives
Alternative Parents
Acetanilides / Phenylpropanes / Aralkylamines / Piperidines / Tertiary carboxylic acid amides / Acetamides / Trialkylamines / Amino acids and derivatives / Azacyclic compounds / Organopnictogen compounds
show 3 more
Substituents
Amphetamine or derivatives / Acetanilide / Phenylpropane / Anilide / Aralkylamine / Piperidine / Tertiary carboxylic acid amide / Acetamide / Amino acid or derivatives / Carboxamide group
show 15 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

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