α-Methylacetylfentanyl

Identification

Generic Name
α-Methylacetylfentanyl
DrugBank Accession Number
DB01532
Background

α-Methylacetylfentanyl is an analog of fentanyl with opioid analgesic properties. It was categorized under the Schedule I in the US and it was illegally sold in early 1980. α-Methylacetylfentanyl synthesis process is very similar to α-methylfentanyl with the substitution of the acetic anhydride for the production of chemical propionic anhydride in the synthesis.

Type
Small Molecule
Groups
Illicit
Structure
Weight
Average: 336.4705
Monoisotopic: 336.220163528
Chemical Formula
C22H28N2O
Synonyms
  • Acetyl-alpha-methylfentanyl
  • alphamethylacetylfentanyl

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

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 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
Acetamide / Acetanilide / Amine / Amino acid or derivatives / Amphetamine or derivatives / Anilide / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Carbonyl group
show 15 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
0O1GKW2BQO
CAS number
101860-00-8
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

References

General References
Not Available
PubChem Compound
62307
PubChem Substance
46507041
ChemSpider
56102
Wikipedia
%CE%91-Methylacetylfentanyl

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 Solubility0.022 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
Polarizability39.97 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-MSsplash10-0f6x-4690000000-b77f5fce6d8e116924e0
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000j-0049000000-0545b0db6ad8ad539af6
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0169000000-40c1754996c1bb5fd606
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0009000000-1fadf297b0ef769dc1b4
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fg6-5893000000-31274627195f2528ab94
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-7293000000-a01bab4cbbebaf520d92
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00xr-0940000000-7e76b44c43500d0e625a
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]-178.25368
predicted
DeepCCS 1.0 (2019)
[M+H]+180.61165
predicted
DeepCCS 1.0 (2019)
[M+Na]+188.23627
predicted
DeepCCS 1.0 (2019)

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