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alpha-methylthiofentanyl

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Identification

Generic Name
alpha-methylthiofentanyl
DrugBank Accession Number
DB01470
Background

alpha-methylthiofentanyl is an opioid analgesic that is an analog of fentanyl.

Type
Small Molecule
Groups
Illicit
Structure
3D
Similar Structures
Weight
Average: 356.525
Monoisotopic: 356.192234218
Chemical Formula
C21H28N2OS
Synonyms
  • alpha-methylthiofentanyl
  • α-methylthiofentanyl
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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 anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Anilides
Direct Parent
Anilides
Alternative Parents
Aralkylamines / Piperidines / Thiophenes / Tertiary carboxylic acid amides / Heteroaromatic compounds / 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 / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Heteroaromatic compound
show 13 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
NF684LIF79
CAS number
103963-66-2
InChI Key
YPOXDUYRRSUFFG-UHFFFAOYSA-N
InChI
InChI=1S/C21H28N2OS/c1-3-21(24)23(18-8-5-4-6-9-18)19-11-13-22(14-12-19)17(2)16-20-10-7-15-25-20/h4-10,15,17,19H,3,11-14,16H2,1-2H3
IUPAC Name
N-phenyl-N-{1-[1-(thiophen-2-yl)propan-2-yl]piperidin-4-yl}propanamide
SMILES
CCC(=O)N(C1CCN(CC1)C(C)CC1=CC=CS1)C1=CC=CC=C1

References

General References
Not Available
PubChem Compound
62309
PubChem Substance
46508575
ChemSpider
56104
ChEMBL
CHEMBL2365807
Wikipedia
Alphamethylthiofentanyl

Clinical Trials

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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 Solubility0.0186 mg/mLALOGPS
logP4.48ALOGPS
logP4.14Chemaxon
logS-4.3ALOGPS
pKa (Strongest Basic)8.98Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area23.55 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity104.9 m3·mol-1Chemaxon
Polarizability41.34 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9877
Blood Brain Barrier+0.9898
Caco-2 permeable+0.624
P-glycoprotein substrateSubstrate0.6665
P-glycoprotein inhibitor IInhibitor0.665
P-glycoprotein inhibitor IINon-inhibitor0.6481
Renal organic cation transporterInhibitor0.5291
CYP450 2C9 substrateNon-substrate0.7737
CYP450 2D6 substrateNon-substrate0.7648
CYP450 3A4 substrateSubstrate0.632
CYP450 1A2 substrateNon-inhibitor0.7647
CYP450 2C9 inhibitorNon-inhibitor0.756
CYP450 2D6 inhibitorNon-inhibitor0.7472
CYP450 2C19 inhibitorInhibitor0.6574
CYP450 3A4 inhibitorNon-inhibitor0.7862
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5135
Ames testNon AMES toxic0.8402
CarcinogenicityNon-carcinogens0.8713
BiodegradationNot ready biodegradable0.9289
Rat acute toxicity2.9487 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9488
hERG inhibition (predictor II)Inhibitor0.6533
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/MSsplash10-0zfr-0009000000-22fb013ed4772691d21f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0009000000-fccc67a57fffe78c0f38
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4j-9074000000-eb795dec8202eb7dfd91
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0pb9-0029000000-33265a7f00e37c452af3
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00dl-4692000000-8f8dee50a06771b6e616
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fba-6794000000-33e455c5c016e1e2adb8
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]-179.90315
predicted
DeepCCS 1.0 (2019)
[M+H]+182.26117
predicted
DeepCCS 1.0 (2019)
[M+Na]+189.72664
predicted
DeepCCS 1.0 (2019)

Drug created at July 31, 2007 13:09 / Updated at June 24, 2020 01:34