3-Methylthiofentanyl

Identification

Name
3-Methylthiofentanyl
Accession Number
DB01439
Type
Small Molecule
Groups
Experimental, Illicit
Description

3-Methyl-thiofentanyl is an opioid analgesic that is an analogue of fentanyl.

Structure
Thumb
Synonyms
  • 3-Methyl-thiofentanyl
Categories
Not Available
UNII
C9C204973M
CAS number
86052-04-2
Weight
Average: 356.525
Monoisotopic: 356.192234218
Chemical Formula
C21H28N2OS
InChI Key
SRARDYUHGVMEQI-UHFFFAOYSA-N
InChI
InChI=1S/C21H28N2OS/c1-3-21(24)23(18-8-5-4-6-9-18)20-12-14-22(16-17(20)2)13-11-19-10-7-15-25-19/h4-10,15,17,20H,3,11-14,16H2,1-2H3
IUPAC Name
N-{3-methyl-1-[2-(thiophen-2-yl)ethyl]piperidin-4-yl}-N-phenylpropanamide
SMILES
CCC(=O)N(C1CCN(CCC2=CC=CS2)CC1C)C1=CC=CC=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action

3-Methylthiofentanyl binds to the mu, delta, and kappa opioid receptors. These ultimately lead to decreased pain sensation as well as a number of side effects, such as euphoria, sedation, depressed breathing.

TargetActionsOrganism
AMu-type opioid receptor
agonist
Human
ADelta-type opioid receptor
agonist
Human
AKappa-type opioid receptor
agonist
Human
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

Side effects of fentanyl analogues are similar to those of fentanyl itself, which include itching, nausea and potentially serious respiratory depression which can be life-threatening.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
3-Methylthiofentanyl Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB61718
PubChem Compound
62296
PubChem Substance
46506995
ChemSpider
56092
ChEBI
53763
ChEMBL
CHEMBL2365680
Wikipedia
3-Methylthiofentanyl

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 Solubility0.018 mg/mLALOGPS
logP4.32ALOGPS
logP4.21ChemAxon
logS-4.3ALOGPS
pKa (Strongest Basic)9.07ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.55 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity104.9 m3·mol-1ChemAxon
Polarizability39.97 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9896
Blood Brain Barrier+0.9826
Caco-2 permeable+0.6364
P-glycoprotein substrateSubstrate0.6543
P-glycoprotein inhibitor IInhibitor0.7429
P-glycoprotein inhibitor IINon-inhibitor0.51
Renal organic cation transporterInhibitor0.5207
CYP450 2C9 substrateNon-substrate0.7735
CYP450 2D6 substrateNon-substrate0.7406
CYP450 3A4 substrateSubstrate0.6614
CYP450 1A2 substrateNon-inhibitor0.7207
CYP450 2C9 inhibitorNon-inhibitor0.6618
CYP450 2D6 inhibitorNon-inhibitor0.7754
CYP450 2C19 inhibitorInhibitor0.6434
CYP450 3A4 inhibitorNon-inhibitor0.6258
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.572
Ames testNon AMES toxic0.8565
CarcinogenicityNon-carcinogens0.8682
BiodegradationNot ready biodegradable0.9549
Rat acute toxicity2.8704 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9351
hERG inhibition (predictor II)Inhibitor0.6674
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 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
Anilide / Aralkylamine / Piperidine / Tertiary carboxylic acid amide / Heteroaromatic compound / Thiophene / Amino acid or derivatives / Carboxamide group / Tertiary amine / Tertiary aliphatic amine
show 13 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
piperidines, monocarboxylic acid amide, thiophenes, anilide (CHEBI:53763)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Voltage-gated calcium channel activity
Specific Function
Receptor for endogenous opioids such as beta-endorphin and endomorphin. Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone...
Gene Name
OPRM1
Uniprot ID
P35372
Uniprot Name
Mu-type opioid receptor
Molecular Weight
44778.855 Da
References
  1. You HJ, Colpaert FC, Arendt-Nielsen L: The novel analgesic and high-efficacy 5-HT1A receptor agonist F 13640 inhibits nociceptive responses, wind-up, and after-discharges in spinal neurons and withdrawal reflexes. Exp Neurol. 2005 Jan;191(1):174-83. [PubMed:15589524]
  2. Scott LJ, Perry CM: Remifentanil: a review of its use during the induction and maintenance of general anaesthesia. Drugs. 2005;65(13):1793-823. [PubMed:16114980]
  3. Scott LJ, Perry CM: Spotlight on remifentanil for general anaesthesia. CNS Drugs. 2005;19(12):1069-74. [PubMed:16332149]
  4. Dosen-Micovic L, Ivanovic M, Micovic V: Steric interactions and the activity of fentanyl analogs at the mu-opioid receptor. Bioorg Med Chem. 2006 May 1;14(9):2887-95. Epub 2006 Jan 11. [PubMed:16376082]
  5. Dardonville C, Fernandez-Fernandez C, Gibbons SL, Ryan GJ, Jagerovic N, Gabilondo AM, Meana JJ, Callado LF: Synthesis and pharmacological studies of new hybrid derivatives of fentanyl active at the mu-opioid receptor and I2-imidazoline binding sites. Bioorg Med Chem. 2006 Oct 1;14(19):6570-80. Epub 2006 Jun 23. [PubMed:16797997]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  7. Hajiha M, DuBord MA, Liu H, Horner RL: Opioid receptor mechanisms at the hypoglossal motor pool and effects on tongue muscle activity in vivo. J Physiol. 2009 Jun 1;587(Pt 11):2677-92. doi: 10.1113/jphysiol.2009.171678. Epub 2009 Apr 29. [PubMed:19403616]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Opioid receptor activity
Specific Function
G-protein coupled receptor that functions as receptor for endogenous enkephalins and for a subset of other opioids. Ligand binding causes a conformation change that triggers signaling via guanine n...
Gene Name
OPRD1
Uniprot ID
P41143
Uniprot Name
Delta-type opioid receptor
Molecular Weight
40368.235 Da
References
  1. Rodrigues AR, Castro MS, Francischi JN, Perez AC, Duarte ID: Participation of ATP-sensitive K+ channels in the peripheral antinociceptive effect of fentanyl in rats. Braz J Med Biol Res. 2005 Jan;38(1):91-7. Epub 2005 Jan 18. [PubMed:15665994]
  2. Poonawala T, Levay-Young BK, Hebbel RP, Gupta K: Opioids heal ischemic wounds in the rat. Wound Repair Regen. 2005 Mar-Apr;13(2):165-74. [PubMed:15828941]
  3. Sahin AS, Duman A, Atalik EK, Ogun CO, Sahin TK, Erol A, Ozergin U: The mechanisms of the direct vascular effects of fentanyl on isolated human saphenous veins in vitro. J Cardiothorac Vasc Anesth. 2005 Apr;19(2):197-200. [PubMed:15868528]
  4. Darwish M, Tempero K, Kirby M, Thompson J: Pharmacokinetics and dose proportionality of fentanyl effervescent buccal tablets in healthy volunteers. Clin Pharmacokinet. 2005;44(12):1279-86. [PubMed:16372825]
  5. Darwish M, Kirby M, Robertson P Jr, Tracewell W, Jiang JG: Pharmacokinetic properties of fentanyl effervescent buccal tablets: a phase I, open-label, crossover study of single-dose 100, 200, 400, and 800 microg in healthy adult volunteers. Clin Ther. 2006 May;28(5):707-14. [PubMed:16861092]
  6. Hajiha M, DuBord MA, Liu H, Horner RL: Opioid receptor mechanisms at the hypoglossal motor pool and effects on tongue muscle activity in vivo. J Physiol. 2009 Jun 1;587(Pt 11):2677-92. doi: 10.1113/jphysiol.2009.171678. Epub 2009 Apr 29. [PubMed:19403616]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Opioid receptor activity
Specific Function
G-protein coupled opioid receptor that functions as receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as receptor for various synt...
Gene Name
OPRK1
Uniprot ID
P41145
Uniprot Name
Kappa-type opioid receptor
Molecular Weight
42644.665 Da
References
  1. Pascoe JE, Williams KL, Mukhopadhyay P, Rice KC, Woods JH, Ko MC: Effects of mu, kappa, and delta opioid receptor agonists on the function of hypothalamic-pituitary-adrenal axis in monkeys. Psychoneuroendocrinology. 2008 May;33(4):478-86. doi: 10.1016/j.psyneuen.2008.01.006. Epub 2008 Mar 5. [PubMed:18325678]

Drug created on July 31, 2007 07:09 / Updated on October 02, 2017 04:58