{"Abbreviation":["3-MF"],"Aliases":["3-Methylfentanyl","3-Methylfentanil","DEA No. 9813","N-(3-Methyl-1-(2-phenylethyl)-4-piperidinyl)-N-phenylpropanamide","Chebi:61092","Propanamide, N-(3-methyl-1-(2-phenylethyl)-4-piperidinyl)-N-phenyl-","QVU94XE61A","3-methyl-fentanyl","N-(3-methyl-1-(2-phenylethyl)piperidin-4-yl)-N-phenylpropanamide","F-7209","IDS-NM-017","Dtxcid10196448","Ids-nm-017(sect.3)","China White","3-MF","F 7209","Discontinued see: M205505","R-26800","Epitope ID:153511","Schembl2337401","Chembl4748291","HSDB 8379","BDBM641069","DDA99517","N-(3-Methyl-1-(2-phenylethyl)-4-piperidyl)-N-phenylpropanamide","DB01571","NS00007543","NS00096426","C22793","US20230399418, Compound 3-Methylfentanyl","N-(3-Methyl-1-phenethyl-4-piperidyl)propionanilide","Q2030844","N-(3-methyl-1-phenethyl-4-piperidyl)-N-phenylpropanamide"],"CAS":"42045-86-3","ChemicalClasses":["phenethylpiperidine"],"Chirality":"racemic","Classes":["Opioid"],"DTXSID":"30962228","EliminationHalfLife":"","Erowid Experience Reports":[],"Esters":[],"Formating":[],"HMDB ID":"HMDB0243534","HeavyAtomCount":26,"IUPACName":"N-[3-methyl-1-(2-phenylethyl)piperidin-4-yl]-N-phenylpropanamide","InChI":"InChI=1S/C23H30N2O/c1-3-23(26)25(21-12-8-5-9-13-21)22-15-17-24(18-19(22)2)16-14-20-10-6-4-7-11-20/h4-13,19,22H,3,14-18H2,1-2H3","InChIKey":"MLQRZXNZHAOCHQ-UHFFFAOYSA-N","Interactions":"Three fatal poisoning cases due to 3-methylfentanyl are described. In each case, the death was accidental and occurred after injection of the opioid combined with amphetamine, heroin, or other drugs. The victims' ages, ranging from 30 to 41 years, were higher than those typically found in heroin poisonings in Finland. The blood concentrations of cis-3-methylfentanyl, measured here for the first time by a specific tandem mass spectrometric method, ranged from 0.3 to 0.9 ug/L (mean 0.5 ug/L). These values are significantly lower than the levels reported for alpha-methylfentanyl and fentanyl in fatal poisonings. Repeated seizures of fentanyl and its analogs have been reported in Europe close to the Russian border.","MeSH Headers":[{"Id":"M0096647","Link":"https://id.nlm.nih.gov/mesh/M0096647.html","Name":"3-methylfentanyl","Ref":28},{"Id":"DescTree","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":"MeSH Tree","Ref":30},{"Id":"PubMed from MeSH","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":null,"Ref":41},{"Id":"M0001067","Link":"https://id.nlm.nih.gov/mesh/M0001067.html","Name":"Analgesics","Ref":42}],"MeSH Pharmacological Classification":[{"Id":"M0001067","Link":"https://id.nlm.nih.gov/mesh/M0001067.html","Name":"Analgesic","Ref":42}],"Mechanism of Action":"Opiate receptors are coupled with G-protein receptors and function as both positive and negative regulators of synaptic transmission via G-proteins that activate effector proteins. Binding of the opiate stimulates the exchange of GTP for GDP on the G-protein complex. As the effector system is adenylate cyclase and cAMP located at the inner surface of the plasma membrane, opioids decrease intracellular cAMP by inhibiting adenylate cyclase. Subsequently, the release of nociceptive neurotransmitters such as substance P, GABA, dopamine, acetylcholine and noradrenaline is inhibited. Opioids also inhibit the release of vasopressin, somatostatin, insulin and glucagon. Fentanyl's analgesic activity is, most likely, due to its conversion to morphine. Opioids close N-type voltage-operated calcium channels (OP2-receptor agonist) and open calcium-dependent inwardly rectifying potassium channels (OP3 and OP1 receptor agonist). This results in hyperpolarization and reduced neuronal excitability.","Melting Point":"Crystals from isopropanol. MP: 272-8-273.6 °C /3-Methylfentanyl hydrochloride/","Metabolism/Metabolites":"The opioid 3-methylfentanyl, a designer drug of the fentanyl type, was scheduled by the Controlled Substance Act due to its high potency and abuse potential. To overcome this regulation, isofentanyl, another designer fentanyl, was synthesized in a clandestine laboratory and seized by the German police. The aims of the presented study were to identify the phase I and phase II metabolites of 3-methylfentanyl and isofentanyl in rat urine, to identify the cytochrome P450 (CYP) isoenzymes involved in their initial metabolic steps, and, finally, to test their detectability in urine. Using liquid chromatography (LC)-linear ion trap-mass spectrometry (MS(n)), nine phase I and five phase II metabolites of 3-methylfentanyl and 11 phase I and four phase II metabolites of isofentanyl could be identified. The following metabolic steps could be postulated for both drugs: N-dealkylation followed by hydroxylation of the alkyl and aryl moiety, hydroxylation of the propanamide side chain followed by oxidation to the corresponding carboxylic acid, and, finally, hydroxylation of the benzyl moiety followed by methylation. In addition, N-oxidation of isofentanyl could also be observed. All hydroxy metabolites were partly excreted as glucuronides. Using recombinant human isoenzymes, CYP2C19, CYP2D6, CYP3A4, and CYP3A5 were found to be involved in the initial metabolic steps. Our LC-MS(n) screening approach allowed the detection of 0.01 mg/L of 3-methylfentanyl and isofentanyl in spiked urine. However, in urine of rats after the administration of suspected recreational doses, the parent drugs could not be detected, but their common nor metabolite, which should therefore be the target for urine screening.","MolecularFormula":"C\u003csub\u003e23\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eO","MolecularWeight":"350.5 g/mol","PD":"PD008773","Pharmacodynamics":"3-Methylfentanyl exhibits similar pharmacodynamic effects to fentanyl but has been proven to be significantly stronger in these effects due to increased binding affinity to the opioid receptor. Fentanyl, administered alone, has a strong affinity for opioid receptors. 3-methylfentanyl has the potential to be extremely hazardous when used without the prescription and supervision of a medical professional. Ingestion of this drug has resulted in numerous deaths among individuals using the drug recreationally.","PubChemId":61996,"PubChemTitle":"3-Methylfentanyl","Reagents":[],"RefChem":"94894","RefCount":2,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/3-Methylfentanyl","Name":"Mefentanyl","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q122618283","Name":"Mefentanyl","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/DB01571","Name":"Mefentanyl","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/61996","Name":"Mefentanyl","Sub":false}]},{"Name":"Probes \u0026 Drugs","Urls":[{"Link":"https://www.probes-drugs.org/compound/PD008773","Name":"Mefentanyl","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=42045-86-3","Name":"Mefentanyl","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0243534","Name":"Mefentanyl","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/C22793","Name":"Mefentanyl","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID30962228","Name":"Mefentanyl","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 61996, Mefentanyl. 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appreciation"],"Physical Effects":["Respiratory depression","Pain relief","Itchiness","Constipation","Cough suppression","Sedation","Nausea","Pupil constriction","Stomach cramp","Difficulty urinating"],"Visual Effects":["Double vision"]},"Therapeutic Uses":"Analgesics","Title":"Mefentanyl","Wikidata":"Q122618283","Wikipedia":"3-Methylfentanyl","XLogP":4.5}