N-[3-methyl-1-(2-phenylethyl)piperidin-4-yl]-N-phenylpropanamide

• ChemBase ID: 1355
• Molecular Formular: C23H30N2O
• Molecular Mass: 350.4971
• Monoisotopic Mass: 350.23581359
• SMILES: O=C(N(C1C(CN(CC1)CCc1ccccc1)C)c1ccccc1)CC
• Canonical SMILES: CCC(=O)N(C1CCN(CC1C)CCc1ccccc1)c1ccccc1
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[3-methyl-1-(2-phenylethyl)piperidin-4-yl]-N-phenylpropanamide
• IUPAC Traditional name: 3-methylfentanyl
• Synonyms: 3-MF; mefentanyl; DEA No. 9813; 3-Methylfentanyl

Database IDs

• CAS Number: 42045-86-3
• PubChem SID: 46509149; 160964815
• PubChem CID: 61996

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.055677
• LogD (pH = 7.4): 2.609922
• Log P: 4.294822
• Molar Refractivity: 107.8989 cm^3
• Polarizability: 42.146507 Å^3
• Polar Surface Area: 23.55 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.29
• LOG S: -4.37
• Solubility (Water): 1.50e-02 g/l

DETAILS

DrugBank - DB01571

• Drug Groups: illicit; experimental
• Description: 3-Methylfentanyl (3-MF, mefentanyl) is an opioid analgesic that is an analogue of fentanyl. 3-Methylfentanyl is one of the most potent drugs that has been widely sold on the black market, estimated to be between 400-6000 times stronger than morphine depending on which isomer is used (with cis isomer being the more potent one). 3-Methylfentanyl was first discovered in 1974 [4] and subsequently appeared on the street as an alternative to the clandestinely produced fentanyl analogue α-methylfentanyl. However it quickly became apparent that 3-methylfentanyl was much more potent than α-methylfentanyl, and corespondingly even more dangerous. [Wikipedia]
• Pharmacology: 3-Methylfentanyl has similar effects to fentanyl, but is far more potent due to increased binding affinity to its target site. Since fentanyl itself is already highly potent, 3-methylfentanyl is extremely dangerous when used recreationally, and has resulted in many deaths among opiate addicts using the drug.
• Toxicity: 3-Methylfentanyl has resulted in many deaths among opiate addicts using the drug.
• Affected Organisms: Humans and other mammals
• External Links: Wikipedia