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Identification
Name3-Methylfentanyl
Accession NumberDB01571
TypeSmall Molecule
GroupsIllicit
Description3-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 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]
Structure
Thumb
Synonyms
3-MF
mefentanyl
External Identifiers
  • DEA No. 9813
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIQVU94XE61A
CAS number42045-86-3
WeightAverage: 350.4971
Monoisotopic: 350.235813592
Chemical FormulaC23H30N2O
InChI KeyMLQRZXNZHAOCHQ-UHFFFAOYSA-N
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
IUPAC Name
N-[3-methyl-1-(2-phenylethyl)piperidin-4-yl]-N-phenylpropanamide
SMILES
CCC(=O)N(C1CCN(CCC2=CC=CC=C2)CC1C)C1=CC=CC=C1
Pharmacology
IndicationNot Available
Structured Indications Not Available
Pharmacodynamics3-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.
Mechanism of actionOpiate 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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Mu-type opioid receptorProteinyes
agonist
HumanP35372 details
Delta-type opioid receptorProteinyes
agonist
HumanP41143 details
Kappa-type opioid receptorProteinyes
agonist
HumanP41145 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
Toxicity3-Methylfentanyl has resulted in many deaths among opiate addicts using the drug.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9808
Blood Brain Barrier+0.9875
Caco-2 permeable+0.695
P-glycoprotein substrateSubstrate0.6788
P-glycoprotein inhibitor IInhibitor0.8087
P-glycoprotein inhibitor IINon-inhibitor0.735
Renal organic cation transporterInhibitor0.5413
CYP450 2C9 substrateNon-substrate0.8205
CYP450 2D6 substrateNon-substrate0.699
CYP450 3A4 substrateSubstrate0.6768
CYP450 1A2 substrateNon-inhibitor0.6901
CYP450 2C9 inhibitorNon-inhibitor0.8046
CYP450 2D6 inhibitorNon-inhibitor0.5713
CYP450 2C19 inhibitorNon-inhibitor0.7282
CYP450 3A4 inhibitorNon-inhibitor0.6426
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6191
Ames testNon AMES toxic0.8872
CarcinogenicityNon-carcinogens0.8297
BiodegradationNot ready biodegradable0.9033
Rat acute toxicity2.9798 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8516
hERG inhibition (predictor II)Inhibitor0.6605
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.015 mg/mLALOGPS
logP4.29ALOGPS
logP4.29ChemAxon
logS-4.4ALOGPS
pKa (Strongest Basic)9.08ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.55 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity107.9 m3·mol-1ChemAxon
Polarizability41.64 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as fentanyls. These are compounds containing the fentanyl moiety or a derivative, which is based on a N-(1-(2-phenylethyl)-4-piperidinyl)-N-phenylpropanamide skeleton.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPiperidines
Sub ClassFentanyls
Direct ParentFentanyls
Alternative Parents
Substituents
  • Fentanyl
  • Anilide
  • Phenethylamine
  • Aralkylamine
  • 4-aminopiperidine
  • Benzenoid
  • Monocyclic benzene moiety
  • Tertiary carboxylic acid amide
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxamide group
  • Azacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available

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. Agonist binding to the receptor induces coupling to an inactive GDP-bound heterotrimeric G-protein complex and subsequent exchange of GDP for GTP in the G-protein alpha subunit leading to dissociati...
Gene Name:
OPRM1
Uniprot ID:
P35372
Molecular Weight:
44778.855 Da
References
  1. Subramanian G, Paterlini MG, Portoghese PS, Ferguson DM: Molecular docking reveals a novel binding site model for fentanyl at the mu-opioid receptor. J Med Chem. 2000 Feb 10;43(3):381-91. [PubMed:10669565 ]
  2. Jin WQ, Xu H, Zhu YC, Fang SN, Xia XL, Huang ZM, Ge BL, Chi ZQ: Studies on synthesis and relationship between analgesic activity and receptor affinity for 3-methyl fentanyl derivatives. Sci Sin. 1981 May;24(5):710-20. [PubMed:6264594 ]
  3. Wang ZX, Zhu YC, Chen XJ, Ji RY: [Stereoisomers of 3-methylfentanyl: synthesis, absolute configuration and analgesic activity]. Yao Xue Xue Bao. 1993;28(12):905-10. [PubMed:8030414 ]
  4. Zhu J, Yin J, Law PY, Claude PA, Rice KC, Evans CJ, Chen C, Yu L, Liu-Chen LY: Irreversible binding of cis-(+)-3-methylfentanyl isothiocyanate to the delta opioid receptor and determination of its binding domain. J Biol Chem. 1996 Jan 19;271(3):1430-4. [PubMed:8576134 ]
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 nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Signaling leads to the inhibition of adenylate cyclase activity. Inhibits neurot...
Gene Name:
OPRD1
Uniprot ID:
P41143
Molecular Weight:
40368.235 Da
References
  1. Jin WQ, Xu H, Zhu YC, Fang SN, Xia XL, Huang ZM, Ge BL, Chi ZQ: Studies on synthesis and relationship between analgesic activity and receptor affinity for 3-methyl fentanyl derivatives. Sci Sin. 1981 May;24(5):710-20. [PubMed:6264594 ]
  2. Wang ZX, Zhu YC, Chen XJ, Ji RY: [Stereoisomers of 3-methylfentanyl: synthesis, absolute configuration and analgesic activity]. Yao Xue Xue Bao. 1993;28(12):905-10. [PubMed:8030414 ]
  3. Zhu J, Yin J, Law PY, Claude PA, Rice KC, Evans CJ, Chen C, Yu L, Liu-Chen LY: Irreversible binding of cis-(+)-3-methylfentanyl isothiocyanate to the delta opioid receptor and determination of its binding domain. J Biol Chem. 1996 Jan 19;271(3):1430-4. [PubMed:8576134 ]
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 synthetic opioids and for the psychoactive diterpene salvinorin A. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates th...
Gene Name:
OPRK1
Uniprot ID:
P41145
Molecular Weight:
42644.665 Da
References
  1. Jin WQ, Xu H, Zhu YC, Fang SN, Xia XL, Huang ZM, Ge BL, Chi ZQ: Studies on synthesis and relationship between analgesic activity and receptor affinity for 3-methyl fentanyl derivatives. Sci Sin. 1981 May;24(5):710-20. [PubMed:6264594 ]
  2. Wang ZX, Zhu YC, Chen XJ, Ji RY: [Stereoisomers of 3-methylfentanyl: synthesis, absolute configuration and analgesic activity]. Yao Xue Xue Bao. 1993;28(12):905-10. [PubMed:8030414 ]
  3. Zhu J, Yin J, Law PY, Claude PA, Rice KC, Evans CJ, Chen C, Yu L, Liu-Chen LY: Irreversible binding of cis-(+)-3-methylfentanyl isothiocyanate to the delta opioid receptor and determination of its binding domain. J Biol Chem. 1996 Jan 19;271(3):1430-4. [PubMed:8576134 ]
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Drug created on July 31, 2007 07:10 / Updated on August 17, 2016 12:23