Banner
targets (3)
for drugs
Identification
Name 3-Methylfentanyl
Accession Number DB01571
Type small molecule
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]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • 3-MF
  • DEA No. 9813
  • mefentanyl
Synonyms
3-MF
DEA No. 9813
mefentanyl
Salts Not Available
Brand names Not Available
Brand mixtures Not Available
Categories
  • Hypnotics and Sedatives
  • Analgesics
CAS number 42045-86-3
Weight Average: 350.4971
Monoisotopic: 350.235813592
Chemical Formula C23H30N2O
InChI Key InChIKey=MLQRZXNZHAOCHQ-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
Plain Text
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Fentanyls
Substructures
  • Amino Ketones
  • Benzene and Derivatives
  • Aliphatic and Aryl Amines
  • Acetanilides
  • Fentanyls
  • Phenethylamines
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Anilines
  • Piperidines
Pharmacology
Indication Not Available
Pharmacodynamics 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.
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.
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 3-Methylfentanyl has resulted in many deaths among opiate addicts using the drug.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Melting point Not Available
Experimental Properties Not Available
Predicted Properties
Property Value Source
water solubility 1.50e-02 g/l ALOGPS
logP 4.29 ALOGPS
logP 4.29 ChemAxon Molconvert
logS -4.4 ALOGPS
pKa 0 ChemAxon Molconvert
hydrogen acceptor count 2 ChemAxon Molconvert
hydrogen donor count 0 ChemAxon Molconvert
polar surface area 23.55 ChemAxon Molconvert
rotatable bond count 6 ChemAxon Molconvert
refractivity 107.9 ChemAxon Molconvert
polarizability 41.64 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
PubChem Compound 61996 Link_out
PubChem Substance 46509149 Link_out
ChemSpider 55844 Link_out
ChEBI 61092 Link_out
ChEMBL 61092 Link_out
Wikipedia http://en.wikipedia.org/wiki/3-Methylfentanyl Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Mu-type opioid receptor

Pharmacological action: yes
Actions: agonist

Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for beta-endorphin

Organism class: human
UniProt ID: P35372 Link_out
Gene: OPRM1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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
  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
  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

2. Delta-type opioid receptor

Pharmacological action: yes
Actions: agonist

Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Highly stereoselective. receptor for enkephalins

Organism class: human
UniProt ID: P41143 Link_out
Gene: OPRD1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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
  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

3. Kappa-type opioid receptor

Pharmacological action: yes
Actions: agonist

Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for dynorphins. May play a role in arousal and regulation of autonomic and neuroendocrine functions

Organism class: human
UniProt ID: P41145 Link_out
Gene: OPRK1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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
  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
Comments
Drug created on July 31, 2007 07:10 / Updated on February 14, 2012 11:48