U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C22H27FN2O
Molecular Weight 354.461
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of p-Fluorofentanyl

SMILES

CCC(=O)N(C1CCN(CCC2=CC=CC=C2)CC1)C3=CC=C(F)C=C3

InChI

InChIKey=KXUBAVLIJFTASZ-UHFFFAOYSA-N
InChI=1S/C22H27FN2O/c1-2-22(26)25(20-10-8-19(23)9-11-20)21-13-16-24(17-14-21)15-12-18-6-4-3-5-7-18/h3-11,21H,2,12-17H2,1H3

HIDE SMILES / InChI

Description

Parafluorofentanyl is a selective mu-opioid agonist, an analog of fentanyl, developed by Janssen. The drug was not developed for human use but is produced and abused illegally.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
4.2 nM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
On a black market, parafluorofentanyl is distributed in form of capsules and tablets containing the drug in the range of 33.8-408.7 ug. In preclinical studies parafluorofentanyl was administered to rats subcutaneously.
Route of Administration: Other
In Vitro Use Guide
The potency of parafluorofentanyl with respect to cloned hMOR was investigated using the heterologous expression in X. laevis. Receptor subtype was individually coexpressed with GIRK1/GIRK2 channels and RGS4, mimicking the native neuronal G protein-mediated pathway of K1 channel activation. The two-microelectrode voltage-clamp technique was then used to measure the opioid receptor-activated GIRK1/GIRK2 channel response as the increase of the inward K1 current at 270 mV, evoked by the application of increasing concentrations of opioid ligands. Parafluorofentanyl activated hMOR with EC50 of 4.2 nM.