Ohmefentanyl

Ohmefentanyl

Clinical data
ATC code	none
Legal status
Legal status	CA: Schedule I DE: Anlage I (Controlled) UK: Class A US: Schedule I UN: Psychotropic Schedule I
Identifiers
IUPAC name N-[1-(2-hydroxy-2-phenylethyl)-3-methylpiperidin-4-yl]-N-phenylpropanamide
CAS Number	78995-14-9 Y
PubChem CID	62279
DrugBank	DB01570
ChemSpider	56080 Y
UNII	Y8263089ZX
ChEMBL	CHEMBL333410
Chemical and physical data
Formula	C23H30N2O2
Molar mass	366.497 g/mol
3D model (Jmol)	Interactive image
SMILES CCC(=O)N(C1CCN(CC1C)CC(C2=CC=CC=C2)O)C3=CC=CC=C3
InChI InChI=1S/C23H30N2O2/c1-3-23(27)25(20-12-8-5-9-13-20)21-14-15-24(16-18(21)2)17-22(26)19-10-6-4-7-11-19/h4-13,18,21-22,26H,3,14-17H2,1-2H3 Y Key:FRPRNNRJTCONEC-UHFFFAOYSA-N Y

Ohmefentanyl (also known as β-hydroxy-3-methylfentanyl, OMFand RTI-4614-4) is an extremely potent opioid analgesic drug which selectively binds to the µ-opioid receptor.

Ohmefentanyl is one of the most potent μ-opioid receptor agonists known, comparable to super-potent opioids such as carfentanil and etorphine which are used for tranquilizing large animals such as elephants in veterinary medicine. In mouse studies, the most active isomer 3R,4S,βS-ohmefentanyl was 28 times more powerful as a painkiller than fentanyl, the chemical from which it is derived, and 6300 times more effective than morphine. Ohmefentanyl has three stereogenic centers and eight stereoisomers, which are named F9201–F9208. Researchers are studying the different pharmaceutical properties of these isomers.

The 4"-fluoro analogue (i.e. substituted on the phenethyl ring) of the 3R,4S,βS isomer of ohmefentanyl is one of the most potent opioid agonists yet discovered, possessing an analgesic potency approximately 18,000-fold greater than morphine. Other analogues with potency higher than that of ohmefentanyl itself include the 2'-fluoro derivative (i.e. substituted on the aniline phenyl ring), and derivatives where the N-propionyl group was replaced by N-methoxyacetyl or 2-furamide groups, or a carboethoxy group is added to the 4-position of the piperidine ring. The latter is listed as being up to 30,000 times more potent than morphine.

Side effects of fentanyl analogs are similar to those of fentanyl itself, which include itching, nausea and potentially serious respiratory depression, which can be life-threatening. Fentanyl analogs have killed hundreds of people throughout Europe and the former Soviet republics since the most recent resurgence in use began in Estonia in the early 2000s, and novel derivatives continue to appear.