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Ohmefentanyl


Ohmefentanyl
Systematic (IUPAC) name
N-[(3R,4S)-1-[(2S)-2-hydroxy-2-phenyl-ethyl] -3-methyl-4-piperidyl]-N-phenyl-propanamide
Identifiers
CAS number	78995-14-9
ATC code	?
PubChem	62279
Chemical data
Formula	C₂₃H₃₀N₂O₂
Mol. mass	366.497 g/mol
SMILES	search in eMolecules, PubChem
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	?

Ohmefentanyl (β-hydroxy-3-methylfentanyl) is an extremely potent analgesic drug which selectively binds to the µ-opioid receptor.

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Ohmefentanyl is one of the most potent μ-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.^[1]. Ohmefentanyl has three stereogenic centers and so has eight stereoisomers, which are named F9201-F9208. Researchers are studying the different pharmaceutical properties of these isomers.^[2].

The 4"-fluoro analogue of the 3R,4S,βS isomer of ohmefentanyl is the most powerful opioid yet discovered, possessing an analgesic potency approximately 18,000-fold greater than morphine.^[3]

References

^ Guo GW, He Y, Jin WQ, Zou Y, Zhu YC, Chi ZQ. "Comparison of physical dependence of ohmefentanyl stereoisomers in mice." Life Sciences. 2000;67(2):113-20. PMID 10901279
^ Liu ZH, He Y, Jin WQ, Chen XJ, Shen QX, Chi ZQ. "Effect of chronic treatment of ohmefentanyl stereoisomers on cyclic AMP formation in Sf9 insect cells expressing human mu-opioid receptors." Life Sciences. 2004 Apr 30;74(24):3001-8. PMID 15051423
^ Zou Yong, Wu Hao, Yuan Weifang, Dai Qiyuan, Chen Xinjian, Jin Wenqia, Zhu Youcheng. "Synthesis and analgesic activity of stereoisomers of cis-fluoro-ohmefentanyl." Pharmazie. 58 (2003) 5. PMID 12779044

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Morphinans

Butorphanol • Cyclorphan • Dextro-3-hydroxy-N-allylmorphinan • Dextrorphan • Drotebanol • Levargorphan • Levallorphan • Levorphanol • Levorphan • Levophenacylmorphan • Levomethorphan • Norlevorphanol • Oxilorphan • Phenomorphan • Racemethorphan • Racemorphan

Benzomorphans

Bremazocine • Cyclazocine • Dezocine • Ethylketocyclazocine • Ketazocine • Metazocine • Pentazocine • Phenazocine

4-Phenylpiperidines

Pethidines (Meperidines)	Anileridine • Benzethidine • Carperidine • Difenoxin • Diphenoxylate • Etoxeridine (Carbetidine) • Furethidine • Hydroxypethidine (Bemidone) • Morpheridine • Oxpheneridine (Carbamethidine) • Pethidine (Meperidine) • Pethidine Intermediate A • Pethidine Intermediate B (Norpethidine) • Pethidine Intermediate C (Pethidinic Acid) • Pheneridine • Phenoperidine • Piminodine • Properidine (Ipropethidine) • Sameridine • WIN-7681
Prodines	Allylprodine • α-meprodine • α-prodine • β-meprodine • β-prodine • Meprodine • MPPP • PEPAP • Prodine • Prosidol • Trimeperidine
Ketobemidones	Acetoxyketobemidone • Ketobemidone • Methylketobemidone • Propylketobemidone
Others	Alvimopan • Loperamide • Picenadol

Open Chain Opioids

Amidones	Dextromethadone • Dipipanone • Isomethadone • Levomethadone • Methadone • Methadone Intermediate • Norpipanone • Phenadoxone (Heptazone) • Pipidone
Methadols	Acetylmethadol • α-methadol • α-acetylmethadol • β-methadol • β-acetylmethadol • Dimepheptanol • Levo-α-acetylmethadol • Noracymethadol
Moramides	Dextromoramide • Levomoramide • Moramide Intermediate • Racemoramide
Thiambutenes	Diethylthiambutene • Dimethylthiambutene • Ethylmethylthiambutene
Phenalkoxams	Dextropropoxyphene • Dimenoxadol • Dioxaphetyl Butyrate • Levopropoxyphene • Propoxyphene
Ampromides	Diampromide • Phenampromide • Propiram
Others	Lefetamine