Ohmefentanyl

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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	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.

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]

[edit] References

1. ^ 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
2. ^ 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
3. ^ 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

[edit] See also

• Opioid
• Fentanyl
• Signal transduction
• Regulation of gene expression
• Protein kinase

[edit] External links

• MeSH Ohmefentanyl

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