Ohmefentanyl

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Ohmefentanyl
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Identifiers
CAS Number
PubChem CID
E number{{#property:P628}}
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Chemical and physical data
FormulaC23H30N2O2
Molar mass366.497 g/mol
3D model (JSmol)


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]

File:OMF.png
Molecular structure of four ohmefentanyl isomers


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

See also

External links


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