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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 none
PubChem 62279
Chemical data
Formula C 23H30N2O2  
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 potent opioid yet discovered, possessing an analgesic potency approximately 18,000-fold greater than morphine.[3]

Molecular structure of four ohmefentanyl isomers

References

  1. ^ Guo, GW; He; Jin; Zou; Zhu; Chi (2000). "Comparison of physical dependence of ohmefentanyl stereoisomers in mice". Life sciences 67 (2): 113–20. PMID 10901279.   edit
  2. ^ Liu, Z.; He, Y.; Jin, W.; Chen, X.; Shen, Q.; Chi, Z. (2004). "Effect of chronic treatment of ohmefentanyl stereoisomers on cyclic AMP formation in Sf9 insect cells expressing human mu-opioid receptors". Life sciences 74 (24): 3001–3008. doi:10.1016/j.lfs.2003.10.027. PMID 15051423.   edit
  3. ^ Yong, Z; Hao; Weifang; Qiyuan; Xinjian; Wenqiao; Youcheng (2003). "Synthesis and analgesic activity of stereoisomers of cis-fluoro-ohmefentanyl". Die Pharmazie 58 (5): 300–2. PMID 12779044.   edit

See also

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