Allylnorpethidine

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Allylnorpethidine
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Systematic (IUPAC) name
ethyl 4-phenyl-1-prop-2-enylpiperidine-4-carboxylate
Identifiers
CAS Number 2372-70-5
ATC code none
PubChem CID 16915
Synonyms Allylnorpethidine, WIN-7681
Chemical data
Formula C17H23NO2
Molar mass 273.37 g/mol[[Script error: No such module "String".]]
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Allylnorpethidine (WIN-7681) is a 4-phenylpiperidine derivative that is related to the opioid analgesic drug pethidine (meperidine).

Allylnorpethidine is an analogue of pethidine where the N-methyl group has been replaced by allyl. In many other opioid derivatives, placing an allyl substituent on the nitrogen instead of a methyl will reverse the normal opioid effects, to produce μ-opioid antagonists which among other things reverse the respiratory depression caused by opioid agonists such as morphine. This is not true with allylnorpethidine, as while it does partially reverse the respiratory depression produced by morphine[1] it is actually an active analgesic and has no antagonistic properties[2][3] when administered alone, so is instead a partial agonist.

References

  1. ↑ Costa PJ, Bonnycastle DD. The Effect of Levallorphan Tartrate, Nalorphine HCl, and WIN 7681 (1-allyl-4-phenyl-4-carboethoxypiperidine) on Respiratory Depression and Analgesia Induced by some active Analgetics. Journal of Pharmacology and Experimental Therapeutics. 1955; 113(3):310-318.
  2. ↑ Casy AF, Parfitt RT (1986). Opioid Analgesics: Chemistry and Receptors. pp. pp239. ISBN 0-306-42130-5. 
  3. ↑ Stenlake JB (1979). Foundations of Molecular Pharmacology. pp. pp152. ISBN 0-485-11171-3. (online version)


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