Allylnorpethidine

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IUPAC_name = ethyl 4-phenyl-1-prop-2-enylpiperidine-4-carboxylate

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CAS_number = 2372-70-5
synonyms = Allylnorpethidine, WIN-7681
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PubChem = 16915
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C = 17 | H = 23 | N = 1 | O = 2
molecular_weight = 273.37 g/mol
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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Allylnorpethidine is an analogue of pethidine where the N-methyl group has been replaced by allyl.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 [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.] it is actually an active analgesic and has no antagonistic properties [cite book
author=Casy AF, Parfitt RT
title=Opioid Analgesics: Chemistry and Receptors
year=1986
isbn=0-306-42130-5
pages=pp239] [cite book
author=Stenlake JB
title=Foundations of Molecular Pharmacology
year=1979
isbn=0-485-11171-3
pages=pp152( [http://books.google.com/books?id=2cobQ8n27McC&pg=PA152&lpg=PA152&dq=allylnorpethidine&source=web&ots=Kzv2HhwDRZ&sig=iBO6Pkmpc0hedvoubzdS8eZo4mo online version] )] when administered alone, so is instead a partial agonist.

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