Allylnorpethidine

Allylnorpethidine

Systematic (IUPAC) name
ethyl 4-phenyl-1-prop-2-enylpiperidine-4-carboxylate
Clinical data
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	2372-70-5
ATC code	None
PubChem	CID 16915
ChemSpider	16026 Y
Synonyms	Allylnorpethidine, WIN-7681
Chemical data
Formula	C17H23NO2
Mol. mass	273.37 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C17H23NO2/c1-3-12-18-13-10-17(11-14-18,16(19)20-4-2)15-8-6-5-7-9-15/h3,5-9H,1,4,10-14H2,2H3 Y Key:YUNKDDDGCRLMAF-UHFFFAOYSA-N Y
Y(what is this?)  (verify)

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Allylnorpethidine is an analogue of pethidine where the N-methyl group has been replaced by allyl.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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