N-Methylcarfentanil

N-Methylcarfentanil

Systematic (IUPAC) name
Methyl 1-methyl-4-(N-phenylpropionamido)piperidine-4-carboxylate
Clinical data
Pregnancy cat.	?
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Pharmacokinetic data
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Identifiers
ATC code	?
ChemSpider	26231037 Y
Chemical data
Formula	C17H24N2O3
Mol. mass	304.384 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C17H24N2O3/c1-4-15(20)19(14-8-6-5-7-9-14)17(16(21)22-3)10-12-18(2)13-11-17/h5-9H,4,10-13H2,1-3H3 Y Key:KKEVIELPQLXPRR-UHFFFAOYSA-N Y
Y(what is this?)  (verify)

N-Methylcarfentanil (R-32395) is an opioid analgesic drug related to the highly potent animal tranquilizer carfentanil, but several thousand times weaker, being only slightly stronger than morphine. It was first synthesised by a team of chemists at Janssen Pharmaceutica led by Paul Janssen, who were investigating the structure-activity relationships of the fentanyl family of drugs. They found that replacing the phenethyl group attached to the piperidine nitrogen of fentanyl with a smaller methyl group, made it so much weaker that it was inactive as an analgesic in animals. However the same change made to the more potent analogue carfentanil retained reasonable opioid receptor activity, reflecting the higher binding affinity produced by the 4-carbomethoxy group.^[1][2][3]

References

1. ^ Cometta-Morini C, Maguire PA, Loew GH (January 1992). "Molecular determinants of mu receptor recognition for the fentanyl class of compounds". Molecular Pharmacology 41 (1): 185–96. PMID 1310142. 
2. ^ Maguire, P.; Tsai, N.; Kamal, J.; Comettamorini, C.; Upton, C.; Loew, G. (1992). "Pharmacological profiles of fentanyl analogs at μ, δ and κ opiate receptors". European Journal of Pharmacology 213 (2): 219–225. doi:10.1016/0014-2999(92)90685-W. PMID 1355735.  edit
3. ^ Dukhovich FS, Darkhovskii MB, Gorbatova EN, Kurochkin VK. Molecular recognition: pharmacological aspects. 2004, Nova Science Publishers, New York. p 81. ISBN 1590338871