Fentanyl tropane

{{Short description|Chemical compound}} {{cs1 config |name-list-style=vanc |display-authors=6}} {{drugbox | drug_name = Fentanyl tropane | image = Tropafentanyl.svg | image_class = skin-invert-image | legal_UK = | legal_DE = | C = 24 | H = 30 | N = 2 | O = 1 | IUPAC_name = N-phenyl-N-[(1R,5S)-8-(2-phenylethyl)-8-azabicyclo[3.2.1]octan-3-yl]propanamide | CAS_number_Ref = {{cascite|correct|CAS}} | CAS_number = 76754-18-2 | ChemSpiderID = 58131720 | PubChem = 118718255 | UNII = | ChEMBL = 3349244 | smiles = CCC(=O)N(C1C[C@H]2CC[C@@H](C1)N2CCC3=CC=CC=C3)C4=CC=CC=C4 | StdInChI = 1S/C24H30N2O/c1-2-24(27)26(20-11-7-4-8-12-20)23-17-21-13-14-22(18-23)25(21)16-15-19-9-5-3-6-10-19/h3-12,21-23H,2,13-18H2,1H3/t21-,22+,23? | StdInChIKey = OLHSRBZZORBSLQ-AIZNXBIQSA-N }}

'''Fentanyl tropane''' ('''tropafentanyl''') is an opioid derivative which is an analogue of fentanyl, where the central piperidine ring has been bridged with a two carbon chain to form a tropane ring. It is made from tropinone in a similar manner to how fentanyl is made from 4-piperidone, and has two isomers, with the 3β isomer being around half the potency of fentanyl while the 3α isomer is much weaker, only around the same potency as morphine.<ref name="pmid513063">{{cite journal | vauthors = Riley TN, Bagley JR | title = 4-Anilidopiperidine analgesics. 2. A study of the conformational aspects of the analgesic activity of the 4-anilidopiperidines utilizing isomeric N-substituted 3-(propananilido)nortropane analogues | journal = Journal of Medicinal Chemistry | volume = 22 | issue = 10 | pages = 1167–71 | date = October 1979 | pmid = 513063 | doi = 10.1021/jm00196a004 }}</ref><ref>{{ cite book | vauthors = Lednicer D | title = Central Analgetics | year = 1982 | page = 188-189 | publisher = Wiley | isbn = 0-471-08314-3 }}</ref>

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Category:Designer drugs Category:Opioids Category:Tropanes Category:Anilides