# Fentanyl tropane

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> Markdown URL: https://mediated.wiki/source/Fentanyl_tropane.md
> Source: https://en.wikipedia.org/wiki/Fentanyl_tropane
> Source revision: 1327037675
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{{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](/source/opioid) derivative which is an analogue of [fentanyl](/source/fentanyl), where the central [piperidine](/source/piperidine) ring has been bridged with a two carbon chain to form a [tropane](/source/tropane) ring. It is made from [tropinone](/source/tropinone) in a similar manner to how fentanyl is made from [4-piperidone](/source/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](/source/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>

== See also ==
* [Fentanyl azepane](/source/Fentanyl_azepane)
* [Secofentanyl](/source/Secofentanyl)
* [Phenaridine](/source/Phenaridine)
* [List of fentanyl analogues](/source/List_of_fentanyl_analogues)

== References ==
{{reflist}}

{{Opioids}}

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

{{analgesic-stub}}

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Adapted from the Wikipedia article [Fentanyl tropane](https://en.wikipedia.org/wiki/Fentanyl_tropane) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Fentanyl_tropane?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.