title: Energy-dependent collision-induced dissociation study of buprenorphine and its synthetic precursors.
abstract: The collision-induced dissociation (CID) of protonated buprenorphine ([M+H](+) ) and four related compounds was studied by electrospray quadrupole/time-of-flight mass spectrometry (ESI-QTOF MS). The fragmentation pathways were investigated by using energy-dependent CID and pseudo-MS(3) (in-source CID combined with tandem mass spectrometry (MS/MS)) methods. The first steps of the fragmentation are the parallel losses of the substituents from the non-aromatic ring moieties. Depending on the applied collision energies, a large number of further fragment ions arising from the cross-ring cleavages of the core-ring structure were observed. Based on the experimental results, a generalized fragmentation scheme was developed for the five buprenorphine derivatives highlighting the differences for the alternatively substituted compounds. The collision-energy-dependent fragmentation profile of buprenorphine is visualized in a two-dimensional plot to aid its fingerprint identification.
authors.affiliation: Department of Applied Chemistry, University of Debrecen, H-4032 Debrecen, Egyetem tér 1, Hungary.
authors.forename: Bernadett
authors.initials: B
authors.lastname: Biri
authors.forename: József
authors.initials: J
authors.lastname: Kalmár
authors.forename: Lajos
authors.initials: L
authors.lastname: Nagy
authors.forename: Attila
authors.initials: A
authors.lastname: Sipos
authors.forename: Miklós
authors.initials: M
authors.lastname: Zsuga
authors.forename: Sándor
authors.initials: S
authors.lastname: Kéki
mesh_terms: D002047:Buprenorphine / Q000138:chemical synthesis / Q000737:chemistry*; D002626:Chemistry, Pharmaceutical; D010880:Piperidines / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods*; D053719:Tandem Mass Spectrometry / Q000379:methods*
chemical_list: D010880:Piperidines; D002047:Buprenorphine; C032727:piperidine