Electrospray ionization mass and tandem mass spectra of a series of N-pyrazolylmethyl and N-triazolylmethyl N-phenylpiperazines: new dopaminergic ligands with potential antipsychotic properties

Recently, two analogous series of N‐pyrazolylmethyl and N‐triazolylmethyl N‐phenylpiperazines have been prepared and found to be potential antipsychotic drugs acting as new selective ligands of the dopamine D2 receptor. Herein we report a systematic study of their high‐resolution electrospray ioniza...

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Bibliographic Details
Published in:Journal of mass spectrometry. 2005-06, Vol.40 (6), p.815-820
Main Authors: Santos, Leonardo S., Padilha, Monica Costa, de Aquino Neto, Francisco Radler, Santos Pereira, Alberto dos, Menegatti, Ricardo, Manssour Fraga, Carlos Alberto, Barreiro, Eliezer J., Eberlin, Marcos N.
Format: Article
Language:English
Subjects:
Antipsychotic Agents - chemistry
antipsychotic drugs
Biological and medical sciences
Catecholaminergic system
Dopamine Antagonists - chemistry
dopamine receptor ligands
ion chemistry
Ligands
Medical sciences
Neuropharmacology
Neurotransmitters. Neurotransmission. Receptors
Pharmacology. Drug treatments
Piperazines - chemistry
Psycholeptics: tranquillizer, neuroleptic
Psychology. Psychoanalysis. Psychiatry
Psychopharmacology
Receptors, Dopamine - chemistry
Spectrometry, Mass, Electrospray Ionization - methods
tandem mass spectrometry
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Summary:Recently, two analogous series of N‐pyrazolylmethyl and N‐triazolylmethyl N‐phenylpiperazines have been prepared and found to be potential antipsychotic drugs acting as new selective ligands of the dopamine D2 receptor. Herein we report a systematic study of their high‐resolution electrospray ionization mass and tandem mass spectra in which the main dissociation routes of their protonated molecules are determined and rationalized. The ESI‐MS/MS data is very characteristic for both series allowing straightforward isomeric differentiation. A single and dominant fragment ion for the pyrazole series and four major fragment ions for the triazole series are useful for selective reaction MS monitoring of these potential drugs in biological fluids. Copyright © 2005 John Wiley & Sons, Ltd.
ISSN:1076-5174
1096-9888
DOI:10.1002/jms.857