title: Identification of a probable new adrenergic agonist by nuclear magnetic resonance and mass spectrometry.
abstract: In animal production, it is consolidated the synthesis and the illegal use of growth promoters of new generation, able to skip routine screening and confirmatory analysis. In this work it is reported the nuclear magnetic resonance (NMR) and the mass spectrometry identification of a probable new adrenergic drug found in a feed premix. The substance was selectively purified on alpha 1 acid glycoprotein affinity columns; then its structure was first achieved by recording the 13C NMR spectrum that gave the total number of carbons of the molecule, successively sorted by DEPT experiments into quaternary, CH, CH2, and CH3 groups. However, the complete assignments of all resonances were derived from the bi-dimensional analysis and the crucial indications from the 1H-13C reverse experiments. Further characterisation was performed by atmospheric pressure chemical ionisation both in positive and negative ion mode, matching the molecular ion and the fragmentation pattern with those of most recently described new adrenergic agonists. After the loss of a ter-butylic group, the structure shows an internal symmetry along with the presence of Chlorine clusters. The proposed formula of the compound, the 8,8'-diamino-9,9'-dichloro-1-terbutyl-1,1',4,4-tetrahydro-5H,5'H-2,2'-bi-1-benzazepine-5,5'-dione, partially resembles that of Zilpaterol for the presence of a heterocyclic ring; Further work is in progress to characterise the structure-activity relationship.
authors: Department of Toxicological Chemistry, University of Sassari, Sassari, Italy.
authors: Gianpiero
authors: G
authors: Boatto
authors: Nicola
authors: N
authors: Culeddu
authors: Cecilia
authors: C
authors: Testa
authors: Bruno
authors: B
authors: Neri
authors: Gianfranco
authors: G
authors: Brambilla
authors: Jorge
authors: J
authors: Barbosa
authors: Clara
authors: C
authors: Cruz
mesh_terms: D000322:Adrenergic Agonists / Q000494:pharmacology*; D000821:Animal Feed / Q000032:analysis; D000818:Animals; D002713:Chlorine / Q000737:chemistry; D002846:Chromatography, Affinity; D004350:Drug Residues / Q000032:analysis; D004983:Ethanolamines / Q000737:chemistry; D005504:Food Analysis / Q000379:methods; D007477:Ions; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D013058:Mass Spectrometry / Q000379:methods*; D008956:Models, Chemical; D013329:Structure-Activity Relationship; D013552:Swine; D014297:Trimethylsilyl Compounds / Q000032:analysis
chemical_list: D000322:Adrenergic Agonists; D004983:Ethanolamines; D007477:Ions; D014297:Trimethylsilyl Compounds; C475840:Zilpaterol; D002713:Chlorine