Optimization of the derivatization procedure for the separation of the stereoisomers of 1,3-dimethylamylamine (1,3-DMAA) by gas chromatography - preliminary data

Authors

  • Maria Mexia-de-Almeida Associate Laboratory i4HB – Institute for Health and Bioeconomy, University Institute of Health Sciences – CESPU, 4585-116 Gandra, Portugal; UCIBIO – Applied Molecular Biosciences Unit, Translational Toxicology Research Laboratory, University Institute of Health Sciences (1H-TOXRUN, IUCS-CESPU), 4585-116 Gandra, Portugal
  • Diana Dias da Silva Associate Laboratory i4HB – Institute for Health and Bioeconomy, University Institute of Health Sciences – CESPU, 4585-116 Gandra, Portugal; UCIBIO – Applied Molecular Biosciences Unit, Laboratory of Toxicology, Faculty of Pharmacy, University of Porto, 4050-313 Porto, Portugal; Associate Laboratory i4HB ‒ Institute for Health and Bioeconomy, University of Porto, 4050-313 Porto, Portugal; REQUIMTE/LAQV, ESS, Polytechnic of Porto, Rua Dr. António Bernardino de Almeida, 400 4200-072, Porto; UCIBIO – Applied Molecular Biosciences Unit, Forensics and Biomedical Sciences Research Laboratory, University Institute of Health Sciences (1H-TOXRUN, IUCS-CESPU), 4585-116 Gandra, Portugal
  • Ricardo Jorge Dinis-Oliveira Associate Laboratory i4HB – Institute for Health and Bioeconomy, University Institute of Health Sciences – CESPU, 4585-116 Gandra, Portugal; UCIBIO – Applied Molecular Biosciences Unit, Translational Toxicology Research Laboratory, University Institute of Health Sciences (1H-TOXRUN, IUCS-CESPU), 4585-116 Gandra, Portugal
  • Cláudia Ribeiro Associate Laboratory i4HB – Institute for Health and Bioeconomy, University Institute of Health Sciences – CESPU, 4585-116 Gandra, Portugal; UCIBIO – Applied Molecular Biosciences Unit, Translational Toxicology Research Laboratory, University Institute of Health Sciences (1H-TOXRUN, IUCS-CESPU), 4585-116 Gandra, Portugal

DOI:

https://doi.org/10.48797/sl.2024.230

Keywords:

Poster

Abstract

Background: 1,3-Dimethylamylamine (1,3-DMAA), also known as methylhexanamine, is a central nervous system stimulant with structural similarities with amphetamines and therefore presenting overlapping biological and detrimental effects [1]. Despite being banned, the presence of 1,3-DMAA in doping controls and dietary supplements continues to be of significant concern. This molecule has two stereogenic centres and thus four stereoisomers [2]. It is widely recognized that enantiomers may exhibit different biological activity, including pharmacokinetics, pharmacodynamics, and toxicity. Consequently, the development of analytical methods for enantioselective separation of 1,3-DMAA is crucial for an accurate determination of the risks associated with each of these stereoisomers. Objective: To develop an indirect method by gas chromatography coupled to mass spectrometry (GC-MS) for the separation and identification of the stereoisomers of the 1,3-DMAA. Methods: 1,3-DMAA was regenerated with sodium hydroxide, extracted with 0.1% triethylamine in hexane and then derivatized using the enantiomeric pure reagent (R)-(-)-α-methoxy-α-(trifluoromethyl)phenylacetyl chloride ((R)-MTPA-Cl). Subsequently, the sample was evaporated, reconstituted in anhydrous ethyl acetate, and analyzed by GC-MS. The chromatographic conditions were established using a capillary column containing 5% diphenyl-95% dimethylpolysiloxane (30 m × 0.25 mm × 0.25 µm), an injector temperature set to 280 ºC, with a temperature ramp starting at 140 ºC and increasing up to 215 ºC at a flow rate of 1 mL/min to a total run of 12.32 min. Results: As preliminary data indicate, the derivatization procedure allowed the formation of 4 diastereomers of 1,3-DMAA. The chromatographic conditions were optimised, allowing for the separation of the four diastereomers within 12 min. Conclusions: Derivatization and chromatographic conditions were established for enantioselective separation of 1,3-DMAA by GC-MS. Further validation of the method will be crucial for understanding the diastereomers' differential pharmacokinetics and pharmacodynamics, and consequently, the perils associated with their presence in food supplement samples.

References

1. Rodrigues, A.N.; Dinis-Oliveira, R.J. Pharmacokinetic and Toxicological Aspects of 1,3-Dimethylamylamine with Clinical and Forensic Relevance. Psychoactives (2023), 2, 222–241.

2. Vorce, S.P.; Holler, J.M.; Cawrse, B.M.; Magluilo, J. Dimethylamylamine: A Drug Causing Positive Immunoassay Results for Amphetamines. J Anal Toxicol (2011), 35,183–187.

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Published

2024-05-01

How to Cite

Mexia-de-Almeida, M., Dias da Silva, D., Dinis-Oliveira, R. J., & Ribeiro, C. (2024). Optimization of the derivatization procedure for the separation of the stereoisomers of 1,3-dimethylamylamine (1,3-DMAA) by gas chromatography - preliminary data. Scientific Letters, 1(Sup 1). https://doi.org/10.48797/sl.2024.230

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