Publication
Optimization of the derivatization procedure for the separation of the stereoisomers of 1,3-dimethylamylamine (1,3-DMAA) by gas chromatography - preliminary data
| dc.contributor.author | Almeida, Maria Mexia de | |
| dc.contributor.author | Silva, Diana Dias da | |
| dc.contributor.author | Oliveira, Ricardo Jorge Dinis | |
| dc.contributor.author | Ribeiro, Cláudia | |
| dc.contributor.author | Dias da Silva, Diana Cristina | |
| dc.date.accessioned | 2025-10-28T14:46:14Z | |
| dc.date.available | 2025-10-28T14:46:14Z | |
| dc.date.issued | 2024-05-01 | |
| dc.description.abstract | 1,3-Dimethylamylamine (1,3-DMAA),also known as methylhexanamine, is a central nervous system stimulant with structural similarities with amphetamines and therefore presenting over-lapping biological and detrimental effects [1]. Despite being banned, the presence of 1,3-DMAA in dop-ing controls and dietary supplements continues to be of significant concern. This molecule has two stere-ogenic centres and thus four stereoisomers [2]. It is widely recognized that enantiomers may exhibit dif-ferent 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. 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. 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 chroma-tographic conditions were established using a capillary column containing 5% diphenyl-95% dime-thylpolysiloxane (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 diastere-omers of 1,3-DMAA. The chromatographic conditions were optimised, allowing for the separation of the four diastereomers within 12 min. 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. | por |
| dc.identifier.citation | Mexia-de-Almeida, M., Silva, D. D. da, 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 | |
| dc.identifier.doi | 10.48797/sl.2024.230 | |
| dc.identifier.issn | 2795-5117 | |
| dc.identifier.uri | http://hdl.handle.net/10400.22/30694 | |
| dc.language.iso | eng | |
| dc.peerreviewed | yes | |
| dc.publisher | IUCS-CESPU Publishing | |
| dc.relation.hasversion | https://publicacoes.cespu.pt/index.php/sl/article/view/230 | |
| dc.rights.uri | http://creativecommons.org/licenses/by/4.0/ | |
| dc.subject | Enantioselectivity | |
| dc.subject | Dietary supplements | |
| dc.subject | Chromatographic analysis | |
| dc.title | Optimization of the derivatization procedure for the separation of the stereoisomers of 1,3-dimethylamylamine (1,3-DMAA) by gas chromatography - preliminary data | por |
| dc.type | conference poster | |
| dspace.entity.type | Publication | |
| oaire.citation.conferenceDate | 2024-05 | |
| oaire.citation.conferencePlace | Porto | |
| oaire.citation.issue | Sup1 | |
| oaire.citation.title | Scientific Letters - III TOXRUN International Congress | |
| oaire.citation.volume | 1 | |
| oaire.version | http://purl.org/coar/version/c_970fb48d4fbd8a85 | |
| person.familyName | Dias da Silva | |
| person.givenName | Diana Cristina | |
| person.identifier.ciencia-id | 7715-CF06-F0B5 | |
| person.identifier.orcid | 0000-0002-7331-9157 | |
| relation.isAuthorOfPublication | 1f32faf1-efa5-4ea0-982d-a755e1940abf | |
| relation.isAuthorOfPublication.latestForDiscovery | 1f32faf1-efa5-4ea0-982d-a755e1940abf |