## 3 Results and Discussion  
In this work, we analyzed the alkaloid and nitrogenated compounds profile of \(C\). _macromeris_ plants and cell cultures. In previous reports, we presented the phenolic profile of this plant species, thereby finding that the in vitro cultures had the potential for a biosynthesis of the selected compounds [32; 33; 34; 36]. Regarding the alkaloid and nitrogenated compound profiles analyzed in this work, the chromatographic profile (Figure 1) indicated the presence of 78 compounds. Among the detected compounds, 61 of them were identified. Within the identified compounds, the in vitro plants presented 24 metabolites, the greenhouse plants a total of 21, and the callus tissue 16 compounds. On the other hand, since the spectrometric evidence existent in the literature did not match with the generated spectrometric information, 17 compounds were not identified. It has been proposed that this \(C\). _macromeris_ is traditionally employed for healing stomach disorders and for hallucinogenic purposes; nevertheless, for this last activity, few reports exist in the literature. In this work, we were not able to find psychotropic metabolites that may support the hallucinogenic functionality; nevertheless, some of the identified compounds are structurally related to alkaloids with recognized pharmacological properties. Figure 1: _Cont._  
Figure 1: UHPLC profiles of the alkaloid and nitrogenated compounds present in _C. macromeris_. The separation profile was obtained using extracts prepared with aerial (**a**) and radicular (**b**) sections of the plants cultivated under in vitro conditions for 12 weeks. The aerial (**c**) and radicular (**d**) sections of plants growing under greenhouse conditions for one year were also analyzed and compared with the callus tissue (**e**) collected after nine weeks of culture. Compounds **6**, **11**, and **14** were assigned as N-methyltyramine and their derivatives (compounds **2**, **3**, **7**, **9**, **10**, and **12**). The parental ion for this metabolite corresponded to \(m/z\): 152.1072 and the generated fragments at \(m/z\): 121.0651 ([M + H-CH\({}_{4}\)N]+) and 103.0546 ([M + H-CH\({}_{4}\)N-OH]+) are characteristic of methyltyramine [37; 38]. These compounds were mainly detected in the radicular sections of the plants; however, the callus tissue also included two of their derivatives (compounds **3** and **9**; see Table 1). This compound is a phenethylamine that has been previously reported in other natural sources, such as _Citrus aurantium_[39], and its activities against gastrointestinal disorders have been proposed [40]. Similarly, compounds **4**, **13**, **15**, **17**, **18**, **19**, **21**, **26**, and **42** were detected in both the aerial and radicular sections of the in vitro and greenhouse plants, and it was identified as salosoline. For this metabolite, the pseudomolecular ion at \(m/z\): 194.1175 generated fragments at \(m/z\): 148.0759, 121.0651, 118.0654, and 104.0497 (see Figure 2a). This metabolite is structurally related to anhalamine and heliamine, two tyrosine-derived alkaloids. In addition, it is structurally related to macromerine and normacromerine, two alkaloids previously reported in _C. macromeris_[41]. Other cacti species such as _Echinocereus merkeri_ have reported the presence of this metabolite [42], and its activities as an antihypertensive agent have been proposed [43]. This compound was not detected in the callus tissue (or may be present but in concentrations below the detection limits). Compounds **5** and **16** were assigned as benzocaine isomers. The fragmentation pattern analysis of these compounds indicated that the pseudomolecular ion at \(m/z\): 166.0868 generated one fragment at \(m/z\): 123.0446, which was produced by the loss of amino and one methyl group. Another fragment at \(m/z\): 107.0495 was also generated by the cleavage of the amino group and C\({}_{2}\)H\({}_{6}\)O tail.