## 3 Results and Discussion
These metabolites were assigned as 3,4-didehydrochromen-2-one derivatives since their signals revealed that they contained the basic structure of 3,4-didehydrochromen-2-one, but at a higher molecular mass. Toluic acid (peaks **54**, **55**, and **57**) and its derivatives (peaks **45**, **59**, **61**, **64**, **65**, and **66**) were predominantly detected in the in vitro cultures (as indicated in Table 1). The parental ion at \(m/z\): 137.0601 for the toluic acid generated fragments at \(m/z\): 107.0495 and 109.0652 resulting from the loss of one methyl group and the subsequent elimination of one hydroxyl group, respectively. Additionally, another fragment at \(m/z\): 121.0652 was observed due to the loss of oxygen. The characteristic fragment ions of toluic acid were also detected for its derivatives in the mass spectrum. Additionally, two picen isomers (peaks **56** and **58**) were detected in all systems. The pseudomolecular ion at \(m/z\): 299.1123 of the picen generated fragments at \(m/z\): 137.0601, 121.0652, and 107.0496. The fragments at \(m/z\): 137.0601 and 121.0652 were generated due to the loss of the glycosidic moiety from the basic phenolic structure and the subsequent elimination of one water molecule, respectively. On the other hand, the fragment at \(m/z\): 121.0652 was produced by the loss of hexose along with water and one methyl group. Lauryldiethanolamine isomers, compounds **60** and **63**, were identified based on their respective parental ion at a \(m/z\): 274.2755, which generated fragment ions at \(m/z\): 256.2643 and 230.2486. These fragments were observed due to the loss of water and the subsequent elimination of one ethyl group, respectively. Another fragment at \(m/z\): 102.0916 was produced by the loss of a C\({}_{6}\)H\({}_{24}\) radical. Similarly, compound **62**, identified as 4-amino-2-dodecylethrahydro-3-furanol, exhibited a fragment at \(m/z\): 254.2491, which was generated by the loss of water. Four alibendol isomers (compounds **68**, **69**, **70**, and **72**) were detected in all the analyzed tissues. For this metabolite, the pseudomolecular ion at \(m/z\): 252.1243 generated fragments at \(m/z\): 196.0610, which was produced by losing one methyl and C\({}_{3}\)H\({}_{6}\) radical. Similarly, fragments at \(m/z\): 122.0600 ([M+H-C\({}_{2}\)H\({}_{7}\)O-H\({}_{2}\)O-CH\({}_{4}\)O-C\({}_{3}\)H\({}_{6}\)]\({}^{+}\))and 178.0504 ([M+H-OH-CH\({}_{3}\)-C\({}_{3}\)H\({}_{6}\)]\({}^{+}\)) were also observed. Finally, compound **77**, identified as 2-[dodecyl(methyl)amino] acetic acid, was exclusively detected in the callus tissue, with a fragment at \(m/z\): 240.2334 generated due to the loss of water. According to our analyses, no alkaloids with strong psychotropic properties reported in the literature were found in the C. _macromeris_ plant extracts. On the other hand, in the callus tissue, we observed molecules that were structurally related to alkaloids with recognized psychotropic properties such as 3,4,5-triethoxypheneethylamine, which is corelatedwith the mescaline present in _Lophophora williamsii_[45]. [PERSON], [PERSON], [PERSON], [PERSON], and [PERSON] [41] evaluated the presence of alkaloids in one herbal product that was sold as incense in Japan, and they identified, using chromatographic and spectrometric approaches, two hallucinogenic phenethylamines (normacromerine and macromerine); additionally, by means of DNA sequence analyses, they found that the psychotropic product may include _C. macromeris_ as one of its constituents. Similarly, in a series of papers, [PERSON] and [PERSON] [47], [PERSON] et al. [48], and [PERSON] [49] reported the presence of alkaloids such as macromerine and normacromerine in _C. macromeris_ sp. Runyonii, suggesting that--in past decades--this plant species was promoted as a natural and legal psychedelic agent; nevertheless, we did not find the reported molecules, suggesting that among the varieties there may exist phytochemical differences.