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Triptamina sustituida

Estructura de las triptaminas sustituidas. La triptamina se obtiene cuando R4=R5=RN1 = RN2 = Rα=H.
La estructura de las triptaminas sustituidas con todas las posiciones etiquetadas.

Las triptaminas sustituidas , o análogos de la serotonina , son compuestos orgánicos que pueden considerarse derivados de la propia triptamina . Las estructuras moleculares de todas las triptaminas contienen un anillo indólico , unido a un grupo amino (NH2 ) a través de una cadena lateral etilo (−CH2–CH2−) . En las triptaminas sustituidas, el anillo indólico, la cadena lateral y/o el grupo amino se modifican sustituyendo otro grupo por uno de los átomos de hidrógeno (H).

Las triptaminas más conocidas son la serotonina , un importante neurotransmisor , y la melatonina , una hormona que interviene en la regulación del ciclo sueño-vigilia. Los alcaloides de triptamina se encuentran en hongos , plantas y animales ; y a veces los utilizan los seres humanos por los efectos neurológicos o psicotrópicos de la sustancia. Entre los ejemplos destacados de alcaloides de triptamina se incluyen la psilocibina (de los " hongos psilocibios ") y la DMT . En América del Sur, la dimetiltriptamina se obtiene de numerosas fuentes vegetales, como la chacruna , y se utiliza a menudo en brebajes de ayahuasca . También se han elaborado muchas triptaminas sintéticas , incluido el fármaco para la migraña sumatriptán y las drogas psicodélicas . Un estudio de 2022 ha descubierto que la variedad de triptaminas presentes en los hongos silvestres puede afectar al impacto terapéutico. [1]

La estructura de la triptamina, en particular su anillo indólico, puede formar parte de la estructura de algunos compuestos más complejos, como por ejemplo: LSD , ibogaína , mitragynina y yohimbina . Ann y Alexander Shulgin publicaron una investigación exhaustiva de docenas de compuestos de triptamina bajo el título TiHKAL .

Lista de triptaminas sustituidas

List of substituted α-alkyltryptamines

α-Alkyltryptamines are a group of substituted tryptamines which possess an alkyl group, such as a methyl or ethyl group, attached at the alpha carbon, and in most cases no substitution on the amine nitrogen.[19][20][21] α-Alkylation of tryptamine makes it much more metabolically stable and resistant to degradation by monoamine oxidase, resulting in increased potency and greatly lengthened half-life.[21] This is analogous to α-methylation of phenethylamine into amphetamine.[21]

Many α-alkyltryptamines are drugs, acting as monoamine releasing agents, non-selective serotonin receptor agonists, and/or monoamine oxidase inhibitors,[22][23][24][25] and produce psychostimulant, entactogen, and/or psychedelic effects.[19][20][21] The most well-known of these agents are α-methyltryptamine (αMT) and α-ethyltryptamine (αET), both of which were used clinically as antidepressants for a brief period of time in the past and are abused as recreational drugs.[20][21] In accordance with its action as a dual releasing agent of serotonin and dopamine, αET has been found to produce serotonergic neurotoxicity similarly to amphetamines like MDMA and PCA, and the same is also likely to hold true for other serotonin and dopamine-releasing α-alkyltryptamines such as αMT, 5-MeO-αMT, and various others.[26]

Related compounds

A number of related compounds are known, with a similar structure but having the indole core flipped and/or replaced with related cores such as indoline, indazole, benzothiophene, or benzofuran. These similarly are primarily active as agonists at the 5-HT2 family of serotonin receptors, with applications in the treatment of glaucoma, cluster headaches or as anorectics.

Further reading

See also

References

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