<\/figure><\/div>\n\n\n\nFigure 1.<\/strong> Numbered substitutions on the tryptamine core<\/em><\/p>\n\n\n\nFigure 1 (above) illustrates ten positions at which tryptamines can be modified to create structural analogs. Since 2016, CaaMTech has worked on first making compounds within the above genus and then correlating structural variations between those compounds with changes in a compound\u2019s properties. <\/p>\n\n\n\n
For example, removing one of the methyl groups from psilocin at R1, R2, or R3 results in norpsilocin. Unlike psilocin, norpsilocin does not elicit a head twitch response (HTR) when administered to mice, suggesting that this one structural modification eliminates the compound\u2019s \u201cpsychedelic\u201d properties. Understanding how these and other structural variations can be used to create particular pharmacological properties requires comparing many pure, well-characterized compounds.<\/p>\n\n\n\n
\u201cI\u2019m really proud of this publication because it illustrates CaaMTech\u2019s work in modifying each of the different positions around the tryptamine core,\u201d explains CaaMTech CEO, Dr. Andrew Chadeayne. \u201cWith more compounds, we can make more comparisons, and better decisions.\u201d<\/p>\n\n\n\n
The paper illustrates tryptamine analogs (Figure 2, below) with modifications at five different positions: R5, R6, R7, R8, R9, and R10 in Figure 1. Previous work has exhaustively evaluated variations to the other positions. To allow for direct comparisons between the compounds without needing to account for potential differences between salt forms, the nine structures published in the paper are all hydrochloride salts. Notably, the nine structures in the paper are also all primary amines, making them near analogs of serotonin (5-HT or 5-hydroxytryptamine), which is the neurotransmitter targeted by psychedelic drugs, many antidepressants (e.g. SSRIs), and migraine drugs. <\/p>\n\n\n\n
<\/figure><\/div>\n\n\n\nFigure 2.<\/strong> Nine serotonin analogs crystallographically characterized by CaaMTech<\/em><\/p>\n\n\n\n\u201cGiven the importance of serotonin, the limited set of crystallographic data for compounds like these is surprising,\u201d said Dr. David R. Manke, Professor at UMass Dartmouth and co-author of the paper. \u201cWe have come across several situations where solving the crystal structure reveals unexpected discrepancies in a compound\u2019s molecular weight, which could introduce errors in biological studies.\u201d<\/p>\n\n\n\n
\n\n\n\nPham, D. N. K., Belanger, Z. S., Chadeayne, A. R., Golen, J. A., & Manke, D. R. (2021). The crystalline forms of nine hydrochloride salts of substituted tryptamines. Acta Crystallographica Section C Structural Chemistry, 77(10). https:\/\/doi.org\/10.1107\/s2053229621008950<\/a><\/li><\/ol>\n\n\n\n<\/p>\n","protected":false},"excerpt":{"rendered":"
Serotonin is a tryptamine-based human neurotransmitter responsible for a variety of complex biological functions<\/p>\n","protected":false},"author":1,"featured_media":365,"comment_status":"open","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[5],"tags":[],"acf":[],"_links":{"self":[{"href":"https:\/\/caam.tech\/wp-json\/wp\/v2\/posts\/362"}],"collection":[{"href":"https:\/\/caam.tech\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/caam.tech\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/caam.tech\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/caam.tech\/wp-json\/wp\/v2\/comments?post=362"}],"version-history":[{"count":0,"href":"https:\/\/caam.tech\/wp-json\/wp\/v2\/posts\/362\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/caam.tech\/wp-json\/wp\/v2\/media\/365"}],"wp:attachment":[{"href":"https:\/\/caam.tech\/wp-json\/wp\/v2\/media?parent=362"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/caam.tech\/wp-json\/wp\/v2\/categories?post=362"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/caam.tech\/wp-json\/wp\/v2\/tags?post=362"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}