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4-HO-TMT

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4-HO-TMT
Clinical data
Other names4-OH-TMT; 4-Hydroxy-N,N,N-trimethyltryptamine; 4-HO-N,N,N-TMT; Dephosphorylated aeruginascin; Dephosphorylaeruginascin
Drug classSerotonin receptor agonist
Identifiers
  • 2-(4-hydroxy-1H-indol-3-yl)ethyl-trimethylazanium
PubChem CID
ChemSpider
ChEBI
Chemical and physical data
FormulaC13H19N2O+
Molar mass219.308 g·mol−1
3D model (JSmol)
  • C[N+](C)(C)CCC1=CNC2=C1C(=CC=C2)O
  • InChI=1S/C13H18N2O/c1-15(2,3)8-7-10-9-14-11-5-4-6-12(16)13(10)11/h4-6,9,14H,7-8H2,1-3H3/p+1
  • Key:RMPOMMZKJNCOTM-UHFFFAOYSA-O

4-HO-TMT, or 4-OH-TMT, also known as 4-hydroxy-N,N,N-trimethyltryptamine or as dephosphorylated aeruginascin, is a substituted tryptamine derivative and the active form of aeruginascin (4-PO-TMT), analogously to how psilocin (4-HO-DMT) is the active form of psilocybin (4-PO-DMT).[1][2][3][4][5] 4-HO-TMT is closely related to bufotenidine, the N-trimethyl analogue of serotonin.[1]

Like psilocin, 4-HO-DMT shows affinity for the serotonin 5-HT1A, 5-HT2A, and 5-HT2B receptors.[1][5][4] However, its affinities for these receptors are lower than those of psilocin (by 8-, 6-, and 26-fold, respectively).[1][5][4] Additionally, in another study, the EC50Tooltip half-maximal effective concentration value of 4-HO-TMT in activating the serotonin 5-HT2A receptor was 324-fold lower than that of psilocin (6800 and 21 nM, respectively).[2] Similarly to psilocin, 4-HO-TMT does not bind to the serotonin 5-HT3 receptor.[1] This was in contrast to predictions, as the related compound bufotenidine is a strong and selective serotonin 5-HT3 receptor agonist.[1]

4-HO-TMT is a quaternary trimethyl ammonium compound, and as a result, is less likely to be able to cross the blood–brain barrier (BBB) and enter the central nervous system than other tryptamines.[1][4] Accordingly, 4-HO-TMT showed no ability to cross an artificial BBB-like membrane in a study.[2] In rodents, 4-HO-TMT showed no head-twitch response (a behavioral proxy of psychedelic effects), hypolocomotion, or hypothermia, in contrast to psilocin and norpsilocin, but similarly to aeruginascin.[3]

A synthetic prodrug of 4-HO-TMT, 4-AcO-TMT, has been developed.[1][5] It is analogous to psilacetin (4-AcO-DMT), a prodrug of psilocin.[1][5]

References

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  1. ^ a b c d e f g h i Chadeayne AR, Pham DN, Reid BG, Golen JA, Manke DR (July 2020). "Active Metabolite of Aeruginascin (4-Hydroxy-N,N,N-trimethyltryptamine): Synthesis, Structure, and Serotonergic Binding Affinity". ACS Omega. 5 (27): 16940–16943. doi:10.1021/acsomega.0c02208. ISSN 2470-1343. PMC 7365549. PMID 32685863.
  2. ^ a b c Rakoczy RJ, Runge GN, Sen AK, Sandoval O, Wells HG, Nguyen Q, Roberts BR, Sciortino JH, Gibbons WJ, Friedberg LM, Jones JA, McMurray MS (October 2024). "Pharmacological and behavioural effects of tryptamines present in psilocybin-containing mushrooms". Br J Pharmacol. 181 (19): 3627–3641. doi:10.1111/bph.16466. PMID 38825326.
  3. ^ a b Glatfelter GC, Pottie E, Partilla JS, Sherwood AM, Kaylo K, Pham DN, Naeem M, Sammeta VR, DeBoer S, Golen JA, Hulley EB, Stove CP, Chadeayne AR, Manke DR, Baumann MH (November 2022). "Structure-Activity Relationships for Psilocybin, Baeocystin, Aeruginascin, and Related Analogues to Produce Pharmacological Effects in Mice". ACS Pharmacol Transl Sci. 5 (11): 1181–1196. doi:10.1021/acsptsci.2c00177. PMC 9667540. PMID 36407948.
  4. ^ a b c d Chue, P.; Andreiev, A.; Bucuci, E.; Els, C.; Chue, J. (2022). "A Review of Aeruginascin and Potential Entourage Effect in Hallucinogenic Mushrooms". European Psychiatry. 65 (S1). Royal College of Psychiatrists: S885. doi:10.1192/j.eurpsy.2022.2297. ISSN 0924-9338.
  5. ^ a b c d e Glatfelter GC, Pham DN, Walther D, Golen JA, Chadeayne AR, Baumann MH, Manke DR (July 2022). "Synthesis, Structural Characterization, and Pharmacological Activity of Novel Quaternary Salts of 4-Substituted Tryptamines". ACS Omega. 7 (28): 24888–24894. doi:10.1021/acsomega.2c03476. PMC 9301952. PMID 35874244.
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