4-HO-TMT

Clinical data
Other names	4-OH-TMT; 4-hydroxy-N,N,N-trimethyltryptammonium; 4-Hydroxy-N,N,N-trimethyltryptamine; 4-HO-N,N,N-TMT; Dephosphorylated aeruginascin; Dephosphorylaeruginascin
Drug class	Serotonin receptoragonist
ATC code	None
Identifiers
IUPAC name 2-(4-hydroxy-1H-indol-3-yl)ethyl-trimethylazanium
CAS Number	262285-41-6 Y
PubChemCID	17868117
ChemSpider	13318696
ChEBI	CHEBI:193061
Chemical and physical data
Formula	C13H19N2O+
Molar mass	219.308 g·mol−1
3D model (JSmol)	Interactive image
SMILES C[N+](C)(C)CCC1=CNC2=C1C(=CC=C2)O
InChI 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, or4-OH-TMT, also known as4-hydroxy-N,N,N-trimethyltryptammonium or asdephosphorylated aeruginascin, is asubstituted tryptaminederivative and theactive form ofaeruginascin (4-PO-TMT), analogously to howpsilocin (4-HO-DMT) is the active form ofpsilocybin (4-PO-DMT).^{[1][2][3][4][5]} 4-HO-TMT is closely related tobufotenidine, theN-trimethylanalogue ofserotonin.^[1]

Likepsilocin, 4-HO-TMT showsaffinity for theserotonin5-HT_1A,5-HT_2A, and5-HT_2B 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, theEC₅₀Tooltip half-maximal effective concentration value of 4-HO-TMT in activating the serotonin 5-HT_2A receptor was 324-fold lower than that of psilocin (6,800 nM and 21 nM, respectively).^[2] Similarly to psilocin, 4-HO-TMT does not bind to the serotonin5-HT₃ receptor.^[1] This was in contrast to predictions, as the related compound bufotenidine is a strong andselective serotonin 5-HT₃ receptoragonist.^[1]

4-HO-TMT is aquaternarytrimethyl ammonium compound, and as a result, is less likely to be able to cross theblood–brain barrier (BBB) and enter thecentral nervous system than other tryptamines.^[1][4] Accordingly, 4-HO-TMT showed no ability to cross an artificial BBB-likemembrane in a study.^[2] In rodents, 4-HO-TMT showed nohead-twitch response (a behavioral proxy ofpsychedelic effects),hypolocomotion, orhypothermia, in contrast to psilocin andnorpsilocin, but similarly to aeruginascin.^[3]

Asyntheticprodrug of 4-HO-TMT, 4-AcO-TMT, has been developed.^[1][5] It is analogous topsilacetin (4-AcO-DMT), a prodrug of psilocin.^[1][5]

• Substituted tryptamine

• 4-OH-TMT⁺ - Isomer Design

• Drugs not assigned an ATC code
• Dimethylamino compounds
• Human drug metabolites
• 4-Hydroxytryptamines
• Mycotoxins
• Non-hallucinogenic 5-HT2A receptor agonists
• Peripherally selective drugs
• Quaternary ammonium compounds
• Serotonin receptor agonists
• N,N,N-Trialkyltryptamines
• Tryptamine alkaloids

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• Short description matches Wikidata
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