4-HO-NALT

{{Short description|Chemical compound}}

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{{Drugbox

| IUPAC_name = 3-[2-(Prop-2-enylamino)ethyl]-1H-indol-4-ol

| image = 4-HO-NALT_structure.png

| width = 240

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| CAS_number = 2767428-88-4

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| PubChem = 166468743

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| C=13 | H=16 | N=2 | O=1

| smiles = C=CCNCCC1=CNC2=C1C(=CC=C2)O

| StdInChI = 1S/C13H16N2O/c1-2-7-14-8-6-10-9-15-11-4-3-5-12(16)13(10)11/h2-5,9,14-16H,1,6-8H2

| StdInChIKey = QOFKSOQRTVFMAL-UHFFFAOYSA-N

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4-Hydroxy-N-allyltryptamine (4-HO-NALT) is a tryptamine derivative developed by modification of norpsilocin (4-HO-NMT). It produces a head-twitch response in mice consistent with psychedelic-like activity, as do the corresponding ethyl, propyl, isopropyl and benzyl derivatives (4-HO-NET, 4-HO-NPT, 4-HO-NiPT and 4-HO-NBnT), but the bulkier t-butyl and cyclohexyl derivatives are inactive.{{cite journal | vauthors = Sherwood AM, Burkhartzmeyer EK, Williamson SE, Baumann MH, Glatfelter GC | title = Psychedelic-like Activity of Norpsilocin Analogues | journal = ACS Chemical Neuroscience | volume = 15 | issue = 2 | pages = 315–327 | date = January 2024 | pmid = 38189238 | pmc = 10797613 | doi = 10.1021/acschemneuro.3c00610 }}

Image:4-HO-NET, 4-HO-NPT, 4-HO-NiPT & 4-HO-NBnT structure.png