| Drug Name: | Norpsilocin |
| Width: | 200px |
| Cas Number: | 28363-70-4 |
| Pubchem: | 14107683 |
| Chemspiderid: | 27283888 |
| Chembl: | 4648350 |
| Iupac Name: | 3-[2-(methylamino)ethyl]-1H-indol-4-ol |
| C: | 11 |
| H: | 14 |
| N: | 2 |
| O: | 1 |
| Smiles: | CNCCC1=CNC2=C1C(=CC=C2)O |
| Stdinchi: | 1S/C11H14N2O/c1-12-6-5-8-7-13-9-3-2-4-10(14)11(8)9/h2-4,7,12-14H,5-6H2,1H3 |
| Stdinchikey: | MTJOWJUQGYWRHT-UHFFFAOYSA-N |
Norpsilocin, also known as 4-hydroxy-N-methyltryptamine (4-HO-NMT), is a tryptamine alkaloid recently discovered in 2017 in the psychedelic mushroom Psilocybe cubensis.[1] [2] It is hypothesized to be a dephosphorylated metabolite of baeocystin.
Norpsilocin was found to be a near full agonist of the 5-HT2A receptor and was found to be more potent than psilocin.[3] [4] It also has affinity for other serotonin receptors. Moreover, it has been found to cross the blood–brain barrier in animals and to have good metabolic stability similarly to psilocin.[5]
Surprisingly however, norpsilocin failed to induce the head-twitch response, a behavioral proxy of psychedelic effects, in animals. Likewise, norbaeocystin and aeruginascin failed to induce the head-twitch response. Only psilocybin was effective in this regard. In any case, norbaeocystin showed antidepressant-like activity (forced swim test) similarly to psilocybin and fluoxetine in spite of its putative non-hallucinogenic nature. Norpsilocin itself was not tested in this assay.
Norpsilocin is being evaluated under the developmental code name PLZ-1017 for the possible treatment of pervasive developmental disorders in children.[6]