28363-70-4
Chemical Structure
Norpsilocin
Synonym(s): 4-Hydroxy-N-methyltryptamine; 4-HO-NMT
- CAS No.: 28363-70-4
- Formula:C11H14N2O
- Molecular Weight:190.24
InChIKey: MTJOWJUQGYWRHT-UHFFFAOYSA-N
SMILES: OC1=CC=CC2=C1C(CCNC)=CN2
Biological Activity: Norpsilocin (4-hydroxy-N-methyltrypt amine; 4-HO-NMT) is a natural tryptamine alkaloid isolated from the hallucinogenic mushroom Psilocybe cubensis. Norpsilocin activates human 5-HT2 receptors (5-HT2A: EC50 = 8.4 nM; 5-HT2B = 12.8 nM; 5-HT2C = 39.6 nM) and displays binding affinity toward 5-HT1 receptors (5-HT1B: Ki = 212 nM; 5-HT1D = 48.9 nM; 5-HT1E = 81.7 nM). Norpsilocin induces β-arrestin recruitment at the 5-HT1B receptor. Norpsilocin fails to produce psychedelic-like effects in mice, whereas high doses can induce hypothermia in vivo. Norpsilocin acts as an important research tool for exploring the structure–activity relationship of tryptamine hallucinogens and the pharmacology of serotonin receptors[1][2][3][4].
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Norpsilocin | Norpsilocin (4-hydroxy-N-methyltrypt amine; 4-HO-NMT) is a natural tryptamine alkaloid isolated from the hallucinogenic mushroom Psilocybe cubensis. Norpsilocin activates human 5-HT2 receptors (5-HT2A: EC50 = 8.4 nM; 5-HT2B = 12.8 nM; 5-HT2C = 39.6 nM) and displays binding affinity toward 5-HT1 receptors (5-HT1B: Ki = 212 nM; 5-HT1D = 48.9 nM; 5-HT1E = 81.7 nM). Norpsilocin induces β-arrestin recruitment at the 5-HT1B receptor. Norpsilocin fails to produce psychedelic-like effects in mice, whereas high doses can induce hypothermia in vivo. Norpsilocin acts as an important research tool for exploring the structure–activity relationship of tryptamine hallucinogens and the pharmacology of serotonin receptors. | |||||||||||||||||||||
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References
- [1]. Lenz C, et al. Identification of ω-N-Methyl-4-hydroxytryptamine (Norpsilocin) as a Psilocybe Natural Product. Journal of natural products. 2017 Oct 27;80(10):2835-2838.
- [2]. Sherwood AM, et al. Synthesis and Biological Evaluation of Tryptamines Found in Hallucinogenic Mushrooms: Norbaeocystin, Baeocystin, Norpsilocin, and Aeruginascin. J Nat Prod. 2020 Feb 28;83(2):461-467. [Content Brief]
- [3]. Sherwood AM, et al. Psychedelic-like Activity of Norpsilocin Analogues. ACS chemical neuroscience. 2024 Jan 17;15(2):315-327.
