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Referencia número: HY-N20747

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Norpsilocin

(Synonyms: 4-Hydroxy-N-methyltryptamine; 4-HO-NMT)

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: K_i = 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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No. CAS: 28363-70-4
Fòrmula: C₁₁H₁₄N₂O
Peso molecular:190.24

Almacenamiento:

Please store the product under the recommended conditions in the Certificate of Analysis.

Norpsilocin Chemical Structure

No. CAS: 28363-70-4

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Fluorescent Dye

Strong Fluorescence Signal / Multi-Disciplinary Applications / High Fluorescence Specificity

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- Descripciòn
- IC₅₀ & Target
- Cellular Effect
- In Vitro
- In Vivo
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Actividad biológica

Descripciòn

IC₅₀ & Target^[3]^[2]

5-HT_1B Receptor

212 nM (Ki)

5-HT_1D Receptor

48.9 nM (Ki)

5-HT_1E Receptor

81.7 nM (Ki)

5-HT_2A Receptor

8.4 nM (EC₅₀)

5-HT_2B Receptor

12.8 nM (EC₅₀)

5-HT_2C Receptor

39.6 nM (EC₅₀)

5-HT_5A Receptor

111 nM (Ki)

5-HT₆ Receptor

305 nM (Ki)

Ver todos los productos específicos de isoformas 5-HT Receptor :

Cellular Effect

Cell Line	Type	Value	Description	References
T-REx-293	EC50	8.4 nM	Agonist activity in Gq-mediated calcium flux assay using human 5-HT₂ₐ receptor-expressing Flp-In T-REx 293 cells, measured as peak fluorescence normalized to 5-HT (100%) baseline after single treatment with norpsilocin. Agonist activity in Gq-mediated calcium flux assay using human 5-HT₂ₐ receptor-expressing Flp-In T-REx 293 cells, measured as peak fluorescence normalized to 5-HT (100%) baseline after single treatment with norpsilocin.	32077284
T-REx-293	EC50	19 nM	Agonist activity in Gq-mediated calcium flux assay using mouse 5-HT₂ₐ receptor-expressing Flp-In T-REx 293 cells, measured as peak fluorescence normalized to 5-HT (100%) baseline after single treatment with norpsilocin. Agonist activity in Gq-mediated calcium flux assay using mouse 5-HT₂ₐ receptor-expressing Flp-In T-REx 293 cells, measured as peak fluorescence normalized to 5-HT (100%) baseline after single treatment with norpsilocin.	32077284

In Vitro

Norpsilocin (4-hydroxy-N-methyltrypt amine; 4-HO-NMT) (18 h) is isolated as an amorphous, colorless solid from Psilocybe cubensis FSU12407 carpophores^[1].
Norpsilocin (18 h) is a consistent natural product across multiple Psilocybe cubensis strains, with its relative concentration in carpophores increasing under aqueous, room-temperature processing conditions that promote dephosphorylation^[1].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

Norpsilocin (4-hydroxy-N-methyltrypt amine; 4-HO-NMT) (10-30 mg/kg; s.c.; single dose) does not elicit psychedelic-like HTR activity in mice at doses up to 30 mg/kg, but induces hypothermia at high doses^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:

C57BL/6J (male and female, 8 weeks old)^[3]
Dosage:

10 mg/kg; 30 mg/kg
Administration:

s.c.; single dose
Result:

Did not induce psychedelic-like head twitch response activity at doses up to and including 30 mg/kg.
Produced dose-related hypothermia at doses of 10 and 30 mg/kg.

Chemical Information

No. CAS 28363-70-4
Peso molecular 190.24
Fòrmula C₁₁H₁₄N₂O
SMILES

OC1=CC=CC2=C1C(CCNC)=CN2
Synonyms

4-Hydroxy-N-methyltryptamine; 4-HO-NMT
Structure Classification
- Alkaloids
- Indole Alkaloids
- Phenols
- Monophenols
Initial Source
- Microorganisms
Psilocybe cubensis
Envío

Room temperature in continental US; may vary elsewhere.
Almacenamiento

Please store the product under the recommended conditions in the Certificate of Analysis.

Pureza y Documentación

Instrucciones de manejo (2659 KB)

Referencias

[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.

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Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

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100 mg

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Actividad biológica
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Norpsilocin

Ver todos los productos específicos de isoformas 5-HT Receptor

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Norpsilocin Related Classifications

HY-N20747 Related Classifications