Norpsilocin
Norpsilocin 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.
For research use only. We do not sell to patients.
- CAS No.: 28363-70-4
- Formula: C11H14N2O
- Molecular Weight:190.24
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Storage:
Please store the product under the recommended conditions in the Certificate of Analysis.
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Biological Activity
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Chemical Information
- Purity & Documentation
- References
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Help & FAQs
All 5-HT Receptor Isoforms
More
Biological Activity
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5-HT1B Receptor 212 nM (Ki) |
5-HT1D Receptor 48.9 nM (Ki) |
5-HT1E Receptor 81.7 nM (Ki) |
5-HT2A Receptor 8.4 nM (EC50) |
5-HT2B Receptor 12.8 nM (EC50) |
5-HT2C Receptor 39.6 nM (EC50) |
5-HT5A Receptor 111 nM (Ki) |
5-HT6 Receptor 305 nM (Ki) |
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Cell Line
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Type | Value | Description | References |
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| T-REx-293 | EC50 |
8.4 nM
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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.
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32077284 |
| T-REx-293 | EC50 |
19 nM
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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.
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32077284 |
Norpsilocin (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.
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:C57BL/6J (male and female, 8 weeks old)[3]
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Dosage:10 mg/kg; 30 mg/kg
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Administration:s.c.; single dose
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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
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CAS No. 28363-70-4
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Molecular Weight 190.24
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Formula C11H14N2O
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SMILES
OC1=CC=CC2=C1C(CCNC)=CN2
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Structure Classification
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Initial Source
Psilocybe cubensis
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Purity & Documentation
References
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Norpsilocin Related Classifications
HY-N20747 Related Classifications
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