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1-Methylpsilocin

Potent and selective 5-HT2C agonist CAS# 1465-16-3

1-Methylpsilocin

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Chemical structure

1-Methylpsilocin

3D structure

Chemical Properties of 1-Methylpsilocin

Cas No. 1465-16-3 SDF Download SDF
PubChem ID 44404883 Appearance Powder
Formula C13H18N2O M.Wt 218.29
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble to 100 mM in DMSO and to 10 mM in ethanol
Chemical Name 3-[2-(dimethylamino)ethyl]-1-methylindol-4-ol
SMILES CN1C=C(C2=C1C=CC=C2O)CCN(C)C
Standard InChIKey MZZRFEIDRWKTKJ-UHFFFAOYSA-N
Standard InChI InChI=1S/C13H18N2O/c1-14(2)8-7-10-9-15(3)11-5-4-6-12(16)13(10)11/h4-6,9,16H,7-8H2,1-3H3
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of 1-Methylpsilocin

DescriptionPotent and selective 5-HT2C agonist (IC50 values are 12 and 633 nM for 5-HT2C and 5-HT2A receptors respectively). Displays high affinity for the 5-HT2B receptor (Ki = 38 nM) but acts as an inverse agonist. Active in vivo; inhibits scratching in a mouse model of OCD.

1-Methylpsilocin Dilution Calculator

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1-Methylpsilocin Molarity Calculator

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Preparing Stock Solutions of 1-Methylpsilocin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.5811 mL 22.9053 mL 45.8106 mL 91.6212 mL 114.5265 mL
5 mM 0.9162 mL 4.5811 mL 9.1621 mL 18.3242 mL 22.9053 mL
10 mM 0.4581 mL 2.2905 mL 4.5811 mL 9.1621 mL 11.4527 mL
50 mM 0.0916 mL 0.4581 mL 0.9162 mL 1.8324 mL 2.2905 mL
100 mM 0.0458 mL 0.2291 mL 0.4581 mL 0.9162 mL 1.1453 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on 1-Methylpsilocin

Support for 5-HT2C receptor functional selectivity in vivo utilizing structurally diverse, selective 5-HT2C receptor ligands and the 2,5-dimethoxy-4-iodoamphetamine elicited head-twitch response model.[Pubmed:23353901]

Neuropharmacology. 2013 Jul;70:112-21.

There are seemingly conflicting data in the literature regarding the role of serotonin (5-HT) 5-HT2C receptors in the mouse head-twitch response (HTR) elicited by the hallucinogenic 5-HT2A/2B/2C receptor agonist 2,5-dimethoxy-4-iodoamphetamine (DOI). Namely, both 5-HT2C receptor agonists and antagonists, regarding 5-HT2C receptor-mediated Gq-phospholipase C (PLC) signaling, reportedly attenuate the HTR response. The present experiments tested the hypothesis that both classes of 5-HT2C receptor compounds could attenuate the DOI-elicited-HTR in a single strain of mice, C57Bl/6J. The expected results were considered in accordance with ligand functional selectivity. Commercially-available 5-HT2C agonists (CP 809101, Ro 60-0175, WAY 161503, mCPP, and 1-Methylpsilocin), novel 4-phenyl-2-N,N-dimethyl-aminotetralin (PAT)-type 5-HT2C agonists (with 5-HT2A/2B antagonist activity), and antagonists selective for 5-HT2A (M100907), 5-HT2C (SB-242084), and 5-HT2B/2C (SB-206553) receptors attenuated the DOI-elicited-HTR. In contrast, there were differential effects on locomotion across classes of compounds. The 5-HT2C agonists and M100907 decreased locomotion, SB-242084 increased locomotion, SB-206553 resulted in dose-dependent biphasic effects on locomotion, and the PATs did not alter locomotion. In vitro molecular pharmacology studies showed that 5-HT2C agonists potent for attenuating the DOI-elicited-HTR also reduced the efficacy of DOI to activate mouse 5-HT2C receptor-mediated PLC signaling in HEK cells. Although there were differences in affinities of a few compounds at mouse compared to human 5-HT2A or 5-HT2C receptors, all compounds tested retained their selectivity for either receptor, regardless of receptor species. Results indicate that 5-HT2C receptor agonists and antagonists attenuate the DOI-elicited-HTR in C57Bl/6J mice, and suggest that structurally diverse 5-HT2C ligands result in different 5-HT2C receptor signaling outcomes compared to DOI.

Differential contributions of serotonin receptors to the behavioral effects of indoleamine hallucinogens in mice.[Pubmed:21148021]

J Psychopharmacol. 2011 Nov;25(11):1548-61.

Psilocin (4-hydroxy-N,N-dimethyltryptamine) is a hallucinogen that acts as an agonist at 5-HT(1A), 5-HT(2A), and 5-HT(2C) receptors. Psilocin is the active metabolite of psilocybin, a hallucinogen that is currently being investigated clinically as a potential therapeutic agent. In the present investigation, we used a combination of genetic and pharmacological approaches to identify the serotonin (5-HT) receptor subtypes responsible for mediating the effects of psilocin on head twitch response (HTR) and the behavioral pattern monitor (BPM) in C57BL/6J mice. We also compared the effects of psilocin with those of the putative 5-HT(2C) receptor-selective agonist 1-Methylpsilocin and the hallucinogen and non-selective serotonin receptor agonist 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT). Psilocin, 1-Methylpsilocin, and 5-MeO-DMT induced the HTR, effects that were absent in mice lacking the 5-HT(2A) receptor gene. When tested in the BPM, psilocin decreased locomotor activity, holepoking, and time spent in the center of the chamber, effects that were blocked by the selective 5-HT(1A) antagonist WAY-100635 but were not altered by the selective 5-HT(2C) antagonist SB 242,084 or by 5-HT(2A) receptor gene deletion. 5-MeO-DMT produced similar effects when tested in the BPM, and the action of 5-MeO-DMT was significantly attenuated by WAY-100635. Psilocin and 5-MeO-DMT also decreased the linearity of locomotor paths, effects that were mediated by 5-HT(2C) and 5-HT(1A) receptors, respectively. In contrast to psilocin and 5-MeO-DMT, 1-Methylpsilocin (0.6-9.6 mg/kg) was completely inactive in the BPM. These findings confirm that psilocin acts as an agonist at 5-HT(1A), 5-HT(2A), and 5-HT(2C) receptors in mice, whereas the behavioral effects of 1-Methylpsilocin indicate that this compound is acting at 5-HT(2A) sites but is inactive at the 5-HT(1A) receptor. The fact that 1-Methylpsilocin displays greater pharmacological selectivity than psilocin indicates that 1-Methylpsilocin represents a potentially useful alternative to psilocybin for development as a potential therapeutic agent.

SAR of psilocybin analogs: discovery of a selective 5-HT 2C agonist.[Pubmed:16061378]

Bioorg Med Chem Lett. 2005 Oct 15;15(20):4555-9.

An SAR study of psilocybin and psilocin derivatives reveals that 1-Methylpsilocin is a selective agonist at the h5-HT(2C) receptor. The corresponding phosphate derivative, 1-methylpsilocybin, shows efficacy in an animal model for obsessive-compulsive disorder, as does 4-fluoro-N,N-dimethyltryptamine. These results suggest a new area for development of novel 5-HT(2C) agonists with applications for drug discovery.

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