Record Information |
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Version | 2.0 |
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Creation Date | 2009-07-03 21:03:18 UTC |
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Update Date | 2014-12-24 20:25:31 UTC |
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Accession Number | T3D2458 |
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Identification |
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Common Name | Psilocin |
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Class | Small Molecule |
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Description | Psilocin (4-OH-DMT), an aromatic compound, sometimes also spelled psilocine, psilocyn, or psilotsin, is a psychedelic mushroom alkaloid. It is found in most psychedelic mushrooms together with its phosphorylated counterpart psilocybin. Psilocin is a Schedule I drug under the Convention on Psychotropic Substances. The mind-altering effects of psilocin are highly variable and subjective, but resemble those caused by LSD and mescaline. The effects typically last anywhere from three to eight hours depending on certain variables (such as metabolism, food interaction); however the effects can seem to last much longer due to psilocin's ability to distort the perception of time. Sulfur analogs are known with a benzothienyl replacement as well as 4-SH-DMT. N1-methylpsilocin is a functionally 5-HT2C receptor preferring agonists. 4-fluoro-N,N-dimethyltryptamine is known. O-Acetylpsilocin is an acetylized analog of psilocin, also known as 4-AcO-DMT. Additionally, substitution of a methyl group at the dimethylated nitrogen with an isopropyl or ethyl group yields 4-HO-MIPT (4-Hydroxy-N-Methyl-N-Isopropyltryptamine) and 4-HO-MET (4-Hydroxy-N-Methyl-N-Ethyltryptamine), respectively. |
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Compound Type | - Amine
- Food Toxin
- Fungal Toxin
- Metabolite
- Mycotoxin
- Natural Compound
- Organic Compound
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Chemical Structure | |
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Synonyms | Synonym | 3-(2-(Dimethylamino)ethyl)indol-4-ol | 3-[2-(Dimethylamino)ethyl]-1H-Indol-4-ol | 3-[2-(Dimethylamino)ethyl]-Indol-4-ol | 4-Hydroxy-N,N-dimethyltryptamine | N,N-Dimethyl-4-Hydroxytryptamine | Psilocine | Psilotsin |
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Chemical Formula | C12H16N2O |
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Average Molecular Mass | 204.268 g/mol |
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Monoisotopic Mass | 204.126 g/mol |
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CAS Registry Number | 520-53-6 |
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IUPAC Name | 3-[2-(dimethylamino)ethyl]-1H-indol-4-ol |
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Traditional Name | psilocin |
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SMILES | CN(C)CCC1=CNC2=C1C(O)=CC=C2 |
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InChI Identifier | InChI=1S/C12H16N2O/c1-14(2)7-6-9-8-13-10-4-3-5-11(15)12(9)10/h3-5,8,13,15H,6-7H2,1-2H3 |
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InChI Key | InChIKey=SPCIYGNTAMCTRO-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as tryptamines and derivatives. Tryptamines and derivatives are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Indoles and derivatives |
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Sub Class | Tryptamines and derivatives |
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Direct Parent | Tryptamines and derivatives |
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Alternative Parents | |
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Substituents | - Tryptamine
- Hydroxyindole
- 3-alkylindole
- Indole
- Alkaloid or derivatives
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Aralkylamine
- Substituted pyrrole
- Benzenoid
- Pyrrole
- Heteroaromatic compound
- Tertiary aliphatic amine
- Tertiary amine
- Azacycle
- Hydrocarbon derivative
- Organopnictogen compound
- Organic oxygen compound
- Amine
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Exogenous |
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Cellular Locations | |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | |
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Biological Roles | |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Solid |
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Appearance | White powder. |
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Experimental Properties | Property | Value |
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Melting Point | 174.5°C | Boiling Point | Not Available | Solubility | Not Available | LogP | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0a4i-9000000000-62ea72268c3ac8349f99 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0a4i-9000000000-62ea72268c3ac8349f99 | JSpectraViewer | MoNA | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4i-9200000000-4cca4e47c3bcf0ef37fc | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-0a4i-9030000000-8686b03317e1e073c475 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-0390000000-30b1cea064c20727c677 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-08fr-0940000000-3d03cc820b34ad7de95c | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01qa-2900000000-6a888d817b451f311e43 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0090000000-b5141a6d394f0df7c3ea | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-1290000000-19a265b5ec7903ebc866 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-052f-5900000000-47f31324e343d436c5c1 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-0190000000-f79ac11f836485a9a33e | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0bt9-3960000000-13e401841c5ab05a231a | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9300000000-3a3674a946d2718b7443 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0090000000-32999cb59116f2b8b325 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0890000000-c3fa63e2f7ddbfec26ec | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-0900000000-f18009588fc5bfaa3db9 | JSpectraViewer | MS | Mass Spectrum (Electron Ionization) | splash10-0a4i-9110000000-58fd69735c607f0dbac4 | JSpectraViewer | MoNA | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer |
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Toxicity Profile |
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Route of Exposure | Oral, dermal, inhalation, and parenteral (contaminated drugs). (1) |
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Mechanism of Toxicity | Psilocin acts as a partial agonist at the 5-HT2A serotonin receptor in the brain where it mimics the effects of serotonin (5-HT). It is an 5-HT1A and 5-HT2A/2C agonist. (2) |
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Metabolism | Not Available |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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Uses/Sources | Psilocin is a psychedelic (hallucinogenic) mushroom alkaloid. It is found in most psychedelic mushrooms together with its phosphorylated counterpart psilocybin. Psilocin is the pharmacologically active agent in the body after ingestion of psilocybin or psychedelic mushrooms. (2) |
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Minimum Risk Level | Not Available |
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Health Effects | Psilocin is neurotoxic and can cause hallucinations. (2) |
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Symptoms | Psilocin may cause tachycardia, dilated pupils, restlessness or arousal, euphoria, open and closed eye visuals, synesthesia, increased body temperature, headache, sweating and chills, and nausea. (2) |
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Treatment | Not Available |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | Not Available |
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HMDB ID | HMDB42000 |
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PubChem Compound ID | 4980 |
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ChEMBL ID | CHEMBL65547 |
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ChemSpider ID | 4807 |
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KEGG ID | C08312 |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | 8613 |
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BioCyc ID | Not Available |
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CTD ID | C009105 |
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Stitch ID | Psilocin |
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PDB ID | Not Available |
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ACToR ID | Not Available |
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Wikipedia Link | Psilocin |
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References |
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Synthesis Reference | Not Available |
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MSDS | T3D2458.pdf |
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General References | - Peraica M, Domijan AM: Contamination of food with mycotoxins and human health. Arh Hig Rada Toksikol. 2001 Mar;52(1):23-35. [11370295 ]
- Wikipedia. Psilocin. Last Updated 22 July 2009. [Link]
- Wikipedia. Mushroom poisoning. Last Updated 10 August 2009. [Link]
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Gene Regulation |
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Up-Regulated Genes | Not Available |
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Down-Regulated Genes | Not Available |
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