Psilocin
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Basic Info
| Common Name | Psilocin(F04689) |
| 2D Structure | |
| 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. |
| FRCD ID | F04689 |
| CAS Number | 520-53-6 |
| PubChem CID | 4980 |
| Formula | C12H16N2O |
| IUPAC Name | 3-[2-(dimethylamino)ethyl]-1H-indol-4-ol |
| InChI Key | SPCIYGNTAMCTRO-UHFFFAOYSA-N |
| InChI | 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 |
| Canonical SMILES | CN(C)CCC1=CNC2=C1C(=CC=C2)O |
| Isomeric SMILES | CN(C)CCC1=CNC2=C1C(=CC=C2)O |
| Wikipedia | Psilocin |
| Synonyms |
PSILOCIN
Psilocine
Psilotsin
4-Hydroxy-N,N-dimethyltryptamine
520-53-6
Psilocyn
3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol
3-(2-(Dimethylamino)ethyl)indol-4-ol
N,N-Dimethyl-4-Hydroxytryptamine
UNII-CMS88KUW0G
|
| Classifies |
Fungal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Indoles and derivatives |
| Subclass | Tryptamines and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Tryptamines and derivatives |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| 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 |
| Description | This compound belongs to the class of organic compounds known as tryptamines and derivatives. These are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 204.273 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 3 |
| Complexity | 208 |
| Monoisotopic Mass | 204.126 |
| Exact Mass | 204.126 |
| XLogP | 2.1 |
| Formal Charge | 0 |
| Heavy Atom Count | 15 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9327 |
| Human Intestinal Absorption | HIA+ | 0.9891 |
| Caco-2 Permeability | Caco2+ | 0.5093 |
| P-glycoprotein Substrate | Substrate | 0.7158 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9724 |
| Inhibitor | 0.5433 | |
| Renal Organic Cation Transporter | Inhibitor | 0.5921 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6766 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7589 |
| CYP450 2D6 Substrate | Substrate | 0.5462 |
| CYP450 3A4 Substrate | Substrate | 0.6161 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.5973 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9025 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.5680 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8931 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9011 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7317 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.7592 |
| Non-inhibitor | 0.6453 | |
| AMES Toxicity | Non AMES toxic | 0.6146 |
| Carcinogens | Non-carcinogens | 0.9602 |
| Fish Toxicity | High FHMT | 0.7519 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.7637 |
| Honey Bee Toxicity | Low HBT | 0.6145 |
| Biodegradation | Not ready biodegradable | 0.9928 |
| Acute Oral Toxicity | III | 0.5942 |
| Carcinogenicity (Three-class) | Non-required | 0.6845 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.9601 | LogS |
| Caco-2 Permeability | 0.7054 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.5635 | LD50, mol/kg |
| Fish Toxicity | 1.3552 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.0799 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Fungal hallucinogens psilocin, ibotenic acid, and muscimol: analytical methods and biologic activities. | Ther Drug Monit | 2013 Aug | 23851905 |
Targets
- General Function:
- Serotonin receptor activity
- Specific Function:
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling inhibits adenylate cyclase activity and activates a phosphatidylinositol-calcium second messenger system that regulates the release of Ca(2+) ions from intracellular stores. Plays a role in the regulation of 5-hydroxytryptamine release and in the regulation of dopamine and 5-hydroxytryptamine metabolism. Plays a role in the regulation of dopamine and 5-hydroxytryptamine levels in the brain, and thereby affects neural activity, mood and behavior. Plays a role in the response to anxiogenic stimuli.
- Gene Name:
- HTR1A
- Uniprot ID:
- P08908
- Molecular Weight:
- 46106.335 Da
- Mechanism of Action:
- 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.
References
- Wikipedia. Psilocin. Last Updated 22 July 2009. : http://en.wikipedia.org/wiki/Psilocin
- General Function:
- Virus receptor activity
- Specific Function:
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling activates phospholipase C and a phosphatidylinositol-calcium second messenger system that modulates the activity of phosphatidylinositol 3-kinase and promotes the release of Ca(2+) ions from intracellular stores. Affects neural activity, perception, cognition and mood. Plays a role in the regulation of behavior, including responses to anxiogenic situations and psychoactive substances. Plays a role in intestinal smooth muscle contraction, and may play a role in arterial vasoconstriction.(Microbial infection) Acts as a receptor for human JC polyomavirus/JCPyV.
- Gene Name:
- HTR2A
- Uniprot ID:
- P28223
- Molecular Weight:
- 52602.58 Da
- Mechanism of Action:
- 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.
References
- Wikipedia. Psilocin. Last Updated 22 July 2009. : http://en.wikipedia.org/wiki/Psilocin
- General Function:
- Serotonin receptor activity
- Specific Function:
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-iodophenyl-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling activates a phosphatidylinositol-calcium second messenger system that modulates the activity of phosphatidylinositol 3-kinase and down-stream signaling cascades and promotes the release of Ca(2+) ions from intracellular stores. Regulates neuronal activity via the activation of short transient receptor potential calcium channels in the brain, and thereby modulates the activation of pro-opiomelacortin neurons and the release of CRH that then regulates the release of corticosterone. Plays a role in the regulation of appetite and eating behavior, responses to anxiogenic stimuli and stress. Plays a role in insulin sensitivity and glucose homeostasis.
- Gene Name:
- HTR2C
- Uniprot ID:
- P28335
- Molecular Weight:
- 51820.705 Da
- Mechanism of Action:
- 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.
References
- Wikipedia. Psilocin. Last Updated 22 July 2009. : http://en.wikipedia.org/wiki/Psilocin