Psilocybin
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Basic Info
| Common Name | Psilocybin(F04688) |
| 2D Structure | |
| Description | Psilocybin (pronounced /ˌsaɪlɵˈsaɪbɪn/ SYE-lə-SYE-bin) (also known as psilocybine) is a hallucinogenic (entheogenic, psychedelic) indole of the tryptamine family, found in psilocybin mushrooms. It is present in hundreds of species of fungi, including those of the genus Psilocybe, such as Psilocybe cubensis and Psilocybe semilanceata, but also reportedly isolated from a dozen or so other genera. Psilocybin mushrooms are commonly called "sacred mushrooms," "magic mushrooms," or more simply "shrooms". Possession, and in some cases usage, of psilocybin or psilocin has been outlawed in most countries across the globe. Proponents of its usage consider it to be an entheogen and a tool to supplement various types of practices for transcendence, including in meditation, psychonautics, and psychedelic psychotherapy. The intensity and duration of entheogenic effects of psilocybin mushrooms are highly variable, depending on species/cultivar of mushrooms, dosage, individual physiology, and set and setting. Though psilocybin rarely attracts much attention from mainstream media, when it does the focus tends to be on the recreational use, generally excluding any other uses of the drug. (L1143) |
| FRCD ID | F04688 |
| CAS Number | 520-52-5 |
| PubChem CID | 10624 |
| Formula | C12H17N2O4P |
| IUPAC Name | [3-[2-(dimethylamino)ethyl]-1H-indol-4-yl] dihydrogen phosphate |
| InChI Key | QVDSEJDULKLHCG-UHFFFAOYSA-N |
| InChI | InChI=1S/C12H17N2O4P/c1-14(2)7-6-9-8-13-10-4-3-5-11(12(9)10)18-19(15,16)17/h3-5,8,13H,6-7H2,1-2H3,(H2,15,16,17) |
| Canonical SMILES | CN(C)CCC1=CNC2=C1C(=CC=C2)OP(=O)(O)O |
| Isomeric SMILES | CN(C)CCC1=CNC2=C1C(=CC=C2)OP(=O)(O)O |
| Wikipedia | Psilocybin |
| Synonyms |
O-Phosphoryl-4-hydroxy-N,N-dimethyltryptamine
Psilocybin
Psilocybine
Indocybin
Psilocibin
Psilocin phosphate ester
Psilotsibin
Teonanacatl
Psilocibina
Psilocybinum
|
| 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 - Aryl phosphate - Aryl phosphomonoester - 3-alkylindole - Indole - Alkaloid or derivatives - Aralkylamine - Organic phosphoric acid derivative - Phosphoric acid ester - Substituted pyrrole - Benzenoid - Pyrrole - Heteroaromatic compound - Tertiary aliphatic amine - Tertiary amine - Azacycle - Amine - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Organooxygen compound - Organonitrogen compound - Organic oxide - Hydrocarbon derivative - 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 | 284.252 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 5 |
| Complexity | 347 |
| Monoisotopic Mass | 284.093 |
| Exact Mass | 284.093 |
| XLogP | -1.6 |
| Formal Charge | 0 |
| Heavy Atom Count | 19 |
| 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+ | 0.9381 |
| Human Intestinal Absorption | HIA+ | 0.8112 |
| Caco-2 Permeability | Caco2- | 0.5820 |
| P-glycoprotein Substrate | Substrate | 0.7245 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9257 |
| Non-inhibitor | 0.9344 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.6361 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6594 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7331 |
| CYP450 2D6 Substrate | Non-substrate | 0.6936 |
| CYP450 3A4 Substrate | Substrate | 0.6278 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.6897 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8028 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8238 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7766 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8303 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7735 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.6618 |
| Non-inhibitor | 0.6642 | |
| AMES Toxicity | Non AMES toxic | 0.6433 |
| Carcinogens | Non-carcinogens | 0.9111 |
| Fish Toxicity | High FHMT | 0.9090 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.7510 |
| Honey Bee Toxicity | High HBT | 0.5890 |
| Biodegradation | Not ready biodegradable | 0.9822 |
| Acute Oral Toxicity | III | 0.5527 |
| Carcinogenicity (Three-class) | Non-required | 0.6098 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.0088 | LogS |
| Caco-2 Permeability | -0.1503 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.7087 | LD50, mol/kg |
| Fish Toxicity | 1.1450 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.3895 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Exploring Hallucinogen Pharmacology and Psychedelic Medicine with Zebrafish Models. | Zebrafish | 2016 Oct | 27002655 |
| 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:
- Psilocybin is rapidly dephosphorylated in the body to psilocin which then acts as a partial agonist at the 5-HT2A serotonin receptor in the brain where it mimics the effects of serotonin (5-HT). Psilocin is an 5-HT1A and 5-HT2A/2C agonist.
References
- Wikipedia. Psilocybin. Last Updated 5 July 2009. : http://en.wikipedia.org/wiki/Psilocybin
- 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:
- Psilocybin is rapidly dephosphorylated in the body to psilocin which then acts as a partial agonist at the 5-HT2A serotonin receptor in the brain where it mimics the effects of serotonin (5-HT). Psilocin is an 5-HT1A and 5-HT2A/2C agonist.
References
- Wikipedia. Psilocybin. Last Updated 5 July 2009. : http://en.wikipedia.org/wiki/Psilocybin
- 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:
- Psilocybin is rapidly dephosphorylated in the body to psilocin which then acts as a partial agonist at the 5-HT2A serotonin receptor in the brain where it mimics the effects of serotonin (5-HT). Psilocin is an 5-HT1A and 5-HT2A/2C agonist.
References
- Wikipedia. Psilocybin. Last Updated 5 July 2009. : http://en.wikipedia.org/wiki/Psilocybin