Details
Stereochemistry | ACHIRAL |
Molecular Formula | C12H17N2O4P |
Molecular Weight | 284.2481 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C)CCC1=CNC2=CC=CC(OP(O)(O)=O)=C12
InChI
InChIKey=QVDSEJDULKLHCG-UHFFFAOYSA-N
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)
Molecular Formula | C12H17N2O4P |
Molecular Weight | 284.2481 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Psilocybin is a naturally occurring psychedelic prodrug compound produced by more than 200 species of mushrooms, collectively known as psilocybin mushrooms. Once ingested, psilocybin is rapidly metabolized to the psilocin, which then acts on serotonin receptors in the brain. Psilocybin was identified as the active hallucinogenic compound in magic mushrooms in 1959, but humans have used assorted psilocybin mushrooms in religious ceremonies since prehistoric times. In the 1960's psilocybin was marketed for use as a treatment for various psychoses, however, it was withdrawn from the market when the regulatory environment changed. Recently there has been as renewed interest in studying the medicinal uses of psilocybin for treatment of anxiety, depression, migraine headaches, addictions, and other neuropsychiatric conditions.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P28223 Gene ID: 3356.0 Gene Symbol: HTR2A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26841800 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
16 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28353056 |
0.3 mg/kg single, oral dose: 0.3 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
PSILOCIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
26 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28353056 |
0.45 mg/kg single, oral dose: 0.45 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
PSILOCIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
37.6 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28353056 |
0.6 mg/kg single, oral dose: 0.6 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
PSILOCIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
140 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28353056 |
0.3 mg/kg single, oral dose: 0.3 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
PSILOCIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
213 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28353056 |
0.45 mg/kg single, oral dose: 0.45 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
PSILOCIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
267 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28353056 |
0.6 mg/kg single, oral dose: 0.6 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
PSILOCIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28353056 |
0.3 mg/kg single, oral dose: 0.3 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
PSILOCIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28353056 |
0.45 mg/kg single, oral dose: 0.45 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
PSILOCIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28353056 |
0.6 mg/kg single, oral dose: 0.6 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
PSILOCIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
PubMed
Title | Date | PubMed |
---|---|---|
Brain mechanisms of hallucinogens and entactogens. | 2001 Dec |
|
Morphological and chemical analysis of magic mushrooms in Japan. | 2003 Dec 17 |
|
Effects of the 5-HT2A agonist psilocybin on mismatch negativity generation and AX-continuous performance task: implications for the neuropharmacology of cognitive deficits in schizophrenia. | 2003 Jan |
|
[Levels of psilocybin and psilocin in various types of mushrooms]. | 2003 Jul |
|
Mushrooms: toxins right in your own backyard. | 2003 Oct |
|
The Meixner test in the detection of alpha-amanitin and false-positive reactions caused by psilocin and 5-substituted tryptamines. | 2004 Aug |
|
Psilocybin impairs high-level but not low-level motion perception. | 2004 Aug 26 |
|
Development of a psilocin immunoassay for serum and blood samples. | 2004 Dec |
|
Transient reinforcing effects of phenylisopropylamine and indolealkylamine hallucinogens in rhesus monkeys. | 2004 Mar |
|
Acute psychological and physiological effects of psilocybin in healthy humans: a double-blind, placebo-controlled dose-effect study. | 2004 Mar |
|
Forensic analysis of hallucinogenic fungi: a DNA-based approach. | 2004 Mar 10 |
|
Psychedelic drugs: the ups and downs of ecstasy. | 2004 May 13 |
|
[Hallucinogenic mushrooms]. | 2005 |
|
Severe rhabdomyolysis, acute renal failure and posterior encephalopathy after 'magic mushroom' abuse. | 2005 Dec |
|
[Hallucinogenic fungi (Psylocibe). Part I. Characteristics, results of consumption, recognition]. | 2005 Jul-Sep |
|
Liquid chromatography-mass spectrometric and liquid chromatography-tandem mass spectrometric determination of hallucinogenic indoles psilocin and psilocybin in "magic mushroom" samples. | 2005 Mar |
|
Using psilocybin to investigate the relationship between attention, working memory, and the serotonin 1A and 2A receptors. | 2005 Oct |
|
SAR of psilocybin analogs: discovery of a selective 5-HT 2C agonist. | 2005 Oct 15 |
|
The determination of psilocin and psilocybin in hallucinogenic mushrooms by HPLC utilizing a dual reagent acidic potassium permanganate and tris(2,2'-bipyridyl)ruthenium(II) chemiluminescence detection system. | 2006 Jan |
|
Response of cluster headache to psilocybin and LSD. | 2006 Jun 27 |
|
Safety, tolerability, and efficacy of psilocybin in 9 patients with obsessive-compulsive disorder. | 2006 Nov |
|
Phylogenetic relationship of psychoactive fungi based on rRNA gene for a large subunit and their identification using the TaqMan assay (II). | 2006 Nov 10 |
|
Psilocybin links binocular rivalry switch rate to attention and subjective arousal levels in humans. | 2007 Dec |
|
[Automutilation after consumption of hallucinogenic mushrooms]. | 2007 Dec 29 |
|
Effects of psilocybin on time perception and temporal control of behaviour in humans. | 2007 Jan |
|
[Hallucinogenic fungi (psilocybe). Part II. Identification of Psilocybe semilanceata by PCR]. | 2007 Jul-Sep |
|
[Prof. Günther Hole on his self-experiments. "What did I actually endure?"]. | 2007 Mar 15 |
|
Psilocybin-induced stimulus control in the rat. | 2007 Oct |
|
The effects of the preferential 5-HT2A agonist psilocybin on prepulse inhibition of startle in healthy human volunteers depend on interstimulus interval. | 2007 Sep |
|
Albert Hofmann, the father of LSD (1906-2008). | 2008 |
|
Between prohibitions: patterns and meanings of magic mushroom use in the UK. | 2008 |
|
Effects of varied doses of psilocybin on time interval reproduction in human subjects. | 2008 Apr 11 |
|
Mystical-type experiences occasioned by psilocybin mediate the attribution of personal meaning and spiritual significance 14 months later. | 2008 Aug |
|
The structure of human serotonin 2c G-protein-coupled receptor bound to agonists and antagonists. | 2008 Aug |
|
Hallucinogen-like effects of N,N-dipropyltryptamine (DPT): possible mediation by serotonin 5-HT1A and 5-HT2A receptors in rodents. | 2008 Jan |
|
[Hallucinogen-induced psychological disorders]. | 2008 Jun |
|
Unrecognized magic mushroom abuse in a 28-year-old man. | 2008 Oct |
|
Analysis of mushroom exposures in Texas requiring hospitalization, 2005-2006. | 2009 Jun |
|
Apical regional wall motion abnormalities reminiscent to Tako-Tsubo cardiomyopathy following consumption of psychoactive fungi. | 2009 May 1 |
|
Return of a problem child. | 2009 Oct |
|
Availability of websites offering to sell psilocybin spores and psilocybin. | 2009 Sep |
|
Sensorimotor gating depends on polymorphisms of the serotonin-2A receptor and catechol-O-methyltransferase, but not on neuregulin-1 Arg38Gln genotype: a replication study. | 2009 Sep 15 |
|
Micro-solid phase extraction coupled with high-performance liquid chromatography-tandem mass spectrometry for the determination of stimulants, hallucinogens, ketamine and phencyclidine in oral fluids. | 2010 Aug 24 |
|
Psychometric evaluation of the altered states of consciousness rating scale (OAV). | 2010 Aug 31 |
|
Hallucinogens as medicine. | 2010 Dec |
|
Forensic analysis of hallucinogenic mushrooms and khat (Catha edulis Forsk) using cation-exchange liquid chromatography. | 2010 Feb 25 |
|
Comparative study of ATR and transflection IR spectroscopic techniques for the analysis of hallucinogenic mushrooms. | 2010 Feb 25 |
|
Glucuronidation of psilocin and 4-hydroxyindole by the human UDP-glucuronosyltransferases. | 2010 Mar |
|
Turn on, tune in, but don't drop out: The impact of neo-liberalism on magic mushroom users' (in)ability to imagine collectivist social worlds. | 2010 Nov |
|
The hallucinogenic world of tryptamines: an updated review. | 2015 Aug |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT03341689
In a clinical trial for the treatment of migraines patients where given either 0.0143 mg/kg or 0.143 mg/kg of psilocybin in capsule form.
Route of Administration:
Oral
Substance Class |
Chemical
Created
by
admin
on
Edited
Thu Jul 06 22:18:39 UTC 2023
by
admin
on
Thu Jul 06 22:18:39 UTC 2023
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Record UNII |
2RV7212BP0
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Record Status |
Validated (UNII)
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NCI_THESAURUS |
C47794
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NCI_THESAURUS |
C221
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DEA NO. |
7437
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FDA ORPHAN DRUG |
843421
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D011562
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208-294-4
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PSILOCYBIN
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SUB10158MIG
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C62529
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TARGET -> AGONIST |
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Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PRODRUG |
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