Details
Stereochemistry | ACHIRAL |
Molecular Formula | C12H17N2O4P |
Molecular Weight | 284.2486 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C)CCc1c[nH]c2cccc(c12)OP(=O)(O)O
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 | 284.2486 |
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 In the 1960's psilocybin was marketed for use as a treatment for various psychoses, however, it was withdrawn from the market when the regulatory environment changed.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 |
|
[Psychoactive mushrooms - an update]. | 2001 Dec |
|
The detection of psilocin in human urine. | 2001 May |
|
Persistent psychosis after a single ingestion of 'ecstasy'. | 2001 Nov-Dec |
|
Possible mechanisms of panic attack and schizophrenia via APUD system. | 2002 Feb |
|
Synthetic studies of psilocin analogs having either a formyl group or bromine atom at the 5- or 7-position. | 2002 Jan |
|
Mismatch negativity predicts psychotic experiences induced by NMDA receptor antagonist in healthy volunteers. | 2002 Mar 1 |
|
Synthesis of a psilocin hapten and a protein-hapten conjugate. | 2002 Sep |
|
Renal excretion profiles of psilocin following oral administration of psilocybin: a controlled study in man. | 2002 Sep 5 |
|
[Discrimination of psychoactive fungi (commonly called "magic mushrooms") based on the DNA sequence of the internal transcribed spacer region]. | 2003 Feb |
|
Concise large-scale synthesis of psilocin and psilocybin, principal hallucinogenic constituents of "magic mushroom". | 2003 Jun |
|
Poly(dimethylsiloxane) electrospray devices fabricated with diamond-like carbon-poly(dimethylsiloxane) coated SU-8 masters. | 2003 May |
|
Optimized glucuronide hydrolysis for the detection of psilocin in human urine samples. | 2003 Nov 5 |
|
Mushrooms: toxins right in your own backyard. | 2003 Oct |
|
Development of a psilocin immunoassay for serum and blood samples. | 2004 Dec |
|
Acute psychological and physiological effects of psilocybin in healthy humans: a double-blind, placebo-controlled dose-effect study. | 2004 Mar |
|
Poisonings resulting from the ingestion of magic mushrooms in Kraków. | 2005 |
|
Hallucinogen persisting perception disorder after psilocybin consumption: a case study. | 2005 Aug |
|
Investigation into the temporal stability of aqueous standard solutions of psilocin and psilocybin using high performance liquid chromatography. | 2006 Apr-Jun |
|
Psilocybin can occasion mystical-type experiences having substantial and sustained personal meaning and spiritual significance. | 2006 Aug |
|
Not imagining it. Research into hallucinogens cautiously resumes. | 2006 Nov |
|
Psilocybin links binocular rivalry switch rate to attention and subjective arousal levels in humans. | 2007 Dec |
|
[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 |
|
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 |
|
Mystical-type experiences occasioned by psilocybin mediate the attribution of personal meaning and spiritual significance 14 months later. | 2008 Aug |
|
[Hallucinogen-induced psychological disorders]. | 2008 Jun |
|
Apical regional wall motion abnormalities reminiscent to Tako-Tsubo cardiomyopathy following consumption of psychoactive fungi. | 2009 May 1 |
|
Availability of websites offering to sell psilocybin spores and psilocybin. | 2009 Sep |
|
Hallucinogens as medicine. | 2010 Dec |
|
Forensic analysis of hallucinogenic mushrooms and khat (Catha edulis Forsk) using cation-exchange liquid chromatography. | 2010 Feb 25 |
|
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
Sat Jun 26 04:37:00 UTC 2021
by
admin
on
Sat Jun 26 04:37:00 UTC 2021
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Record UNII |
2RV7212BP0
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Record Status |
Validated (UNII)
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Record Version |
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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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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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CHEMBL194378
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DB11664
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2RV7212BP0
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7365
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520-52-5
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M9305
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METABOLITE ACTIVE -> PRODRUG |