Basic information
- CAS
520-53-6- Standard SMILES
CN(C)CCc1c[nH]c2cccc(O)c12- InChIKey
SPCIYGNTAMCTRO-UHFFFAOYSA-N- Molecular formula
- C12H16N2O
- Average molar mass
- 204.27 g/mol
- Monoisotopic mass
- 204.12626314
Overview
Psilocin is a tryptamine alkaloid that is N,N-dimethyltryptamine carrying an additional hydroxy substituent at position 4. A hallucinogenic alkaloid isolated in trace amounts from Psilocybe mushrooms (also known as Teonancatl or "magic mushrooms"). It has a role as a hallucinogen, a serotonergic agonist, a drug metabolite, a fungal metabolite and a human xenobiotic metabolite. It is a member of phenols, a tryptamine alkaloid, a tertiary amino compound and a member of hydroxyindoles. It is functionally related to a N,N-dimethyltryptamine. It is a conjugate base of a psilocinium.
Names & identifiers
- Preferred name
- Psilocin
- IUPAC
- 3-[2-(dimethylamino)ethyl]-1H-indol-4-ol
- English name
- PSILOCIN
- Molecular formula
- C12H16N2O
- Molecular weight
- 204.27
Names & synonyms
PSILOCINPsilocine4-Hydroxy-N,N-dimethyltryptaminePsilotsinPsilocyn520-53-63-[2-(Dimethylamino)ethyl]-1H-indol-4-ol3-(2-(Dimethylamino)ethyl)indol-4-ol4-HO-DMTN,N-Dimethyl-4-HydroxytryptamineDTXSID5048899CMS88KUW0G
Show more names
CX 59cx-59psylocinGMP Psilocin4-hydroxy DMTPsilocin (CRM)
3-(2-(Dimethylamino)ethyl)-1H-indol-4-olCHEBI:8613DTXCID5028825(3-(2-dimethylamino)ethyl)indol-4-olRefChem:870285208-296-5CHEMBL655471H-Indol-4-ol, 3-[2-(dimethylamino)ethyl]-
Database identifiers
- CAS
520-53-6- PubChem CID
- 4980
- DTXSID
DTXSID5048899- ChEMBL
CHEMBL65547- ChEBI
CHEBI:8613- UNII
- CMS88KUW0G
- EC Number
- 208-296-5
- Nikkaji
- J12.982H
Properties
Computed structural properties
- XLogP
- 2.1
- Topological polar surface area
- 39.3 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 3
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 208
Experimental & physicochemical properties
Drugs
DEA NFLIS-Drug Category -> Psychedelics
DEA Schedule I Controlled Substance -> Hallucinogenic substances
Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds
Human DrugsPharmaceuticals
Melting Point174.5 °C
Physical DescriptionSolid
Collision Cross Section144.8 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
Physicochemical properties
- Melting point
- 173 · 173-176°
- Boiling point
- 342.77 °C · 342.77°C (rough estimate)
- Density
- 1.0565 · 1.0565 (rough estimate)
- refractive index
- 1.6 · 1.6000 (estimate)
- Flash point
- 11 °C · 11 °C
- storage temp.
- 20 °C · −20°C
- solubility
- 100 mM · Soluble to 100 mM in DMSO
- pka
- 10.01 · 10.01±0.40(Predicted)
- FDA UNII
- 88 KUW0G · CMS88KUW0G
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302
- Precautionary statements
- 264 · P264-P270-P301+P312-P330-P501
- Hazard Codes
- Xn,T,F
- Risk Statements
- 22 · 22-39/23/24/25-23/24/25-11
- Safety Statements
- 36 · 36/37/39-45-36/37-16-7
- RIDADR
- 1230 · UN 1230 3/PG 2
- WGK Germany
- 3 · 3
- RTECS
- 2625000 · NM2625000
- HazardClass
- 6.1 · 6.1(b)
- PackingGroup
- III
- Toxicity
- 50 intraperitoneal · LD50 intraperitoneal in mouse: 196mg/kg
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory InformationDEA schedule I controlled substance
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
Health EffectsPsilocin is neurotoxic and can cause hallucinations. (L1673)
Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity SummaryPsilocin 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. (L1673)
Signs and SymptomsPsilocin may cause tachycardia, dilated pupils, restlessness or arousal, euphoria, open and closed eye visuals, synesthesia, increased body temperature, headache, sweating and chills, and nausea. (L1673)
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Safety data
- wgk
- 3
- rtecs
- NM2625000
- ridadr
- UN 1230 3/PG 2
- Toxicity
- LD50 intraperitoneal in mouse: 196mg/kg
- risk_code
- 22-39/23/24/25-23/24/25-11
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,T,F
- safety_code
- 36/37/39-45-36/37-16-7
- hazard_class
- 6.1(b)
- packing_group
- III
- Hazard statements
- H302
- Precautionary statements
- P264-P270-P301+P312-P330-P501
Chemistry & industry
Pharmacology
Metabolism/MetabolitesPsilocin has known human metabolites that include (2S,3S,4S,5R)-6-[[3-[2-(dimethylamino)ethyl]-1H-indol-4-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid.
MeSH Pharmacological Classification
Drugs capable of inducing illusions, hallucinations, delusions, paranoid ideations, and other alterations of mood and thinking. Despite the name, the feature that distinguishes these agents from other classes of drugs is their capacity to induce states of altered perception, thought, and feeling that are not experienced otherwise.
Uses & manufacturing
Uses
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. (L1673)
Use ClassificationPharmaceuticals
Applications
UsesThe minor hallucinogenic component of the Teonanacatl mushroom. Psilocin is the 4-hydroxy analog of Psilocybin, formed by metabolic dephosphorylation of Psilocybin and is an active neurochemical. Psychomimetic. Controlled substance (hallucinogen).
Additional notes
DefinitionAn indole derivative. An alkaloid from certain mush- rooms; a hallucinogenic drug.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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