Grundinformationen
- CAS
520-53-6- Standard-SMILES
CN(C)CCc1c[nH]c2cccc(O)c12- InChIKey
SPCIYGNTAMCTRO-UHFFFAOYSA-N- Summenformel
- C12H16N2O
- Durchschnittliche Molmasse
- 204,27 g/mol
- Monoisotopische Masse
- 204,12626314
Überblick
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.
Namen und Bezeichner
- Bevorzugter Name
- Psilocin
- IUPAC
- 3-[2-(dimethylamino)ethyl]-1H-indol-4-ol
- Lokaler Name
- 3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol
- Englischer Name
- PSILOCIN
- Summenformel
- C12H16N2O
- Molmasse
- 204.27
Namen und Synonyme
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
Weitere Namen anzeigen
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]-
Datenbank-Bezeichner
- CAS
520-53-6- PubChem CID
- 4980
- DTXSID
DTXSID5048899- ChEMBL
CHEMBL65547- ChEBI
CHEBI:8613- UNII
- CMS88KUW0G
- EC Number
- 208-296-5
- Nikkaji
- J12.982H
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 2,1
- Polarare Oberfläche (TPSA)
- 39,3 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 15
- Formalladung
- 0
- Komplexität
- 208
Experimentelle und physikochemische Eigenschaften
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)]
Physikochemische Eigenschaften
- Schmelzpunkt
- 173 · 173-176°
- Siedepunkt
- 342.77 °C · 342.77°C (rough estimate)
- Dichte
- 1.0565 · 1.0565 (rough estimate)
- Brechungsindex
- 1.6 · 1.6000 (estimate)
- Flammpunkt
- 11 °C · 11 °C
- storage temp.
- 20 °C · −20°C
- Löslichkeit
- 100 mM · Soluble to 100 mM in DMSO
- pka
- 10.01 · 10.01±0.40(Predicted)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
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.
Gefahrenhinweise
Regulatory InformationDEA schedule I controlled substance
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxikologische Informationen
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).
Sicherheitsdaten
- wgk
- 3
- ridadr
- UN 1230 3/PG 2
- RTECS-Nr.
- NM2625000
- risk_code
- 22-39/23/24/25-23/24/25-11
- Toxizität
- LD50 intraperitoneal in mouse: 196mg/kg
- hazard_code
- Xn,T,F
- safety_code
- 36/37/39-45-36/37-16-7
- hazard_class
- 6.1(b)
- packing_group
- III
Chemie und Industrie
Pharmakologische Informationen
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.
Verwendung und Herstellung
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
Anwendungen
VerwendenThe 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).
Ergänzende Hinweise
DefinitionAn indole derivative. An alkaloid from certain mush- rooms; a hallucinogenic drug.
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