基本情報
- CAS
520-53-6- 標準SMILES
CN(C)CCc1c[nH]c2cccc(O)c12- InChIKey
SPCIYGNTAMCTRO-UHFFFAOYSA-N- 分子式
- C12H16N2O
- 平均分子量
- 204.27 g/mol
- 単同位体質量
- 204.12626314
概要
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.
名称と識別子
- 優先名称
- Psilocin
- IUPAC
- 3-[2-(dimethylamino)ethyl]-1H-indol-4-ol
- 現地名
- 3-(2-ジメチルアミノエチル)-4-ヒドロキシ-1H-インドール
- 英語名
- PSILOCIN
- 分子式
- C12H16N2O
- 分子量
- 204.27
名称と別名
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
名称をさらに表示
3-(2-ジメチルアミノエチル)-4-ヒドロキシ-1H-インドールサイロシンシロシン4-ヒドロキシ-N,N-ジメチル-1H-インドール-3-エタンアミンプシロシン4-ヒドロキシ-N,N-ジメチルトリプタミン3-[2-(ジメチルアミノ)エチル]-1H-インドール-4-オール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]-
データベース識別子
- CAS
520-53-6- PubChem CID
物性
構造計算による物性
- XLogP
- 2.1
- 極性表面積
- 39.3 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 2
- 回転可能結合数
- 3
- 重原子数
- 15
- 形式電荷
- 0
- 複雑度
- 208
実験および物理化学的性質
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)]
物理化学的性質
- 融点
- 173 · 173-176°
- 沸点
- 342.77 °C · 342.77°C (rough estimate)
- 比重(密度)
- 1.0565 · 1.0565 (rough estimate)
- 屈折率
- 1.6 · 1.6000 (estimate)
- 闪点
- 11 °C · 11 °C
- 貯蔵温度
- 20 °C · −20°C
- 溶解性
- 100 mM · Soluble to 100 mM in DMSO
- 酸解離定数(Pka)
- 10.01 · 10.01±0.40(Predicted)
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
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.
危険有害性情報
Regulatory InformationDEA schedule I controlled substance
Hazard Classes and CategoriesAcute Tox. 4 (100%)
毒性情報
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).
安全データ
- wgk
- 3
- rtecs
- NM2625000
化学と産業
薬理情報
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.
用途と製造
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
応用分野
使用The 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).
補足説明
定義An indole derivative. An alkaloid from certain mush- rooms; a hallucinogenic drug.
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