3-[2-(dimethylamino)ethyl]-1H-indol-4-ol

• ChemBase编号: 130311
• 分子式: C12H16N2O
• 平均质量: 204.26824
• 单一同位素质量: 204.12626314
• SMILES: Oc1cccc2c1c(c[nH]2)CCN(C)C
• Canonical SMILES: CN(CCc1c[nH]c2c1c(O)ccc2)C
• InChI: InChI=1S/C12H16N2O/c1-14(2)7-6-9-8-13-10-4-3-5-11(15)12(9)10/h3-5,8,13,15H,6-7H2,1-2H3
• InChIKey: SPCIYGNTAMCTRO-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 3-[2-(dimethylamino)ethyl]-1H-indol-4-ol
• IUPAC传统名: psilocin
• 别名: 4-羟基-N,N-二甲基色胺 溶液; 4-羟基-N,N-二甲基色胺; 3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol; Psilocyn; Psilocin solution; 4-hydroxy-''N'',''N''-dimethyltryptamine; Psilocin; 4-Hydroxy-N,N-dimethyltryptamine; Psilocin

登记号

• CAS号: 520-53-6
• EC号: 200-659-6; 208-296-5
• MDL号: MFCD00079228
• PubChem SID: 24898489; 162224590; 24898305
• PubChem CID: 4980
• CHEBI ID: 8613
• CHEMBL: 65547
• Chemspider ID: 4807
• KEGG ID: C08312
• 维基百科标题: Psilocin

理论计算性质

• Acid pKa: 8.971079
• 质子受体: 2
• 质子供体: 2
• LogD (pH = 5.5): -1.3831663
• LogD (pH = 7.4): -0.095287494
• Log P: 1.1496978
• 摩尔折射率: 62.4231 cm^3
• 极化性: 25.000689 Å^3
• 极化表面积: 39.26 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: 173-176 °C (343.4-348.8°F)
• 闪点: 11 °C; 51.8 °F

安全信息

• RTECS编号: NM2625000
• 欧盟危险性物质标志: 易燃性(Flammable) (F); 有毒(Toxic) (T); 有害性(Harmful) (Xn)
• 联合国危险货物编号: 1230
• 德国WGK号: 1; 3
• 联合国危险货物等级: 3
• 联合国危险货物包装类别(PG): 2
• 危险公开号: 11-23/24/25-39/23/24/25; 22
• 安全公开号: 36/37/39; 7-16-36/37-45
• GHS危险品标识: GHS02; GHS06; GHS07; GHS08
• GHS警示词: Danger; Warning
• GHS危险声明: H225-H301-H311-H331-H370; H302
• GHS警示性声明: P210-P260-P280-P301 + P310-P311
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1230 3/PG 2
• 毒品管制信息: Home Office Schedule 1; stupéfiant; kontrollierte Droge in Deutschland; USDEA Schedule I; Home Office Schedule 1; stupéfiant; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada
• 保存温度: -20°C

药理学性质

• 给药途径: Oral, IV
• 排泄: Kidneys/Urine
• 半衰期: 2–3 hours
• 代谢: Liver
• 法定药品分级: Class A(NZ); Class A(UK); S9 (Australia); Schedule I (US); Schedule III (Canada)
• 相关基因信息: human ... HTR1A(3350)rat ... Htr2a(29595), Htr2c(25187)

产品相关信息

• 浓度: 100 μg/mL in methanol
• 级别: drug standard

详细说明

Sigma Aldrich - P2279

Biochem/physiol Actions
Hallucinogen originally isolated from the mushroom, Psilocybe mexicana, non-selective serotonin receptor agonist.

Toronto Research Chemicals - P839630

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).

参考文献

• Hofmann, et al.: Experientia, 14, 397 (1958)
• Callahan, P., et al.: J. Pharmacol. Exp. Ther., 246, 866 (1958)
• Appel, J., et al.: Eur. J. Pharmacol., 159, 41 (1958)
• Blair, J., et al.: J. Med. Chem., 43, 4701 (1958)