({3-[2-(dimethylamino)ethyl]-1H-indol-4-yl}oxy)phosphonic acid

• ChemBase编号: 129168
• 分子式: C12H17N2O4P
• 平均质量: 284.248141
• 单一同位素质量: 284.09259366
• SMILES: CN(C)CCc1c[nH]c2cccc(OP(=O)(O)O)c12
• Canonical SMILES: CN(CCc1c[nH]c2c1c(ccc2)OP(=O)(O)O)C
• InChI: 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)
• InChIKey: QVDSEJDULKLHCG-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: ({3-[2-(dimethylamino)ethyl]-1H-indol-4-yl}oxy)phosphonic acid
• IUPAC传统名: psilocybin
• 别名: Psilocybin; 3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol 4-Dihydrogen Phosphate Ester; 4-Phosphoryl-N,N-dimethyltryptamine; Cy 39; Indocybin; Psilocybine; O-Phosphoryl-4-hydroxy-N,N-dimethyltryptamine; Psilocine Phosphate; 3-[2-(Dimethylamino)ethyl]-1H-indol-4-yl phosphate; Psilocybin

登记号

• CAS号: 520-52-5
• EC号: 208-294-4
• MDL号: MFCD01310431
• Beilstein号: 273158
• PubChem SID: 162223465
• PubChem CID: 10624
• CHEBI ID: 8614
• CHEMBL: 194378
• Chemspider ID: 10178
• KEGG ID: C07576
• 医学主题词(MeSH): Psilocybine
• 维基百科标题: Psilocybin

理论计算性质

• Acid pKa: 1.7443777
• 质子受体: 4
• 质子供体: 3
• LogD (pH = 5.5): -0.15883611
• LogD (pH = 7.4): -0.89353734
• Log P: -0.13636683
• 摩尔折射率: 73.296 cm^3
• 极化性: 29.192675 Å^3
• 极化表面积: 85.79 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: H2O: >20 mg/mL; Methanol (Hot),; soluble in methanol ; slightly soluble in ethanol ; negligible in chloroform, benzene; soluble in water; Water
• 外观: solid; White to Off-White Solid
• 熔点: 226-2280C

安全信息

• 保存条件: Controlled Substance, -20°C Freezer
• RTECS编号: NM3150000
• 德国WGK号: 3
• 半数致死量: 285 mg/kg (mouse, i.v.); 280 mg/kg (rat, i.v.); 12.5 mg/kg (rabbit, i.v.)
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 毒品管制信息: USDEA Schedule I; 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, intravenous
• 依赖倾向: Low
• 排泄: Renal
• 半衰期: oral: 163±64 min; intravenous: 74.1±19.6 min
• 代谢: Hepatic
• 法定药品分级: Class A (UK); S9 (Australia); Schedule I (US); Schedule III (Canada)

产品相关信息

• 纯度: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C12H17N2O4P

详细说明

Sigma Aldrich - P0100

Biochem/physiol Actions
Psilocybin is a hallucinogenic serotonin 1A and 2A agonist and psychotomimetic. It is the minor hallucinogenic component of Teonanácatl, the sacred mushroom of Mexico. Psilocybin produces muscle relaxation, dilation of pupils, vivid visual and auditory distortions, and emotional disturbances.

Toronto Research Chemicals - P839650

The major of two hallucinogenic components of Teonanacatl, the sacred mushroom of Mexico, the other component being Psilocin. 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)