3-[2-(dimethylamino)ethyl]-1H-indol-5-ol

• ChemBase编号: 1251
• 分子式: C12H16N2O
• 平均质量: 204.26824
• 单一同位素质量: 204.12626314
• SMILES: Oc1cc2c(CCN(C)C)c[nH]c2cc1
• Canonical SMILES: CN(CCc1c[nH]c2c1cc(O)cc2)C
• InChI: InChI=1S/C12H16N2O/c1-14(2)6-5-9-8-13-12-4-3-10(15)7-11(9)12/h3-4,7-8,13,15H,5-6H2,1-2H3
• InChIKey: VTTONGPRPXSUTJ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 3-[2-(dimethylamino)ethyl]-1H-indol-5-ol
• IUPAC传统名: mappin
• 别名: 3-[2-(Dimethylamino)ethyl]-1H-indol-5-ol; 3-(β-Dimethylaminoethyl)-5-hydroxyindole; 5-Hydroxy-N,N-dimethyltryptamine; Bufotenin; Cinobufotenine; Dimethylserotonin; Mappin; Mappine; N,N-Dimethylserotonin; NSC 89593; Bufotenine; Bufotenine; N,N-dimethyl-5-hydroxytryptamine; 5-hydroxy-dimethyltryptamine; cebilcin; Bufotenin

登记号

• CAS号: 487-93-4
• PubChem SID: 160964711; 46507174
• PubChem CID: 10257
• CHEBI ID: 3210
• CHEMBL: 416526
• Chemspider ID: 9839
• DrugBank ID: DB01445
• IUPHAR配体索引: 144
• KEGG ID: C08299
• 维基百科标题: Bufotenin

理论计算性质

JChem

• Acid pKa: 9.232412
• 质子受体: 2
• 质子供体: 2
• LogD (pH = 5.5): -1.3982623
• LogD (pH = 7.4): -0.15401816
• Log P: 1.2922695
• 摩尔折射率: 62.4231 cm^3
• 极化性: 24.996414 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

ALOGPS 2.1

• Log P: 2.04
• LOG S: -1.81
• 溶解度: 3.20e+00 g/l

分子性质

理化性质

• 溶解度: Methanol
• 外观: Yellow Solid
• 熔点: 146-147 °C (294.8-296.6°F); 62-64°C
• 沸点: 320°C (608°F)

安全信息

• 保存条件: Refrigerator, Under Inert Atmosphere

药理学性质

• 给药途径: Parenteral
• 法定药品分级: Schedule I (US)

详细说明

DrugBank - DB01445

• Drug Groups: illicit; experimental
• Description: A hallucinogenic serotonin analog found in frog or toad skins, mushrooms, higher plants, and mammals, especially in the brains, plasma, and urine of schizophrenics. Bufotenin has been used as a tool in CNS studies and misused as a psychedelic.
• Pharmacology: Bufotenin is a tryptamine related to the neurotransmitter serotonin.
• Toxicity: Ingestion of Bufo toad venom and eggs by humans has resulted in several reported cases of poisoning, some of which resulted in death. The acute toxicity of bufotenin in rodents has been calculated to have an LD50 of between 200 and 300 mg/kg, which by comparison, is comparable to the LD50 for intravenous morphine (200-300 mg/kg) in mice. Death occurs by respiratory arrest.
• Affected Organisms: Humans and other mammals
• Biotransformation: Orally administered bufotenine undergoes extensive first-pass metabolism by the enzyme monoamine oxidase.
• Absorption: Rapidly absorbed following intravenous administration.
• References: Pomilio AB, Vitale AA, Ciprian-Ollivier J, Cetkovich-Bakmas M, Gomez R, Vazquez G: Ayahoasca: an experimental psychosis that mirrors the transmethylation hypothesis of schizophrenia. J Ethnopharmacol. 1999 Apr;65(1):29-51. [Pubmed] ; Ciprian-Ollivier J, Cetkovich-Bakmas MG: Altered consciousness states and endogenous psychoses: a common molecular pathway? Schizophr Res. 1997 Dec 19;28(2-3):257-65. [Pubmed] ; Carpenter WT Jr, Fink EB, Narasimhachari N, Himwich HE: A test of the transmethylation hypothesis in acute schizophrenic patients. Am J Psychiatry. 1975 Oct;132(10):1067-71. [Pubmed] ; Takeda N, Ikeda R, Ohba K, Kondo M: Bufotenine reconsidered as a diagnostic indicator of psychiatric disorders. Neuroreport. 1995 Nov 27;6(17):2378-80. [Pubmed] ; Sponheim E, Myhre AM, Reichelt KL, Aalen OO: [Urine peptide patterns in children with milder types of autism] Tidsskr Nor Laegeforen. 2006 May 25;126(11):1475-7. [Pubmed]
• External Links: Wikipedia

Toronto Research Chemicals - B689525

Controlled substance (hallucinogen).

参考文献

• Pomilio AB, Vitale AA, Ciprian-Ollivier J, Cetkovich-Bakmas M, Gomez R, Vazquez G: Ayahoasca: an experimental psychosis that mirrors the transmethylation hypothesis of schizophrenia. J Ethnopharmacol. 1999 Apr;65(1):29-51. Pubmed
• Ciprian-Ollivier J, Cetkovich-Bakmas MG: Altered consciousness states and endogenous psychoses: a common molecular pathway? Schizophr Res. 1997 Dec 19;28(2-3):257-65. Pubmed
• Carpenter WT Jr, Fink EB, Narasimhachari N, Himwich HE: A test of the transmethylation hypothesis in acute schizophrenic patients. Am J Psychiatry. 1975 Oct;132(10):1067-71. Pubmed
• Takeda N, Ikeda R, Ohba K, Kondo M: Bufotenine reconsidered as a diagnostic indicator of psychiatric disorders. Neuroreport. 1995 Nov 27;6(17):2378-80. Pubmed
• Sponheim E, Myhre AM, Reichelt KL, Aalen OO: [Urine peptide patterns in children with milder types of autism] Tidsskr Nor Laegeforen. 2006 May 25;126(11):1475-7. Pubmed
• Stoll, et al.: Helv. Chim. Acta, 38, 1452 (1955)
• Bhattacharya, S., et al.: Indian. J. Physiol. Pharmacol., 15, 133 (1955)
• Falkenberg, G., et al.: Acta Crystallogr., 28B, 3219 (1955)