7-methoxy-1-methyl-3H,4H,9H-pyrido[3,4-b]indole

• ChemBase编号: 102502
• 分子式: C13H14N2O
• 平均质量: 214.26306
• 单一同位素质量: 214.11061308
• SMILES: COc1cc2c(cc1)c1c([nH]2)C(=NCC1)C
• Canonical SMILES: COc1ccc2c(c1)[nH]c1c2CCN=C1C
• InChI: InChI=1S/C13H14N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-4,7,15H,5-6H2,1-2H3
• InChIKey: RERZNCLIYCABFS-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 7-methoxy-1-methyl-3H,4H,9H-pyrido[3,4-b]indole
• IUPAC传统名: harmaline; 7-methoxy-1-methyl-3H,4H,9H-pyrido[3,4-b]indole
• 别名: 1-甲基-7-甲氧基-3,4-二氢-β-咔啉; 3,4-二氢骆驼蓬碱; 7-甲氧基-1-甲基-4,9-二氢-3H-吡啶并[3,4-b]吲哚; O-甲基骆驼蓬酚; 骆驼蓬灵; 1-Methyl-7-methoxy-3,4-dihydro-β-carboline; Dihydroharmine; Harmalol methyl ether; 4,9-Dihydro-7-methoxy-1-methyl-3H-pyrido[3,4-b]indole; HARMALINE; Harmidine; NSC 407285; 1-Methyl-7-methoxy-3,4-dihydro-β-carboline; Harmaline; 1-Methyl-7-methoxy-3,4-dihydro-β-carboline hydrochloride

登记号

• CAS号: 304-21-2; 6027-98-1
• EC号: 206-152-6
• MDL号: MFCD00004955
• Beilstein号: 207310
• PubChem SID: 24873687; 162088113
• PubChem CID: 5280951
• CHEBI ID: 28172
• CHEMBL: 340807
• Chemspider ID: 10211258
• KEGG ID: C06536
• 美国药典/FDA物质标识码: CN58I4TOET
• 维基百科标题: Harmaline

理论计算性质

• Acid pKa: 14.954947
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): -0.750205
• LogD (pH = 7.4): 1.0009356
• Log P: 1.6682112
• 摩尔折射率: 64.1514 cm^3
• 极化性: 25.353348 Å^3
• 极化表面积: 37.38 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

理化性质

• 外观: Powder
• 熔点: 232–234 °C; 232-234 °C(lit.)

安全信息

• 保存条件: 0°C
• RTECS编号: MG8750000; UU9800000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: R:36/37/38
• 安全公开号: S:20-25-26-37/39
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 毒品管制信息: regulated under CDSA - not available from Sigma-Aldrich Canada; stupéfiantregulated under CDSA - not available from Sigma-Aldrich Canada

药理学性质

• 相关基因信息: human ... ADRA1A(148), ADRA1B(147), ADRA2A(150), ADRA2B(151), ADRA2C(152), ADRB1(153), ADRB2(154), CHRM1(1128), CHRM2(1129), CHRM3(1131), CHRM4(1132), CHRM5(1133), DRD1(1812), DRD5(1816), HTR1A(3350), HTR1B(3351), HTR1D(3352), HTR2C(3358), HTR3A(3359), HTR5A(3361), HTR6(3362), HTR7(3363), SLC6A2(6530), SLC6A4(6532), SLC9A2(6549), SLC9A5(6553)rat ... Drd2(24318), Drd3(29238), Drd4(25432), Htr2a(29595), Maoa(29253), Maob(25750), Slc9a1(24782), Slc9a3(24784)
• 生物活性机理: CNS stimulant; MAO inhibitor

产品相关信息

• 纯度: 97%; 98.5
• 生物来源: Alkaloid from Peganum harmala, Passiflora incarnata, Banisteria caapi and some Banisteriopsis spp. (Zygophyllaceae, Passifloraceae, Malphigiaceae)
• 应用领域: Component of a S. American hallucinogenic drink; Possesses antiparkinsonian props.
• Empirical Formula (Hill Notation): C13H14N2O

详细说明

MP Biomedicals - 02101915

Free Base
Crystalline
Fluoresces blue in solution.

MP Biomedicals - 02151225

Hydrochloride
Crystalline
Dihydrate
Monoamine oxidase inhibitor

MP Biomedicals - 05211576

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 51330

Biochem/physiol Actions
中枢神经系统兴奋剂；可通过 NMDA 受体起作用
包装
1 g in glass bottle
Application
Reactant for preparation of:
• Acylated harmalines via Friedel-Crafts reaction1
• Phenacyl derivatives of 1-methyl-7-methoxy-β-carbolines as central nervous system affectors2
• Palladium harmaline DMSO chloro complex as anti-tumor agent3Natural product scaffold in preparation of:
• Trypanothione reductase inhibitors†

Sigma Aldrich - 286036

Biochem/physiol Actions
中枢神经系统兴奋剂；可通过 NMDA 受体起作用
Application
Reactant for preparation of:
• Acylated harmalines via Friedel-Crafts reaction1
• Phenacyl derivatives of 1-methyl-7-methoxy-β-carbolines as central nervous system affectors2
• Palladium harmaline DMSO chloro complex as anti-tumor agent3Natural product scaffold in preparation of:
• Trypanothione reductase inhibitors†

参考文献

• Fischer, O., Ber., 1889, 22, 637, (synth)
• Spth, E. et al., Ber., 1930, 63, 120, (Me ether, synth)
• Konovalova, R. et al., Arch. Pharm. (Weinheim, Ger.), 1935, 273, 156, (synth)
• Spenser, I.D., Can. J. Chem., 1959, 37, 1851, (derivs, synth, uv, ir)
• Robinson, B., Chem. Ind. (London), 1965, 605, (Me ether, pmr)
• Allen, J.R.F. et al., Phytochemistry, 1980, 19, 1573, (occur, bibl)
• Coune, C.A. et al., Phytochemistry, 1980, 19, 2009, (cmr)
• Verpoorte, R. et al., Org. Magn. Reson., 1984, 22, 328, (cmr)
• Biondic, M.C. et al., J.C.S. Perkin 2, 1992, 1049, (Me ether, uv)