475-81-0

• 常用中文名：(+)-海罂粟碱
• 常用英文名：Glaucine
• CAS号：475-81-0
• 分子式：C₂₁H₂₅NO₄
• 分子量：355.427
• 相关类别： 天然产物 生物碱
• 发布时间：2018-06-21 12:19:27
• 更新时间：2024-01-03 08:38:56
• Glaucine (O,O-Dimethylisoboldine) 是一种从 Glaucium flavum Crantz 中分离的生物碱,具有镇咳,支气管扩张和抗炎作用。 Glaucine 是一种选择性的,具有口服活性的磷酸二酯酶 4 (PDE4) 抑制剂,在人支气管和多形核白细胞中的 Ki 为 3.4 µM。Glaucine 还是一种非选择性的 α-肾上腺素受体 (α-adrenoceptor) 拮抗剂,一种 Ca2+ 进入阻滞剂以及弱多巴胺 D1 和 D2 受体拮抗剂。Glaucine 具有抗氧化和抗病毒活性。

名称

• 中文名: 海罂粟碱
• 英文名: (S)-1,2,9,10-Tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline
• 中文别名: 海罌粟鹼; 脱氢海罂粟碱
• 英文别名: (6aS)-1,2,9,10-Tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline; 4H-Dibenzo[de,g]quinoline, 5,6,6a,7-tetrahydro-1,2,9,10-tetramethoxy-6-methyl-, (S)-; (S)-5,6,6a,7-Tetrahydro-1,2,9,10-tetramethoxy-6-methyl-4H-dibenzo[de,g]quinoline; (+)-Glaucine; 4H-Dibenzo[de,g]quinoline, 5,6,6a,7-tetrahydro-1,2,9,10-tetramethoxy-6-methyl-, (6aS)-; d-Glaucine; 6aα-Aporphine, 1,2,9,10-tetramethoxy-; Glaucine; EINECS 207-501-5

物化性质

• 密度: 1.2±0.1 g/cm3
• 沸点: 487.0±45.0 °C at 760 mmHg
• 熔点: 246-247ºC
• 分子式: C₂₁H₂₅NO₄
• 分子量: 355.427
• 闪点: 140.2±25.9 °C
• 精确质量: 355.178345
• PSA: 40.16000
• LogP: 3.86
• 外观性状: 棕色粉末
• 蒸汽压: 0.0±1.2 mmHg at 25°C
• 折射率: 1.576
• 储存条件: 2-8℃，干燥，密闭

生物活性

• 描述: Glaucine (O,O-Dimethylisoboldine) 是一种从 Glaucium flavum Crantz 中分离的生物碱,具有镇咳,支气管扩张和抗炎作用。 Glaucine 是一种选择性的,具有口服活性的磷酸二酯酶 4 (PDE4) 抑制剂,在人支气管和多形核白细胞中的 Ki 为 3.4 µM。Glaucine 还是一种非选择性的 α-肾上腺素受体 (α-adrenoceptor) 拮抗剂,一种 Ca2+ 进入阻滞剂以及弱多巴胺 D1 和 D2 受体拮抗剂。Glaucine 具有抗氧化和抗病毒活性。
• 相关类别:
  信号通路 >> 跨膜转运 >> 钙通道
  信号通路 >> 抗感染 >> 流感病毒
  信号通路 >> 代谢酶/蛋白酶 >> 磷酸二酯酶(PDE)
  研究领域 >> 感染
  信号通路 >> G 蛋白偶联受体/G 蛋白 >> 肾上腺素能受体
  信号通路 >> G 蛋白偶联受体/G 蛋白 >> 多巴胺受体
  研究领域 >> 炎症/免疫
  信号通路 >> 神经信号通路 >> 多巴胺受体
• 靶点:

  Ki: 3.4 µM (Phosphodiesterase 4 (PDE4))[1] α-adrenoceptor[1] Ca2+ channel[1] Dopamine D1/D2 receptors[2]

• 参考文献:

  [1]. J Cortijo, et al. Bronchodilator and Anti-Inflammatory Activities of Glaucine: In Vitro Studies in Human Airway Smooth Muscle and Polymorphonuclear Leukocytes. Br J Pharmacol. 1999 Aug;127(7):1641-51.

  [2]. Golo M J Meyer, et al. Studies on the in Vivo Contribution of Human Cytochrome P450s to the Hepatic Metabolism of Glaucine, a New Drug of Abuse. Biochem Pharmacol. 2013 Nov 15;86(10):1497-506.

  [3]. Maya Spasova, et al. Cinnamoyl- And Hydroxycinnamoyl Amides of Glaucine and Their Antioxidative and Antiviral Activities. Bioorg Med Chem. 2008 Aug 1;16(15):7457-61.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : CE0925000 CHEMICAL NAME : 6a-alpha-Aporphine, 1,2,9,10-tetramethoxy- CAS REGISTRY NUMBER : 475-81-0 LAST UPDATED : 199512 DATA ITEMS CITED : 7 MOLECULAR FORMULA : C21-H25-N-O4 MOLECULAR WEIGHT : 355.47 HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 545 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 46(4),100,1983 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 143 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 46(4),100,1983 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 434 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 46(4),100,1983 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 167 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 46(4),100,1983 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 430 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 31,44,1968 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - guinea pig DOSE/DURATION : 140 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 46(4),100,1983 ** OTHER MULTIPLE DOSE TOXICITY DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 6300 mg/kg/12W-I TOXIC EFFECTS : Liver - liver function tests impaired REFERENCE : FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 46(4),100,1983

安全

• 危害码 (欧洲): Xi
• 海关编码: 2933990090

合成路线

海关

海关编码	2933990090
中文概述	2933990090. 其他仅含氮杂原子的杂环化合物. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:20.0%
申报要素	品名, 成分含量, 用途, 乌洛托品请注明外观, 6－己内酰胺请注明外观, 签约日期
Summary	2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%