N-methylpavine | 5531-95-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 栗碱生物碱
• 英文名称: N-methylpavine
• 英文别名: (+7-)-N-methylpavine；(+/-)-Argemonine；argemonine；2,3,8,9-tetramethoxy-13-methyl-5,6,11,12-tetrahydro-5,11-epiazano-dibenzo[a,e]cyclooctene；Norargemonin-methylether；4,5,12,13-tetramethoxy-17-methyl-17-azatetracyclo[7.7.1.02,7.010,15]heptadeca-2,4,6,10,12,14-hexaene
• CAS: 5531-95-3
• 化学式: C₂₁H₂₅NO₄
• 分子量: 355.434
• InChiKey: QEOWCPFWLCIQSL-UHFFFAOYSA-N

物化性质

• 熔点：
  132 °C
• 沸点：
  446.0±45.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  罂粟碱 在 盐酸 、 lithium aluminium tetrahydride 、 甲酸 作用下， 以 乙醚 为溶剂， 反应 9.83h， 生成 N-methylpavine
  参考文献：
  名称：

  Langhals, Elke; Langhals, Heinz; Ruechardt, Christoph, Chemische Berichte, 1984, vol. 117, # 4, p. 1436 - 1454

  摘要：

  DOI：

文献信息

• Aryl Radical Cyclizations:  One-Pot Syntheses of Protoberberine and Pavine Alkaloids
  作者：Kazuhiko Orito、Yoshitaka Satoh、Hidetoshi Nishizawa、Rika Harada、Masao Tokuda

  DOI：10.1021/ol006213a

  日期：2000.8.1

  2-(2'-bromo-beta-phenethyl)isoquinolinium bromides 6 and their nor- and homoanalogues (10,11) induced 6-, 5-, and 7-exo radical closures in a one-pot manner to give protoberberines 2, dibenzo[b,g]indolizidine 14a and, dibenzo[a, h]-1-azabicyclo[5.4.0]undecane 15a, respectively. A one-pot radical cyclization of 1-(2'-bromobenzyl)isoquinoline methiodide 18a gave a pavine alkaloid, (+/-)-algemonine (19a).

  在沸腾的苯中用AIBN-Bu（3）SnH处理2-（2'-溴-β-苯乙基）异咔唑7，得到的8-氧代丁苯橡胶3的收率很高。对2-（2'-溴-β-苯乙基）溴化异喹啉鎓6及其正和类似物（10,11）的类似处理以一锅方式诱导6-，5-和7-exo自由基封闭分别得到原小ber碱2，二苯并[b，g]吲哚唑烷14a和二苯并[a，h] -1-氮杂双环[5.4.0]十一烷15a。一锅法将1-（2'-溴苄基）异喹啉甲硫醇18a进行自由基环化，得到了一种牛类生物碱（+/-）-金刚烷（19a）。
• An efficient synthesis of argemonine, a pavine alkaloid
  作者：Somsak Ruchirawat、Anucha Namsa-aid

  DOI：10.1016/s0040-4039(00)02233-4

  日期：2001.2

  A method for the synthesis of 1,2-dihydroisoquinoline derivatives is described and the conversion of the 1,2-dihydroisoquinoline intermediate to a pavine alkaloid via palladium-induced intramolecular hydroarylation reaction and radical cyclization is presented.

  描述了一种合成1,2-二氢异喹啉衍生物的方法，并提出了通过钯诱导的分子内加氢芳基化反应和自由基环化反应将1,2-二氢异喹啉中间体转化为猪生物碱的方法。
• A new route to the pavine (5,6,11,12-tetrahydro-5,11-imino-13-methyldibenzo[a,e]cyclo-octene) skeleton: synthesis of (±)-argemonine
  作者：Takashi Nomoto、Hiroaki Takayama

  DOI：10.1039/c39820001113

  日期：——

  A new route to the pavine skeleton was investigated starting from the readily accessible tetrahydro-6,12-methanodibenz[c,f]azocine (1,RH or Me); an efficient synthesis of a typical pavine alkaloid (±)-argemonine (6, R = OMe) from (1, R = OMe) was accomplished in 53% overall yield.

  从容易获得的四氢-6,12-甲二苯并[ c，f ]偶氮星（1，R H或Me）开始研究了一条通往猪骨架的新途径。从（1，R = OMe）高效合成典型的牛类生物碱（±）-精氨酸（6，R = OMe）的总产率为53％。
• Methods of producing nor-opioid and nal-opioid benzylisoquinoline alkaloids
  申请人：Antheia, Inc.

  公开号：US10738335B2

  公开（公告）日：2020-08-11

  A method of demethylizing an opioid to a nor-opioid is provided. The method comprises contacting an opioid with at least one enzyme. Contacting the opioid with the at least one enzyme converts the opioid to a nor-opioid. A method of converting a nor-opioid to a nal-opioid is provided. The method comprises contacting a nor-opioid with at least one enzyme. Contacting the nor-opioid with the at least one enzyme converts the nor-opioid to a nal-opioid.

  本发明提供了一种将阿片类药物去甲基化为非阿片类药物的方法。该方法包括将阿片类药物与至少一种酶接触。将阿片与至少一种酶接触可将阿片转化为去甲阿片。提供了一种将去甲阿片转化为正阿片的方法。该方法包括将去甲阿片与至少一种酶接触。将去甲阿片与至少一种酶接触可将去甲阿片转化为正阿片。
• Herbal composition for treating various disorders including psoriasis, a process for preparation thereof and method for treatment of such disorders
  申请人：LUPIN LIMITED

  公开号：US20030194456A1

  公开（公告）日：2003-10-16

  The invention provides a novel herbal composition containing the extracts of the leaves and/or stem of Argemone mexicana plant, optionally containing the extracts of the fruits of Cuminum cyminum , which exhibits useful in vitro, in vivo and interesting immunological and pharmacological activities; a process for preparation thereof; and a method of treatment of psoriasis and related immunological and biological disorders by administration of the said novel herbal composition. The useful in vitro, in vivo and interesting immunological and pharmacological activities exhibited by the extracts and fractions of the leaves and/or stem of Argemone mexicana plant include immunosuppression, lymphoproliferation inhibition, cytokine modulation such as IL-2 inhibition, IFNgamma inhibition, IL-10 induction, keratinocyte proliferation inhibition, keratolytic activity, endothelial cell proliferation inhibition, inhibition of cell adhesion molecule expression such as ICAM-1, MEST inhibition, and enzymes inhibition such as p60src Tyrosine kinase, which are known to be involved in anti-psoriatic activity. The novel herbal composition(s) is useful in the treatment of various disorders, such as psoriasis including plaque psoriasis, gutatte psoriasis, pustular psoriasis and psoriasis of the nails; dermatitis and scleroderma; eczema; inflammatory disorders and other autoimmune diseases like psoriatic arthritis, rheumatoid arthritis, Crohn's disease, multiple sclerosis, irritable bowel disease, ankylosing spondilitis, systemic lupus erythremetosus and Sjogren's syndrome; allergies like asthma and chronic obstructive pulmonary disease and is safe, well-tolerated, non-toxic, with minimal and reversible adverse reactions or side effects, and most importantly, with minimal relapse or recurrence of the disease following completion of a treatment regimen. The invention also describes the presence of phosphodiesterase (III, IV and V) inhibition and 5-Lipoxygenase inhibition in the aqueous, ethanolic or aqueous-ethanolic extracts of fruits of Cuminum cyminum plant.

  本发明提供了一种新型草药组合物，其中含有以下植物的叶子和/或茎的提取物 Argemone mexicana 植物的叶和/或茎的提取物，可选择含有 孜然 本发明提供了一种新型草药组合物，该组合物具有有用的体外、体内和有趣的免疫学和药理学活性；其制备方法；以及通过服用所述新型草药组合物治疗银屑病和相关免疫学和生物学疾病的方法。墨西哥刺五加（Argemone mexicana）叶和/或茎的提取物和馏分在体外、体内和有趣的免疫学和药理学方面表现出的有用活性。 Argemone mexicana 包括免疫抑制、淋巴细胞增殖抑制、细胞因子调节（如 IL-2 抑制、IFNgamma 抑制、IL-10 诱导）、角质细胞增殖抑制、角质溶解活性、内皮细胞增殖抑制、细胞粘附分子表达抑制（如 ICAM-1）、MEST 抑制、酶抑制（如 p60src 酪氨酸激酶），已知这些活性参与了抗银屑病活性。新型草药组合物可用于治疗各种疾病，如银屑病，包括斑块型银屑病、银屑病、脓疱型银屑病和指甲银屑病；皮炎和硬皮病；湿疹；炎症性疾病和其他自身免疫性疾病，如银屑病关节炎、类风湿性关节炎、克罗恩病、多发性硬化症、肠易激综合征、强直性脊柱炎、系统性红斑狼疮和 Sjogren 综合征；过敏症，如哮喘和慢性阻塞性肺病，并且安全、耐受性好、无毒、不良反应或副作用极小且可逆，最重要的是，在完成治疗方案后，疾病的复发或复发率极低。本发明还描述了孜然果实的水提取物、乙醇提取物或水乙醇提取物中存在磷酸二酯酶（III、IV 和 V）抑制作用和 5-脂氧合酶抑制作用。 孜然 植物。