131-01-1

• 常用中文名：地舍平
• 常用英文名：Deserpidine
• CAS号：131-01-1
• 分子式：C₃₂H₃₈N₂O₈
• 分子量：578.653
• 相关类别： 原料药 循环系统用药 抗高血压病药
• 发布时间：2018-08-05 15:59:25
• 更新时间：2024-01-14 11:16:37
• Deserpidine (Harmonyl) 是与 Reserpine 相关的从 Rauwolfia canescens 的根中分离的生物碱。Deserpidine 被用作抗高血压药和镇定剂。Deserpidine 是一种竞争性血管紧张素转化酶 (ACE) 抑制剂。Deserpidine 还减少了肾上腺皮质血管紧张素 II 诱导的醛固酮分泌。

名称

• 中文名: 蛇根平定
• 英文名: deserpidine
• 中文别名: 地舍平; 17-甲氧基-18-[(3,4,5-三甲氧基苯甲酰)氧]育亨烷-16-甲酸甲酯; 去甲氧利血平
• 英文别名: methyl (3β,16β,17α,18β,20α)-17-methoxy-18-{[(3,4,5-trimethoxyphenyl)carbonyl]oxy}yohimban-16-carboxylate; DESERPIDINE; canescine; (3b,16b,17a,18b,20a)-17-Methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-3,20-yohimban-16-carboxylic Acid Methyl Ester; MFCD00078228; Harmonyl; Recanescin; Canescin; Deserpidin; Methyl-(1S,2R,3R,4aS,13bR,14aS)-2-methoxy-3-{[(3,4,5-trimethoxyphenyl)carbonyl]oxy}-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydroindolo[2',3':3,4]pyrido[1,2-b]isochinolin-1-carboxylat; (1S,2R,3R,4aS,13bR,14aS)-2-méthoxy-3-{[(3,4,5-triméthoxyphényl)carbonyl]oxy}-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodécahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoléine-1-carboxylate de méthyle; Yohimban-16-carboxylic acid, 17-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3b,16b,17a,18b,20a)-; Desepridine; 11-desmethoxyreserpine; 17a-Methoxy-18b-[(3,4,5-trimethoxybenzoyl)oxy]-3b,20a-yohimban-16b-carboxylic Acid Methyl Ester; 17-methoxy-18-(3,4,5-trimethoxy-benzoyloxy)-yohimbane-16-carboxylic acid methyl ester; Raunormin; Methyl (3β,16β,17α,18β,20α)-17-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate; 17α-Methoxy-18β-[(3,4,5-trimethoxybenzoyl)oxy]-3β,20α-yohimban-16β-carboxylic acid methyl ester; Yohimban-16-carboxylic acid, 17-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3β,16β,17α,18β,20α)-; methyl (1R,15S,17R,18R,19S,20S)-18-methoxy-17-(3,4,5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate; EINECS 205-004-8; recanescine; Raunormine; Deserpidic Acid Methyl Ester 3,4,5-Trimethoxybenzoate; methyl (1S,2R,3R,4aS,13bR,14aS)-2-methoxy-3-{[(3,4,5-trimethoxyphenyl)carbonyl]oxy}-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylate

物化性质

• 密度: 1.3±0.1 g/cm3
• 沸点: 676.1±55.0 °C at 760 mmHg
• 熔点: ~275 °C (dec.)(lit.)
• 分子式: C₃₂H₃₈N₂O₈
• 分子量: 578.653
• 闪点: 362.7±31.5 °C
• 精确质量: 578.262817
• PSA: 108.55000
• LogP: 4.19
• 外观性状: 白色晶体粉末
• 蒸汽压: 0.0±2.1 mmHg at 25°C
• 折射率: 1.626
• 储存条件: -20°C
• 水溶解性: slightly soluble
• 分子结构:

  1、 摩尔折射率：154.57

  2、 摩尔体积（cm³/mol）：436.6

  3、 等张比容（90.2K）：1215.8

  4、 表面张力（dyne/cm）：60.0

  5、 极化率（10-24cm3）：61.27

• 计算化学:

  1.疏水参数计算参考值（XlogP）:无

  2.氢键供体数量:1

  3.氢键受体数量:9

  4.可旋转化学键数量:9

  5.互变异构体数量:无

  6.拓扑分子极性表面积109

  7.重原子数量:42

  8.表面电荷:0

  9.复杂度:953

  10.同位素原子数量:0

  11.确定原子立构中心数量:6

  12.不确定原子立构中心数量:0

  13.确定化学键立构中心数量:0

  14.不确定化学键立构中心数量:0

  15.共价键单元数量:1

生物活性

• 描述: Deserpidine (Harmonyl) 是与 Reserpine 相关的从 Rauwolfia canescens 的根中分离的生物碱。Deserpidine 被用作抗高血压药和镇定剂。Deserpidine 是一种竞争性血管紧张素转化酶 (ACE) 抑制剂。Deserpidine 还减少了肾上腺皮质血管紧张素 II 诱导的醛固酮分泌。
• 相关类别:
  信号通路 >> 代谢酶/蛋白酶 >> 血管紧张素转换酶(ACE)
  研究领域 >> 代谢疾病
  研究领域 >> 神经疾病
• 靶点:

  Angiotensin converting enzyme (ACE)[3]

• 体外研究: 地塞米松是一种有效的神经节阻断剂,与利血平的区别在于C-11处没有甲氧基。德西匹定已被用于治疗高血压和精神病。此外,德塞匹丁似乎是其他心脏疾病的控制者[1][2]。
• 参考文献:

  [1]. Varchi G, et al. Synthesis of deserpidine from reserpine. J Nat Prod. 2005 Nov;68(11):1629-31.

  [2]. Zhang H, et al. Liquid chromatography/tandem mass spectrometry method for the quantification of deserpidine in human plasma: Application to a pharmacokinetic study. J Chromatogr B Analyt Technol Biomed Life Sci. 2009 Oct 1;877(27):3221-5.

  [3]. Fulton SC, et al. Comparison of the effectiveness of deserpidine, reserpine, and alpha-methyltyrosine on brain biogenic amines. Fed Proc. 1976 Dec;35(14):2558-62.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : ZG0875000 CHEMICAL NAME : 3-beta,20-alpha-Yohimban-16-beta-carboxylic acid, 18-beta-hydroxy-17-alpha-methoxy-, methyl ester, 3,4,5-trimethoxybenzoate (ester) CAS REGISTRY NUMBER : 131-01-1 BEILSTEIN REFERENCE NO. : 0101820 LAST UPDATED : 199612 DATA ITEMS CITED : 12 MOLECULAR FORMULA : C32-H38-N2-O8 MOLECULAR WEIGHT : 578.72 WISWESSER LINE NOTATION : T F6 D5 C666 EM ON&&TTTJ SOVR CO1 DO1 EO1& TO1 UVO1 HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 15 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : 27ZQAG "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972 Volume(issue)/page/year: -,104,1972 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 500 mg/kg TOXIC EFFECTS : Behavioral - coma Lungs, Thorax, or Respiration - dyspnea Gastrointestinal - hypermotility, diarrhea REFERENCE : JAPMA8 Journal of the American Pharmaceutical Association, Scientific Edition. (Washington, DC) V.29-49, 1940-60. For publisher information, see JPMSAE. Volume(issue)/page/year: 44,688,1955 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 60 mg/kg TOXIC EFFECTS : Behavioral - coma Lungs, Thorax, or Respiration - dyspnea Gastrointestinal - hypermotility, diarrhea REFERENCE : JAPMA8 Journal of the American Pharmaceutical Association, Scientific Edition. (Washington, DC) V.29-49, 1940-60. For publisher information, see JPMSAE. Volume(issue)/page/year: 44,688,1955 ** OTHER MULTIPLE DOSE TOXICITY DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 25690 mg/kg/4W-C TOXIC EFFECTS : Related to Chronic Data - death REFERENCE : JAPMA8 Journal of the American Pharmaceutical Association, Scientific Edition. (Washington, DC) V.29-49, 1940-60. For publisher information, see JPMSAE. Volume(issue)/page/year: 44,688,1955 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Mammal - dog DOSE/DURATION : 80 mg/kg/4D-I TOXIC EFFECTS : Related to Chronic Data - death REFERENCE : JAPMA8 Journal of the American Pharmaceutical Association, Scientific Edition. (Washington, DC) V.29-49, 1940-60. For publisher information, see JPMSAE. Volume(issue)/page/year: 44,688,1955 ** TUMORIGENIC DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Human - woman DOSE/DURATION : 16 mg/kg/9Y-C TOXIC EFFECTS : Tumorigenic - neoplastic by RTECS criteria Skin and Appendages - tumors REFERENCE : LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 2,672,1974 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 54 mg/kg/77W-C TOXIC EFFECTS : Tumorigenic - Carcinogenic by RTECS criteria Liver - tumors Blood - lymphoma, including Hodgkin's disease REFERENCE : COREAF Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. (Paris, France) V.1-261, 1835-1965. For publisher information, see CRASEV. Volume(issue)/page/year: 254,1535,1962 ** REPRODUCTIVE DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Unreported DOSE : 4950 mg/kg SEX/DURATION : female 6-16 day(s) after conception TOXIC EFFECTS : Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) REFERENCE : CRSBAW Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. (SPPIF, B.P.22, F-41353 Vineuil, France) V.1- 1849- Volume(issue)/page/year: 155,2291,1961 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Unreported DOSE : 1600 ug/kg SEX/DURATION : female 1 day(s) pre-mating TOXIC EFFECTS : Reproductive - Fertility - other measures of fertility REFERENCE : AJOGAH American Journal of Obstetrics and Gynecology. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63146) V.1- 1920- Volume(issue)/page/year: 83,1405,1962 *** REVIEWS *** TOXICOLOGY REVIEW CLPTAT Clinical Pharmacology and Therapeutics (St. Louis). (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63146) V.1- 1960- Volume(issue)/page/year: 5,480,1964 TOXICOLOGY REVIEW ADVPA3 Advances in Pharmacology. (New York, NY) V.1-6, 1962-68. For publisher information, see AVPCAQ. Volume(issue)/page/year: 4,263,1966 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X9135 No. of Facilities: 35 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 430 (estimated) No. of Female Employees: 239 (estimated)

安全

• 危险品运输编码: UN 9111
• WGK德国: 3

合成路线

4521-61-3 54290-61-8 ~90% 131-01-1

文献：INDENA S.P.A. Patent: WO2005/95394 A1, 2005 ; Location in patent: Page/Page column 10-11 ;

4521-61-3 ~% 131-01-1

文献：Journal of the American Chemical Society, , vol. 77, p. 4084,4086 Journal of the American Chemical Society, , vol. 77, p. 4335,4340

61-54-1 ~% 131-01-1

文献：Bulletin de la Societe Chimique de France, , p. 673,676 Annales Pharmaceutiques Francaises, , vol. 17, p. 15,21

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