Atropine 阿托品

CAS 51-55-8 MFCD00022622

化学结构图

51-55-8
SMILES: CN1[C@H]2CC[C@@H]1C[C@H](OC(=O)C(CO)c1ccccc1)C2

化学属性

Mol. FormulaC17H23NO3
Mol. Weight289.41
Melting Point115-118 °C
Appearance powder 50 白色结晶性粉末，无臭，无味。Mp114-116℃，在高真空下，于93-110℃升华。本品在各溶剂中的溶解度分别为：80℃热水(1：90)，乙醇(1：2)，氯仿(1：1)，乙醚(1：25)，溶于苯和稀酸溶液。低毒，LD (大鼠，经口) 622mg/kg。
SolubilityH2O: 2 mg/mL

别名和识别编码

Chemical NameAtropine
CAS Number51-55-8
MDL NumberMFCD00022622
Synonym Atropin-flexiolen (8-甲基-8-氮杂双环[3.2.1]辛-3-基) endo-(+/-)-α-(羟甲基)苯乙酸酯 茄碱 莨菪鹼 颠茄碱 间甲氧基苯甲醛 alpha-(Hydroxymethyl)benzeneacetic acid 1alphah,5alphah-tropan-3alpha-ol(+-)-tropate(ester) 茄苷 (+,-)-tropyltropate DL-HYOSCYAMINE 龙葵碱 TIMTEC-BB SBB005985 1alphaH,5alphaH-Tropan-3alpha-ol (.+/-.)-tropate (ester) 2-Phenylhydracrylic acid 3-alpha-tropanyl ester 阿托品 Atropin Eyesules 2-phenylhydracrylicacid3-alpha-tropanylester 曼陀羅鹼 (+,-)-Tropyl tropate (8-甲基-8-氮杂双环[3.2.1]辛-3-基) endo-(+/-)-α-(羟甲基)苯乙酸酯 莨菪碱 龙葵碱 alpha-(Hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo(3.2.1)oct-3-yl ester 1alphaH,5alphaH-Tropan-3alpha-ol (± 3-甲氧基苯甲醛 HYOSCYAMINE Atropina 1-alpha-H,5-alpha-H-Tropan-3-alpha-ol (.+/-.)-tropate (+/-)-HYOSCYAMINE 顛茄鹼 endo-(+/-)-alpha-(Hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester (8-甲基-8-氮杂双环[3.2.1]辛-3-基) 3-羟基-2-苯基-丙酸酯 莨菪碱 Atropinol 托品鹼 茄灵 (8-甲基-8-氮杂双环[3.2.1]辛-3-基) ENDO-(+/-)-ALPHA-(羟甲基)苯乙酸酯 ATROPINE alpha-(hydroxymethyl)benzeneaceticacid8-methyl-8-azabicyclo(3.2.1)oct-3-yl 1-alpha-h,5-alpha-h-tropan-3-alpha-ol(+-)-tropate(ester)
Beilstein Registry Number91260
EC Number200-104-8
PubChem Substance ID174174
Chemical Name Translation阿托品
Merck Number875
Wiswesser Line NotationT56 A ANTJ A1 GOVYR&1Q
LabNetwork Molecule IDLN00238411
InChIInChI=1S/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15?,16?
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分类

  • {SNA} Analytical Standards, Analytical/Chromatography, Chromatography, EP Standards, EP Standards A - B, Pharmaceutical Standards,
  • {SNA} AN-AZ, Antagonists, Approved Therapeutics/Drug Candidates, Bioactive Small Molecules, Cell Signaling and Neuroscience, Cholinergics, Neuroscience, Neurotransmission, Neurotransmitters, Pfizer Compounds, 细胞生物学
  • {SNA} AN-
  • {Chemicalbook} 生物化学品: 生化试剂: 生物碱
  • {SNA} Analytical Standards, Chromatography, EP Standards, EP Standards A - B, Pharmaceutical Standards, Pharmacopeia Standards, 分析/色谱
  • {SNA} AN-AZ, Bioactive Small Molecules,

相关文献及参考

  • [2]. Carr BJ, et al. Myopia-Inhibiting Concentrations of Muscarinic Receptor Antagonists Block Activation of Alpha2A-Adrenoceptors In Vitro. Invest Ophthalmol Vis Sci. 2018 Jun 1;59(7):2778-2791.
  • Beil. 21 ,V,1,235
  • Merck 14 ,875
  • Trovero, F., et al., Pharmacological profile of CEB-1957 and atropine toward brain muscarinic receptors and comparative study of their efficacy against sarin poisoning. Toxicol. Appl. Pharmacol. 150 , 321-327, (1998) 摘要
  • Walch, L., et al., Evidence for a M 1 muscarinic receptor on the endothelium of human pulmonary veins. Br. J. Pharmacol. 130 , 73-78, (2000) 摘要
  • Zwart, R., and Vijverberg, H.P., Potentiation and inhibition of neuronal nicotinic receptors by atropine: competitive and noncompetitive effects. Mol. Pharmacol. 52 , 886-895, (1997)
  • [1]. P
  • [1]. Perera RK, et al. Atropine augments cardiac contractility by inhibiting cAMP-specific phosphodiesterase type 4. Sci Rep. 2017 Nov 9;7(1):15222.

安全信息

RTECSCK0700000
GHS Symbol
Precautionary statements
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P301+P310
  • P284 Wear respiratory protection.? 佩戴呼吸保护装置。
  • P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P310 Immediately call a POISON CENTER or doctor/physician. 立即呼救解毒中心或医生/医师。
Hazard statements
  • H300+H330
  • H330 Fatal if inhaled 吸入致命
  • H300 Fatal if swallowed 吞食致命
WGK Germany3
Signal word Danger
Personal Protective Equipment Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
Hazard Codes T+
Safety Statements
  • S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时，立即求医（可能时出示标签）；
  • S25 Avoid contact with eyes 避免眼睛接触；
Risk Statements
  • R26/28 Very toxic by inhalation and if swallowed 吸入及吞食都有剧毒
UN Number 1544 
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intramuscular
SPECIES OBSERVED        : Human - man
DOSE/DURATION           : 175 ug/kg
TOXIC EFFECTS :
   Behavioral - hallucinations, distorted perceptions
REFERENCE :
   FEPRA7 Federation Proceedings, Federation of American Societies for
   Experimental Biology. (Bethesda, MD)  V.1-46, 1942-87.
   Volume(issue)/page/year: 32,250,1973

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intramuscular
SPECIES OBSERVED        : Human
DOSE/DURATION           : 1 ug/kg
TOXIC EFFECTS :
   Sense Organs and Special Senses (Eye) - mydriasis (pupillary dilation)
REFERENCE :
   85IVAW "Possible Long-Term Health Effects of Short-Term Exposure to Chemical
   Agents," National Research Council, 3 vols., Washington, DC, National
   Academy Press, 1982-85  Volume(issue)/page/year: 1,L1,1982

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Amphibian - frog
DOSE/DURATION           : 1 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   HBAMAK "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." (Leipzig,
   Ger. Dem. Rep.)  Volume(issue)/page/year: 4,1311,1935

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intradermal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 550 mg/kg
TOXIC EFFECTS :
   Behavioral - excitement
   Behavioral - ataxia
   Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
   AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans
   Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium)  V.4-   
   1898-  Volume(issue)/page/year: 59,149,1938

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Unreported
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 1600 ug/kg
SEX/DURATION            : female 1 day(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Fertility - other measures of fertility
REFERENCE :
   FESTAS Fertility and Sterility.  (American Fertility Soc., 608 13th Ave. S,
   Birmingham, AL 35282) V.1-    1950-  Volume(issue)/page/year: 12,346,1961

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Human - woman
DOSE                    : 20 ug/kg
SEX/DURATION            : female 26-39 week(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - cardiovascular
   (circulatory) system
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: 82,1055,1961

其他信息

  • 储运特性:通风低温干燥; 与库房食品原料分开存放
  • 方法二:可从茄科东莨菪属植物唐古特山莨菪或喜马拉雅山莨菪的根中提取，也可以人工合成得到。
  • 药代动力学:口服后很快由胃肠道吸收并迅速分布到全身组织，也能通过胎盘进入胎儿循环。临床研究表明，肌内注射2mg后，24小时内有85～88%经尿排出。其中约5%以原形出现，33%则为其代谢产物; 在粪便及其他分泌物中仅有少量排出。
  • 使用方法:阿托品主要用于内脏平滑肌痉挛所致的绞痛(以缓解胃肠道平滑肌痉挛的效果较好)，0.3mg口服或0.5mg皮下、肌内或静注; 虹膜睫状体炎：0.5～1%液滴眼; 全身麻醉前给药，以减少呼吸道及唾液分泌，0.5mg皮下注射; 锑剂中毒所致的阿斯综合征：2mg静注及1～2mg皮下注射，以后
  • 阿托品价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 K1132001 颠茄碱 1g 461元
  • 图谱信息:阿托品(51-55-8)Raman光谱 阿托品(51-55-8)核磁图( 1 HNMR) 阿托品(51-55-8)质谱(MS) 阿托品(51-55-8)核磁图( 13 CNMR) 阿托品(51-55-8)红外图谱(IR2) 阿托品(51-55-8)红外图谱(IR1)
  • Sigma Aldrich:51-55-8(sigmaaldrich)
  • 方法一:颠茄叶经提取莨菪碱(左旋体)，再经消旋化、重结晶精制而得。
  • 可燃性危险特性:可燃; 燃烧产生有毒氮氧化物烟雾; 病人用药副作用; 视觉改变; 瞳孔放大,肌肉无力
  • 下游产品:硫酸阿托品
  • 毒性分级:高毒
  • 用途一:临床作为解痉药物，并作为检定金的试剂。
  • 概述:阿托品是从茄科植物颠茄(Atropa bell-adonna)、曼陀罗(Datura stramonium)或莨菪 (Hyosc-yamus niger)等中提取的生物碱。天然存在的是不稳定的左旋茛菪碱(L-hyoscyamine)经化学处理后，得稳定的消旋体即阿托品。也可化学合成，常用其硫酸盐。白色结晶性粉末、无臭、味苦，易溶于水和醇。遇碱性药物可引起分解。阿托品能阻断M-胆碱受体，从而拮抗乙酰胆碱或其拟似药的M样作用(毒蕈碱样作用)。 主要作用如下： (1) 松弛平滑肌：本品有松弛许多内脏平滑肌的作用，对过度活动或处于痉挛状态的平滑肌则有明显松弛作用，而对正常活动的平滑肌影响较小。 (2) 抑制腺体分泌：通过阻断M-胆碱受体抑制腺体分泌。对唾液腺及汗腺的抑制作用最明显。也可使泪腺和呼吸道腺体的分泌大大减少，但对胃酸分泌的影响则较小。 (3) 对眼的作用：阿托品通过阻断瞳孔括约肌及睫状肌的M-胆碱受体而表现为散瞳、升高眼内压及调节麻痹。这三种作用都有重要临床意义。 (4) 对心血管的作用： 较大剂量(1～2mg) 阿托品能解除迷走神经对心脏的抑制，因而使心率加快。大剂量能扩张皮肤及内脏血管，解除小动脉痉挛。其扩张血管及解除小血管痉挛的机理不明。 (5) 兴奋中枢神经系统： 大剂量时出现烦躁不安、多言及谵妄等。中毒剂量(超过10mg)则可产生幻觉、定向障碍、不随意运动及惊厥等。
  • 参考质量标准:含量≥99%；mp114-118℃；要求比旋光度合格；检测还原高锰酸钾物质、灼烧残渣等杂质含量。
  • 副作用:副作用有口干、视力模糊、心悸
  • 使用方法:阿托品主要用于内脏平滑肌痉挛所致的绞痛(以缓解胃肠道平滑肌痉挛的效果较好)，0.3mg口服或0.5mg皮下、肌内或静注; 虹膜睫状体炎：0.5～1%液滴眼; 全身麻醉前给药，以减少呼吸道及唾液分泌，0.5mg皮下注射; 锑剂中毒所致的阿斯综合征：2mg静注及1～2mg皮下注射，以后每半小时静注1mg，病情好转后改用每2～4小时肌注1mg，直到心率达每分钟100次并恢复节律性心律; 房室传导阻滞：0.5～1mg静注，每4～6小时一次; 感染中毒性休克：在补充血容量前提下，1～2mg用葡萄糖液稀释后静注，每10～20分钟一次; 有机磷酸酯类中毒：轻度中毒者0.5～1mg肌注，每日3次;中度中毒者1～2mg肌注或静
  • 用途二:阿托品是副交感神经

系列性分类

  1. Life Science 生命科学
  2. Cell Biology 细胞生物学
  3. Bioactive Small Molecules - Cell Biology
  4. AN-AZ - Bioactive Small Molecules
  1. Life Science 生命科学
  2. Cell Biology 细胞生物学
  3. Cell Signaling and Neuroscience - Cell Biology
  4. Approved Therapeutics/Drug Candidates - Cell Signaling and Neuroscience
  5. Pfizer Compounds - Approved Therapeutics/Drug Candidates
  1. Analytical & Chromatography 分析化学与色谱
  2. Analytical Standards
  3. Chromatography - Analytical Standards
  4. Life Sciences Standards - Chromatography
  5. Biotoxins - Life Sciences Standards
  6. Phytotoxins - Biotoxins
  1. Life Science 生命科学
  2. Biochemistry / Glyco-Chemistry
  3. Alkaloids
  1. Medical Research Areas
  2. GPCR & G Protein
  3. mAChR  (毒蕈碱型乙酰胆碱受体)
  1. Medical Research Areas
  2. Metabolism
  3. Endogenous Metabolite  (内源性代谢物)

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