Scopolamine - analytical standard , CAS No.51-34-3

CAS: 51-34-3 Cat. No.: P303845 Formula: C₁₇H₂₁NO₄ Peso molecolare: 303.35 Numero EC: 200-090-3 PubChem CID: 3000322

GRADE & PURITY Analytical standard

Synonyms

Hyoscine | Scopine (-)-tropate | Scopine tropate

Storage

Store at 2-8°C,Protected from light,Argon charged

Shipped In

Wet ice

Panoramica

Product Describtion:

Scopolamine (Skopolamin) is a tropane alkaloid derived from plants of the nightshade family, specifically Hyoscyamus niger and Atropa belladonna, with anticholinergic, antiemetic and antivertigo properties.

Product Application:

Scopolamine is an acetylcholine antagonist. Used in treatment of motion sickness; antiemetic; antispasmodic; mydriatic; preanesthetic medicant.

Specifications

Sinonimi

Hyoscine | Scopine (-)-tropate | Scopine tropate

Specifiche e purezza

analytical standard

Condizioni di conservazione di stoccaggio

Store at 2-8°C,Protected from light,Argon charged

Spedito in

Wet ice

Questo prodotto richiede spedizione a catena fredda. I servizi di terra e altri servizi economici non sono disponibili.

Grado

Standard analitico

Tipo di azione

INHIBITOR

Nomi e identificatori

• Pubchem Sid: 504762274
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504762274
• Sorrisi canonici: CN1C2CC(CC1C3C2O3)OC(=O)C(CO)C4=CC=CC=C4
• IUPAC Name: [(1R,2R,4S,5S)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl] (2S)-3-hydroxy-2-phenylpropanoate
• InChIKey: STECJAGHUSJQJN-USLFZFAMSA-N
• INCHI: 1S/C17H21NO4/c1-18-13-7-11(8-14(18)16-15(13)22-16)21-17(20)12(9-19)10-5-3-2-4-6-10/h2-6,11-16,19H,7-9H2,1H3/t11?,12-,13-,14+,15-,16+/m1/s1
• Isomeri SMILES: CN1[C@@H]2CC(C[C@H]1[C@H]3[C@@H]2O3)OC(=O)[C@H](CO)C4=CC=CC=C4
• PubChem CID: 3000322
• Peso molecolare: 303.35

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Classe Hydroxy acids and derivatives
      • Subclass Beta hydroxy acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Classe: Hydroxy acids and derivatives
• Subclass: Beta hydroxy acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Beta hydroxy acids and derivatives
• Alternative Parents: Piperidines Benzene and substituted derivatives Morpholines N-alkylpyrrolidines Trialkylamines Amino acids and derivatives Carboxylic acid esters Azacyclic compounds Oxacyclic compounds Dialkyl ethers Epoxides Monocarboxylic acids and derivatives Primary alcohols Carbonyl compounds Hydrocarbon derivatives Organopnictogen compounds Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Beta-hydroxy acid - Monocyclic benzene moiety - Morpholine - Oxazinane - Piperidine - N-alkylpyrrolidine - Benzenoid - Pyrrolidine - Amino acid or derivatives - Carboxylic acid ester - Tertiary amine - Tertiary aliphatic amine - Oxacycle - Organoheterocyclic compound - Azacycle - Carboxylic acid derivative - Dialkyl ether - Oxirane - Ether - Monocarboxylic acid or derivatives - Primary alcohol - Organopnictogen compound - Organonitrogen compound - Organooxygen compound - Amine - Organic oxide - Carbonyl group - Organic oxygen compound - Organic nitrogen compound - Alcohol - Hydrocarbon derivative - Aromatic heteropolycyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as beta hydroxy acids and derivatives. These are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Obiettivi associati (umani)

CHRM3 Tclin Muscarinic acetylcholine receptor M3 (0 Activities)

Discover Target: CHRM3

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CHRM4 Tclin Muscarinic acetylcholine receptor M4 (0 Activities)

Discover Target: CHRM4

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CHRM2 Tclin Muscarinic acetylcholine receptor M2 (0 Activities)

Discover Target: CHRM2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CHRM1 Tclin Muscarinic acetylcholine receptor M1 (0 Activities)

Discover Target: CHRM1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Proprietà chimiche e fisiche

• Solubilità: Chloroform (Slightly), DMSO (Sparingly), Ethanol (Slightly), Methanol (Slightly)；Soluble in MeCN
• Sensibilità: light sensitive；moisture sensitive
• Punto di infiammabilità (°C): 232.2ºC
• Punto di ebollizione (°C): 460.3ºC at 760 mmHg
• Punto di fusione (°C): 59ºC
• Peso molecolare: 303.350 g/mol
• XLogP3: 0.900
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 303.147 Da
• Monoisotopic Mass: 303.147 Da
• Topological Polar Surface Area: 62.300 Ų
• Heavy Atom Count: 22
• Formal Charge: 0
• Complexity: 418.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Riferimenti

1. Leilei Pan, Shuifeng Xiao, Zichao Xu, Wenping Li, Long Zhao, Ling Zhang, Ruirui Qi, Junqin Wang, Yiling Cai.  (2023)  Orexin-A attenuated motion sickness through modulating neural activity in hypothalamus nuclei.  BRITISH JOURNAL OF PHARMACOLOGY,      [PMID:38129941] [10.1111/bph.16307]

2. Xi Zhu, Yangjing Lv, Miaoliang Fan, Jianan Guo, Yujia Zhang, Bianbian Gao, Changjun Zhang, Yuanyuan Xie.  (2023)  Exploration of the novel phthalimide-hydroxypyridinone derivatives as multifunctional drug candidates against Alzheimer’s disease.  BIOORGANIC CHEMISTRY,      [PMID:37690318] [10.1016/j.bioorg.2023.106817]

3. Changjun Zhang, Yujia Zhang, Yangjing Lv, Jianan Guo, Bianbian Gao, Yi Lu, Anjie Zang, Xi Zhu, Tao Zhou, Yuanyuan Xie.  (2023)  Chromone-based monoamine oxidase B inhibitor with potential iron-chelating activity for the treatment of Alzheimer’s disease.  JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY,      [PMID:36519319] [10.1080/14756366.2022.2134358]

4. Jingru Zheng, Yuanhong Gao, Jie Ding, Na Sun, Songyi Lin.  (2022)  Antarctic krill peptides improve scopolamine-induced memory impairment in mice.  Food Bioscience,      [PMID:] [10.1016/j.fbio.2022.101987]

5. Wang Yue, Wu Xinyan, Yang Kailin, Liu Qing, Jiang Baoping, Yang Runmei, Xiao Peigen, He Chunnian.  (2022)  Integrating network pharmacology analysis and pharmacodynamic evaluation for exploring the active components and molecular mechanism of moutan seed coat extract to improve cognitive impairment.  Frontiers in Pharmacology,      [PMID:36034803] [10.3389/fphar.2022.952876]

6. Chuansheng Yao, Xiaoying Jiang, Rui Zhao, Zhichao Zhong, Jiamin Ge, Junlong Zhu, Xiang-Yang Ye, Yuanyuan Xie, Zhen Liu, Tian Xie, Renren Bai.  (2022)  HDAC1/MAO-B dual inhibitors against Alzheimer’s disease: Design, synthesis and biological evaluation of N-propargylamine-hydroxamic acid/o-aminobenzamide hybrids.  BIOORGANIC CHEMISTRY,      [PMID:35305483] [10.1016/j.bioorg.2022.105724]

7. Yue Zhao, Zhiqiang Lu, Xiaomeng Xu, Na Sun, Songyi Lin.  (2022)  Sea Cucumber-Derived Peptide Attenuates Scopolamine-Induced Cognitive Impairment by Preventing Hippocampal Cholinergic Dysfunction and Neuronal Cell Death.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:34989228] [10.1021/acs.jafc.1c07232]

8. Zhiqiang Lu, Xiaomeng Xu, Dongmei Li, Na Sun, Songyi Lin.  (2021)  Comprehensive Analysis of Mouse Hippocampal Lysine Acetylome Mediated by Sea Cucumber Peptides Preventing Memory Impairment.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:34633809] [10.1021/acs.jafc.1c05155]

9. Min Wang, Longji Fang, Tongtong Liu, Xuejie Chen, Yan Zheng, Yilong Zhang, Shiming Chen, Zeng Li.  (2021)  Discovery of 7-O-1, 2, 3-triazole hesperetin derivatives as multi-target-directed ligands against Alzheimer's disease.  CHEMICO-BIOLOGICAL INTERACTIONS,      [PMID:33905740] [10.1016/j.cbi.2021.109489]

10. Yilei Song, Xiangyu Wang, Xingrong Wang, Jianze Wang, Qiulian Hao, Jifu Hao, Xueqin Hou.  (2021)  Osthole-Loaded Nanoemulsion Enhances Brain Target in the Treatment of Alzheimer’s Disease via Intranasal Administration.  Oxidative Medicine and Cellular Longevity,      [PMID:33564364] [10.1155/2021/8844455]

11. Jianan Guo, Zhisheng Mi, Xiaoying Jiang, Changjun Zhang, Zili Guo, Linzi Li, Jinping Gu, Tao Zhou, Renren Bai, Yuanyuan Xie.  (2020)  Design, synthesis and biological evaluation of potential anti-AD hybrids with monoamine oxidase B inhibitory and iron-chelating effects.  BIOORGANIC CHEMISTRY,      [PMID:33353806] [10.1016/j.bioorg.2020.104564]

12. Xu Yi, Zhang Shuai, Sun Qiang, Wang Xu-Qiao, Chai Ya-Ni, Mishra Chandan, Chandra Shah Ram, Ai Jing.  (2020)  Cholinergic Dysfunction Involvement in Chronic Cerebral Hypoperfusion-Induced Impairment of Medial Septum–dCA1 Neurocircuit in Rats.  Frontiers in Cellular Neuroscience,      [PMID:33132852] [10.3389/fncel.2020.586591]

13. Shuangshuang Liu, Yue Li, Fan Yi, Qing Liu, Naihong Chen, Xiaoli He, Chunnian He, Peigen Xiao.  (2020)  Resveratrol oligomers from Paeonia suffruticosa protect mice against cognitive dysfunction by regulating cholinergic, antioxidant and anti-inflammatory pathways.  JOURNAL OF ETHNOPHARMACOLOGY,      [PMID:32442589] [10.1016/j.jep.2020.112983]

14. Huimin Wu, Longfei Lin, Xueying Du, Lingling Zhang, Xingbin Yin, Xiaoxv Dong, Xiaofeng Hao, Like Xie, Changhai Qu, Jian Ni.  (2020)  Study on the potential effective ingredients of Xiaosheng prescription for dry eye disease.  BIOMEDICINE & PHARMACOTHERAPY,      [PMID:32428832] [10.1016/j.biopha.2020.110051]

15. Zhijie Bao, Penglin Zhang, Jin Chen, Jie Gao, Songyi Lin, Na Sun.  (2020)  Egg yolk phospholipids reverse scopolamine–induced spatial memory deficits in mice by attenuating cholinergic damage.  Journal of Functional Foods,      [PMID:] [10.1016/j.jff.2020.103948]

16. Xiaomeng Xu, Rong Liang, Dongmei Li, Chengyao Jiang, Songyi Lin.  (2020)  Evaluation of sea cucumber peptides-assisted memory activity and acetylation modification in hippocampus of test mice based on scopolamine-induced experimental animal model of memory disorder.  Journal of Functional Foods,      [PMID:] [10.1016/j.jff.2020.103909]

17. Huihong Zeng, Huan Li, Mengzhen Yue, Ying Fan, Jiaoqi Cheng, Xincheng Wu, Rui Xu, Wuping Yang, Manjun Li, Jiahui Tang, Hongping Chen, Bohai Kuang, Guangqin Fan, Qingxian Zhu, Lijian Shao.  (2019)  Isoprenaline protects intestinal stem cells from chemotherapy-induced damage.  BRITISH JOURNAL OF PHARMACOLOGY,  177  (3): (687-700).  [PMID:31648381] [10.1111/bph.14883]

18. Yu-Min Xu, Xin-Chen Wang, Ting-Ting Xu, Hong-Ying Li, Shang-Yan Hei, Na-Chuan Luo, Hong Wang, Wei Zhao, Shu-Huan Fang, Yun-Bo Chen, Li Guan, Yong-Qi Fang, Shi-Jie Zhang, Qi Wang, Wei-Xiong Liang.  (2019)  Kai Xin San ameliorates scopolamine-induced cognitive dysfunction.  Neural Regeneration Research,      [PMID:30688265] [10.4103/1673-5374.249227]

19. Jing Zhang, Jun Wang, Gui-Sheng Zhou, Ya-Jie Tan, Hui-Juan Tao, Jia-Qian Chen, Zong-Jin Pu, Jia-Yan Ma, Wen She, An Kang, Yue Zhu, Pei Liu, Zhen-Hua Zhu, Xu-Qin Shi, Yu-Ping Tang, Jin-Ao Duan.  (2019)  Studies of the Anti-amnesic Effects and Mechanisms of Single and Combined Use of Donepezil and Ginkgo Ketoester Tablet on Scopolamine-Induced Memory Impairment in Mice.  Oxidative Medicine and Cellular Longevity,      [PMID:30911351] [10.1155/2019/8636835]

20. Sun Kaiyue, Bai Yuting, Zhao Rong, Guo Zijiao, Su Xiang, Li Peiqi, Yang Pengyu.  (2018)  Neuroprotective effects of matrine on scopolamine-induced amnesia via inhibition of AChE/BuChE and oxidative stress.  METABOLIC BRAIN DISEASE,  34  (1): (173-181).  [PMID:30406376] [10.1007/s11011-018-0335-y]

21. Yao Chen, Jie Zhu, Jun Mo, Hongyu Yang, Xueyang Jiang, Hongzhi Lin, Kai Gu, Yuqiong Pei, Liang Wu, Renxiang Tan, Jing Hou, Jingyi Chen, Yang Lv, Yaoyao Bian, Haopeng Sun.  (2018)  Synthesis and bioevaluation of new tacrine-cinnamic acid hybrids as cholinesterase inhibitors against Alzheimer’s disease.  JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY,      [PMID:29278947] [10.1080/14756366.2017.1412314]

22. Liang Meng, Pinjia Meng, Bugang Tang, Qingqing Zhang, Yanji Wang.  (2013)  Molecularly imprinted photonic hydrogels for fast screening of atropine in biological samples with high sensitivity.  FORENSIC SCIENCE INTERNATIONAL,      [PMID:23890610] [10.1016/j.forsciint.2013.04.008]

23. Bao-Yuan Hou.  (2012)  Ameliorative Effects of Curculigoside from Curculigo orchioides Gaertn on Learning and Memory in Aged Rats.  MOLECULES,  17  (9): (10108-10118).  [PMID:22922281] [10.3390/molecules170910108]

24. Yao Chen, Jianfei Sun, Lei Fang, Mei Liu, Sixun Peng, Hong Liao, Jochen Lehmann, Yihua Zhang.  (2012)  Tacrine–Ferulic Acid–Nitric Oxide (NO) Donor Trihybrids as Potent, Multifunctional Acetyl- and Butyrylcholinesterase Inhibitors.  JOURNAL OF MEDICINAL CHEMISTRY,      [PMID:22512543] [10.1021/jm300106z]

25. Hong Yao, Giuseppe Uras, Pengfei Zhang, Shengtao Xu, Ying Yin, Jie Liu, Shuai Qin, Xinuo Li, Stephanie Allen, Renren Bai, Qi Gong, Haiyan Zhang, Zheying Zhu, Jinyi Xu.  (2021)  Discovery of Novel Tacrine–Pyrimidone Hybrids as Potent Dual AChE/GSK-3 Inhibitors for the Treatment of Alzheimer’s Disease.  JOURNAL OF MEDICINAL CHEMISTRY,      [PMID:34024109] [10.1021/acs.jmedchem.1c00160]

26. Qi Li, Ying Chen, Shuaishuai Xing, Qinghong Liao, Baichen Xiong, Yuanyuan Wang, Weixuan Lu, Siyu He, Feng Feng, Wenyuan Liu, Yao Chen, Haopeng Sun.  (2021)  Highly Potent and Selective Butyrylcholinesterase Inhibitors for Cognitive Improvement and Neuroprotection.  JOURNAL OF MEDICINAL CHEMISTRY,      [PMID:33973470] [10.1021/acs.jmedchem.1c00167]

27. Dan Liu, Honghua Zhang, Yuying Wang, Wencheng Liu, Gaofeng Yin, Degui Wang, Junfang Li, Tao Shi, Zhen Wang.  (2021)  Design, synthesis, and biological evaluation of carbamate derivatives of N-salicyloyl tryptamine as multifunctional agents for the treatment of Alzheimer's disease.  EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY,      [PMID:34923430] [10.1016/j.ejmech.2021.114044]

28. Xiaona Sun, Yujin Wang, Zhichao Lei, Shasha Yue, Li Chen, Jianbo Sun.  (2022)  Development of 5-hydroxyl-1-azabenzanthrone derivatives as dual binding site and selective acetylcholinesterase inhibitors.  EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY,      [PMID:35303485] [10.1016/j.ejmech.2022.114210]

29. Zhiqiang Lu, Yuan Gao, Zhijie Bao, Songyi Lin.  (2024)  A novel neuroprotective peptide against cognitive disorder in mice by regulating hippocampal oxidative stress and synaptic plasticity.  Food Bioscience,      [PMID:] [10.1016/j.fbio.2024.104575]

30. Xiaomeng Xu, Jingqi Yang, Zhiqiang Lu, Jie Ding, Songyi Lin.  (2024)  Folic acid ameliorated the scopolamine-induced memory impairment in mice and the neuroprotective mechanisms.  Food Bioscience,      [PMID:] [10.1016/j.fbio.2024.104351]

31. Xin Li, Kai Zheng, Hao Chen, Wei Li.  (2024)  Ginsenoside Re Regulates Oxidative Stress through the PI3K/Akt/Nrf2 Signaling Pathway in Mice with Scopolamine-Induced Memory Impairments.  CURRENT ISSUES IN MOLECULAR BIOLOGY,  46  (10): (11359-11374).  [PMID:39451557] [10.3390/cimb46100677]

32. Baoxin Zhang, Jingqin Tian, Na Jiang, Guozhu Chai, Hong Quan, Xinghao Han, Hongjun Xie, Fangyuan Zhang, Zhihua Liao, Min Chen, Chao Wang, Xiaozhong Lan.  (2025)  Optimization of Tropane Alkaloids Extraction from Utilizing Response Surface Methodology and Quality Assessment through UPLC Fingerprinting.  ACS Omega,  10  (25): (27137).  [PMID:40621034] [10.1021/acsomega.5c02397]