Atropine - Moligand™, 10mM in DMSO , Muscarinic acetylcholine receptor M2 antagonist, CAS No.51-55-8, Muscarinic acetylcholine receptor M2 antagonist

CAS: 51-55-8 Cat. No.: A424427 分子式: C₁₇H₂₃NO₃ 分子量: 289.37 Beilstein Registry Number: 91260 EC番号: 200-104-8

GRADE & PURITY Moligand™, 10mM in DMSO

Synonyms

(1R,3r,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate | alpha-(Hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo(3.2.1)oct-3-yl ester | Atropine, >=95.0% (NT) | InChI=1/C11H8Cl2N2O/c12-8-1-2-9(10(13)5-8)11(16)6-15-4-3-14-7-15

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Specifications

同義語

(1R,3r,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate | alpha-(Hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo(3.2.1)oct-3-yl ester | Atropine, >=95.0% (NT) | InChI=1/C11H8Cl2N2O/c12-8-1-2-9(10(13)5-8)11(16)6-15-4-3-14-7-15

仕様と純度

Moligand™, 10mM in DMSO

生化学的・生理学的メカニズム

Competitive nonselective antagonist at central and peripheral muscarinic acetylcholine receptors.Potent, competitive, non-selective mAChR antagonist (IC 50 = 2.5 nM). Induces mydriasis. Shows antimuscarinic and anticholinergic effects in vivo . Orally act

保管条件

Store at -80°C

入荷

Dry ice packs + Cold packs

この製品は冷冷この冷このこの製品の運送が必要です。地上およびその他の経済サービスは利用できません。

等級

Moligand™

アクションタイプ

ANTAGONIST

作用メカニズム

Muscarinic acetylcholine receptor M2 antagonist

製品の性質

• ALogP: 1.8

名前と識別子

• パブケム・シド: 528763338
• カノニカル・スマイル: CN1C2CCC1CC(C2)OC(=O)C(CO)C3=CC=CC=C3
• IUPAC Name: [(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate
• InChIKey: RKUNBYITZUJHSG-PJPHBNEVSA-N
• INCHI: 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?
• 異性体SMILES: CN1[C@@H]2CC[C@H]1CC(C2)OC(=O)C(CO)C3=CC=CC=C3
• WGKドイツ: 3
• RTECS: CK0700000
• 分子量: 289.37
• Beilstein: 91260
• Reaxy-Rn: 91256
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=91256&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Alkaloids and derivatives
    • 分類 Tropane alkaloids

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• 分類: Tropane alkaloids
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Tropane alkaloids
• Alternative Parents: Beta hydroxy acids and derivatives Piperidines N-alkylpyrrolidines Benzene and substituted derivatives Trialkylamines Carboxylic acid esters Amino acids and derivatives Monocarboxylic acids and derivatives Azacyclic compounds Primary alcohols Organopnictogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Tropane alkaloid - Beta-hydroxy acid - Monocyclic benzene moiety - Hydroxy acid - Piperidine - Benzenoid - N-alkylpyrrolidine - Pyrrolidine - Amino acid or derivatives - Carboxylic acid ester - Tertiary aliphatic amine - Tertiary amine - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Azacycle - Organoheterocyclic compound - Organonitrogen compound - Amine - Hydrocarbon derivative - Organic oxide - Alcohol - Carbonyl group - Organopnictogen compound - Organic oxygen compound - Organooxygen compound - Organic nitrogen compound - Primary alcohol - Aromatic heteropolycyclic compound
• 説明: This compound belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]octane.
• 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

関連ターゲット（人間）

CHRM5 Tclin Muscarinic acetylcholine receptor M5 (9 Activities)

Discover Target: CHRM5

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

CHRM4 Tclin Muscarinic acetylcholine receptor M4 (8 Activities)

Discover Target: CHRM4

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

化学的性質と物理的性質

• 感度: Light & Air sensitive.
• 分子量: 289.400 g/mol
• XLogP3: 1.800
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 289.168 Da
• Monoisotopic Mass: 289.168 Da
• Topological Polar Surface Area: 49.800 Ų
• Heavy Atom Count: 21
• Formal Charge: 0
• Complexity: 353.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

参考文献

1. Dianfa Zhao, Jie Liu, Yunshan Zhou, Lijuan Zhang, Yuxu Zhong, Yang Yang, Baoquan Zhao, Mengru Yang, Yong’an Wang.  (2023)  Penetrating the Blood–Brain Barrier for Targeted Treatment of Neurotoxicant Poisoning by Nanosustained-Released 2-PAM@VB1-MIL-101-NH2(Fe).  ACS Applied Materials & Interfaces,      [PMID:36867458] [10.1021/acsami.2c18929]

2. Dianfa Zhao, Jie Liu, Lijuan Zhang, Yunshan Zhou, Yuxu Zhong, Yang Yang, Chengcheng Huang, Yong’an Wang.  (2021)  Loading and Sustained Release of Pralidoxime Chloride from Swellable MIL-88B(Fe) and Its Therapeutic Performance on Mice Poisoned by Neurotoxic Agents.  INORGANIC CHEMISTRY,      [PMID:34969248] [10.1021/acs.inorgchem.1c03227]

3. Xue Zhao, Xiaoying Fu, Xinyi Yuan, Aerduosi Shayiranbieke, Ru Xu, Fang Cao, Jianping Ren, Qi Liang, Xinfeng Zhao.  (2021)  Development and characterization of a selective chromatographic approach to the rapid discovery of ligands binding to muscarinic-3 acetylcholine receptor.  JOURNAL OF CHROMATOGRAPHY A,      [PMID:34365202] [10.1016/j.chroma.2021.462443]

4. Si Tang, Jing Zhu, Dong Zhao, Huaheng Mo, Zhaofu Zeng, Mengqing Xiong, Minglin Dong, Ke Hu.  (2020)  Effects of the excitation or inhibition of basal forebrain cholinergic neurons on cognitive ability in mice exposed to chronic intermittent hypoxia.  BRAIN RESEARCH BULLETIN,      [PMID:32905806] [10.1016/j.brainresbull.2020.08.027]

5. Yushi Ding, Suyun Yu, Zhonghong Wei, Rui Deng, Peng Chen, Yifan Sun, Qi Jia, Xiaoman Li, Yuanyuan Wu, Wenxing Chen, Kurt S. Zanker, Aiyun Wang, Yin Lu.  (2020)  Relieving Sore Throat Formula Exerts a Therapeutic Effect on Pharyngitis through Immunoregulation and NF-κB Pathway.  MEDIATORS OF INFLAMMATION,      [PMID:32508523] [10.1155/2020/2929163]

6. Ke Chen, Yilei Zhao, Ting Liu, Zhaohao Su, Huiliang Yu, Leanne Lai Hang Chan, Tiejun Liu, Dezhong Yao.  (2020)  Monocular Visual Deprivation and Ocular Dominance Plasticity Measurement in the Mouse Primary Visual Cortex.  Jove-Journal of Visualized Experiments,      [PMID:32090984] [10.3791/60600]

7. Lianfang Chen, Junjie Ou, Hongwei Wang, Zhongshan Liu, Mingliang Ye, Hanfa Zou.  (2016)  Tailor-Made Stable Zr(IV)-Based Metal–Organic Frameworks for Laser Desorption/Ionization Mass Spectrometry Analysis of Small Molecules and Simultaneous Enrichment of Phosphopeptides.  ACS Applied Materials & Interfaces,      [PMID:27427857] [10.1021/acsami.6b06225]

8. Ji-Hong Chen, Qian Zhang, Yuanjie Yu, Kongling Li, Hong Liao, Longying Jiang, Lu Hong, Xiaohui Du, Xinghai Hu, Sifeng Chen, Sheng Yin, Qingmin Gao, Xiangdong Yin, Hesheng Luo, Jan D. Huizinga.  (2013)  Neurogenic and Myogenic Properties of Pan-Colonic Motor Patterns and Their Spatiotemporal Organization in Rats.  PLoS One,  8  (4): (e60474).  [PMID:23577116] [10.1371/journal.pone.0060474]

9. Shuo Li, Alhamdu Adamu, Yucai Ye, Fankai Gao, Rulin Mi, Guofang Xue, Zhaojun Wang.  (2024)  (+)-Borneol inhibits neuroinflammation and M1 phenotype polarization of microglia in epileptogenesis through the TLR4-NFκB signaling pathway.  Frontiers in Neuroscience,      [PMID:39605791] [10.3389/fnins.2024.1497102]

10. Cunzheng Zhang, Yuzhu Chen, Ruqiao Duan, Yiming Zhang, Haonan Zheng, Jindong Zhang, Tao Zhang, Jingxian Xu, Kailong Li, Fei Pei, Liping Duan.  (2025)  Preconception maternal gut dysbiosis affects enteric nervous system development and disease susceptibility in offspring via the GPR41–GDNF/RET/SOX10 signaling pathway.  iMeta,      [PMID:40236770] [10.1002/imt2.70012]

11. Huang Xiaomin, Wang Ting, Wang Ludan, Sun Yantao, Zhang Ziru, Zhang Yajun.  (2024)  Two-point immobilization of M3 muscarinic receptor: a method for recognizing receptor antagonists in natural products.  BMC Chemistry,  18  (1): (1-15).  [PMID:38702791] [10.1186/s13065-024-01198-z]

12. Cai-Feng Zhang, Xiao-Li Zhang, Jun-Hui Zhang, Yue Zhang, Jin Song, Jin-Xia Zhu.  (2026)  Activation of the dopamine D2 receptor enhances colonic motility via disinhibition of somatostatinergic signalling in rodents.  EUROPEAN JOURNAL OF PHARMACOLOGY,      [PMID:] [10.1016/j.ejphar.2026.179278]