Atropine - Moligand™, ≥99% , Muscarinic acetylcholine receptor M2 antagonist, CAS No.51-55-8, Muscarinic acetylcholine receptor M2 antagonist

CAS: 51-55-8 Cat. No.: A135946 Molecular Weight: 289.37 Beilstein Registry Number: 91260 EC Number: 200-104-8

GRADE & PURITY Moligand™, ≥99%

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

Shipped In

Wet ice

Specifications

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

Specifications & Purity

Moligand™, ≥99%

Biochemical and Physiological Mechanisms

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

Storage

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

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

ANTAGONIST

Mechanism of action

Muscarinic acetylcholine receptor M2 antagonist

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Toxic, refer to SDS for further information. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥99%

Product Properties

• ALogP: 1.8

Names and Identifiers

• Pubchem Sid: 504757676
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504757676
• Canonical Smiles: 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?
• Isomeric SMILES: CN1[C@@H]2CC[C@H]1CC(C2)OC(=O)C(CO)C3=CC=CC=C3
• WGK Germany: 3
• RTECS: CK0700000
• Molecular Weight: 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
    • Class Tropane alkaloids

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Class: 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
• Description: 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

Associated Targets(Human)

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)

CHRM3 Tclin Muscarinic acetylcholine receptor M3 (6 Activities)

Discover Target: CHRM3

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)

CHRM2 Tclin Muscarinic acetylcholine receptor M2 (21 Activities)

Discover Target: CHRM2

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

CHRM1 Tclin Muscarinic acetylcholine receptor M1 (10 Activities)

Discover Target: CHRM1

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

ADRA2A Tclin Alpha-2A adrenergic receptor (0 Activities)

Discover Target: ADRA2A

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

Chemical and Physical Properties

• Solubility: Soluble in dilute aqueous acid, ethanol.
• Sensitivity: Light & Air sensitive.
• Molecular Weight: 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

References

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]