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 Formula: C₁₇H₂₃NO₃ 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|Tropine (+/-)-tropate|ATROPINE [MART.]|ATROPINE [USP MONOGRAPH]|[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate|ropine tropate|8-Methyl-8-azabicyclo[3.2.1]oct-3-yl 3-hydroxy-2-phenylpropanoate|beta-Phenyl-gamma-oxypropionsaeure-tropyl-ester|Tropic acid, 3-alpha-tropanyl ester|[(1S,5R)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 3-hydroxy-2-phenyl-propanoate|Atropina [Italian]|ATROPINE [GREEN BOOK]|ATROPINE [USP-RS]|Atropen (TN)|ATROPINE [EP IMPURITY]|ATROPINE, (+/-)-|endo-(+/-)-alpha-(Hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester|hyoscyamine|Benzeneacetic acid, alpha-(hydroxymethyl)-8-methyl-8-azabicyclo(3,2,1)oct-3-yl ester, endo-(+-)-|HOE-2960|beta-Phenyl-gamma-oxypropionsaeure-tropyl-ester [German]|(3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl 3-hydroxy-2-phenylpropanoate|Atropin-flexiolen|(3-ENDO)-8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL TROPATE|Atropine ((+/-)-Hyoscyamin)|Benzeneacetic acid, alpha-(hydroxymethyl)-, (3-endo)-8-methyl-8-azabicyclo(3.2.1)oct-3-yl ester|CP-52223|Atropen|ATROPINE [ORANGE BOOK]|Atropinum|Eyesules|(+/-)-Atropine|Articaine hydrochloride (JAN/USP)|Troyl tropate|(+,-)-Tropyl tropate|beta-Phenyl-gamma-oxypropionsaure-tropyl-ester [German]|Tropine tropate;DL-Hyoscyamine|ATROPINE|Atropine sulfate|Opera_ID_1088|3-tropoyloxytropane|Tropine tropate|(3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl tropate|Atropin|dl-Tropyltropate|Atropina|ATROPINE [EP MONOGRAPH]|DL-Tropyl tropate|2-Phenylhydracrylic acid 3-alpha-tropanyl ester|ATNAA COMPONENT ATROPINE|Atropin [German]|ATROPINE ((+/-)-)|DUODOTE COMPONENT ATROPINE|Isopto-atropine|Tropic acid, ester with tropine|(+-)-atropine|ATROPINE [WHO-DD]|1-alpha-H,5-alpha-H-Tropan-3-alpha-ol (+-)-tropate (ester) (8CI)|Atropine [USP:BAN]|DL-Tropanyl 2-hydroxy-1-phenylpropionate|beta-Phenyl-gamma-oxypropionsaure-tropyl-ester|Tropine, tropate (ester)|1-alpha-H,5-alpha-H-Tropan-3-alpha-ol (+-)-tropate (ester)|1alphaH,5alphaH-Tropan-3alpha-ol (+-)-tropate (ester)|ATROPINUM [HPUS]|Atropine (USP)|8-Methyl-8-azabicyclo[3.2.1]oct-3-yl tropate|ATROPINE [VANDF]|Protamine & Atropine|(+-)-hyoscyamine|dl-Hyoscyamine

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 | Tropine (+/-)-tropate | ATROPINE [MART.] | ATROPINE [USP MONOGRAPH] | [(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate | ropine tropate | 8-Methy Show more

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