Mefloquine Hydrochloride - ≥98%(HPLC) , CAS No.51773-92-3

CAS: 51773-92-3 Cat. No.: M157854 Molecular Weight: 414.78 EC Number: 257-412-0

GRADE & PURITY ≥98%(HPLC)

Synonyms

M2313 | 4-Quinolinemethanol, .alpha,-[(2R)-2-piperidinyl]-2,8-bis(trifluoromethyl)-, (.alpha.S)-, hydrochloride (1:1) | 4-Quinolinemethanol, alpha-(2R)-2-piperidinyl-2,8-bis(trifluoromethyl)-, monohydrochloride, (alphaS)-rel- | Mefloquine hydrochloride [U

Storage

Room temperature

Shipped In

Normal

Overview

Mefloquine hydrochloride is a quinoline antimalarial drug that is structurally related to the antiarrhythmic agent quinidine.

Specifications

Synonyms

M2313 | 4-Quinolinemethanol, .alpha, -[(2R)-2-piperidinyl]-2, 8-bis(trifluoromethyl)-, (.alpha.S)-, hydrochloride (1:1) | 4-Quinolinemethanol, alpha-(2R)-2-piperidinyl-2, 8-bis(trifluoromethyl)-, monohydrochloride, (alphaS)-rel- | Mefloquine hydrochloride [U

Specifications & Purity

≥98%(HPLC)

Biochemical and Physiological Mechanisms

Cx36 and Cx50 gap channel blocker (IC50values are 0.3 and 1.1 μM, resepctively). Blocks gap junctional-coupling between interneurons in neocortical slices. Also antimalarial. Bind 80S ribosome ofPlasmodium falciparumto inhibit protein synthesis. Improves

Storage

Room temperature

Shipped In

Normal

Purity

≥98%(HPLC)

Names and Identifiers

• Pubchem Sid: 488183677
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488183677
• Canonical Smiles: C1CCNC(C1)C(C2=CC(=NC3=C2C=CC=C3C(F)(F)F)C(F)(F)F)O.Cl
• IUPAC Name: (S)-[2,8-bis(trifluoromethyl)quinolin-4-yl]-[(2R)-piperidin-2-yl]methanol;hydrochloride
• InChIKey: WESWYMRNZNDGBX-YLCXCWDSSA-N
• INCHI: 1S/C17H16F6N2O.ClH/c18-16(19,20)11-5-3-4-9-10(15(26)12-6-1-2-7-24-12)8-13(17(21,22)23)25-14(9)11;/h3-5,8,12,15,24,26H,1-2,6-7H2;1H/t12-,15+;/m1./s1
• Isomeric SMILES: C1CCN[C@H](C1)[C@H](C2=CC(=NC3=C2C=CC=C3C(F)(F)F)C(F)(F)F)O.Cl
• WGK Germany: 3
• RTECS: VC0308000
• Alternate CAS: 53230-10-7;49752-90-1
• Molecular Weight: 414.78
• Reaxy-Rn: 6836041
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=6836041&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Quinolines and derivatives
      • Subclass 4-quinolinemethanols

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Quinolines and derivatives
• Subclass: 4-quinolinemethanols
• Intermediate Tree Nodes: Not available
• Direct Parent: 4-quinolinemethanols
• Alternative Parents: Aralkylamines Pyridines and derivatives Piperidines Benzenoids Heteroaromatic compounds Secondary alcohols 1,2-aminoalcohols Dialkylamines Azacyclic compounds Organopnictogen compounds Organofluorides Hydrochlorides Hydrocarbon derivatives Aromatic alcohols Alkyl fluorides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 4-quinolinemethanol - Aralkylamine - Piperidine - Pyridine - Benzenoid - Heteroaromatic compound - 1,2-aminoalcohol - Secondary alcohol - Secondary aliphatic amine - Secondary amine - Azacycle - Alcohol - Hydrocarbon derivative - Organopnictogen compound - Organic oxygen compound - Organooxygen compound - Organonitrogen compound - Organofluoride - Organohalogen compound - Organic nitrogen compound - Amine - Alkyl halide - Aromatic alcohol - Alkyl fluoride - Hydrochloride - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as 4-quinolinemethanols. These are organoheterocyclic compounds containing a quinoline moiety substituted at the 4-position with a methanol.
• 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)

PTH1R Tclin Parathyroid hormone receptor (47172 Activities)

Discover Target: PTH1R

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SLC2A1 Tchem Glucose transporter (14755 Activities)

Discover Target: SLC2A1

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GLP1R Tclin Glucagon-like peptide 1 receptor (111429 Activities)

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Huh-7 (12904 Activities)

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HepG2 (196354 Activities)

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UBE2N Tchem Ubiquitin-conjugating enzyme E2 N (1570 Activities)

Discover Target: UBE2N

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

Discover Target: TDP1

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SMAD3 Tchem Mothers against decapentaplegic homolog 3 (68039 Activities)

Discover Target: SMAD3

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GMNN Tbio Geminin (128009 Activities)

Discover Target: GMNN

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ATAD5 Tbio ATPase family AAA domain-containing protein 5 (122566 Activities)

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ATXN2 Tbio Ataxin-2 (54410 Activities)

Discover Target: ATXN2

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Associated Targets(non-human)

ampC Beta-lactamase AmpC (62480 Activities)

Discover Target: ampC

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Pseudomonas aeruginosa (123386 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Staphylococcus aureus (210822 Activities)

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Acinetobacter baumannii (41033 Activities)

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Escherichia coli (133304 Activities)

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Plasmodium falciparum (966862 Activities)

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Cryptococcus neoformans (21258 Activities)

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Candida albicans (78123 Activities)

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Plasmodium berghei (192651 Activities)

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ht1 Hexose transporter 1 (14071 Activities)

Discover Target: ht1

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botA Botulinum neurotoxin type A (1303 Activities)

Discover Target: botA

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solvent:ethanol, Max Conc. mg/mL: 41.48, Max Conc. mM: 100; Solvent:DMSO, Max Conc. mg/mL: 20.74, Max Conc. mM: 50
• Melt Point(°C): 253 °C
• Molecular Weight: 414.800 g/mol
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 2
• Exact Mass: 414.093 Da
• Monoisotopic Mass: 414.093 Da
• Topological Polar Surface Area: 45.200 Ų
• Heavy Atom Count: 27
• Formal Charge: 0
• Complexity: 483.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• 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: 2

XLogP3

References

1. Lancheng Wang, Huimin Zhou, Kun Yan, Peng Xu, Bin Di, Chi Hu, Mengxiang Su.  (2021)  Using dual exonucleases to finely distinguish structural adjustment of aptamers for small-molecule detection.  RSC Advances,  11  (52): (32898-32903).  [PMID:35493548] [10.1039/D1RA05551H]