Hydroquinine - ≥95%(HPLC), sum of enantiomers , CAS No.522-66-7

CAS: 522-66-7 Cat. No.: H101601 Molecular Weight: 326.43 Beilstein Registry Number: 91444 EC Number: 208-334-0

GRADE & PURITY ≥95%(HPLC), sum of enantiomers

Synonyms

DTXSID70878516 | QUINIDINE SULFATE IMPURITY C [WHO-IP] | (8alpha,9R)-10,11-Dihydro-6'-methoxycinchonan-9-ol | D70296 | Epitope ID:141487 | NSC 41799 | MEGxp0_001893 | QUININE BISULFATE HEPTAHYDRATE IMPURITY C [WHO-IP] | DB13718 | AKOS015920285 | (R)-[(2S,

Storage

Room temperature

Shipped In

Normal

Specifications

Synonyms

DTXSID70878516 | QUINIDINE SULFATE IMPURITY C [WHO-IP] | (8alpha, 9R)-10, 11-Dihydro-6'-methoxycinchonan-9-ol | D70296 | Epitope ID:141487 | NSC 41799 | MEGxp0_001893 | QUININE BISULFATE HEPTAHYDRATE IMPURITY C [WHO-IP] | DB13718 | AKOS015920285 | (R)-[(2S,

Specifications & Purity

≥95%(HPLC), sum of enantiomers

Storage

Room temperature

Shipped In

Normal

Purity

≥95%(HPLC)

Names and Identifiers

• Pubchem Sid: 488187650
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488187650
• Canonical Smiles: CCC1CN2CCC1CC2C(C3=C4C=C(C=CC4=NC=C3)OC)O
• IUPAC Name: (R)-[(2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
• InChIKey: LJOQGZACKSYWCH-WZBLMQSHSA-N
• INCHI: 1S/C20H26N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h4-6,8,11,13-14,19-20,23H,3,7,9-10,12H2,1-2H3/t13-,14-,19-,20+/m0/s1
• Isomeric SMILES: CC[C@H]1CN2CC[C@H]1C[C@H]2[C@@H](C3=C4C=C(C=CC4=NC=C3)OC)O
• WGK Germany: 3
• Molecular Weight: 326.43
• Beilstein: 91444
• Reaxy-Rn: 91438
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=91438&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Alkaloids and derivatives
    • Class Cinchona alkaloids

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Class: Cinchona alkaloids
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Cinchona alkaloids
• Alternative Parents: 4-quinolinemethanols Quinuclidines Anisoles Aralkylamines Alkyl aryl ethers Pyridines and derivatives Piperidines Heteroaromatic compounds Trialkylamines Secondary alcohols 1,2-aminoalcohols Azacyclic compounds Organopnictogen compounds Hydrocarbon derivatives Aromatic alcohols
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Cinchonan-skeleton - 4-quinolinemethanol - Quinoline - Anisole - Quinuclidine - Alkyl aryl ether - Aralkylamine - Piperidine - Pyridine - Benzenoid - Heteroaromatic compound - 1,2-aminoalcohol - Tertiary aliphatic amine - Tertiary amine - Secondary alcohol - Ether - Azacycle - Organoheterocyclic compound - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Hydrocarbon derivative - Organopnictogen compound - Amine - Alcohol - Organic oxygen compound - Aromatic alcohol - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as cinchona alkaloids. These are alkaloids structurally characterized by the presence of the cinchonan skeleton, which consists of a quinoline linked to an azabicyclo[2.2.2]octane moiety.
• 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)

F2 Tclin Thrombin (11687 Activities)

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ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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PGR Tclin Progesterone receptor (8562 Activities)

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CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

Discover Target: CHRM2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

Discover Target: HTR1A

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ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

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AR Tclin Androgen Receptor (11781 Activities)

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CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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GABRA1 Tclin GABA receptor alpha-1 subunit (399 Activities)

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MAOA Tclin Monoamine oxidase A (11911 Activities)

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DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

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SLC6A4 Tclin Serotonin transporter (12625 Activities)

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ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

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OPRM1 Tclin Mu opioid receptor (19785 Activities)

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DRD3 Tclin Dopamine D3 receptor (14368 Activities)

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SLC6A3 Tclin Dopamine transporter (10535 Activities)

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KCNH2 Tclin HERG (29587 Activities)

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PDE3A Tclin Phosphodiesterase 3A (3309 Activities)

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HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)

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TBXA2R Tclin Thromboxane A2 receptor (5717 Activities)

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PDE4A Tclin Phosphodiesterase 4A (1943 Activities)

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ADORA3 Tchem Adenosine A3 receptor (15931 Activities)

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HRH3 Tclin Histamine H3 receptor (10389 Activities)

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KDR Tclin Vascular endothelial growth factor receptor 2 (20924 Activities)

Discover Target: KDR

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MES-SA (905 Activities)

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MES-SA/Dx5 (643 Activities)

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Associated Targets(non-human)

Streptococcus pneumoniae (31063 Activities)

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Plasmodium berghei (192651 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Melt Point(°C): 168-176°C
• Molecular Weight: 326.400 g/mol
• XLogP3: 3.100
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 326.199 Da
• Monoisotopic Mass: 326.199 Da
• Topological Polar Surface Area: 45.600 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 432.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• 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

References

1. Guo Qing, Gan Jun, Wang En-ze, Wei Yu-ming, Xu Jie, Xu Yun, Zhang Fei-fei, Cui Meng, Jia Meng-xing, Kong Ming-jian, Tang Qiong-yao, Zhang Zhe.  (2025)  Electrophysiological characterization of human KCNT1 channel modulators and the therapeutic potential of hydroquinine and tipepidine in KCNT1 mutation-associated epilepsy mouse model.  ACTA PHARMACOLOGICA SINICA,      [PMID:39870847] [10.1038/s41401-024-01457-8]