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    Cinchonan-9-ol, 6'-methoxy-, monohydrochloride, (8-alpha,9R)-

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    2D Structure
    Also known as: Quinine hcl, 130-89-2, Quinine muriate, Chinimetten, Quinine monohydrochloride, Fema no. 2976
    Molecular Formula
    C20H25ClN2O2
    Molecular Weight
    360.9  g/mol
    InChI Key
    LBSFSRMTJJPTCW-DSXUQNDKSA-N
    FDA UNII
    7CS0WNO31M
    An alkaloid derived from the bark of the cinchona tree. It is used as an antimalarial drug, and is the active ingredient in extracts of the cinchona that have been used for that purpose since before 1633. Quinine is also a mild antipyretic and analgesic and has been used in common cold preparations for that purpose. It was used commonly and as a bitter and flavoring agent, and is still useful for the treatment of babesiosis. Quinine is also useful in some muscular disorders, especially nocturnal leg cramps and myotonia congenita, because of its direct effects on muscle membrane and sodium channels. The mechanisms of its antimalarial effects are not well understood.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol;hydrochloride
    2.1.2 InChI
    InChI=1S/C20H24N2O2.ClH/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;/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3;1H/t13-,14-,19-,20+;/m0./s1
    2.1.3 InChI Key
    LBSFSRMTJJPTCW-DSXUQNDKSA-N
    2.1.4 Canonical SMILES
    COC1=CC2=C(C=CN=C2C=C1)C(C3CC4CCN3CC4C=C)O.Cl
    2.1.5 Isomeric SMILES
    COC1=CC2=C(C=CN=C2C=C1)[C@H]([C@@H]3C[C@@H]4CCN3C[C@@H]4C=C)O.Cl
    2.2 Other Identifiers
    2.2.1 UNII
    7CS0WNO31M
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Biquinate

    2. Bisulfate, Quinine

    3. Hydrochloride, Quinine

    4. Legatrim

    5. Myoquin

    6. Quinamm

    7. Quinbisan

    8. Quinbisul

    9. Quindan

    10. Quinimax

    11. Quinine

    12. Quinine Bisulfate

    13. Quinine Lafran

    14. Quinine Sulfate

    15. Quinine Sulphate

    16. Quinine-odan

    17. Quinoctal

    18. Quinson

    19. Quinsul

    20. Strema

    21. Sulfate, Quinine

    22. Sulphate, Quinine

    23. Surquina

    2.3.2 Depositor-Supplied Synonyms

    1. Quinine Hcl

    2. 130-89-2

    3. Quinine Muriate

    4. Chinimetten

    5. Quinine Monohydrochloride

    6. Fema No. 2976

    7. Ccris 2002

    8. Einecs 205-001-1

    9. 7549-43-1

    10. 7cs0wno31m

    11. Anhydrous Quinine Hydrochloride

    12. Quinine Hydrochloride Anhydrous

    13. Ai3-62121

    14. Quinine, Hydrochloride (2:1)

    15. Quinine Hydrochloride Dihydrate

    16. (r)-[(2s,4s,5r)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol;hydrochloride

    17. Chininum Muriaticum

    18. Quinine Chloride

    19. Quinine Hydrochloride Hydrate

    20. 6119-47-7

    21. Cinchonan-9-ol, 6'-methoxy-, Hydrochloride (1:1), (8alpha,9r)-

    22. (r)-(6-methoxyquinolin-4-yl)((1s,2s,4s,5r)-5-vinylquinuclidin-2-yl)methanol Hydrochloride

    23. 30860-23-2

    24. Chinine Hydrochloride

    25. Quinine, Hydrochloride

    26. Fema No. 2976, Dihydrate-

    27. Einecs 231-437-7

    28. Unii-7cs0wno31m

    29. Quinine, Monohydrochloride

    30. Quininehcl

    31. Quinini Hydrochloridum

    32. (8alpha,9r)-6'-methoxycinchonan-9-ol Monohydrochloride

    33. 6'-methoxycinchonan-9-ol Monohydrochloride, (8alpha,9r)-

    34. Cinchonan-9-ol, 6'-methoxy-, Monohydrochloride, (8alpha,9r)-

    35. Quinine Hydrochloride (1:1)

    36. Schembl184367

    37. Chembl588046

    38. Dtxsid7044213

    39. Tcmdc-123484

    40. Tcmdc-125479

    41. Cinchonan-9-ol, 6'-methoxy-, Hydrochloride, (8alpha,9r)-

    42. Cinchonan-9-ol, 6'-methoxy-, Hydrochloride, (8.alpha.,9r)-

    43. Cinchonan-9-ol, 6'-methoxy-, Monohydrochloride, (8-alpha,9r)-

    44. Quinine Hydrochloride [fhfi]

    45. Mfcd00078498

    46. Akos016002029

    47. Cinchonan-9-ol, 6'-methoxy-, Monohydrochloride, Dihydrate, (8alpha,9r)-

    48. Quinine Hydrochloride [who-dd]

    49. 6'-methoxycinchonan-9-ol Hydrochloride

    50. As-70722

    51. Quinine Monohydrochloride Anhydrous

    52. Quinine Hydrochloride Anhydrous [mi]

    53. A51181

    54. Q27268091

    55. (8.alpha.,9r)-6'-methoxycinchonan-9-ol Hydrochloride

    56. Cinchonan-9-ol, 6'-methoxy-, Hydrochloride (1:?), (8alpha,9r)-

    57. (r)-(6-methoxyquinolin-4-yl)((2s,4s,5r)-5-vinylquinuclidin-2-yl)methanol Hydrochloride

    58. (r)-[(2s,4s,5r)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol Hydrochloride

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 360.9 g/mol
    Molecular Formula C20H25ClN2O2
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count4
    Exact Mass360.1604557 g/mol
    Monoisotopic Mass360.1604557 g/mol
    Topological Polar Surface Area45.6 Ų
    Heavy Atom Count25
    Formal Charge0
    Complexity457
    Isotope Atom Count0
    Defined Atom Stereocenter Count4
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Analgesics, Non-Narcotic

    A subclass of analgesic agents that typically do not bind to OPIOID RECEPTORS and are not addictive. Many non-narcotic analgesics are offered as NONPRESCRIPTION DRUGS. (See all compounds classified as Analgesics, Non-Narcotic.)

    Muscle Relaxants, Central

    A heterogeneous group of drugs used to produce muscle relaxation, excepting the neuromuscular blocking agents. They have their primary clinical and therapeutic uses in the treatment of muscle spasm and immobility associated with strains, sprains, and injuries of the back and, to a lesser degree, injuries to the neck. They have been used also for the treatment of a variety of clinical conditions that have in common only the presence of skeletal muscle hyperactivity, for example, the muscle spasms that can occur in MULTIPLE SCLEROSIS. (From Smith and Reynard, Textbook of Pharmacology, 1991, p358) (See all compounds classified as Muscle Relaxants, Central.)

    Antimalarials

    Agents used in the treatment of malaria. They are usually classified on the basis of their action against plasmodia at different stages in their life cycle in the human. (From AMA, Drug Evaluations Annual, 1992, p1585) (See all compounds classified as Antimalarials.)