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    Also known as: 88637-37-0, 2-(benzhydryloxy)-n,n-dimethylethanamine 2-hydroxypropane-1,2,3-tricarboxylate, Diphenhydramine citrate [usp], Diphenhydramine (citrate), 2-benzhydryloxy-n,n-dimethylethanamine;2-hydroxypropane-1,2,3-tricarboxylic acid, 4od433s209
    Molecular Formula
    C23H29NO8
    Molecular Weight
    447.5  g/mol
    InChI Key
    SPCKHVPPRJWQRZ-UHFFFAOYSA-N
    FDA UNII
    4OD433S209
    Diphenhydramine Citrate
    A histamine H1 antagonist used as an antiemetic, antitussive, for dermatoses and pruritus, for hypersensitivity reactions, as a hypnotic, an antiparkinson, and as an ingredient in common cold preparations. It has some undesired antimuscarinic and sedative effects.
    1 2D Structure

    Diphenhydramine Citrate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-benzhydryloxy-N,N-dimethylethanamine;2-hydroxypropane-1,2,3-tricarboxylic acid
    2.1.2 InChI
    InChI=1S/C17H21NO.C6H8O7/c1-18(2)13-14-19-17(15-9-5-3-6-10-15)16-11-7-4-8-12-16;7-3(8)1-6(13,5(11)12)2-4(9)10/h3-12,17H,13-14H2,1-2H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
    2.1.3 InChI Key
    SPCKHVPPRJWQRZ-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CN(C)CCOC(C1=CC=CC=C1)C2=CC=CC=C2.C(C(=O)O)C(CC(=O)O)(C(=O)O)O
    2.2 Other Identifiers
    2.2.1 UNII
    4OD433S209
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 2-diphenylmethoxy-n,n-dimethylethylamine

    2. Allerdryl

    3. Benadryl

    4. Benhydramin

    5. Benylin

    6. Benzhydramine

    7. Citrate, Diphenhydramine

    8. Dimedrol

    9. Diphenhydramine

    10. Diphenhydramine Citrate (1:1)

    11. Diphenhydramine Hydrochloride

    12. Diphenylhydramin

    13. Diphenylhydramine

    14. Dormin

    15. Hydrochloride, Diphenhydramine

    2.3.2 Depositor-Supplied Synonyms

    1. 88637-37-0

    2. 2-(benzhydryloxy)-n,n-dimethylethanamine 2-hydroxypropane-1,2,3-tricarboxylate

    3. Diphenhydramine Citrate [usp]

    4. Diphenhydramine (citrate)

    5. 2-benzhydryloxy-n,n-dimethylethanamine;2-hydroxypropane-1,2,3-tricarboxylic Acid

    6. 4od433s209

    7. 2-(diphenylmethoxy)-n,n-dimethylethylamine Citrate (1:1)

    8. Diphenhydramine Citrate (usp)

    9. Ethanamine, 2-(diphenylmethoxy)-n,n-dimethyl-, 2-hydroxy-1,2,3-propanetricarboxylate (1:1)

    10. Unii-4od433s209

    11. Einecs 289-432-0

    12. Schembl322306

    13. Chembl1201089

    14. Dtxsid80237211

    15. Bcp12478

    16. 2-(benzhydryloxy)-n,n-dimethylethanamine2-hydroxypropane-1,2,3-tricarboxylate

    17. Akos016005048

    18. Diphenhydramine Citrate [mart.]

    19. Diphenhydramine Citrate [vandf]

    20. 2-benzhydryloxy-n,n-dimethylethanamine,2-hydroxypropane-1,2,3-tricarboxylic Acid

    21. Diphenhydramine Citrate [usp-rs]

    22. Diphenhydramine Citrate [who-dd]

    23. Diphenhydramine Citrate [orange Book]

    24. D03854

    25. Diphenhydramine Citrate [usp Monograph]

    26. 637d370

    27. Q5402419

    28. (2-(diphenylmethoxy)ethyl)dimethylammonium Dihydrogen 2-hydroxypropane-1,2,3-tricarboxylate

    2.4 Create Date
    2005-08-09
    3 Chemical and Physical Properties
    Molecular Weight 447.5 g/mol
    Molecular Formula C23H29NO8
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count11
    Exact Mass447.18931688 g/mol
    Monoisotopic Mass447.18931688 g/mol
    Topological Polar Surface Area145 Ų
    Heavy Atom Count32
    Formal Charge0
    Complexity439
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    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

    Histamine H1 Antagonists

    Drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine. Included here are the classical antihistaminics that antagonize or prevent the action of histamine mainly in immediate hypersensitivity. They act in the bronchi, capillaries, and some other smooth muscles, and are used to prevent or allay motion sickness, seasonal rhinitis, and allergic dermatitis and to induce somnolence. The effects of blocking central nervous system H1 receptors are not as well understood. (See all compounds classified as Histamine H1 Antagonists.)

    Anesthetics, Local

    Drugs that block nerve conduction when applied locally to nerve tissue in appropriate concentrations. They act on any part of the nervous system and on every type of nerve fiber. In contact with a nerve trunk, these anesthetics can cause both sensory and motor paralysis in the innervated area. Their action is completely reversible. (From Gilman AG, et. al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed) Nearly all local anesthetics act by reducing the tendency of voltage-dependent sodium channels to activate. (See all compounds classified as Anesthetics, Local.)

    Sleep Aids, Pharmaceutical

    Drugs used to induce SLEEP, prevent SLEEPLESSNESS, or treat SLEEP INITIATION AND MAINTENANCE DISORDERS. (See all compounds classified as Sleep Aids, Pharmaceutical.)

    Anti-Allergic Agents

    Agents that are used to treat allergic reactions. Most of these drugs act by preventing the release of inflammatory mediators or inhibiting the actions of released mediators on their target cells. (From AMA Drug Evaluations Annual, 1994, p475) (See all compounds classified as Anti-Allergic Agents.)

    Antiemetics

    Drugs used to prevent NAUSEA or VOMITING. (See all compounds classified as Antiemetics.)

    Hypnotics and Sedatives

    Drugs used to induce drowsiness or sleep or to reduce psychological excitement or anxiety. (See all compounds classified as Hypnotics and Sedatives.)

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    05-Mar-2022
    20-Oct-2023
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