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Diphenhydramine Citrate

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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

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 Formula	C₂₃H₂₉NO₈
Molecular Weight	447.5 g/mol
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	11
Exact Mass	447.18931688 g/mol
Monoisotopic Mass	447.18931688 g/mol
Topological Polar Surface Area	145 Å²
Heavy Atom Count	32
Formal Charge	0
Complexity	439
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

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.)