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Chemistry

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Also known as: 147-20-6, Hispril, Diphenylpyrilene, Allergen, Diphenylpyralamine, Lyssipoll

Molecular Formula

C₁₉H₂₃NO

Molecular Weight

281.4 g/mol

InChI Key

OWQUZNMMYNAXSL-UHFFFAOYSA-N

FDA UNII

33361OE3AV

Diphenylpyraline is an antihistamine. Antihistamines used in the treatment of allergy act by competing with histamine for H 1-receptor sites on effector cells. Antihistamines prevent, but do not reverse, responses mediated by histamine alone. Antihistamines antagonize, in varying degrees, most of the pharmacological effects of histamine, including urticaria and pruritus.

1 2D Structure

Diphenylpyraline

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-benzhydryloxy-1-methylpiperidine

2.1.2 InChI

InChI=1S/C19H23NO/c1-20-14-12-18(13-15-20)21-19(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18-19H,12-15H2,1H3

2.1.3 InChI Key

OWQUZNMMYNAXSL-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN1CCC(CC1)OC(C2=CC=CC=C2)C3=CC=CC=C3

2.2 Other Identifiers

2.2.1 UNII

33361OE3AV

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4-diphenylmethoxy-1-methylpiperidine

2. Diphenylpyraline Hydrochloride

3. Diphenylpyraline Maleate (2:1)

4. Lergobine

2.3.2 Depositor-Supplied Synonyms

1. 147-20-6

2. Hispril

3. Diphenylpyrilene

4. Allergen

5. Diphenylpyralamine

6. Lyssipoll

7. Belfene

8. Dayfen

9. Histryl

10. Histyn

11. Mepiben

12. Neargal

13. 4-(diphenylmethoxy)-1-methylpiperidine

14. 4-(benzhydryloxy)-1-methylpiperidine

15. Difenilpiralina

16. Diphenylpyralinum

17. 1-methyl-4-piperidyl Benzhydryl Ether

18. An 1041

19. 4-benzhydryloxy-1-methylpiperidine

20. Diphenylpyraline (inn)

21. 4-(benzhydryloxy)-n-methylpiperidine

22. Piperidine, 4-(diphenylmethoxy)-1-methyl-

23. Chembl1492

24. 4-diphenylmethoxy-1-methylpiperidine

25. N-methylpiperidyl-(4)-benzhydrylaether Salzsauren Salze

26. P 253

27. 1-methyl-4-hydroxypiperidine Benzhydryl Ether

28. Chebi:59788

29. 33361oe3av

30. 4-benzhydryloxy-1-methyl-piperidine

31. Hystryl

32. Diphenylpyraline [inn]

33. Diphenylpyraline [inn:ban]

34. Difenilpiralina [inn-spanish]

35. Diphenylpyralinum [inn-latin]

36. Nsc61825

37. Ncgc00016395-01

38. Cas-132-18-3

39. Einecs 205-686-7

40. Brn 0245467

41. Unii-33361oe3av

42. N-methylpiperidyl-(4)-benzhydrylaether Salzsauren Salze [german]

43. Diafen (salt/mix)

44. Spectrum_001002

45. 4-[(diphenylmethyl)oxy]-1-methylpiperidine

46. Prestwick0_000707

47. Prestwick1_000707

48. Prestwick2_000707

49. Prestwick3_000707

50. Spectrum2_000982

51. Spectrum3_000401

52. Spectrum4_000521

53. Spectrum5_000917

54. Nciopen2_007716

55. Oprea1_289175

56. Bspbio_000893

57. Bspbio_001922

58. Diphenylpyraline [mi]

59. Kbiogr_001121

60. Kbioss_001482

61. 5-21-01-00053 (beilstein Handbook Reference)

62. Divk1c_000851

63. Schembl119077

64. Spbio_001043

65. Spbio_002814

66. Bpbio1_000983

67. Gtpl7165

68. Diphenylpyraline [vandf]

69. Dtxsid3022952

70. Kbio1_000851

71. Kbio2_001482

72. Kbio2_004050

73. Kbio2_006618

74. Kbio3_001142

75. Zinc56643

76. Diphenylpyraline [who-dd]

77. Ninds_000851

78. Bdbm50241333

79. N-methyl-4-(benzhydryloxy)piperidine

80. Akos015889312

81. Ac-9855

82. Db01146

83. Idi1_000851

84. Ncgc00016395-02

85. Ncgc00016395-03

86. Ncgc00178908-01

87. Ncgc00178908-02

88. 4-(diphenylmethoxy)-1-(methyl)piperidine

89. Sbi-0051354.p003

90. Hy-107431

91. Ab00053461

92. Cs-0028462

93. Ft-0657213

94. D07862

95. Ab00053461_14

96. Ab00053461_15

97. A808623

98. L001180

99. Piperidine, 4-(diphenylmethoxy)-1-methyl

100. Q411150

101. Brd-k22936972-003-05-3

102. Brd-k22936972-003-15-2

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₂₃NO
Molecular Weight	281.4 g/mol
XLogP3	3.9
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	4
Exact Mass	281.177964357 g/mol
Monoisotopic Mass	281.177964357 g/mol
Topological Polar Surface Area	12.5 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	268
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	1

4 Drug and Medication Information

4.1 Drug Indication

For use in the treatment of allergic rhinitis, hay fever, and allergic skin disorders.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Diphenylpyraline is an antihistamine that prevents, but does not reverse, responses mediated by histamine alone. Diphenylpyraline antagonizes most of the pharmacological effects of histamine, including urticaria and pruritus. Also, diphenylpyraline may exhibit anticholinergic actions (as do most of the antihistamines) and may thus provide a drying effect on the nasal mucosa.

5.2 ATC Code

R - Respiratory system

R06 - Antihistamines for systemic use

R06A - Antihistamines for systemic use

R06AA - Aminoalkyl ethers

R06AA07 - Diphenylpyraline

5.3 Absorption, Distribution and Excretion

Absorption

Well absorbed after oral administration.

5.4 Metabolism/Metabolites

Hepatic

5.5 Mechanism of Action

Antihistamines such as diphenylpyraline used in the treatment of allergy act by competing with histamine for H1-receptor sites on effector cells. This reduces the effects of histamine, leading to a temporary reduction of allergy symptoms.

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