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2D Structure
Also known as: 341-69-5, Orphenadrine hcl, Mephenamin, Disipal, Mebedrol, Mephenamine
Molecular Formula
C18H24ClNO
Molecular Weight
305.8  g/mol
InChI Key
UQZKYYIKWZOKKD-UHFFFAOYSA-N
FDA UNII
UBY910DUXH

A muscarinic antagonist used to treat drug-induced parkinsonism and to relieve pain from muscle spasm.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
N,N-dimethyl-2-[(2-methylphenyl)-phenylmethoxy]ethanamine;hydrochloride
2.1.2 InChI
InChI=1S/C18H23NO.ClH/c1-15-9-7-8-12-17(15)18(20-14-13-19(2)3)16-10-5-4-6-11-16;/h4-12,18H,13-14H2,1-3H3;1H
2.1.3 InChI Key
UQZKYYIKWZOKKD-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1=CC=CC=C1C(C2=CC=CC=C2)OCCN(C)C.Cl
2.2 Other Identifiers
2.2.1 UNII
UBY910DUXH
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Citrate, Norflex Orphenadrine

2. Citrate, Orphenadrine

3. Disipal

4. Hydrochloride, Orphenadrine

5. Lysantin

6. Mefenamine

7. Mefenamine, Sodium

8. Mephenamine

9. Methyldiphenylhydramine

10. Norflex

11. Norflex Orphenadrine Citrate

12. Orphenadrine

13. Orphenadrine Citrate

14. Orphenadrine Citrate, Norflex

15. Sodium Mefenamine

2.3.2 Depositor-Supplied Synonyms

1. 341-69-5

2. Orphenadrine Hcl

3. Mephenamin

4. Disipal

5. Mebedrol

6. Mephenamine

7. Orphenadrine (hydrochloride)

8. Brocadisipal

9. Mephenamin Hydrochloride

10. Orfenadrin Hydrochloride

11. Mephenamine Hydrochloride

12. Mefenamin Hydrochloride

13. Bf 5930

14. Bg 5930

15. Bs 5930

16. Orphenadrine (chloride)

17. Nsc-82357

18. Uby910duxh

19. Mls000069427

20. N,n-dimethyl-2-(2-methylbenzhydryloxy)ethylamine Hydrochloride

21. 2-dimethylaminoethyl 2-methylbenzhydryl Ether Hydrochloride

22. Beta-dimethylaminoethyl 2-methylbenzhydryl Ether Hydrochloride

23. Smr000058999

24. Mephenamin Forte

25. Ethanamine, N,n-dimethyl-2-((2-methylphenyl)phenylmethoxy)-, Hydrochloride

26. Ethanamine, N,n-dimethyl-2-[(2-methylphenyl)phenylmethoxy]-, Hydrochloride

27. Chebi:60902

28. Sr-01000002975

29. Einecs 206-435-4

30. Unii-uby910duxh

31. Nsc 82357

32. Brocasipal

33. N,n-dimethyl-2-[(2-methylphenyl)-phenylmethoxy]ethanamine;hydrochloride

34. Prestwick_663

35. Disipal (tn)

36. Disipal Hydrochloride

37. Mfcd00012480

38. Orphenadrine Chloride

39. Opera_id_658

40. Orphenedrine Hydrochloride

41. Dsstox_cid_5815

42. Cas-341-69-5

43. Dsstox_rid_77934

44. Dsstox_gsid_25815

45. Regid_for_cid_9568

46. Mls001148572

47. Mls002548882

48. Mls006011645

49. Schembl1235378

50. Chembl1201023

51. Dtxsid5025815

52. Orphenadrine-[d3] Hydrochloride

53. Hms1568p19

54. Hy-b1126

55. Nsc82357

56. Tox21_301927

57. Tox21_500884

58. S5664

59. Akos024307520

60. Wln: 1n1&2oyr&r B1 &gh

61. Ccg-220239

62. Ccg-222188

63. Cs-4723

64. Lp00884

65. Nc00465

66. Ethylamine, N,n-dimethyl-2-((o-methyl-alpha-phenylbenzyl)oxy)-, Hydrochloride

67. Ncgc00089814-04

68. Ncgc00094204-01

69. Ncgc00094204-02

70. Ncgc00255176-01

71. Ncgc00261569-01

72. Ls-14663

73. Orphenadrine Hydrochloride [mart.]

74. Orphenadrine Hydrochloride [vandf]

75. Orphenadrine Hydrochloride [who-dd]

76. Db-048578

77. Eu-0100884

78. Ft-0631984

79. O0406

80. Orphenadrine Hydrochloride, >=98.0% (at)

81. Wln: 1n1 & 2oyr & R B1 & Gh

82. D02599

83. O 3752

84. Orphenadrine Hydrochloride [ep Impurity]

85. Orphenadrine Hydrochloride [orange Book]

86. Orphenadrine Hydrochloride [ep Monograph]

87. J-019475

88. Sr-01000002975-2

89. Sr-01000002975-7

90. Q27129640

91. N,n-dimethyl-2-(phenyl(o-tolyl)methoxy)ethanamine Hydrochloride

92. Ethylamine,n-dimethyl-2-[phenyl-(o-tolyl)methoxy]-, Hydrochloride

93. N,n-dimethyl-2-[(.alpha.-o-tolylbenzyl)oxy]ethylamine Hydrochloride

94. N,n-dimethyl-2-[.alpha.-(o-tolyl)benzyloxy]ethylamine Hydrochloride

95. Ethanamine,n-dimethyl-2-[(2-methylphenyl)phenylmethoxy]-, Hydrochloride

96. Ethylamine,n-dimethyl-2-[.alpha.-(o-tolyl)benzyloxy]-, Hydrochloride

97. N,n-dimethyl-2-(o-methyl-.alpha.-phenylbenzyloxy)ethylamine Hydrochloride

98. Orphenadrine Hydrochloride, European Pharmacopoeia (ep) Reference Standard

99. Ethylamine,n-dimethyl-2-[(o-methyl-.alpha.-phenylbenzyl)oxy]-, Hydrochloride

100. Orphenadrine For Peak Identification, European Pharmacopoeia (ep) Reference Standard

2.4 Create Date
2005-07-28
3 Chemical and Physical Properties
Molecular Weight 305.8 g/mol
Molecular Formula C18H24ClNO
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count6
Exact Mass305.1546421 g/mol
Monoisotopic Mass305.1546421 g/mol
Topological Polar Surface Area12.5 Ų
Heavy Atom Count21
Formal Charge0
Complexity260
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Antiparkinson Agents

Agents used in the treatment of Parkinson's disease. The most commonly used drugs act on the dopaminergic system in the striatum and basal ganglia or are centrally acting muscarinic antagonists. (See all compounds classified as Antiparkinson Agents.)


Cytochrome P-450 CYP2B6 Inhibitors

Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 CYP2B6. (See all compounds classified as Cytochrome P-450 CYP2B6 Inhibitors.)


Parasympatholytics

Agents that inhibit the actions of the parasympathetic nervous system. The major group of drugs used therapeutically for this purpose is the MUSCARINIC ANTAGONISTS. (See all compounds classified as Parasympatholytics.)


Muscarinic Antagonists

Drugs that bind to but do not activate MUSCARINIC RECEPTORS, thereby blocking the actions of endogenous ACETYLCHOLINE or exogenous agonists. Muscarinic antagonists have widespread effects including actions on the iris and ciliary muscle of the eye, the heart and blood vessels, secretions of the respiratory tract, GI system, and salivary glands, GI motility, urinary bladder tone, and the central nervous system. (See all compounds classified as Muscarinic Antagonists.)


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.)


4.2 ATC Code

N - Nervous system

N04 - Anti-parkinson drugs

N04A - Anticholinergic agents

N04AB - Ethers chemically close to antihistamines

N04AB02 - Orphenadrine (chloride)