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Chemistry

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Also known as: 552-79-4, (1r,2s)-2-(dimethylamino)-1-phenylpropan-1-ol, (-)-n-methylephedrine, Dl-methylephedrine, Methylephedrine, (+/-)-, Methylephedrine, dl-

Molecular Formula

C₁₁H₁₇NO

Molecular Weight

179.26 g/mol

InChI Key

FMCGSUUBYTWNDP-ONGXEEELSA-N

FDA UNII

SHS9PGQ2LS

N-methylephedrine is a natural product found in Ephedra intermedia and Ephedra sinica with data available.

1 2D Structure

Methylephedrine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1R,2S)-2-(dimethylamino)-1-phenylpropan-1-ol

2.1.2 InChI

InChI=1S/C11H17NO/c1-9(12(2)3)11(13)10-7-5-4-6-8-10/h4-9,11,13H,1-3H3/t9-,11-/m0/s1

2.1.3 InChI Key

FMCGSUUBYTWNDP-ONGXEEELSA-N

2.1.4 Canonical SMILES

CC(C(C1=CC=CC=C1)O)N(C)C

2.1.5 Isomeric SMILES

C[C@@H]([C@@H](C1=CC=CC=C1)O)N(C)C

2.2 Other Identifiers

2.2.1 UNII

SHS9PGQ2LS

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Methylpseudoephedrine

2. N-methylephedrine

3. N-methylephedrine Hydrochloride, (r*,r*)-(+-)-isomer

4. N-methylephedrine Hydrochloride, (r*,s*)-(+-)-isomer

5. N-methylephedrine Hydrochloride, (r*,s*)-isomer

6. N-methylephedrine Hydrochloride, (r-(r*,s*))-isomer

7. N-methylephedrine Hydrochloride, (s-(r*,r*))-isomer

8. N-methylephedrine, (r*,r*)-isomer

9. N-methylephedrine, (r*,s*)-(+-)-isomer

10. N-methylephedrine, (r*,s*)-isomer

11. N-methylephedrine, (r-(r*,s*))-isomer

12. N-methylephedrine, (s-(r*,r*))-isomer

2.3.2 Depositor-Supplied Synonyms

1. 552-79-4

2. (1r,2s)-2-(dimethylamino)-1-phenylpropan-1-ol

3. (-)-n-methylephedrine

4. Dl-methylephedrine

5. Methylephedrine, (+/-)-

6. Methylephedrine, Dl-

7. Shs9pgq2ls

8. (+/-)-methylephedrine

9. (1r,2s)-2-dimethylamino-1-phenyl-1-propanol

10. (+/-)-n-methylephedrine

11. 60vh42a1kj

12. (1r,2s)-2-(dimethylamino)-1-phenyl-1-propanol

13. N-methyl (-)ephedrine

14. Nsc-760389

15. Tybraine

16. Methylephedrine ((1r,2s)-methylephedrine)

17. (1rs,2rs)-2-dimethylamino-1-phenylpropan-1-ol

18. Einecs 209-022-7

19. Methylephedrine [inn:ban]

20. Unii-60vh42a1kj

21. L-erythro-2-dimethylamino-1-phenylpropanol

22. (1s,2s)-(+)-n-methylephedrine

23. Ncgc00095782-01

24. 1201-56-5

25. L-erythro-alpha-(1-dimethylaminoethyl)benzylalkohol

26. (-)-methylephedrine

27. Methylephedrine (ban)

28. Spectrum_000431

29. Unii-shs9pgq2ls

30. Spectrum2_001196

31. Spectrum3_000671

32. Spectrum4_000739

33. Spectrum5_001055

34. N-methylephedrine Dl-form

35. Dsstox_cid_25992

36. Dsstox_rid_81277

37. Dsstox_gsid_45992

38. Schembl99673

39. Bspbio_002361

40. Kbiogr_001038

41. Kbioss_000911

42. N-methyl(-)ephedrine

43. Zinc491

44. Divk1c_000283

45. Spectrum2300220

46. Spbio_001271

47. N-methylephedrine [mi]

48. Chembl445001

49. Dtxsid7045992

50. Methylephedrine [who-dd]

51. (1r,2s)-(-)n-methylephedrine

52. Hms500o05

53. Kbio1_000283

54. Kbio2_000911

55. Kbio2_003479

56. Kbio2_006047

57. Kbio3_001581

58. Chebi:113556

59. Ninds_000283

60. Hms3264g05

61. Pharmakon1600-02300220

62. N-methyl-(-)ephedrine-[1r,2s]

63. Einecs 214-859-6

64. Tox21_111521

65. Benzenemethanol, Alpha-((1s)-1-(dimethylamino)ethyl)-, (alphar)-

66. Ccg-39547

67. Nsc760389

68. Akos006281830

69. Db11278

70. N-methylephedrine Dl-form [mi]

71. Nsc 760389

72. Idi1_000283

73. N-methylephedrine; Aif; Ce0; Corrdec

74. Ncgc00178692-01

75. Ncgc00178692-02

76. Ncgc00178692-04

77. Ncgc00181086-01

78. Ac-15988

79. Cas-552-79-4

80. (1r,2s)-(-)-n-methylephedrine, 99%

81. Ft-0770746

82. D08206

83. Ab00052416_02

84. Q2331543

85. Brd-k82236108-001-02-3

86. Brd-k82236108-001-03-1

87. Brd-k82236108-001-04-9

88. (r*,s*)-(1)-alpha-(1-(dimethylamino)ethyl)benzyl Alcohol

89. Methylephedrine ((1r,2s)-methylephedrine) 1.0 Mg/ml In Methanol

90. Benzenemethanol, .alpha.-((1r)-1-(dimethylamino)ethyl)-, (.alpha.s)-rel-

91. Benzenemethanol, Alpha-((1s)-1-(dimethylamino)ethyl)-, (.alpha.r)-

92. (1r,2s)-(-)-n--methylephedrine Solution, 1.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₁H₁₇NO
Molecular Weight	179.26 g/mol
XLogP3	1.7
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	3
Exact Mass	179.131014166 g/mol
Monoisotopic Mass	179.131014166 g/mol
Topological Polar Surface Area	23.5 Å²
Heavy Atom Count	13
Formal Charge	0
Complexity	141
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
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

Used as an antitussive and decongestant.

5 Pharmacology and Biochemistry

5.1 Pharmacology

This drugs acts as an antitussive, bronchodilator, and adrenergic receptor agonist. It stimulates the alpha and beta adrenergic receptors, relieving cough and congestion. As with other adrenomimetic amines, the drugs in this class are much less potent than norepinephrine itself. Members of this class of drugs increase both systolic and diastolic blood pressure, cardiac contractility, and cardiac output; in general, however, they do not increase heart rate. Bronchial smooth muscle relaxation of prolonged duration occurs, and pupils dilate.

5.2 Absorption, Distribution and Excretion

Absorption

Methylephedrine is rapidly absorbed following oral administration. Peak plasma concentrations of ephedrine (from which methylephedrine is derived) occur 2-3h after administration. Due to the fact that methylephedrine is a derivative of ephedrine, peak plasma concentrations are likely similar.

Route of Elimination

The primary compound excreted in urine is unchanged methylephedrine (33-40% of dose), followed by the metabolite _methylephedrine-N-oxide_ (15% of dose), and approximately 8% of the dose excreted as ephedrine after 24 hours. About 70% of the dose is excreted in the urine as metabolites over 72 hours. Alkaline urine reduces elimination to 20-35% of the dose.

Volume of Distribution

Ephedrine: 2.5-3.0 L/kg. Methylephedrine is a derivative of ephedrine and quickly distributed throughout the body.

5.3 Metabolism/Metabolites

Methylephedrine is metabolized to give ephedrine and norephedrine.

5.4 Biological Half-Life

3-6 hours (Ephedrine).

5.5 Mechanism of Action

The pharmacology of methylephedrine is similar to that of other members of the ephedra alkaloid class of drugs. These compounds are sympathomimetic amines because they mimic the effects of the catecholamines on the sympathetic nervous system. These alkaloids permeate the blood-brain barrier and have a direct central nervous system stimulant effect with peripheral effects; the peripheral effects are indirect and primarily mediated by norepinephrine release. Methylephedrine expands the bronchia by relaxing the bronchial muscles. The decrease in urination with sympathomimetic use is increased through activation of the alpha-adrenoceptors of the smooth muscles of the bladder.

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API Reference Price

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