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04JA59TNSJ
Also known as: 61-76-7, Phenylephrine hcl, Biomydrin, Nostril, (r)-phenylephrine hydrochloride, L-phenylephrine hydrochloride
Molecular Formula
C9H14ClNO2
Molecular Weight
203.66  g/mol
InChI Key
OCYSGIYOVXAGKQ-FVGYRXGTSA-N
FDA UNII
04JA59TNSJ

An alpha-1 adrenergic agonist used as a mydriatic, nasal decongestant, and cardiotonic agent.
1 2D Structure

04JA59TNSJ

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
3-[(1R)-1-hydroxy-2-(methylamino)ethyl]phenol;hydrochloride
2.1.2 InChI
InChI=1S/C9H13NO2.ClH/c1-10-6-9(12)7-3-2-4-8(11)5-7;/h2-5,9-12H,6H2,1H3;1H/t9-;/m0./s1
2.1.3 InChI Key
OCYSGIYOVXAGKQ-FVGYRXGTSA-N
2.1.4 Canonical SMILES
CNCC(C1=CC(=CC=C1)O)O.Cl
2.1.5 Isomeric SMILES
CNC[C@@H](C1=CC(=CC=C1)O)O.Cl
2.2 Other Identifiers
2.2.1 UNII
04JA59TNSJ
2.3 Synonyms
2.3.1 MeSH Synonyms

1. (r)-3-hydroxy-alpha-((methylamino)methyl)benzenemethanol

2. Metaoxedrin

3. Metasympatol

4. Mezaton

5. Neo Synephrine

6. Neo-synephrine

7. Neosynephrine

8. Phenylephrine

9. Phenylephrine Tannate

10. Tannate, Phenylephrine

2.3.2 Depositor-Supplied Synonyms

1. 61-76-7

2. Phenylephrine Hcl

3. Biomydrin

4. Nostril

5. (r)-phenylephrine Hydrochloride

6. L-phenylephrine Hydrochloride

7. (r)-(-)-phenylephrine Hydrochloride

8. Phenylephrine.hcl

9. Mydfrin

10. Metaoxedrine Chloride

11. Vazculep

12. Neo-synephrine

13. Adrianol

14. Neophryn

15. Prefrin

16. Rhinall

17. Alcon Efrin

18. (-)-phenylephrine Hydrochloride

19. Nci-c55641

20. Efricel

21. Isopto Frin

22. Prefrin Liquifilm

23. (r)-3-(1-hydroxy-2-(methylamino)ethyl)phenol Hydrochloride

24. 3-[(1r)-1-hydroxy-2-(methylamino)ethyl]phenol;hydrochloride

25. Afrin 4 Hour Nasal Spray

26. Nsc-757273

27. 04ja59tnsj

28. Phenylephrine (hydrochloride)

29. Mls000069696

30. Ncgc00024257-04

31. Neosympatol

32. Synethenate

33. Almefrin

34. Consdrin

35. Emagrin

36. Fenilfar

37. Histabid

38. Idrianol

39. Lexatol

40. Oftalfrine

41. Phenistan

42. Pyristan

43. Smr000058497

44. Stanephrin

45. Sucraphen

46. Synasal

47. Fenox

48. Meta-sympatol

49. Alcon-efrin

50. (r)-(-)-1-(3-hydroxyphenyl)-2-methylaminoethanol Hydrochloride

51. [(2r)-2-hydroxy-2-(3-hydroxyphenyl)ethyl]-methylazanium;chloride

52. Dsstox_cid_1142

53. Op-isophrin

54. Dsstox_rid_75972

55. Neo-synesin 1

56. Dsstox_gsid_21142

57. Neooxedrine Chloride

58. 3-[(1r)-1-hydroxy-2-(methylamino)ethyl]phenol Hydrochloride

59. Consdrin Hydrochloride

60. Isophrin Hydrochloride

61. Vasosulf

62. Relief

63. Metaoxedrine Hydrochloride

64. Neosynephrine Hydrochloride

65. Sudafed Pe

66. Chebi:8094

67. Op-isophrin-z

68. Cas-61-76-7

69. Meta-synephrine Hydrochloride

70. Ccris 219

71. Levophenylephrine Hydrochloride

72. Phenylephrine Hydrochloride, L-

73. R-(-)-m-synephrine Hydrochloride

74. D-(-)-phenylephrine Hydrochloride

75. Einecs 200-517-3

76. Unii-04ja59tnsj

77. M-methylaminoethanolphenol Hydrochloride

78. Benzedrex Nasal Spray, Regular

79. Sr-01000075286

80. Mfcd00012605

81. Phenylephrine Hydrochloride [usp:jan]

82. Vicks Sinex Vapospray

83. Neo-synephrine (tn)

84. L-1-(m-hydroxyphenyl)-2-methyl-aminoethanol Hydrochloride

85. Vicks Sinex Nasal Spray

86. 1-m-hydroxy-alpha-(methylaminomethyl)benzyl Alcohol Hydrochloride

87. Opera_id_1786

88. (-)-m-hydroxy-alpha-((methylamino)methyl)benzyl Alcohol Hydrochloride

89. (r)-3-hydroxy-alpha-((methylamino)methyl)benzenemethanol Hydrochloride

90. (-)-alpha-hydroxy-beta-(methylamino)ethyl-alpha-(3-hydroxybenzene) Hydrochloride

91. Benzenemethanol, 3-hydroxy-alpha-((methylamino)methyl)-, Hydrochloride, (-)-

92. Ec 200-517-3

93. Schembl24654

94. Mls006012005

95. Spectrum1500483

96. Phenylephrine Hydrochloride,(s)

97. Chembl1200339

98. Dtxsid3021142

99. L(-)-phenylephrine Hydrochloride

100. Hms1920h08

101. Pharmakon1600-01500483

102. Bcp23410

103. Hy-b0471

104. Tox21_110897

105. Tox21_201261

106. Tox21_302846

107. Tox21_500920

108. Ccg-39113

109. Nsc757273

110. S2569

111. Akos022190146

112. Benzenemethanol, 3-hydroxy-alpha-((methylamino)methyl)-, Hydrochloride (r)-

113. Benzyl Alcohol, M-hydroxy-alpha-((methylamino)methyl)-, Hydrochloride, (-)-

114. Tox21_110897_1

115. Lp00920

116. Nsc 757273

117. Benzenemethanol, 3-hydroxy-alpha-((methylamino)methyl)-, Hydrochloride, (alphar)-

118. Phenylephrine Hydrochloride (jp17/usp)

119. Phenylephrine Hydrochloride [mi]

120. Ncgc00024257-08

121. Ncgc00094231-01

122. Ncgc00256496-01

123. Ncgc00258813-01

124. Ncgc00261605-01

125. Phenylephrine Hydrochloride [jan]

126. Bp166231

127. Bcp0726000237

128. Phenylephrine Hydrochloride [mart.]

129. Phenylephrine Hydrochloride [vandf]

130. Phenylephrine Hydrochloride [usp-rs]

131. Phenylephrine Hydrochloride [who-dd]

132. (r)-(-)-phenylephrine Hydrochloride, Powder

133. Eu-0100920

134. P0398

135. Sw219446-1

136. Vu0239753-6

137. D00511

138. D70603

139. P 6126

140. Phenylephrine Hydrochloride [orange Book]

141. A833410

142. Phenylephrine Hydrochloride [ep Monograph]

143. Phenylephrine Hydrochloride [usp Monograph]

144. Omidria Component Phenylephrine Hydrochloride

145. Q-201561

146. Sr-01000075286-1

147. Phenylephrine Hydrochloride Component Of Omidria

148. Prefrin-a Component Phenylephrine Hydrochloride

149. Q27107758

150. (r)-(-)-phenylephrine Hydrochloride, Analytical Standard

151. Cyclomydril Component Phenylephrine Hydrochloride

152. Phenergan Vc Component Phenylephrine Hydrochloride

153. Phenylephrine Hydrochloride Component Of Prefrin-a

154. Pherazine Vc Component Phenylephrine Hydrochloride

155. Phenylephrine Hydrochloride Component Of Cyclomydril

156. Phenylephrine Hydrochloride Component Of Phenergan Vc

157. Phenylephrine Hydrochloride Component Of Pherazine Vc

158. Promethazine Vc Component Phenylephrine Hydrochloride

159. Phenylephrine Hydrochloride Component Of Promethazine Vc

160. (r)-(-)-phenylephrine Hydrochloride, Tested According To Ph.eur.

161. Advil Congestion Relief Component Phenylephrine Hydrochloride

162. Benzenemethanol, 3-hydroxy-a-[(methylamino)methyl]-, Hydrochloride,(ar)-

163. Phenylephrine Hydrochloride Component Of Advil Congestion Relief

164. Phenylephrine Hydrochloride, British Pharmacopoeia (bp) Reference Standard

165. Phenylephrine Hydrochloride, European Pharmacopoeia (ep) Reference Standard

166. (-)-m-hydroxy-.alpha.-((methylamino)methyl)benzyl Alcohol Hydrochloride

167. Benzenemethanol, 3-hydroxy-.alpha.-((methylamino)methyl)-, Hydrochloride (r)-

168. Benzenemethanol, 3-hydroxy-alpha-((methylamino)methyl)-, Hydrochloride (1:1), (alphar)-

169. Phenylephrine Hydrochloride, Pharmaceutical Secondary Standard; Certified Reference Material

170. Phenylephrine Hydrochloride, United States Pharmacopeia (usp) Reference Standard

171. Phenylephrine Hydrochloride For Peak Identification, European Pharmacopoeia (ep) Reference Standard

172. R-(-)-phenylephrine Hydrochloride Solution, 1.0 Mg/ml In Methanol (as Free Base), Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date
2005-11-20
3 Chemical and Physical Properties
Molecular Weight 203.66 g/mol
Molecular Formula C9H14ClNO2
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Exact Mass203.0713064 g/mol
Monoisotopic Mass203.0713064 g/mol
Topological Polar Surface Area52.5 Ų
Heavy Atom Count13
Formal Charge0
Complexity130
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NamePhenylephrine hydrochloride
Drug LabelNEO-SYNEPHRINE hydrochloride, brand of phenylephrine hydrochloride injectino, is a vasoconstrictor and pressor drug chemically related to epinephrine and ephedrine. NEO-SYNEPHRINE hydrochloride is a synthetic sympathomimetic agent in sterile form f...
Active IngredientPhenylephrine hydrochloride
Dosage FormSolution/drops; Solution
RouteOphthalmic; Iv (infusion)
Strength10mg/ml (10mg/ml); 10%; 2.5%
Market StatusPrescription
CompanyWest Ward Pharm; Paragon Bioteck

2 of 2  
Drug NamePhenylephrine hydrochloride
Drug LabelNEO-SYNEPHRINE hydrochloride, brand of phenylephrine hydrochloride injectino, is a vasoconstrictor and pressor drug chemically related to epinephrine and ephedrine. NEO-SYNEPHRINE hydrochloride is a synthetic sympathomimetic agent in sterile form f...
Active IngredientPhenylephrine hydrochloride
Dosage FormSolution/drops; Solution
RouteOphthalmic; Iv (infusion)
Strength10mg/ml (10mg/ml); 10%; 2.5%
Market StatusPrescription
CompanyWest Ward Pharm; Paragon Bioteck

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Mydriatics

Agents that dilate the pupil. They may be either sympathomimetics or parasympatholytics. (See all compounds classified as Mydriatics.)


Nasal Decongestants

Drugs designed to treat inflammation of the nasal passages, generally the result of an infection (more often than not the common cold) or an allergy related condition, e.g., hay fever. The inflammation involves swelling of the mucous membrane that lines the nasal passages and results in inordinate mucus production. The primary class of nasal decongestants are vasoconstrictor agents. (From PharmAssist, The Family Guide to Health and Medicine, 1993) (See all compounds classified as Nasal Decongestants.)


Sympathomimetics

Drugs that mimic the effects of stimulating postganglionic adrenergic sympathetic nerves. Included here are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters. (See all compounds classified as Sympathomimetics.)


Vasoconstrictor Agents

Drugs used to cause constriction of the blood vessels. (See all compounds classified as Vasoconstrictor Agents.)


Adrenergic alpha-1 Receptor Agonists

Compounds that bind to and activate ADRENERGIC ALPHA-1 RECEPTORS. (See all compounds classified as Adrenergic alpha-1 Receptor Agonists.)


Cardiotonic Agents

Agents that have a strengthening effect on the heart or that can increase cardiac output. They may be CARDIAC GLYCOSIDES; SYMPATHOMIMETICS; or other drugs. They are used after MYOCARDIAL INFARCT; CARDIAC SURGICAL PROCEDURES; in SHOCK; or in congestive heart failure (HEART FAILURE). (See all compounds classified as Cardiotonic Agents.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
alpha-1 Adrenergic Agonist [EPC]; Adrenergic alpha1-Agonists [MoA]
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  • SOLUTION;INTRAVENOUS - 0.5MG/5ML (0.1MG/ML)
  • SOLUTION;INTRAVENOUS - 100MG/10ML (10MG/ML)
  • SOLUTION;INTRAVENOUS - 10MG/ML (10MG/ML)
  • SOLUTION;INTRAVENOUS - 1MG/10ML (0.1MG/ML)
  • SOLUTION;INTRAVENOUS - 50MG/5ML (10MG/ML)
  • SOLUTION;INTRAVENOUS - 100MG/10ML (10MG/ML)
  • SOLUTION;INTRAVENOUS - 10MG/ML (10MG/ML)
  • SOLUTION;INTRAVENOUS - 50MG/5ML (10MG/ML)
  • SOLUTION/DROPS;OPHTHALMIC - 10%
  • SOLUTION/DROPS;OPHTHALMIC - 2.5%
  • TABLET;ORAL - 4MG;200MG;10MG
  • TABLET;ORAL - 200MG;10MG
  • SYRUP;ORAL - 5MG/5ML;6.25MG/5ML
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