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4-Hydroxy-alpha-(methylaminomethyl)benzyl Alcohol

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Chemistry

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Also known as: Oxedrine, 94-07-5, P-synephrine, Parasympatol, Sympaethamine, Sympatol

Molecular Formula

C₉H₁₃NO₂

Molecular Weight

167.20 g/mol

InChI Key

YRCWQPVGYLYSOX-UHFFFAOYSA-N

FDA UNII

PEG5DP7434

Sympathetic alpha-adrenergic agonist with actions like PHENYLEPHRINE. It is used as a vasoconstrictor in circulatory failure, asthma, nasal congestion, and glaucoma.

1 2D Structure

Synephrine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-[1-hydroxy-2-(methylamino)ethyl]phenol

2.1.2 InChI

InChI=1S/C9H13NO2/c1-10-6-9(12)7-2-4-8(11)5-3-7/h2-5,9-12H,6H2,1H3

2.1.3 InChI Key

YRCWQPVGYLYSOX-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CNCC(C1=CC=C(C=C1)O)O

2.2 Other Identifiers

2.2.1 UNII

PEG5DP7434

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Oxedrine

2. Sympaethamin

3. Synephrin

2.3.2 Depositor-Supplied Synonyms

1. Oxedrine

2. 94-07-5

3. P-synephrine

4. Parasympatol

5. Sympaethamine

6. Sympatol

7. Analeptin

8. Sympaethamin

9. Synephrin

10. Synthenate

11. Simpalon

12. (+/-)-synephrine

13. Simpatol

14. Ethaphene

15. Sympathol

16. Dl-synephrine

17. P-oxedrine

18. 4-(1-hydroxy-2-(methylamino)ethyl)phenol

19. 4-[1-hydroxy-2-(methylamino)ethyl]phenol

20. Synefrin

21. Advantra Z

22. 1-(4-hydroxyphenyl)-n-methylethanolamine

23. (rs)-1-(4-hydroxyphenyl)-2-(methylamino)ethanol

24. 1-(4-hydroxyphenyl)-2-methylaminoethanol

25. Nsc 166285

26. Chebi:29081

27. S 38537-9

28. Nsc-166285

29. Nsc-170956

30. Beta-methylamino-alpha-(4-hydroxyphenyl)ethyl Alcohol

31. Peg5dp7434

32. P-hydroxy-alpha-((methylamino)methyl)benzyl Alcohol

33. 4-hydroxy-alpha-((methylamino)methyl)benzenemethanol

34. Mfcd00002370

35. Nsc166285

36. Benzenemethanol, 4-hydroxy-.alpha.-[(methylamino)methyl]-

37. Benzenemethanol, 4-hydroxy-a-[(methylamino)methyl]-, (ar)-

38. 1-(4-hydroxyphenyl)-(2-methylamino)ethanol

39. Wln: Qr Dyq1m1

40. Dsstox_cid_10588

41. Dsstox_rid_78850

42. Synefrin [czech]

43. Dsstox_gsid_30588

44. P-hydroxy-alpha-[(methylamino)methyl]benzyl Alcohol

45. Pentedrin [german]

46. 4-hydroxy-alpha-[(methylamino)methyl]benzenemethanol

47. P-((methylamino)ethanol)phenol

48. P-[(methylamino)ethanol]phenol

49. P-hydroxy-.alpha.-[(methylamino)methyl]benzyl Alcohol

50. Parakorper [german]

51. S-38537-9

52. 1-(4-hydroxyphenyl)-2-(methylamino)ethanol

53. .beta.-methylamino-.alpha.-(4-hydroxyphenyl)ethyl Alcohol

54. Benzyl Alcohol, P-hydroxy-.alpha.-[(methylamino)methyl]-

55. Parakorper

56. P-hydroxyphenyl(methylamino)ethanol

57. P-methylaminoethanolphenol

58. Smr000059111

59. Synepherine

60. 1-(4-hydroxyphenyl)-(n-methylethanol)amine

61. P-hydroxyphenylmethylaminoethanol

62. Benzyl Alcohol, P-hydroxy-alpha-((methylamino)methyl)-, (-)-

63. Oxedrine [inn:ban]

64. ((methylamino)methyl)((4-hydroxyphenyl)carbinol)

65. [(methylamino)methyl][(4-hydroxyphenyl)carbinol]

66. Sr-01000002983

67. P-hydroxy-.alpha.-[(methylamino)methyl]benzylalcohol

68. Einecs 202-300-9

69. (+-)-n-methyloctopamine

70. Unii-peg5dp7434

71. Methylaminomethyl(4-hydroxyphenyl)carbinol

72. Benzenemethanol, 4-hydroxy-alpha-((methylamino)methyl)-

73. Rac-synephrine

74. Benzenemethanol, 4-hydroxy-.alpha.-((methylamino)methyl)-

75. (y)-synephrine

76. Synephrine,(s)

77. Cas-94-07-5

78. Ncgc00016351-01

79. Oxedrine, Sympatol

80. (?)-synephrine

81. Oxedrine (ban)

82. (+/-)synephrine

83. (+,-)-synephrine

84. Nsc 170956

85. Synephrine (oxedrine)

86. Synephrine - Oxedrine

87. Alpha-(4-oxyphenyl)alpha-oxy-beta-methylaminoaethan [german]

88. Synephrine [mi]

89. Prestwick0_001088

90. Prestwick1_001088

91. Prestwick2_001088

92. Prestwick3_001088

93. (.+/-.)-synephrine

94. Synephrine [inci]

95. Oxedrine [mart.]

96. Oxedrine [who-dd]

97. Synephrine [usp-rs]

98. 4-hydroxy-alpha-(methylaminomethyl)benzyl Alcohol

99. Lopac0_001085

100. (+/-)-oxedrine

101. Bspbio_001136

102. Alpha-(4-oxyphenyl)alpha-oxy-beta-methylaminoaethan

103. Mls000069435

104. Mls001424216

105. Chembl33720

106. Schembl146500

107. Spbio_003028

108. Synephrine, Analytical Standard

109. (.+/-.)-n-methyloctopamine

110. Bpbio1_001250

111. Oxedrine [usp Impurity]

112. Dtxsid0030588

113. (+/-)-synephrine, >=98%

114. Benzyl Alcohol, P-hydroxy-alpha-((methylamino)methyl)-

115. Hms1571i18

116. Hms2052g09

117. Hms2098i18

118. Hms2233f20

119. Hms3263i12

120. Hms3264e11

121. Hms3369c13

122. Hms3394g09

123. Hms3656o09

124. Hms3715i18

125. Hms3884d15

126. Pharmakon1600-01506085

127. Albb-025740

128. Hy-n0132

129. Tox21_110390

130. Tox21_200962

131. Tox21_501085

132. ( Inverted Question Mark)-synephrine

133. Bbl015111

134. Bdbm50102660

135. Nsc170956

136. Nsc759316

137. Pdsp1_000167

138. Pdsp2_000166

139. S2362

140. Stk803113

141. Akos004119915

142. Akos016038542

143. Tox21_110390_1

144. Ccg-101098

145. Ccg-205162

146. Db09203

147. Ks-5152

148. Lp01085

149. Nc00348

150. Nsc-759316

151. Sdccgsbi-0051055.p003

152. Ncgc00015924-03

153. Ncgc00015924-04

154. Ncgc00015924-05

155. Ncgc00015924-06

156. Ncgc00015924-08

157. Ncgc00015924-09

158. Ncgc00015924-12

159. Ncgc00015924-13

160. Ncgc00015924-25

161. Ncgc00089788-02

162. Ncgc00089788-03

163. Ncgc00089788-04

164. Ncgc00258515-01

165. Ncgc00261770-01

166. (+)-[(methylamino)methyl]-benzenemethano

167. 4-(1-hydroxy-2-methylamino-ethyl)phenol

168. Bp-12742

169. Synephrine 100 Microg/ml In Acetonitrile

170. Sbi-0051055.p002

171. Ab00514040

172. Cs-0007857

173. Eu-0101085

174. Ft-0618685

175. Ft-0653012

176. N1706

177. S0232

178. Sw197214-5

179. 4-[1-hydroxy-2-(methylamino)ethyl]phenol #

180. 4-hydroxy-a-(methylaminomethyl)benzyl Alcohol

181. 94s075

182. C04548

183. D07148

184. S 0752

185. Ab00384265_11

186. Q421351

187. Q-100668

188. Sr-01000002983-3

189. Sr-01000002983-7

190. Sr-01000002983-8

191. W-100214

192. 4-hydroxy-.alpha.-((methylamino)methyl)benzenemethanol

193. 7336264b-edc9-42c5-939b-ff800ab5bb4a

194. Benzenemethanol, 4-hydroxy-alpha-[(methylamino)methyl]-, 2,3-dihydroxybutanedioate (1:1) (salt)

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₉H₁₃NO₂
Molecular Weight	167.20 g/mol
XLogP3	-0.6
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	3
Exact Mass	167.094628657 g/mol
Monoisotopic Mass	167.094628657 g/mol
Topological Polar Surface Area	52.5 Å²
Heavy Atom Count	12
Formal Charge	0
Complexity	122
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Adrenergic alpha-Agonists

Drugs that selectively bind to and activate alpha adrenergic receptors. (See all compounds classified as Adrenergic alpha-Agonists.)

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.)

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.)

4.2 ATC Code

C - Cardiovascular system

C01 - Cardiac therapy

C01C - Cardiac stimulants excl. cardiac glycosides

C01CA - Adrenergic and dopaminergic agents

C01CA08 - Oxedrine

S - Sensory organs

S01 - Ophthalmologicals

S01G - Decongestants and antiallergics

S01GA - Sympathomimetics used as decongestants

S01GA06 - Oxedrine

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