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Synopsis

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Also known as: Norphenylephrine, 3-(2-amino-1-hydroxyethyl)phenol, 536-21-0, Norphenephrine, Metacardiol, M-octopamine

Molecular Formula

C₈H₁₁NO₂

Molecular Weight

153.18 g/mol

InChI Key

LRCXRAABFLIVAI-UHFFFAOYSA-N

FDA UNII

D2P3M6SRN5

1 2D Structure

Norfenefrine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-(2-amino-1-hydroxyethyl)phenol

2.1.2 InChI

InChI=1S/C8H11NO2/c9-5-8(11)6-2-1-3-7(10)4-6/h1-4,8,10-11H,5,9H2

2.1.3 InChI Key

LRCXRAABFLIVAI-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC(=CC(=C1)O)C(CN)O

2.2 Other Identifiers

2.2.1 UNII

D2P3M6SRN5

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3-octopamine

2. A.s. Cor

3. Alpha-(aminomethyl)-3-hydroxybenzyl Alcohol

4. M-octopamine

5. Norfenefrin Ziethen

6. Norfenefrin-ratiopharm

7. Norfenefrine Citrate (1:1), (r)-(r-(r*,r*))-isomer

8. Norfenefrine Citrate (1:1), (r-(r*,r*))-isomer

9. Norfenefrine Hydrochloride

10. Norfenefrine Hydrochloride, (+,-)-isomer

11. Norfenefrine Hydrochloride, (r)-isomer

12. Norfenefrine Hydrochloride, (s)-isomer

13. Norfenefrine Sulfate

14. Norfenefrine, (+)-isomer

15. Norfenefrine, (+,-)-isomer

16. Norfenefrine, (-)-isomer

17. Norfenefrine, 2h-labeled Cpd

18. Norphenylephrine

19. Novadral

2.3.2 Depositor-Supplied Synonyms

1. Norphenylephrine

2. 3-(2-amino-1-hydroxyethyl)phenol

3. 536-21-0

4. Norphenephrine

5. Metacardiol

6. M-octopamine

7. Normetol

8. Norenol

9. Normetasympathol

10. Dl-norphenylephrine

11. 15308-34-6

12. M-hydroxyphenylethanolamine

13. Norfenefrine [inn]

14. Norfenefrinum

15. R,s-norphenylephrine

16. Dl-m-octopamine

17. 1-(m-hydroxyphenyl)-2-aminoethanol

18. 3-(2-amino-1-hydroxy-ethyl)-phenol

19. (+-)-norphenylephrine

20. Alpha-(aminomethyl)-m-hydroxybenzyl Alcohol

21. 1-(3'-hydroxyphenyl)-2-aminoethanol

22. 1-(3-hydroxyphenyl)-1-hydroxy-2-aminoethane

23. Normezaton; Norphenephrine

24. D2p3m6srn5

25. Wv 569 [as Hydrochloride]

26. (+-)-alpha-(aminomethyl)-m-hydroxybenzyl Alcohol

27. Benzyl Alcohol, Alpha-(aminomethyl)-m-hydroxy-

28. Norfenefrine (inn)

29. Benzenemethanol, Alpha-(aminomethyl)-3-hydroxy-, (+-)-

30. Benzyl Alcohol, Alpha-(aminomethyl)-m-hydroxy-, (+-)-

31. Benzenemethanol, .alpha.-(aminomethyl)-3-hydroxy-

32. Norfenefrina

33. Norfenefrinum [inn-latin]

34. Norfenefrina [inn-spanish]

35. Ncgc00167553-01

36. Einecs 208-626-8

37. Unii-d2p3m6srn5

38. Brn 1211018

39. Norfenefrin

40. Zondel (salt/mix)

41. Novadral (salt/mix)

42. 2-amino-1-(3-hydroxyphenyl)ethan-1-ol

43. Norfenefrine [mi]

44. (.+/-.)-norfenefrine

45. Wv569 Free Base

46. Dl-[2-hydroxy-2-(3-hydroxyphenyl)ethyl]amine

47. Oprea1_016194

48. Wv-569 Free Base

49. 3-13-00-02235 (beilstein Handbook Reference)

50. Norfenefrine [who-dd]

51. Schembl153494

52. Chembl358040

53. Dtxsid3048314

54. Chebi:134779

55. Albb-006272

56. Hy-b1711

57. Bbl028398

58. Stk503797

59. 3-(2-amino-1-hydroxyethyl)phenol #

60. Akos005171592

61. Db13378

62. Fs-4505

63. Ncgc00167553-02

64. 13026-50-1

65. Am100918

66. 3-[(1rs)-2-amino-1-hydroxyethyl]phenol

67. Db-043177

68. Cs-0013711

69. .alpha.-(aminomethyl)-m-hydroxybenzyl Alcohol

70. D08286

71. Benzyl Alcohol, .alpha.-(aminomethyl)-m-hydroxy-

72. Sr-01000944512

73. .alpha.-(aminoethyl)-m-hydroxybenzyl Alcohol

74. Sr-01000944512-1

75. .alpha.-(aminomethyl)-m-hydroxybenzyl Alcohol.

76. Q12746348

77. .alpha.-(aminomethyl)-3-hydroxybenzene Methanol

78. Norphenylephrine Hydrochloride, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₈H₁₁NO₂
Molecular Weight	153.18 g/mol
XLogP3	-0.8
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	2
Exact Mass	153.078978594 g/mol
Monoisotopic Mass	153.078978594 g/mol
Topological Polar Surface Area	66.5 Å²
Heavy Atom Count	11
Formal Charge	0
Complexity	119
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.)

4.2 ATC Code

C - Cardiovascular system

C01 - Cardiac therapy

C01C - Cardiac stimulants excl. cardiac glycosides

C01CA - Adrenergic and dopaminergic agents

C01CA05 - Norfenefrine

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