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Chemistry

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Also known as: (+)-norpseudoephedrine, Pseudonorephedrine, Katine, D-cathine, Norpseudoephedrine, Cathinum

Molecular Formula

C₉H₁₃NO

Molecular Weight

151.21 g/mol

InChI Key

DLNKOYKMWOXYQA-IONNQARKSA-N

FDA UNII

E1L4ZW2F8O

cathine is a natural product found in Catha edulis and Ephedra sinica with data available.

1 2D Structure

Cathine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1S,2S)-2-amino-1-phenylpropan-1-ol

2.1.2 InChI

InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9+/m0/s1

2.1.3 InChI Key

DLNKOYKMWOXYQA-IONNQARKSA-N

2.1.4 Canonical SMILES

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

2.1.5 Isomeric SMILES

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

2.2 Other Identifiers

2.2.1 UNII

E1L4ZW2F8O

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (+)-norpseudoephedrine

2. Benzenemethanol, Alpha-((1r)-1-aminoethyl)-, (alphar)-rel-

3. Cathine Hydrochloride

4. Exponcit

5. Fasupond

6. Fugoa Depot

7. Norpseudoephedrine

8. Norpseudoephedrine Hydrobromide

9. Norpseudoephedrine Hydrochloride

10. Norpseudoephedrine Hydrochloride, (+)-isomer

11. Norpseudoephedrine Hydrochloride, (r*,s*)-(+-)-isomer

12. Norpseudoephedrine Hydrochloride, (r*,s*)-isomer

13. Norpseudoephedrine Hydrochloride, (r-(r*,r*))-isomer

14. Norpseudoephedrine Hydrochloride, (s-(r*,s*))-isomer

15. Norpseudoephedrine Sulfate (2:1), (+)-isomer

16. Norpseudoephedrine Sulfate (2:1), (r-(r*,r*))-isomer

17. Norpseudoephedrine Sulfate, (r-(r*,s*))-isomer

18. Norpseudoephedrine Sulfate, (s-(r*,r*))-isomer

19. Norpseudoephedrine Tartrate, (s-(r*,r*))-(r-(r*,r*))-isomer

20. Norpseudoephedrine, (-)-isomer

21. Norpseudoephedrine, (r*,r*)-(+-)-isomer

22. Norpseudoephedrine, (r*,s*)-isomer

23. Norpseudoephedrine, (r-(r*,s*))-isomer

24. Norpseudoephedrine, (s-(r*,r*))-isomer

25. Norpseudoephedrine, (s-(r*,s*))-isomer

26. Norpseudoephedrine, Conjugate Monoacid, (r-(r*,s*))-isomer

27. Pseudonorephedrine

2.3.2 Depositor-Supplied Synonyms

1. (+)-norpseudoephedrine

2. Pseudonorephedrine

3. Katine

4. D-cathine

5. Norpseudoephedrine

6. Cathinum

7. Exponcit

8. Psi-norephedrine

9. D-norpseudoephedrine

10. D-nor-psi-ephedrine

11. 492-39-7

12. Minusine

13. (1s,2s)-2-amino-1-phenylpropan-1-ol

14. 36393-56-3

15. Cathine [inn]

16. D-(+)-norephedrine

17. Racemic Norpseudoephedrine

18. D-phenylpropanolamine

19. Threo-1-phenyl-1-hydroxy-2-aminopropane

20. Threo-2-amino-1-hydroxy-1-phenylpropane

21. Norpseudoephedrine, D-

22. (+)-norephedrin

23. D-(+)-norpseudoephedrine

24. 27a0hlc3hh

25. E1l4zw2f8o

26. (1s,2s)-pseudonorephedrine

27. Chebi:4109

28. Cathine (inn)

29. L-nor-psi-ephedrine

30. Benzenemethanol, .alpha.-[(1s)-1-aminoethyl]-, (.alpha.s)-

31. (1s,2s)-2-amino-1-phenyl-propan-1-ol

32. L-nor-psi-ephedrin [german]

33. Benzenemethanol, Alpha-((1s)-1-aminoethyl)-, (alphas)-

34. Cathina

35. L-nor-psi-ephedrin

36. (1s,2s)-(+)-norpseudoephedrine

37. Norpseudoephedrine, (+)-

38. Cathinum [inn-latin]

39. Cathina [inn-spanish]

40. Unii-27a0hlc3hh

41. Unii-e1l4zw2f8o

42. Benzenemethanol, .alpha.-(1-aminoethyl)-, [s-(r*,r*)]-

43. Cathin

44. Benzenemethanol, .alpha.-(1-aminoethyl)-, (s-(r*,r*))-

45. Benzenemethanol, .alpha.-((1s)-1-aminoethyl)-, (.alpha.s)-

46. (r*,r*)-alpha-(1-aminoethyl)benzyl Alcohol

47. Nor-psi-ephedrine

48. D-norpseudoephedrin

49. Einecs 207-754-1

50. Einecs 253-014-6

51. Catina

52. Dl-nor-psi-ephedrine

53. Brn 2802895

54. (+)-pseudonorephedrine

55. (1s,2s)-2-amino-1-phenyl-1-propanol

56. Cathine [mart.]

57. Constituent Of Khat Plant

58. Ncgc00016416-01

59. Cathine [who-dd]

60. Cas-154-41-6

61. .omega.-norephedrine

62. Norpseudoephedrine, (+-)-

63. Schembl34132

64. 4-13-00-01874 (beilstein Handbook Reference)

65. Norpseudoephedrine [mi]

66. Zinc1100

67. 492-39-7 (free Base)

68. Dea No. 1230

69. Phenylpropanolamine D-threo-form

70. Benzenemethanol, .alpha.-((1r)-1-aminoethyl)-, (.alpha.r)-rel-

71. Cathine, (+/-)-

72. Chembl1412041

73. Niosh/rc9110000

74. Dtxsid20889399

75. Dtxsid50889347

76. (+/-)-norpseudoephedrine

77. Benzenemethanol, Alpha-((1r)-1-aminoethyl)-, (alphar)-rel-

78. Bdbm50405615

79. Mfcd01711268

80. Pdsp1_001353

81. Pdsp2_001337

82. Akos015891205

83. Db01486

84. As-30504

85. 2-amino-1-phenyl-1-propanol, (+)- #

86. Threo-2-amino-1-phenylpropan-1-ol

87. Phenylpropanolamine D-threo-form [mi]

88. Rc91100000

89. C08300

90. D07627

91. A823766

92. Q423797

93. Benzenemethanol, Alpha-(1-aminoethyl)-, (r*,r*)-

94. J-500428

95. (1s,2s)-(+)-norpseudoephedrine, >=98.0% (nt)

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₉H₁₃NO
Molecular Weight	151.21 g/mol
XLogP3	0.8
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	2
Exact Mass	151.099714038 g/mol
Monoisotopic Mass	151.099714038 g/mol
Topological Polar Surface Area	46.2 Å²
Heavy Atom Count	11
Formal Charge	0
Complexity	110
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 to decrease appetite.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Closely related to ephedrine, cathinone and other amphetamines, it may contribute to the stimulant effect of Catha edulis, although another constituent, cathinone appears to show stronger activity.

5.2 MeSH Pharmacological Classification

Appetite Depressants

Agents that are used to suppress appetite. (See all compounds classified as Appetite Depressants.)

5.3 ATC Code

A - Alimentary tract and metabolism

A08 - Antiobesity preparations, excl. diet products

A08A - Antiobesity preparations, excl. diet products

A08AA - Centrally acting antiobesity products

A08AA07 - Cathine

5.4 Absorption, Distribution and Excretion

Absorption

The mucosa of the oral cavity is considered to be the first absorption segment, where the major proportion of the alkaloids is absorbed (mean +/- SD: 84 +/- 6% for cathine). [PMID: 12848785]

5.5 Biological Half-Life

5.2 +/- 3.4 hours

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