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DSSTox_CID_3526

DSSTox_CID_3526

Synopsis, Chemistry

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Also known as: Benzedrex, Hydromethamphetamine, Propylhexedrin, Dristan, Obesin, Hexahydrodesoxyephedrine

Molecular Formula

C₁₀H₂₁N

Molecular Weight

155.28 g/mol

InChI Key

JCRIVQIOJSSCQD-UHFFFAOYSA-N

FDA UNII

LQU92IU8LL

Propylhexedrine is a propylamine derivative with sympathomimetic property. Propylhexedrine binds to and activates alpha-adrenergic receptors in the mucosa of the respiratory tract, thereby mimicking the actions of norepinephrine and epinephrine. This results in vasoconstriction and reduces swelling and inflammation of the mucous membrane lining, therefore relieving nasal and sinus congestion.

1 2D Structure

DSSTox_CID_3526

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-cyclohexyl-N-methylpropan-2-amine

2.1.2 InChI

InChI=1S/C10H21N/c1-9(11-2)8-10-6-4-3-5-7-10/h9-11H,3-8H2,1-2H3

2.1.3 InChI Key

JCRIVQIOJSSCQD-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(CC1CCCCC1)NC

2.2 Other Identifiers

2.2.1 UNII

LQU92IU8LL

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Benzedrex

2. Propylhexadrine

3. Propylhexedrine Hydrochloride

4. Propylhexedrine Hydrochloride, (s)-isomer

2.3.2 Depositor-Supplied Synonyms

1. Benzedrex

2. Hydromethamphetamine

3. Propylhexedrin

4. Dristan

5. Obesin

6. Hexahydrodesoxyephedrine

7. Dristan Inhaler

8. Chp-depot

9. 1-cyclohexyl-n-methylpropan-2-amine

10. 101-40-6

11. Propylhexadrine

12. Propylhexedrinum

13. Dl-propylhexedrine

14. Methyl-(1-methyl-2-cyclohexylethyl)amine

15. 1-cyclohexyl-2-(methylamino)propane

16. 1-cyclohexyl-n-methyl-2-propanamine

17. (+/-) Propylhexedrine

18. N,alpha-dimethylcyclohexaneethylamine

19. Nsc 32410

20. 1-cyclohexyl-2-methylaminopropan

21. Cyclohexaneethanamine, N,.alpha.-dimethyl-

22. Nsc-32410

23. Lqu92iu8ll

24. Ncgc00182042-01

25. Cyclohexaneethylamine, N-.alpha.-dimethyl-

26. Propilhexedrina

27. Propilesedrina

28. Propilesedrina [dcit]

29. Einecs 202-939-3

30. Unii-lqu92iu8ll

31. Brn 3194303

32. Propylhexedrinum [inn-latin]

33. 1-cyclohexyl-2-methylaminopropan [german]

34. Propilhexedrina [inn-spanish]

35. (+-)-n,alpha-dimethylcyclohexaneethylamine

36. (cyclohexaneethyl)amine, N-alpha-dimethyl-

37. Beta-cyclohexyl-isopropylmethylamin [german]

38. Propylhexedrine [usp:inn:ban]

39. Beta-cyclohexyl-isopropylmethylamin

40. Cyclohexaneethanamine, N,alpha-dimethyl-, (+-)

41. Einecs 222-741-0

42. Dristan Inhaler (tn)

43. Propylhexedrine Dl-form

44. Dsstox_cid_3526

45. Cyclohexaneethylamine, Alpha,n-dimethyl-

46. Propylhexedrine (usp/inn)

47. Dsstox_rid_77064

48. Cyclohexaneethanamine, N,alpha-dimethyl-, (+-)-

49. Dsstox_gsid_23526

50. Schembl28537

51. Propylhexedrine [inn]

52. 3-12-00-00108 (beilstein Handbook Reference)

53. Propylhexedrine [vandf]

54. Propylhexedrine [mart.]

55. Chembl2105275

56. Dtxsid1023526

57. Propylhexedrine [who-dd]

58. Schembl20780004

59. Wln: L6tj A1y1&m1

60. Chebi:134783

61. N-methyl-1-cyclohexylisopropylamine

62. Nsc32410

63. Tox21_113077

64. Propylhexedrine Dl-form [mi]

65. Stk664138

66. Akos005172629

67. .alpha.,n-dimethylcyclohexaneethylamine

68. Cyclohexaneethanamine,.alpha.-dimethyl-

69. Db06714

70. N,.alpha.-dimethylcyclohexaneethylamine

71. Propylhexedrine [usp Monograph]

72. (1-cyclohexylpropan-2-yl)(methyl)amine

73. Ncgc00182042-03

74. Ncgc00182042-04

75. 3595-11-7

76. Cas-101-40-6

77. N-.alpha.-(dimethylcyclohexane)ethylamine

78. Cyclohexaneethylamine, .alpha.,n-dimethyl-

79. Ft-0674106

80. (cyclohexaneethyl)amine, N-.alpha.-dimethyl-

81. N-(2-cyclohexyl-1-methylethyl)-n-methylamine

82. D05637

83. Ab01331925-02

84. (.+/-.)-n,.alpha.-dimethylcyclohexaneethylamine

85. Q408704

86. (+/-)-n,.alpha.-dimethylcyclohexaneethanamine

87. Cyclohexaneethanamine, N,.alpha.-dimethyl-, (.+/-.)

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₁₀H₂₁N
Molecular Weight	155.28 g/mol
XLogP3	3.5
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	3
Exact Mass	155.167399674 g/mol
Monoisotopic Mass	155.167399674 g/mol
Topological Polar Surface Area	12 Å²
Heavy Atom Count	11
Formal Charge	0
Complexity	95
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 Drug and Medication Information

4.1 Drug Indication

It is used to provide temporary symptomatic relief of nasal congestion due to colds, allergies and allergic rhinitis.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Like other monoamine releasing stimulants propylhexedrine is active as a norepinephrine and dopamine releaser in the central nervous system. The acute effects of the drug closely resemble the physiological and psychological effects of an epinephrine-provoked fight-or-flight response, including increased heart rate and blood pressure, vasoconstriction (constriction of the arterial walls), bronchodilation, and hyperglycemia (increased blood sugar).

5.2 Mechanism of Action

Propylhexidrine causes the norepinephrine, dopamine, and serotonin (5HT) transporters to reverse their direction of flow. This inversion leads to a release of these transmitters from the vesicles to the cytoplasm and from the cytoplasm to the synapse. It also antagonizes the action of VMAT2, causing the release of more neurotransmitters.