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Chemistry

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Also known as: Versamine, Mecamine, Revertina, Mecamilamina, Mekamine, 60-40-2

Molecular Formula

C₁₁H₂₁N

Molecular Weight

167.29 g/mol

InChI Key

IMYZQPCYWPFTAG-UHFFFAOYSA-N

A nicotinic antagonist that is well absorbed from the gastrointestinal tract and crosses the blood-brain barrier. Mecamylamine has been used as a ganglionic blocker in treating hypertension, but, like most ganglionic blockers, is more often used now as a research tool.

1 2D Structure

Mecamylamine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N,2,3,3-tetramethylbicyclo[2.2.1]heptan-2-amine

2.1.2 InChI

InChI=1S/C11H21N/c1-10(2)8-5-6-9(7-8)11(10,3)12-4/h8-9,12H,5-7H2,1-4H3

2.1.3 InChI Key

IMYZQPCYWPFTAG-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1(C2CCC(C2)C1(C)NC)C

2.2 Synonyms

2.2.1 Depositor-Supplied Synonyms

1. Versamine

2. Mecamine

3. Revertina

4. Mecamilamina

5. Mekamine

6. 60-40-2

7. 2-methylaminoisocamphane

8. Mevasine

9. 3-methylaminoisocamphane

10. N,2,3,3-tetramethylbicyclo[2.2.1]heptan-2-amine

11. N-methyl-2-isocamphanamine

12. 2-methylamino-2,3,3-trimethylnorbornane

13. N,2,3,3-tetramethyl-2-norbornamine

14. N,2,3,3-tetramethyl-2-norcamphanamine

15. 2-norbornanamine, N,2,3,3-tetramethyl-

16. Bicyclo(2.2.1)heptan-2-amine, N,2,3,3-tetramethyl-

17. Bicyclo[2.2.1]heptan-2-amine, N,2,3,3-tetramethyl-

18. Chebi:6706

19. Chembl267936

20. Mecamylaminum

21. Ncgc00015703-03

22. Mecamilamina [dcit]

23. Mecamilamina [italian]

24. Dsstox_cid_3240

25. Dsstox_rid_76937

26. Dsstox_gsid_23240

27. Mecamylamine [inn:ban]

28. Mecamylaminum [inn-latin]

29. 3-methylaminoisokamfan

30. 3-methylaminoisokamfan [czech]

31. Cas-60-40-2

32. Einecs 200-476-1

33. 3-beta-methylamino-2,2,3-trimethylbicyclo(2.2.1)heptane

34. Inversine (salt/mix)

35. Spectrum_000304

36. Specplus_000736

37. Prestwick0_001111

38. Prestwick1_001111

39. Prestwick2_001111

40. Prestwick3_001111

41. Spectrum3_000736

42. Spectrum4_001257

43. Spectrum5_001616

44. Lopac0_000841

45. Schembl34252

46. Bspbio_001242

47. Bspbio_002292

48. Kbiogr_001814

49. Kbioss_000784

50. Divk1c_006832

51. Spbio_003111

52. Bpbio1_001367

53. Gtpl3990

54. Dtxsid0023240

55. Hy-b1395a

56. Kbio1_001776

57. Kbio2_000784

58. Kbio2_003352

59. Kbio2_005920

60. Kbio3_001512

61. Hms3604d12

62. 107538-05-6

63. Albb-023410

64. Tox21_110198

65. Bdbm50061565

66. Akos003662515

67. Tox21_110198_1

68. Ccg-204924

69. Db00657

70. Sdccgsbi-0050817.p005

71. Ncgc00015703-02

72. Ncgc00015703-04

73. Ncgc00015703-06

74. Ncgc00015703-12

75. Ncgc00162272-01

76. Ncgc00162272-02

77. Sbi-0050817.p004

78. Ab00053764

79. Cs-0013657

80. C07511

81. Ab00053764_03

82. Q3332124

83. Brd-a20119038-001-01-5

84. Brd-a20119038-003-01-1

85. N,2,3,3-tetramethylbicyclo[2.2.1]heptan-2-amine #

86. Methyl-(2,3,3-trimethyl-bicyclo[2.2.1]hept-2-yl)-amine

87. (+)methyl-(2,3,3-trimethyl-bicyclo[2.2.1]hept-2-yl)-amine

88. (-)methyl-(2,3,3-trimethyl-bicyclo[2.2.1]hept-2-yl)-amine

89. 3-.beta.-methylamino-2,2,3-trimethylbicyclo(2.2.1)heptane

90. (+/-)methyl-(2,3,3-trimethyl-bicyclo[2.2.1]hept-2-yl)-amine

91. Methyl(2,3,3-trimethylbicyclo[2.2.1]hept-2-yl)amine Hydrochloride

92. Methyl-(2,3,3-trimethyl-bicyclo[2.2.1]hept-2-yl)-amine(mecamylamine)

2.3 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₁H₂₁N
Molecular Weight	167.29 g/mol
XLogP3	2.6
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	1
Exact Mass	167.167399674 g/mol
Monoisotopic Mass	167.167399674 g/mol
Topological Polar Surface Area	12 Å²
Heavy Atom Count	12
Formal Charge	0
Complexity	197
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	3
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

For the treatment of moderately severe to severe essential hypertension and in uncomplicated cases of malignant hypertension

5 Pharmacology and Biochemistry

5.1 Pharmacology

Mecamylamine is a potent, oral antihypertensive agent and ganglion blocker, and is a secondary amine. Mecamylamine is indicated for the management of moderately severe to severe essential hypertension and in uncomplicated cases of malignant hypertension. Mecamylamine reduces blood pressure in both normotensive and hypertensive individuals. A small oral dosage often produces a smooth and predictable reduction of blood pressure. Although this antihypertensive effect is predominantly orthostatic, the supine blood pressure is also significantly reduced. Mecamylamine crosses the blood-brain and placental barriers.

5.2 MeSH Pharmacological Classification

Antihypertensive Agents

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)

Ganglionic Blockers

Agents having as their major action the interruption of neural transmission at nicotinic receptors on postganglionic autonomic neurons. Because their actions are so broad, including blocking of sympathetic and parasympathetic systems, their therapeutic use has been largely supplanted by more specific drugs. They may still be used in the control of blood pressure in patients with acute dissecting aortic aneurysm and for the induction of hypotension in surgery. (See all compounds classified as Ganglionic Blockers.)

Nicotinic Antagonists

Drugs that bind to nicotinic cholinergic receptors (RECEPTORS, NICOTINIC) and block the actions of acetylcholine or cholinergic agonists. Nicotinic antagonists block synaptic transmission at autonomic ganglia, the skeletal neuromuscular junction, and at central nervous system nicotinic synapses. (See all compounds classified as Nicotinic Antagonists.)

5.3 ATC Code

C - Cardiovascular system

C02 - Antihypertensives

C02B - Antiadrenergic agents, ganglion-blocking

C02BB - Secondary and tertiary amines

C02BB01 - Mecamylamine

5.4 Absorption, Distribution and Excretion

Absorption

Mecamylamine is almost completely absorbed from the gastrointestinal tract

Route of Elimination

Mecamylamine is excreted slowly in the urine in the unchanged form. The rate of its renal elimination is influenced markedly by urinary pH. Alkalinization of the urine reduces, and acidification promotes, renal excretion of mecamylamine. Mecamylamine crosses the blood-brain and placental barriers.

5.5 Mechanism of Action

Mecamylamine is a ganglionic blocker which prevents stimulation of postsynaptic receptors by acetylcholine released from presynaptic nerve endings. The hypotensive effect of Mecamylamine is attributed to reduction in sympathetic tone, vasodilation, and reduced cardiac output, and is primarily postural.

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