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Minaprine

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Chemistry

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Also known as: Cantor, 25905-77-5, Minaprinum, Minaprina, Minaprinum [inn-latin], Minaprina [inn-spanish]

Molecular Formula

C₁₇H₂₂N₄O

Molecular Weight

298.4 g/mol

InChI Key

LDMWSLGGVTVJPG-UHFFFAOYSA-N

FDA UNII

00U7GX0NLM

Minaprine is a psychotropic drug which has proved to be effective in the treatment of various depressive states. Like most antidepressants minaprine antagonizes behavioral despair. Minaprine is an amino-phenylpyridazine antidepressant reported to be relatively free of cardiotoxicity, drowsiness, and weight gain.

1 2D Structure

Minaprine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-methyl-N-(2-morpholin-4-ylethyl)-6-phenylpyridazin-3-amine

2.1.2 InChI

InChI=1S/C17H22N4O/c1-14-13-16(15-5-3-2-4-6-15)19-20-17(14)18-7-8-21-9-11-22-12-10-21/h2-6,13H,7-12H2,1H3,(H,18,20)

2.1.3 InChI Key

LDMWSLGGVTVJPG-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=CC(=NN=C1NCCN2CCOCC2)C3=CC=CC=C3

2.2 Other Identifiers

2.2.1 UNII

00U7GX0NLM

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3-(2-morpholino-ethylamino)-4-methyl-6-phenyl Pyridazine, Dihydrochloride

2. 3-(morpholinoethyl)amino-4-methyl-6-phenylpyridazine

3. Agr 1240

4. Cantor

5. Minaprine Dihydrochloride

6. Minaprine Hydrochloride

2.3.2 Depositor-Supplied Synonyms

1. Cantor

2. 25905-77-5

3. Minaprinum

4. Minaprina

5. Minaprinum [inn-latin]

6. Minaprina [inn-spanish]

7. Agr 1240

8. N-(4-methyl-6-phenyl-3-pyridazinyl)-4-morpholineethanamine

9. 4-morpholineethanamine, N-(4-methyl-6-phenyl-3-pyridazinyl)-

10. 4-(2-((4-methyl-6-phenyl-3-pyridazinyl)amino)ethyl)morpholine

11. 4-methyl-3-(2-morpholinoethylamino)-6-phenylpyridazin

12. Agr-1240

13. 4-methyl-n-(2-morpholin-4-ylethyl)-6-phenylpyridazin-3-amine

14. 00u7gx0nlm

15. Cb-30038

16. 4-methyl-n-(2-morpholinoethyl)-6-phenylpyridazin-3-amine

17. Chembl278819

18. Chebi:51038

19. 25905-77-5 (free Base)

20. Brantur

21. 4-methyl-n-[2-(morpholin-4-yl)ethyl]-6-phenylpyridazin-3-amine

22. 4-[2-[(4-methyl-6-phenyl-3-pyridazinyl)amino]ethyl]morpholine

23. Minaprin Dihydrochloride

24. Chembl536932

25. Cantor (tn)

26. Cb 30038

27. Minaprine (usan/inn)

28. Einecs 247-329-8

29. Cas-25953-17-7

30. Unii-00u7gx0nlm

31. Minaprine [usan:inn:ban]

32. Spectrum_001334

33. Minaprine [inn]

34. Minaprine [mi]

35. Minaprine [usan]

36. Prestwick0_000066

37. Prestwick1_000066

38. Prestwick2_000066

39. Prestwick3_000066

40. Spectrum2_001407

41. Spectrum3_001445

42. Spectrum4_000418

43. Spectrum5_001593

44. Minaprine [who-dd]

45. Schembl49371

46. Bspbio_000251

47. Bspbio_002909

48. Kbiogr_000716

49. Kbioss_001814

50. Divk1c_000063

51. Spbio_001454

52. Spbio_002172

53. Bpbio1_000277

54. Dtxsid5048477

55. Kbio1_000063

56. Kbio2_001814

57. Kbio2_004382

58. Kbio2_006950

59. Kbio3_002409

60. Ninds_000063

61. Hy-b0884

62. (r)-benzyl2-oxooxetan-3-ylcarbamate

63. Bdbm50074289

64. Zinc19796082

65. Akos024287006

66. Cs-4346

67. Db00805

68. Idi1_000063

69. Ncgc00016795-01

70. Ncgc00016795-02

71. Ncgc00016795-03

72. Ncgc00016795-04

73. Sbi-0051647.p002

74. Db-046791

75. Ab00053599

76. Ft-0630519

77. D05039

78. Ab00053599_13

79. L001202

80. Q6863173

81. Brd-k02867583-300-05-5

82. Brd-k02867583-300-06-3

83. 3-(2-morpholinoethylamino)-4-methyl-6-phenylpyridazine

84. 4-methyl-n-[2-(4-morpholinyl)ethyl]-6-phenyl-3-pyridazinamine #

85. (4-methyl-6-phenyl-pyridazin-3-yl)-(2-morpholin-4-yl-ethyl)-amine; Hydrochloride

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₇H₂₂N₄O
Molecular Weight	298.4 g/mol
XLogP3	2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	5
Exact Mass	298.17936134 g/mol
Monoisotopic Mass	298.17936134 g/mol
Topological Polar Surface Area	50.3 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	316
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
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

For the treatment of depression

5 Pharmacology and Biochemistry

5.1 Pharmacology

Minaprine is an amino-phenylpyridazine antidepressant reported to be relatively free of cardiotoxicity, drowsiness, and weight gain. Similar to other antidepressant treatments, minaprine attenuates the beta-adrenergic receptor function. Studies have also shown that minaprine improves memory consolidation and that repeated drug administration leads to potentiation of this effect. Moreover, the effects of minaprine on memory consolidation are related to its dopaminergic action.

5.2 MeSH Pharmacological Classification

Antidepressive Agents

Mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. Several MONOAMINE OXIDASE INHIBITORS are useful as antidepressants apparently as a long-term consequence of their modulation of catecholamine levels. The tricyclic compounds useful as antidepressive agents (ANTIDEPRESSIVE AGENTS, TRICYCLIC) also appear to act through brain catecholamine systems. A third group (ANTIDEPRESSIVE AGENTS, SECOND-GENERATION) is a diverse group of drugs including some that act specifically on serotonergic systems. (See all compounds classified as Antidepressive Agents.)

5.3 ATC Code

N - Nervous system

N06 - Psychoanaleptics

N06A - Antidepressants

N06AX - Other antidepressants

N06AX07 - Minaprine

5.4 Metabolism/Metabolites

Hepatic. Cytochrome P4502D is responsible for the 4-hydroxylation of minaprine to 4-hydroxyminaprine.

Minaprine has known human metabolites that include 4-Hydroxyminaprine.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

5.5 Mechanism of Action

Minaprine binds to serotonin type 2 receptors and to dopamine D1 and D2 type receptors. It also binds to the serotonin reuptake pump. Therefore, minaprine blocks the reuptake of both dopamine and serotonin. It is also, to a slight degree, cholinomimetic. Thus it may exhibit both mood-brightening and nootropic properties. It also acts as a reversible inhibitor of MAO-A (RIMA).It has also been found to inhibit acetylcholinesterase.

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