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Chemistry

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Also known as: 72822-13-0, Dapiprazole hcl, Rev-eyes, Dapiprazole (hydrochloride), Dapiprazolehydrochloride, Glamidolo

Molecular Formula

C₁₉H₂₈ClN₅

Molecular Weight

361.9 g/mol

InChI Key

ZIODNPFQZIHCOE-UHFFFAOYSA-N

FDA UNII

DS9UJN1I0X

Dapiprazole Hydrochloride is an alpha-1-adrenergic antagonist that acts by blocking alpha-adrenergic receptors in the smooth muscle of blood vessels (arteries, arterioles and veins), gastrointestinal tract, and radial smooth muscle of the iris. This prevents smooth muscle contraction and results in vasodilatation. Administered in the eye, dapiprazole hydrochloride produces miosis. In the heart, it may antagonize alpha-1 adrenoreceptors in myocytes causing a mild negative inotropic effect.

1 2D Structure

Dapiprazole Hydrochloride

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-[2-[4-(2-methylphenyl)piperazin-1-yl]ethyl]-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine;hydrochloride

2.1.2 InChI

InChI=1S/C19H27N5.ClH/c1-16-6-2-3-7-17(16)23-14-12-22(13-15-23)11-9-19-21-20-18-8-4-5-10-24(18)19;/h2-3,6-7H,4-5,8-15H2,1H3;1H

2.1.3 InChI Key

ZIODNPFQZIHCOE-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=CC=CC=C1N2CCN(CC2)CCC3=NN=C4N3CCCC4.Cl

2.2 Other Identifiers

2.2.1 UNII

DS9UJN1I0X

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3-(2-(4-(2-methylphenyl)-1-piperazinyl)ethyl)-5,6,7,8,-tetrahydro-1,2,4-triazolo(4,3-a)pyridine Hydrochloride

2. Dapiprazole

3. Remydrial

4. Rev-eyes

2.3.2 Depositor-Supplied Synonyms

1. 72822-13-0

2. Dapiprazole Hcl

3. Rev-eyes

4. Dapiprazole (hydrochloride)

5. Dapiprazolehydrochloride

6. Glamidolo

7. Dapiprazole Monohydrochloride

8. Reversil

9. Af 2139

10. Dapiprazole Hydrochloride [usan]

11. Ds9ujn1i0x

12. Af-2139

13. Remydrial

14. 72822-13-0 (hcl)

15. Dsstox_cid_28595

16. Dsstox_rid_82866

17. Dsstox_gsid_48669

18. 3-(2-(4-(o-tolyl)piperazin-1-yl)ethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine Hydrochloride

19. 5,6,7,8-tetrahydro-3-(2-(4-o-tolyl-1-piperazinyl)ethyl)-s-triazolo(4,3-a)pyridine Monohydrochloride

20. Dapiprazole Hydrochloride (usan)

21. 1,2,4-triazolo(4,3-a)pyridine, 5,6,7,8-tetrahydro-3-(2-(4-(2-methylphenyl)-1-piperazinyl)ethyl)-, Monohydrochloride

22. 5,6,7,8-tetrahydro-3-[2-[4-(2-methylphenyl)-1-piperazinyl]ethyl]-1,2,4-triazolo[4,3-a]pyridine

23. Cas-72822-13-0

24. Unii-ds9ujn1i0x

25. Rev-eyes (tn)

26. Reversil Hydrochloride

27. Glamidolo Hydrochloride

28. Schembl667604

29. Chembl1201044

30. Dtxsid7048669

31. Hy-a0142a

32. Hms3746g11

33. Bcp34410

34. Tox21_113035

35. S5281

36. Akos015966533

37. Tox21_113035_1

38. Ac-8851

39. Ccg-268185

40. Cs-5720

41. Dapiprazole Hydrochloride [mart.]

42. Dapiprazole Hydrochloride [vandf]

43. Ncgc00262927-01

44. 3-[2-[4-(2-methylphenyl)piperazin-1-yl]ethyl]-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine Hydrochloride

45. 3-[2-[4-(2-methylphenyl)piperazin-1-yl]ethyl]-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine,hydrochloride

46. 3-[2-[4-(2-methylphenyl)piperazin-1-yl]ethyl]-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine;hydrochloride

47. As-16932

48. Dapiprazole Hydrochloride [who-dd]

49. Dapiprazole Monohydrochloride [mi]

50. Dapiprazole Hydrochloride, >=98% (hplc)

51. Ft-0665471

52. D03648

53. D82527

54. Dapiprazole Hydrochloride [orange Book]

55. 822d130

56. A837632

57. Q27276579

58. 3-(2-(4-o-tolylpiperazin-1-yl)ethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine Hydrochloride

59. 3-[2-[4-(2-methylphenyl)-1-piperazinyl]ethyl]-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine Hydrochloride

60. 5,6,7,8-tetrahydro-3-(2-(4-(2-methylphenyl)-1-piperazinyl)ethyl)-1,2,4-triazolo(4,3-a)pyridine Monohydrochloride

2.4 Create Date

2006-07-28

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₂₈ClN₅
Molecular Weight	361.9 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	4
Exact Mass	361.2033236 g/mol
Monoisotopic Mass	361.2033236 g/mol
Topological Polar Surface Area	37.2 Å²
Heavy Atom Count	25
Formal Charge	0
Complexity	395
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	2

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Adrenergic alpha-Antagonists

Drugs that bind to but do not activate alpha-adrenergic receptors thereby blocking the actions of endogenous or exogenous adrenergic agonists. Adrenergic alpha-antagonists are used in the treatment of hypertension, vasospasm, peripheral vascular disease, shock, and pheochromocytoma. (See all compounds classified as Adrenergic alpha-Antagonists.)

Antipsychotic Agents

Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus. (See all compounds classified as Antipsychotic Agents.)

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