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Nemonapride

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Chemistry

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Also known as: Emonapride, Emilace, [3h]nemonapride, 75272-39-8, (+)-nemonapride, (2r,3r)-nemonapride

Molecular Formula

C₂₁H₂₆ClN₃O₂

Molecular Weight

387.9 g/mol

InChI Key

KRVOJOCLBAAKSJ-RDTXWAMCSA-N

FDA UNII

Q88T5P3444

1 2D Structure

Nemonapride

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-[(2R,3R)-1-benzyl-2-methylpyrrolidin-3-yl]-5-chloro-2-methoxy-4-(methylamino)benzamide

2.1.2 InChI

InChI=1S/C21H26ClN3O2/c1-14-18(9-10-25(14)13-15-7-5-4-6-8-15)24-21(26)16-11-17(22)19(23-2)12-20(16)27-3/h4-8,11-12,14,18,23H,9-10,13H2,1-3H3,(H,24,26)/t14-,18-/m1/s1

2.1.3 InChI Key

KRVOJOCLBAAKSJ-RDTXWAMCSA-N

2.1.4 Canonical SMILES

CC1C(CCN1CC2=CC=CC=C2)NC(=O)C3=CC(=C(C=C3OC)NC)Cl

2.1.5 Isomeric SMILES

C[C@@H]1[C@@H](CCN1CC2=CC=CC=C2)NC(=O)C3=CC(=C(C=C3OC)NC)Cl

2.2 Other Identifiers

2.2.1 UNII

Q88T5P3444

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Cis-n-(1-benzyl-2-methylpyrrolidin-3-yl)-5-chloro-2-methoxy-4-methylaminobenzamide

2. Emonapride

3. Nemonapride, (cis)-isomer

4. Ym 09151-2

5. Ym 09151-m

6. Ym-09151-2

2.3.2 Depositor-Supplied Synonyms

1. Emonapride

2. Emilace

3. [3h]nemonapride

4. 75272-39-8

5. (+)-nemonapride

6. (2r,3r)-nemonapride

7. N-[(2r,3r)-1-benzyl-2-methylpyrrolidin-3-yl]-5-chloro-2-methoxy-4-(methylamino)benzamide

8. Chebi:64219

9. Q88t5p3444

10. N-(cis-1-benzyl-2-methylpyrrolidin-3-yl)-5-chloro-2-methoxy-4-(methylamino)benzamide

11. 187139-87-3

12. Nemonapride [inn:jan]

13. Ym-09151

14. Unii-q88t5p3444

15. Emilace (tn)

16. Ym-09151-2

17. Nemonapride (jan/inn)

18. Nemonapride [mi]

19. Nemonapride [inn]

20. Nemonapride [jan]

21. (+-)-cis-n-(1-benzyl-2-methyl-3-pyrrolidinyl)-5-chloro-4-(methylamino)-o-anisamide

22. (+-)-cis-n-(1-benzyl-2-methylpyrrolidin-3-yl)-5-chloro-2-methoxy-4-methylaminobenzamide

23. N-(2rs,3rs)-(1-benzyl-2-methyl-3-pyrrolidinyl)-5-chloro-2-methoxy-4-methylaminobenzamide

24. Nemonapride [mart.]

25. Gtpl962

26. Nemonapride [who-dd]

27. Schembl1649724

28. Chembl2261102

29. Dtxsid601116422

30. Zinc538069

31. Bdbm50487259

32. Pdsp1_001527

33. Pdsp2_001511

34. Ncgc00371107-01

35. Benzamide, 5-chloro-2-methoxy-4-(methylamino)-n-((2r,3r)-2-methyl-1-(phenylmethyl)-3-pyrrolidinyl)-, Rel-

36. Benzamide, 5-chloro-2-methoxy-4-(methylamino)-n-(2-methyl-1-(phenylmethyl)-3-pyrrolidinyl)-, Cis-(+-)-

37. Hy-103415

38. B6843

39. Cs-0027847

40. D01468

41. Brd-k47289124-001-02-6

42. (+/-)-cis-n-(1-benzyl-2-methyl-3-pyrrolidinyl)-5-chloro-4-(methylamino)-o-anisamide

43. 5-chloro-2-methoxy-4-(methylamino)-n-[(2r,3r)-2-methyl-1-(phenylmethyl)-3-pyrrolidinyl]benzamide

44. 5-chloro-2-methoxy-4-methylamino-n-[(2r,3r)-2-methyl-1-(phenylmethyl)pyrrolidin-3-yl]benzamide

45. Benzamide, 5-chloro-2-methoxy-4-(methylamino)-n-(2-methyl-1- (phenylmethyl)-3-pyrrolidinyl)-, Cis-(+/-)-

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₂₆ClN₃O₂
Molecular Weight	387.9 g/mol
XLogP3	3.9
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	6
Exact Mass	387.1713548 g/mol
Monoisotopic Mass	387.1713548 g/mol
Topological Polar Surface Area	53.6 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	486
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 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

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.)

Dopamine Antagonists

Drugs that bind to but do not activate DOPAMINE RECEPTORS, thereby blocking the actions of dopamine or exogenous agonists. Many drugs used in the treatment of psychotic disorders (ANTIPSYCHOTIC AGENTS) are dopamine antagonists, although their therapeutic effects may be due to long-term adjustments of the brain rather than to the acute effects of blocking dopamine receptors. Dopamine antagonists have been used for several other clinical purposes including as ANTIEMETICS, in the treatment of Tourette syndrome, and for hiccup. Dopamine receptor blockade is associated with NEUROLEPTIC MALIGNANT SYNDROME. (See all compounds classified as Dopamine Antagonists.)

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