Moxaprindine

Moxaprindine
	File:Moxaprindine.svg
Clinical data
Synonyms	Moxaprindina, Moxaprindinum.
Identifiers
	IUPAC name N1-(2,3-Dihydro-1-methoxy-1H-inden-2-yl)-N3,N3-diethyl-N1-phenyl-1,3-propanediamine;
CAS Number	53076-26-9;
PubChem CID	68699;
ChemSpider	61950;
UNII	5HAF6QO904;
ChEMBL	ChEMBL2104713;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C23H32N2O
Molar mass	352.522 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCN(CC)CCCN(C1CC2=CC=CC=C2C1OC)C3=CC=CC=C3;
	InChI InChI=1S/C23H32N2O/c1-4-24(5-2)16-11-17-25(20-13-7-6-8-14-20)22-18-19-12-9-10-15-21(19)23(22)26-3/h6-10,12-15,22-23H,4-5,11,16-18H2,1-3H3; Key:QQGGXAOUSKREAE-UHFFFAOYSA-N;

Moxaprindine is a Class I antiarrhythmic agent that acts as a sodium channel blocker, used experimentally for treating ventricular and supraventricular arrhythmias. Its pharmacological profile resembles that of aprindine, with high protein binding and potent membrane-stabilizing effects.

Moxaprindine is a promising new antiarrhythmic drug for the treatment of ventricular arrhythmias, but its value and safely in the chronic oral treatment of these arrhythmias remain to be established.^[1]

Moxaprindine could be considered a clinically safer anti-arrhythmic agent than aprindine.^[2]

Pharmacology

The pharmacology is described:

Pharmacology:^[3]^[4]^[5]

Synthesis

The synthesis has been reported:^[6] Patent:^[7] Starting material:^[8] Recent article:^[9]

File:Moxaprindine synthesis.svg

The reaction of 1-Methoxyindan-2-ol [71720-52-0] (1) with mesyl chloride gives 1-methoxy-2-mesyloxy-indane, PC11831595 (2). Displacement of the leaving group by aniline gives 1-methoxy-2-phenylamino-indane [53076-24-7] (3). Alkylation with 3-Chloropropyl(diethyl)amine [104-77-8] (4) in the presence of sodamide completed the synthesis of Moxaprindine (5).

References

↑ Staessen, J., Kesteloot, H. (February 1981). "Moxaprindine in the acute treatment of ventricular arrhythmias in patients with cardiovascular disease". European Journal of Clinical Pharmacology. 19 (3): 167–172. doi:10.1007/BF00561943. PMID 7215413.
↑ Stryckmans, P. A., Ronge‐Collard, E., Delforge, A., Lambert, M., Suciu, S. (October 1982). "Effect of 2 Anti-Arrhythmic Drugs Aprindine and Moxaprindine on the Replication Capacity of Murine and Human Haemopoietic Cells". Scandinavian Journal of Haematology. 29 (4): 331–337. doi:10.1111/j.1600-0609.1982.tb00603.x. PMID 7178839.
↑ Teirlynck, O., Belpaire, F. M., Andreasen, F. (1982). "Binding of Aprindine and Moxaprindine to Human Serum, ?1-Acid Glycoprotien and Serum of Healthy and Diseased Humans". European Journal of Clinical Pharmacology. 22 (5): 472. doi:10.1007/BF00542556.
↑ Teirlynck, O., Belpaire, F. M., Andreasen, F. (1982). "Binding of aprindine and moxaprindine to human serum, ?1-acid glycoprotein and serum of healthy and diseased humans". European Journal of Clinical Pharmacology. 21 (5): 427–431. doi:10.1007/BF00542331. PMID 7075647.
↑ Kesteloot H, van de Werf F, Marchandise B, Sluyts R (1979). "Influence of moxaprindine treatment on ventricular arrhythmias occurring during maximal exercise stress testing". Acta Cardiologica. 34 (5): 301–9. PMID 317204.
↑ Castañer, J., Thorpe, P. J. (1981). "Moxaprindine". Drugs of the Future. 6 (6): 354. doi:10.1358/dof.1981.006.06.1003862. ISSN 0377-8282. Retrieved 3 November 2025.
↑ Pierre Vanhoof, Pierre Clarebout, DE2355039 (1974 to Manuf Prod Pharma).
↑ Shigeru Nakano, Noriko Yoneta, & Takashi Tate, US6127579 (2000 to Ichikawa Gosei Chemical Co Ltd).
↑ Horáková, E., Valtr, J., Dostálová, K., Drabina, P., Váňa, J., Růžička, A., Hanusek, J. (9 April 2019). "A Kinetic Study of the Intramolecular Nitroaldol (Henry) Reaction Giving 2-Nitroindan-1-ols". ChemistrySelect. 4 (13): 3973–3979. doi:10.1002/slct.201900481.

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References

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[1] Staessen, J., Kesteloot, H. (February 1981). "Moxaprindine in the acute treatment of ventricular arrhythmias in patients with cardiovascular disease". European Journal of Clinical Pharmacology. 19 (3): 167–172. doi:10.1007/BF00561943. PMID 7215413.

[2] Stryckmans, P. A., Ronge‐Collard, E., Delforge, A., Lambert, M., Suciu, S. (October 1982). "Effect of 2 Anti-Arrhythmic Drugs Aprindine and Moxaprindine on the Replication Capacity of Murine and Human Haemopoietic Cells". Scandinavian Journal of Haematology. 29 (4): 331–337. doi:10.1111/j.1600-0609.1982.tb00603.x. PMID 7178839.

[3] Teirlynck, O., Belpaire, F. M., Andreasen, F. (1982). "Binding of Aprindine and Moxaprindine to Human Serum, ?1-Acid Glycoprotien and Serum of Healthy and Diseased Humans". European Journal of Clinical Pharmacology. 22 (5): 472. doi:10.1007/BF00542556.

[4] Teirlynck, O., Belpaire, F. M., Andreasen, F. (1982). "Binding of aprindine and moxaprindine to human serum, ?1-acid glycoprotein and serum of healthy and diseased humans". European Journal of Clinical Pharmacology. 21 (5): 427–431. doi:10.1007/BF00542331. PMID 7075647.

[pmid317204-5] Kesteloot H, van de Werf F, Marchandise B, Sluyts R (1979). "Influence of moxaprindine treatment on ventricular arrhythmias occurring during maximal exercise stress testing". Acta Cardiologica. 34 (5): 301–9. PMID 317204.

[6] Castañer, J., Thorpe, P. J. (1981). "Moxaprindine". Drugs of the Future. 6 (6): 354. doi:10.1358/dof.1981.006.06.1003862. ISSN 0377-8282. Retrieved 3 November 2025.

[7] Pierre Vanhoof, Pierre Clarebout, DE2355039 (1974 to Manuf Prod Pharma).

[8] Shigeru Nakano, Noriko Yoneta, & Takashi Tate, US6127579 (2000 to Ichikawa Gosei Chemical Co Ltd).

[9] Horáková, E., Valtr, J., Dostálová, K., Drabina, P., Váňa, J., Růžička, A., Hanusek, J. (9 April 2019). "A Kinetic Study of the Intramolecular Nitroaldol (Henry) Reaction Giving 2-Nitroindan-1-ols". ChemistrySelect. 4 (13): 3973–3979. doi:10.1002/slct.201900481.

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Moxaprindine

Contents

Pharmacology

Synthesis

References

References

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