The most common use for azaperone is in relatively small doses as a "
serenic" (to reduce aggression) in farmed pigs, either to stop them fighting or to encourage sows to accept piglets. Higher doses are used for
anesthesia in combination with other drugs such as
xylazine,
tiletamine and
zolazepam. Azaperone is also used in combination with strong narcotics such as
etorphine or
carfentanil for tranquilizing large animals such as elephants.[2] Use in horses is avoided as adverse reactions may occur.
Azaperone (under the brand name Stresnil) was approved for use in pigs in the USA in 1983, under NADA 115-732.[4]
Synthesis
The alkylation of
2-chloropyridine (1) with
piperazine gives 1-(pyridin-2-yl)piperazine [67980-77-2] (2). The attachement of the sidechain by reaction with 4-chloro-4'-fluorobutyrophenone [3874-54-2] (3) completed the synthesis of azaperone (4).
^"Azaperone Summary Report (2)"(PDF). European Medicines Agency. Committee for Veterinary Medicinal Products. November 1997. Archived from
the original(PDF) on 2017-01-16. Retrieved 2017-01-15.
^"Rules and Regulations"(PDF). Federal Register. 48 (202): 48229. 18 October 1983. Retrieved 2017-01-15.
^Jaen, Juan C.; Caprathe, Bradley W.; Pugsley, Thomas A.; Wise, Lawrence D.; Akunne, Hyacinth (1993). "Evaluation of the effects of the enantiomers of reduced haloperidol, azaperol, and related 4-amino-1-arylbutanols on dopamine and .sigma. receptors". Journal of Medicinal Chemistry. 36 (24): 3929–3936. doi:10.1021/jm00076a022.
^Taghizadeh, M. J., Mohammadnia, M. S., Ghalkhani, M., Sohouli, E. (April 2022). "Improved Method for the Total Synthesis of Azaperone and Investigation of Its Electrochemical Behavior in Aqueous Solution". Chemical Research in Chinese Universities. 38 (2): 546–551.
doi:
10.1007/s40242-021-1061-2.
ISSN1005-9040.
S2CID235614834.
^Soudijn, W.; van Wijngaarden, I. (1968). "A rapid and convenient method for the synthesis of labelled tertiary amines". Journal of Labelled Compounds. 4 (2): 159–163. doi:10.1002/jlcr.2590040209.
The most common use for azaperone is in relatively small doses as a "
serenic" (to reduce aggression) in farmed pigs, either to stop them fighting or to encourage sows to accept piglets. Higher doses are used for
anesthesia in combination with other drugs such as
xylazine,
tiletamine and
zolazepam. Azaperone is also used in combination with strong narcotics such as
etorphine or
carfentanil for tranquilizing large animals such as elephants.[2] Use in horses is avoided as adverse reactions may occur.
Azaperone (under the brand name Stresnil) was approved for use in pigs in the USA in 1983, under NADA 115-732.[4]
Synthesis
The alkylation of
2-chloropyridine (1) with
piperazine gives 1-(pyridin-2-yl)piperazine [67980-77-2] (2). The attachement of the sidechain by reaction with 4-chloro-4'-fluorobutyrophenone [3874-54-2] (3) completed the synthesis of azaperone (4).
^"Azaperone Summary Report (2)"(PDF). European Medicines Agency. Committee for Veterinary Medicinal Products. November 1997. Archived from
the original(PDF) on 2017-01-16. Retrieved 2017-01-15.
^"Rules and Regulations"(PDF). Federal Register. 48 (202): 48229. 18 October 1983. Retrieved 2017-01-15.
^Jaen, Juan C.; Caprathe, Bradley W.; Pugsley, Thomas A.; Wise, Lawrence D.; Akunne, Hyacinth (1993). "Evaluation of the effects of the enantiomers of reduced haloperidol, azaperol, and related 4-amino-1-arylbutanols on dopamine and .sigma. receptors". Journal of Medicinal Chemistry. 36 (24): 3929–3936. doi:10.1021/jm00076a022.
^Taghizadeh, M. J., Mohammadnia, M. S., Ghalkhani, M., Sohouli, E. (April 2022). "Improved Method for the Total Synthesis of Azaperone and Investigation of Its Electrochemical Behavior in Aqueous Solution". Chemical Research in Chinese Universities. 38 (2): 546–551.
doi:
10.1007/s40242-021-1061-2.
ISSN1005-9040.
S2CID235614834.
^Soudijn, W.; van Wijngaarden, I. (1968). "A rapid and convenient method for the synthesis of labelled tertiary amines". Journal of Labelled Compounds. 4 (2): 159–163. doi:10.1002/jlcr.2590040209.