Ractopamine

Ractopamine
Names
Preferred IUPAC name
4-(1-Hydroxy-2-{[4-(4-hydroxyphenyl)butan-2-yl]amino}ethyl)phenol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
MeSH Ractopamine
UNII
  • InChI=1S/C18H23NO3/c1-13(2-3-14-4-8-16(20)9-5-14)19-12-18(22)15-6-10-17(21)11-7-15/h4-11,13,18-22H,2-3,12H2,1H3 checkY
    Key: YJQZYXCXBBCEAQ-UHFFFAOYSA-N checkY
  • InChI=1/C18H23NO3/c1-13(2-3-14-4-8-16(20)9-5-14)19-12-18(22)15-6-10-17(21)11-7-15/h4-11,13,18-22H,2-3,12H2,1H3
    Key: YJQZYXCXBBCEAQ-UHFFFAOYAP
  • OC(c1ccc(O)cc1)CNC(C)CCc2ccc(O)cc2
Properties
C18H23NO3
Molar mass 301.386 g·mol−1
4100 mg/L
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Ractopamine (/rækˈtɒpəmaɪn, -miːn/) is an animal feed additive used to promote leanness and increase food conversion efficiency in farmed animals in several countries, but banned in others. Pharmacologically, it is a phenol-based TAAR1 agonist and β adrenoreceptor agonist that stimulates β1 and β2 adrenergic receptors.[1][2] It is most commonly administered to animals for meat production as ractopamine hydrochloride.[3] It is the active ingredient in products marketed in the US as Paylean for swine, Optaflexx for cattle, and Topmax[4] for turkeys.[5] It was developed by Elanco Animal Health, a former division of Eli Lilly and Company.

As of 2014, according to the Humane Society, the use of ractopamine was “banned or restricted” in 160 countries,[6] including the European Union, China and Russia,[7][8] while 27 other countries, such as Japan, the United States, South Korea, and New Zealand have deemed meat from livestock fed ractopamine safe for human consumption.[9][10][11]

Commercial ractopamine is a mixture of all four possible stereoisomers.[12] It is also a positional isomer of dobutamine, a related drug.

  1. ^ Cite error: The named reference TAAR1 was invoked but never defined (see the help page).
  2. ^ Colbert, WE; Williams, PD; Williams, GD (December 1991). "Beta-adrenoceptor Profile of Ractopamine HCl in Isolated Smooth and Cardiac Muscle Tissues of Rat and Guinea-pig". The Journal of Pharmacy and Pharmacology. 43 (12): 844–7. doi:10.1111/j.2042-7158.1991.tb03192.x. PMID 1687583. S2CID 95388599.
  3. ^ Aroeira, C. N.; Feddern, V.; Gressler, V.; Molognoni, L.; Daguer, H.; Dalla Costa, O. A.; de Lima GJMM; Contreras-Castillo, C. J. (2019). "Determination of ractopamine residue in tissues and urine from pig fed meat and bone meal". Food Additives & Contaminants. Part A, Chemistry, Analysis, Control, Exposure & Risk Assessment. 36 (3): 424–433. doi:10.1080/19440049.2019.1567942. PMID 30785370. S2CID 73496591.
  4. ^ Co, Elanco Animal Health. "Topmax - Elanco Animal Health Co: Veterinary Package Insert". VetLabel.com.[permanent dead link]
  5. ^ LE BIZEC, Bruno (October 2017). "A GENERAL PERSPECTIVE ON THE USE OF WADA PROHIBITED SUBSTANCES FOR ANIMAL HUSBANDRY" (PDF). WADA.
  6. ^ Pacelle, Wayne (July 2014). "Banned in 160 Nations, Why is Ractopamine in U.S. Pork? (Op-Ed)". Live Science. Expert Voices: Op-Ed & Insights.
  7. ^ Bottemiller, Helena (January 25, 2012). "Dispute over drug in feed limiting US meat exports". Bottom Line. Archived from the original on January 26, 2012.
  8. ^ Garina, Anastasia (11 December 2012). "Russia throws poisonous meat back to US". Pravda.ru. Retrieved 14 December 2012.
  9. ^ "The Facts about U.S. Beef and Ractopamine". American Institute in Taiwan. Archived from the original on 10 May 2012. Retrieved 5 March 2012.
  10. ^ AIT- American Institute in Taiwan: 'The Facts about U.S. Beef and Ractopamine' (archived) Accessed January 21, 2018
  11. ^ Environmental Risk Management Authority (22 August 2006). "Environmental Risk Management Authority Decision - Application HSR05114 "PAYLEAN: to import and release this granular premix for use as a feed additive for pigs "". Retrieved 15 January 2020.
  12. ^ Vivian Vezzoni de AlmeidaI; Amoracyr José Costa NuñezII; Valdomiro Shigueru Miyada (May 2012). "Ractopamine as a metabolic modifier feed additive for finishing pigs: a review" (PDF). Brazilian Archives of Biology and Technology. 25 (3). Retrieved 9 December 2014.