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Details

Stereochemistry MIXED
Molecular Formula C18H23NO3.ClH
Molecular Weight 337.841
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RACTOPAMINE HYDROCHLORIDE

SMILES

Cl.CC(CCC1=CC=C(O)C=C1)NCC(O)C2=CC=C(O)C=C2

InChI

InChIKey=JHGSLSLUFMZUMK-UHFFFAOYSA-N
InChI=1S/C18H23NO3.ClH/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;1H

HIDE SMILES / InChI

Molecular Formula C18H23NO3
Molecular Weight 301.3801
Charge 0
Count
Stereochemistry MIXED
Additional Stereochemistry No
Defined Stereocenters 0 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/20590599 | https://www.ncbi.nlm.nih.gov/pubmed/12052723 | https://www.ncbi.nlm.nih.gov/pubmed/10995307 | https://www.ncbi.nlm.nih.gov/pubmed/19648492

Ractopamine is a feed additive to promote leanness in animals raised for their meat. Pharmacologically, it is a TAAR1 agonist and β adrenoreceptor agonist that stimulates β1 and β2 adrenergic receptors. Ractopamine is known to increase the rate of weight gain, improve feed efficiency, and increase carcass leanness in finishing swine. Its use in finishing swine yields about three kilograms of additional lean pork and improves feed efficiency by 10%. Ractopamine is the active ingredient in products known as Paylean for swine and Optaflexx for cattle, developed by Elanco Animal Health, a division of Eli Lilly and Company, for use in food animals for growth promotion. Ractopamine use has been banned in most countries, including the European Union, mainland China and Russia while 27 other countries, such as Japan, the United States, Canada, and South Korea, have deemed meat from livestock fed ractopamine safe for human consumption. Ractopamine is safe for finishing pigs heavier than 240 lb (110 kg) when administered in the diet at concentrations up to 10 ppm and fed for up to 35 days.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
180.0 nM [Ki]
6.97 null [pKd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Effect of a ractopamine feeding program on growth performance and carcass composition in finishing pigs.
2004 Aug
beta-Adrenergic receptor agonists increase apoptosis of adipose tissue in mice.
2004 Jan
Response of barrows to space allocation and ractopamine.
2004 Nov
The effect of dietary ractopamine concentration and duration of feeding on growth performance, carcass characteristics, and meat quality of finishing pigs.
2004 Nov
The effects of ractopamine hydrochloride on lean carcass yields and pork quality characteristics.
2005 Dec
Effects of ractopamine on performance and composition of pigs phenotypically sorted into fat and lean groups.
2005 Jun
Development of a monoclonal antibody-based enzyme-linked immuosorbent assay for the beta-adrenergic agonist zilpaterol.
2005 May 4
Evaluation of the effects of dietary fat, conjugated linoleic acid, and ractopamine on growth performance, pork quality, and fatty acid profiles in genetically lean gilts.
2006 Mar
Effects of steroidal implantation and ractopamine-HCl on nitrogen retention, blood metabolites and skeletal muscle gene expression in Holstein steers.
2007 Oct
Response to ractopamine-HCl in heifers is altered by implant strategy across days on feed.
2007 Sep
Effects of ractopamine supplementation and postmortem aging on longissimus muscle palatability of beef steers differing in biological type.
2008 Jan
Effects of a "step-up" ractopamine feeding program, sex, and social rank on growth performance, hoof lesions, and Enterobacteriaceae shedding in finishing pigs.
2009 Jan
Molecularly imprinted polymer for the determination of trace ractopamine in pork using SPE followed by HPLC with fluorescence detection.
2009 May
Development and validation of a simple method for routine analysis of ractopamine hydrochloride in raw material and feed additives by HPLC.
2009 May-Jun
Simultaneous determination of beta2-agonists in human urine by fast-gas chromatography/mass spectrometry: method validation and clinical application.
2010 Apr
Effect of distillers dried grains with solubles and ractopamine (Paylean) on quality and shelf-life of fresh pork and bacon.
2010 Aug
Effects of ractopamine and trenbolone acetate implants with or without estradiol on growth performance, carcass characteristics, adipogenic enzyme activity, and blood metabolites in feedlot steers and heifers.
2010 Dec
Determination of beta-agonists in pig feed, pig urine and pig liver using capillary electrophoresis with electrochemical detection.
2010 Jun
Determination of beta-adrenergic agonists by hapten microarray.
2010 Jun 30
Development and validation of a liquid chromatography tandem mass spectrometry method for the analysis of beta-agonists in animal feed and drinking water.
2010 Sep 24
Patents

Patents

Sample Use Guides

Ractopamine used in the dose range of 4.5 to 18.0 g/ton
Route of Administration: Oral
CHO-K1 cells were grown to confluence in 24-well plates. The medium was removed and the cells were pre-labelled with [3H]-adenine by incubation for 2 h with 2 mCi/mL [3H]-adenine in serumfree medium (0.5 mL per well). The [3H]-adenine was removed, and each well was washed by the addition and removal of 1 mL serum-free medium. Then, 1 mL serum-free medium containing 1 mM IBMX was added to each well, and the cells were incubated for 15 min. Ractopamine (in 10 mL serum-free medium) was added to each well, and the plates were incubated for 10 min–5 h. The reaction was terminated by the addition of 50 mL concentrated HCl per well. The plates were then frozen, thawed and [3H]-cAMP separated from other 3H-nucleotides by sequential Dowex and alumina column chromatography
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:58:52 GMT 2025
Edited
by admin
on Mon Mar 31 17:58:52 GMT 2025
Record UNII
309G9J93TP
Record Status Validated (UNII)
Record Version
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Name Type Language
EL-737
Preferred Name English
RACTOPAMINE HYDROCHLORIDE
GREEN BOOK   MI   USAN   USP   USP-RS  
USAN  
Official Name English
BENZENEMETHANOL, 4-HYDROXY-.ALPHA.-(((3-(4-HYDROXYPHENYL)-1-METHYLPROPYL)AMINO)METHYL)-, HYDROCHLORIDE
Systematic Name English
RACTOPAMINE HYDROCHLORIDE [GREEN BOOK]
Common Name English
LYO31537
Code English
RACTOPAMINE HYDROCHLORIDE [USAN]
Common Name English
NSC-759638
Code English
RACTOPAMINE HYDROCHLORIDE [USP-RS]
Common Name English
RACTOPAMINE HYDROCHLORIDE [USP IMPURITY]
Common Name English
RACTOPAMINE HYDROCHLORIDE [MI]
Common Name English
EL737
Code English
RACTOPAMINE HCL
Common Name English
LYO-31537
Code English
(±)-ALL-RAC-P-HYDROXY-.ALPHA.-(((3-(P-HYDROXYPHENYL)-1-METHYLPROPYL)AMINO)METHYL)BENZYL ALCOHOL, HYDROCHLORIDE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C48149
Created by admin on Mon Mar 31 17:58:52 GMT 2025 , Edited by admin on Mon Mar 31 17:58:52 GMT 2025
Code System Code Type Description
RS_ITEM_NUM
1598100
Created by admin on Mon Mar 31 17:58:52 GMT 2025 , Edited by admin on Mon Mar 31 17:58:52 GMT 2025
PRIMARY
ChEMBL
CHEMBL509336
Created by admin on Mon Mar 31 17:58:52 GMT 2025 , Edited by admin on Mon Mar 31 17:58:52 GMT 2025
PRIMARY
FDA UNII
309G9J93TP
Created by admin on Mon Mar 31 17:58:52 GMT 2025 , Edited by admin on Mon Mar 31 17:58:52 GMT 2025
PRIMARY
NSC
759638
Created by admin on Mon Mar 31 17:58:52 GMT 2025 , Edited by admin on Mon Mar 31 17:58:52 GMT 2025
PRIMARY
MERCK INDEX
m9478
Created by admin on Mon Mar 31 17:58:52 GMT 2025 , Edited by admin on Mon Mar 31 17:58:52 GMT 2025
PRIMARY Merck Index
USAN
W-117
Created by admin on Mon Mar 31 17:58:52 GMT 2025 , Edited by admin on Mon Mar 31 17:58:52 GMT 2025
PRIMARY
MESH
C060897
Created by admin on Mon Mar 31 17:58:52 GMT 2025 , Edited by admin on Mon Mar 31 17:58:52 GMT 2025
PRIMARY
DRUG BANK
DBSALT001698
Created by admin on Mon Mar 31 17:58:52 GMT 2025 , Edited by admin on Mon Mar 31 17:58:52 GMT 2025
PRIMARY
PUBCHEM
14010333
Created by admin on Mon Mar 31 17:58:52 GMT 2025 , Edited by admin on Mon Mar 31 17:58:52 GMT 2025
PRIMARY
EPA CompTox
DTXSID1046471
Created by admin on Mon Mar 31 17:58:52 GMT 2025 , Edited by admin on Mon Mar 31 17:58:52 GMT 2025
PRIMARY
RXCUI
1311676
Created by admin on Mon Mar 31 17:58:52 GMT 2025 , Edited by admin on Mon Mar 31 17:58:52 GMT 2025
PRIMARY RxNorm
SMS_ID
300000055070
Created by admin on Mon Mar 31 17:58:52 GMT 2025 , Edited by admin on Mon Mar 31 17:58:52 GMT 2025
PRIMARY
CAS
90274-24-1
Created by admin on Mon Mar 31 17:58:52 GMT 2025 , Edited by admin on Mon Mar 31 17:58:52 GMT 2025
PRIMARY
NCI_THESAURUS
C84133
Created by admin on Mon Mar 31 17:58:52 GMT 2025 , Edited by admin on Mon Mar 31 17:58:52 GMT 2025
PRIMARY
DAILYMED
309G9J93TP
Created by admin on Mon Mar 31 17:58:52 GMT 2025 , Edited by admin on Mon Mar 31 17:58:52 GMT 2025
PRIMARY
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