U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
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.
2010-12
Development and validation of a liquid chromatography tandem mass spectrometry method for the analysis of beta-agonists in animal feed and drinking water.
2010-09-24
Aggressiveness and brain amine concentration in dominant and subordinate finishing pigs fed the beta-adrenoreceptor agonist ractopamine.
2010-09
Analysis of the interactions of mixtures of two beta-agonists steroids with bovine serum albumin: a fluorescence spectroscopy and chemometrics investigation.
2010-08
Development of rapid immunoassays for the detection of ractopamine in swine urine.
2010-08
Effect of distillers dried grains with solubles and ractopamine (Paylean) on quality and shelf-life of fresh pork and bacon.
2010-08
Investigation of ractopamine-imprinted polymer for dispersive solid-phase extraction of trace beta-agonists in pig tissues.
2010-07
Effect of ractopamine-HCl supplementation for 28 days on carcass characteristics, muscle fiber morphometrics, and whole muscle yields of six distinct muscles of the loin and round.
2010-07
Determination of beta-adrenergic agonists by hapten microarray.
2010-06-30
Molecular spectroscopic studies on the interaction between ractopamine and bovine serum albumin.
2010-06-05
Determination of beta-agonists in pig feed, pig urine and pig liver using capillary electrophoresis with electrochemical detection.
2010-06
Investigation of ractopamine molecularly imprinted stir bar sorptive extraction and its application for trace analysis of beta2-agonists in complex samples.
2010-05-28
Comparative effects of ractopamine hydrochloride and zilpaterol hydrochloride on growth performance, carcass traits, and longissimus tenderness of finishing steers.
2010-05
Generic sample preparation combined with high-resolution liquid chromatography-time-of-flight mass spectrometry for unification of urine screening in doping-control laboratories.
2010-04
Effects of ractopamine and sex on serum metabolites and skeletal muscle gene expression in finishing steers and heifers.
2010-04
Simultaneous determination of beta2-agonists in human urine by fast-gas chromatography/mass spectrometry: method validation and clinical application.
2010-04
Behavior and peripheral amine concentrations in relation to ractopamine feeding, sex, and social rank of finishing pigs.
2010-03
Effect of dietary protein and lysine fluctuations in the absence and presence of ractopamine on performance and carcass quality of late-finishing pigs.
2010-02
Effects of ractopamine hydrochloride are not confined to mammalian tissue: evidence for direct effects of ractopamine hydrochloride supplementation on fermentation by ruminal microorganisms.
2010-02
Impact of dietary protein on lipid metabolism-related gene expression in porcine adipose tissue.
2010-01-21
Hormonal growth promoting agents in food producing animals.
2010
Influence of beta-agonists (ractopamine HCl and zilpaterol HCl) on fecal shedding of Escherichia coli O157:H7 in feedlot cattle.
2009-12
Development of a colloidal gold-based lateral-flow immunoassay for the rapid simultaneous detection of clenbuterol and ractopamine in swine urine.
2009-12
Ractopamine hydrochloride improves growth performance and carcass composition in immunocastrated boars, intact boars, and gilts.
2009-11
Responses to maternal GH or ractopamine during early-mid pregnancy are similar in primiparous and multiparous pregnant pigs.
2009-10
Highly sensitive and specific liquid chromatography- tandem mass spectrometry method for testing ractopamine in cow and sheep urine.
2009-08-06
Development and validation of a simple method for routine analysis of ractopamine hydrochloride in raw material and feed additives by HPLC.
2009-07-21
Effect of preslaughter feeding and ractopamine hydrochloride supplementation on growth performance, carcass characteristics, and end product quality in market dairy cows.
2009-07
Molecularly imprinted polymer for the determination of trace ractopamine in pork using SPE followed by HPLC with fluorescence detection.
2009-05
Effect of ractopamine-hydrochloride on the fiber type distribution and shelf-life of six muscles of steers.
2009-05
How to decrease ion suppression in a multiresidue determination of beta-agonists in animal liver and urine by liquid chromatography-mass spectrometry with ion-trap detector.
2009-04-01
Simultaneous determination of salbutamol, ractopamine, and clenbuterol in animal feeds by SPE and LC-MS.
2009-04
Effects of a "step-up" ractopamine feeding program, sex, and social rank on growth performance, hoof lesions, and Enterobacteriaceae shedding in finishing pigs.
2009-01
Rapid determination of ractopamine residues in edible animal products by enzyme-linked immunosorbent assay: development and investigation of matrix effects.
2009
Carcass, meat quality, and sensory characteristics of heavy body weight pigs fed ractopamine hydrochloride (Paylean).
2008-12
Differential response of cull cow muscles to the hypertrophic actions of ractopamine-hydrogen chloride.
2008-12
[Simultaneous determination of nine beta-agonist residues in animal derived foods by ultra performance liquid chromatography-tandem mass spectrometry].
2008-11
Interactive effect of ractopamine and dietary fat source on pork quality characteristics of fresh pork chops during simulated retail display.
2008-10
Effect of feedlot management system on response to ractopamine-HCl in yearling steers.
2008-09
Screening procedures for clenbuterol residue determination in raw swine livers using lateral-flow assay and enzyme-linked immunosorbent assay.
2008-04
The effects of ractopamine-hydrogen chloride (Optaflexx) on performance, carcass characteristics, and meat quality of finishing feedlot heifers.
2008-04
Effective monitoring for ractopamine residues in samples of animal origin by SPR biosensor and mass spectrometry.
2008-02-11
[Multi-residue analysis of 10 beta2-agonists in animal tissues using gas chromatography-mass spectrometry].
2008-01
Effects of ractopamine supplementation and postmortem aging on longissimus muscle palatability of beef steers differing in biological type.
2008-01
Effects of ractopamine hydrochloride on performance, rate and variation in feed intake, and acid-base balance in feedlot cattle.
2007-11
Determination method for ractopamine in swine and cattle tissues using LC/MS.
2007-10
Effects of steroidal implantation and ractopamine-HCl on nitrogen retention, blood metabolites and skeletal muscle gene expression in Holstein steers.
2007-10
Interactive effect of ractopamine and dietary fat source on quality characteristics of fresh pork bellies.
2007-10
Effects of pantothenic acid on growth performance and carcass characteristics of growing-finishing pigs fed diets with or without ractopamine hydrochloride.
2007-10
Development and identification of monoclonal antibodies against ractopamine.
2007-06
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
  • Download
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
Related Record Type Details
IMPURITY -> PARENT
limits for Ractopamine Hydrochloride Suspension
USP
IMPURITY -> PARENT
limits for Ractopamine Hydrochloride Suspension
USP
IMPURITY -> PARENT
limits for Ractopamine Hydrochloride Suspension
USP
IMPURITY -> PARENT
limits for Ractopamine Hydrochloride Suspension
USP
IMPURITY -> PARENT
limits for Ractopamine Hydrochloride Suspension
USP
IMPURITY -> PARENT
limits for Ractopamine Hydrochloride Suspension
USP
IMPURITY -> PARENT
limits for Ractopamine Hydrochloride Suspension
USP
IMPURITY -> PARENT
limits for Ractopamine Hydrochloride Suspension
USP
IMPURITY -> PARENT
limits for Ractopamine Hydrochloride Suspension
USP
IMPURITY -> PARENT
limits for Ractopamine Hydrochloride Suspension
USP
IMPURITY -> PARENT
limits for Ractopamine Hydrochloride Suspension
USP
IMPURITY -> PARENT
limits for Ractopamine Hydrochloride Suspension
USP
Related Record Type Details
ACTIVE MOIETY