Clenbuterol

Basic Info

Common NameClenbuterol(F05773)
2D Structure
FRCD IDF05773
CAS Number37148-27-9
PubChem CID2783
FormulaC12H18Cl2N2O
IUPAC Name

1-(4-amino-3,5-dichlorophenyl)-2-(tert-butylamino)ethanol

InChI Key

STJMRWALKKWQGH-UHFFFAOYSA-N

InChI

InChI=1S/C12H18Cl2N2O/c1-12(2,3)16-6-10(17)7-4-8(13)11(15)9(14)5-7/h4-5,10,16-17H,6,15H2,1-3H3

Canonical SMILES

CC(C)(C)NCC(C1=CC(=C(C(=C1)Cl)N)Cl)O

Isomeric SMILES

CC(C)(C)NCC(C1=CC(=C(C(=C1)Cl)N)Cl)O

Synonyms
        
            clenbuterol
        
            Planipart
        
            37148-27-9
        
            Clenbuterolum
        
            Clenbuterolum [INN-Latin]
        
            Monores
        
            dl-Clenbuterol
        
            NAB-365
        
            (+/-)-clenbuterol
        
            Clenbuterol [BAN:INN]
Classifies
                

                  
                    Veterinary Drug
                  
                    Illegal Additives
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassHalobenzenes
Intermediate Tree NodesChlorobenzenes
Direct ParentDichlorobenzenes
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
Substituents1,3-dichlorobenzene - Aniline or substituted anilines - Aralkylamine - Aryl chloride - Aryl halide - 1,2-aminoalcohol - Secondary alcohol - Secondary aliphatic amine - Secondary amine - Hydrocarbon derivative - Primary amine - Organooxygen compound - Organonitrogen compound - Organochloride - Organohalogen compound - Organic nitrogen compound - Aromatic alcohol - Alcohol - Organic oxygen compound - Amine - Organopnictogen compound - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as dichlorobenzenes. These are compounds containing a benzene with exactly two chlorine atoms attached to it.

Properties

Property NameProperty Value
Molecular Weight277.189
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count3
Rotatable Bond Count4
Complexity233
Monoisotopic Mass276.08
Exact Mass276.08
XLogP2.2
Formal Charge0
Heavy Atom Count17
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.8631
Human Intestinal AbsorptionHIA+0.9484
Caco-2 PermeabilityCaco2+0.5375
P-glycoprotein SubstrateSubstrate0.5588
P-glycoprotein InhibitorNon-inhibitor0.8863
Non-inhibitor0.9627
Renal Organic Cation TransporterNon-inhibitor0.9052
Distribution
Subcellular localizationMitochondria0.5945
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8142
CYP450 2D6 SubstrateNon-substrate0.6830
CYP450 3A4 SubstrateNon-substrate0.5835
CYP450 1A2 InhibitorNon-inhibitor0.9045
CYP450 2C9 InhibitorNon-inhibitor0.9070
CYP450 2D6 InhibitorNon-inhibitor0.9231
CYP450 2C19 InhibitorNon-inhibitor0.9025
CYP450 3A4 InhibitorNon-inhibitor0.8310
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.5428
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9704
Non-inhibitor0.8546
AMES ToxicityNon AMES toxic0.8858
CarcinogensNon-carcinogens0.5199
Fish ToxicityHigh FHMT0.8812
Tetrahymena Pyriformis ToxicityHigh TPT0.9934
Honey Bee ToxicityLow HBT0.7797
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityIII0.6399
Carcinogenicity (Three-class)Non-required0.5674
Model Value Unit
Absorption
Aqueous solubility-2.8515LogS
Caco-2 Permeability1.0475LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.6024LD50, mol/kg
Fish Toxicity1.2343pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.5077pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
HoneyJapan0. residue was detected
Other Aquatic AnimalJapan0. residue was detected
CrustaceansJapan0. residue was detected
Shelled MolluscasJapan0. residue was detected
Other FishJapan0. residue was detected
PerciformesJapan0. residue was detected
AnguilliformesJapan0. residue was detected
SalmoniformesJapan0. residue was detected
Other Poultry,EggsJapan0. residue was detected
Chicken,EggsJapan0. residue was detected
Other Poultry Animals,Edible OffalJapan0. residue was detected
Chicken,Edible OffalJapan0. residue was detected
Other Poultry Animals,KidneyJapan0. residue was detected
Chicken,KidneyJapan0. residue was detected
Other Poultry Animals,LiverJapan0. residue was detected
Chicken,LiverJapan0. residue was detected
Other Poultry Animals,FatJapan0. residue was detected
Chicken,FatJapan0. residue was detected
Other Poultry Animals,MuscleJapan0. residue was detected
Chicken,MuscleJapan0. residue was detected

References

TitleJournalDatePubmed ID
A fluorometric clenbuterol immunoassay based on the use of organic/inorganichybrid nanoflowers modified with gold nanoclusters and artificial antigen.Mikrochim Acta2018 Jul 729982940
Detection of prohibited substances in equine hair by ultra-high performanceliquid chromatography-triple quadrupole mass spectrometry - application to dopingcontrol samples.Drug Test Anal2018 Feb 1229430877
Mechanism of surface plasmon resonance sensing by indirect competitive inhibitionimmunoassay using Au nanoparticle labeled antibody.Talanta2017 Sep 128602280
Identification of Buctopamine and Mebuctopamine, a β2 Receptor Agonist and ItsMetabolite, in Swine Hair and Feed Additives.J Agric Food Chem2017 May 1728453289
Electrochemical non-enzyme sensor for detecting clenbuterol (CLB) based onMoS2-Au-PEI-hemin layered nanocomposites.Biosens Bioelectron2017 Mar 1527151438
Detection of β-agonists in pork tissue with novel electrospun nanofibers-basedsolid-phase extraction followed ultra-high performance liquidchromatography/tandem mass spectrometry.Food Chem2017 Jul 1528274437
A Case Series of Clenbuterol Toxicity Caused by Adulterated Heroin.J Emerg Med2016 Sep27431866
The Potential of Various Living Tissues for Monitoring Clenbuterol Abuse inFood-Producing Chinese Simmental Beef Cattle.J Anal Toxicol2016 Jan-Feb26487642
A Rapid Colorimetric Sensor of Clenbuterol Based on Cysteamine-Modified GoldNanoparticles.ACS Appl Mater Interfaces2016 Jan 1326673452
Rapid screening of toxic salbutamol, ractopamine, and clenbuterol in pork sample by high-performance liquid chromatography-UV method.J Food Drug Anal2016 Apr28911579
The potential of circulating extracellular small RNAs (smexRNA) in veterinarydiagnostics-Identifying biomarker signatures by multivariate data analysis.Biomol Detect Quantif2015 Sep 1927077039
Mutagenicity and DNA-damaging potential of clenbuterol and its metabolite4-amino-3,5-dichlorobenzoic acid in vitro.Food Chem Toxicol2015 Mar25595371
Metabolomic analysis of swine urine treated with β2-agonists by ultra-highperformance liquid chromatography-quadrupole time-of-flight mass spectrometry.J Chromatogr A2015 Jun 2625980694
Ultratrace LC-MS/MS analysis of segmented calf hair for retrospective assessment of time of clenbuterol administration in Agriforensics.J Agric Food Chem2015 Jan 2125537490
Development and validation of a sensitive method for simultaneous determination of eight β₂-agonists in pork by ultrasonic-assisted extraction and liquid chromatography/tandem mass spectrometry.J Chromatogr Sci2015 Jan24771052
Development and Application of a Method for Rapid and Simultaneous Determination of Three β-agonists (Clenbuterol, Ractopamine, and Zilpaterol) using LiquidChromatography-tandem Mass Spectrometry.Korean J Food Sci Anim Resour201526761809
Evaluation of matrix solid-phase dispersion extraction for 11 β-agonists in swinefeed by liquid chromatography with electrospray ionization tandem massspectrometry.J Sep Sci2014 Sep24981594
Comparison of accumulation of clenbuterol and salbutamol residues in animalinternal tissues, non-pigmented eyes and hair.J Anal Toxicol2014 Nov-Dec24990876
Ultrasensitive and quantitative detection of a new β-agonist phenylethanolamine Aby a novel immunochromatographic assay based on surface-enhanced Raman scattering(SERS).J Agric Food Chem2014 Nov 1225343225
Sample preincubation strategy for sensitive and quantitative detection ofclenbuterol in swine urine using a fluorescent microsphere-basedimmunochromatographic assay.J Food Prot2014 Nov25364937