Terbutaline (CED0003767)

Record Information
Version1.0
Creation Date2016-05-25 18:23:22 UTC
Update Date2026-08-18 19:58:43 UTC
Accession NumberCHEM022194
Identification
Common NameTerbutaline
ClassSmall Molecule
Description
Terbutaline is an organic compound with the chemical formula C12H19NO3 and an average molecular weight of 225.28 g/mol. Terbutaline belongs to the benzenediols, a subclass of phenols within the organic compounds. It acts as an agonist/antagonist of the Beta-1 adrenergic receptor (ADRB1), Beta-2 adrenergic receptor (ADRB2), and Beta-3 adrenergic receptor (ADRB3). The compound is utilized in healthcare, pharmaceuticals, and veterinary products as a drug for obstructive airway diseases. It has been found in or released from 18 recorded sources. These sources include drinking water and water supply; food preservation within food, food processing, and cookware; and floors within building and construction. Other recorded sources include electrical and electronic equipment, such as hybrid capacitors, electrodes, line transmission systems, conductive bodies characterized by the conductive materials, and electrically stimulated smoking devices. Additionally, it is found in household cleaning and consumer products, including pipe accessories, cigar cigarettes, perfumes within detergents and soaps, non-electric simulated smoking devices, and other smoking requisites. Exposure to terbutaline can occur through subcutaneous, respiratory, oral, and intramuscular routes.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
TerbutalinaChEBI
TerbutalinumChEBI
AsthmasianKegg
TerbutalinHMDB
Terbutaline sulfateHMDB
Alpharma brand OF terbutaline sulfateHMDB
AsthmoprotectHMDB
AstraZeneca brand OF terbutaline sulfateHMDB
ButalitabHMDB
Kendrick brand OF terbutaline sulfateHMDB
TerbulHMDB
Terbutalin stadaHMDB
CT-Arzneimittel brand OF terbutaline sulfateHMDB
AstraZeneca brand OF terbutalineHMDB
BrethaireHMDB
BrethineHMDB
Hexal brand OF terbutaline sulfateHMDB
Hoechst brand OF terbutaline sulfateHMDB
Lagap brand OF terbutaline sulfateHMDB
Lindopharm brand OF terbutaline sulfateHMDB
MonoventHMDB
Novartis brand OF terbutaline sulfateHMDB
Stadapharm brand OF terbutaline sulfateHMDB
Terbutalin alHMDB
Terbutalin ratiopharmHMDB
Terbutalin-ratiopharmHMDB
Terbutaline astrazeneca brandHMDB
CT Arzneimittel brand OF terbutaline sulfateHMDB
Azupharma brand OF terbutaline sulfateHMDB
BricanylHMDB
Bricanyl saHMDB
ButaliretHMDB
ContimitHMDB
Dermapharm brand OF terbutaline sulfateHMDB
TedipulmoHMDB
TerbasminHMDB
Pharma-stern brand OF terbutaline sulfateHMDB
Ratiopharm brand OF terbutaline sulfateHMDB
Terbutalin von CTHMDB
Aliud brand OF terbutaline sulfateHMDB
ArubendolHMDB
Estedi brand OF terbutaline sulfateHMDB
Fatol brand OF terbutaline sulfateHMDB
TazikenHMDB
TerbuturmantHMDB
Chemical FormulaC12H19NO3
Average Molecular Mass225.284 g/mol
Monoisotopic Mass225.136 g/mol
CAS Registry Number23031-25-6
IUPAC Name5-[2-(tert-butylamino)-1-hydroxyethyl]benzene-1,3-diol
Traditional Nameterbutaline
SMILESCC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1
InChI IdentifierInChI=1S/C12H19NO3/c1-12(2,3)13-7-11(16)8-4-9(14)6-10(15)5-8/h4-6,11,13-16H,7H2,1-3H3
InChI KeyXWTYSIMOBUGWOL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as resorcinols. Resorcinols are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydroxyl groups at positions 1 and 3.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct ParentResorcinols
Alternative Parents
Substituents
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Monocyclic benzene moiety
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Aromatic alcohol
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.84 g/LALOGPS
logP0.55ALOGPS
logP0.44ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)8.86ChemAxon
pKa (Strongest Basic)9.76ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area72.72 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity63.04 m³·mol⁻¹ChemAxon
Polarizability24.78 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-000i-9600000000-883d61ad257dffc64a5dNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0a4i-4009200000-9ae8a659f4d6ab038c42Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0290000000-8c26dbc913131cf49bc4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-3148282c5452a80b16c3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-9122151a6e70e6f2b536Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0090000000-aab7f309385309d8884bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0920000000-1e85cd2bf4a0358c22d7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-82b70479a4e38921e06bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-2900000000-aff994ffd107ef3b6e71Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a6r-7900000000-cfe77aa0133facea1c75Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-1a0ccd393797b19105a0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0190000000-f9271bb736a512dbdbabNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-a70c8697ca7633839444Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a6r-1900000000-4a9c0ddb9af4ce93b4aeNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a6r-6900000000-0cc68c4a50196d6ffab6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-9400000000-e1cec349ffb2fcd3ebe2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a6r-1900000000-66b082864419c2ddb9d5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-a70c8697ca7633839444Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a6r-6900000000-0cc68c4a50196d6ffab6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-9400000000-e1cec349ffb2fcd3ebe2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a6r-1900000000-4a9c0ddb9af4ce93b4aeNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0190000000-f9271bb736a512dbdbabNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-9122151a6e70e6f2b536Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0290000000-8c26dbc913131cf49bc4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-3148282c5452a80b16c3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-9400000000-b4d699243189b10de1beNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a6r-1900000000-31d8965927b3f4a0a5f4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a6r-0290000000-9796f2ff21f424e4e05eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0zg0-1940000000-233ca9ad582e2ad95cd5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0k9i-5900000000-92f8d44ebccabc74764fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-1190000000-b64eabaa2feb653f341aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05fr-4490000000-0e761dccb9282646875dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0abi-9800000000-c64d63f8e4a1c43cef38Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0920000000-1ec6d7b60f5b070516dbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-1900000000-06423c7a4c0de2fede30Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9400000000-de6181abea4a00bd96d3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0090000000-76ec0345fdc4b4d17e50Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0490000000-6818d9c1bd30449228d6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-6900000000-672993a0437267d57527Not AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
985.0Log mg/kg[550:1800]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
115Drinking waterDrinking water & water supplyNot Available
391Drugs for obstructive airway diseasesHealthcare, pharmaceuticals & veterinary productsNot Available
497FloorsBuilding & ConstructionNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
566Tobacco PipesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
651Purses Money Bags WalletsTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
3 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Beta-2 adrenergic receptor structureClick to view 3D structureBeta-2 adrenergic receptorP07550HumansPredicted (SEA)1.24559
Click to view 3D structureBeta-2 adrenergic receptorQ28044Bos taurusPredicted (SEA)0.0778492
Click to view 3D structureBeta-2 adrenergic receptorQ8K4Z4Cavia porcellusPredicted (SEA)2.72472
Beta-1 adrenergic receptor structureClick to view 3D structureBeta-1 adrenergic receptorP08588HumansPredicted (SEA)9.18621
Click to view 3D structureBeta-2 adrenergic receptorP10608Rattus norvegicusPredicted (SEA)2.33548
Click to view 3D structureBeta-1 adrenergic receptorP18090Rattus norvegicusPredicted (SEA)5.2159
Click to view 3D structureBeta-1 adrenergic receptorB0FL73Cavia porcellusPredicted (SEA)6.38364
Click to view 3D structureTaste receptor type 2 member 50P59544HumansPredicted (SEA)1.40129
Click to view 3D structureTaste receptor type 2 member 45P59539HumansPredicted (SEA)1.40129
Click to view 3D structureTaste receptor type 2 member 42Q7RTR8HumansPredicted (SEA)1.40129
Click to view 3D structureTaste receptor type 2 member 41P59536HumansPredicted (SEA)1.40129
Click to view 3D structureTaste receptor type 2 member 7Q9NYW3HumansPredicted (SEA)1.40129
Click to view 3D structureTaste receptor type 2 member 30P59541HumansPredicted (SEA)1.40129
Click to view 3D structureTaste receptor type 2 member 60P59551HumansPredicted (SEA)1.40129
Click to view 3D structureTaste receptor type 2 member 19P59542HumansPredicted (SEA)1.40129
Click to view 3D structureTaste receptor type 2 member 20P59543HumansPredicted (SEA)1.40129
Click to view 3D structureTaste receptor type 2 member 1Q9NYW7HumansPredicted (SEA)1.40129
Click to view 3D structureTaste receptor type 2 member 40P59535HumansPredicted (SEA)1.40129
Click to view 3D structureTaste receptor type 2 member 3Q9NYW6HumansPredicted (SEA)1.40129
Click to view 3D structureTaste receptor type 2 member 13Q9NYV9HumansPredicted (SEA)1.40129
Click to view 3D structureTaste receptor type 2 member 39P59534HumansPredicted (SEA)1.40129
Click to view 3D structureTaste receptor type 2 member 5Q9NYW4HumansPredicted (SEA)1.40129
Click to view 3D structureTaste receptor type 2 member 9Q9NYW1HumansPredicted (SEA)1.40129
Click to view 3D structureTaste receptor type 2 member 43P59537HumansPredicted (SEA)1.40129
Click to view 3D structure5-hydroxytryptamine receptor 1AP19327Rattus norvegicusPredicted (SEA)272.628
Concentrations
Not Available
External Links
DrugBank IDDB00871
HMDB IDHMDB0015009
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTerbutaline
Chemspider ID5210
ChEBI ID9449
PubChem Compound ID5403
Kegg Compound IDC07129
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12423672
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=12569076
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21618259
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21996060
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22310877
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22363704
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22765375
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22767151
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22782385
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22813780
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22872661
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22988932
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=23075357
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=23126237
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=23204625
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=23283786
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=23299764
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=23325598
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=23341043
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=8298802
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=9596106
22. Hochhaus G, Mollmann H: Pharmacokinetic/pharmacodynamic characteristics of the beta-2-agonists terbutaline, salbutamol and fenoterol. Int J Clin Pharmacol Ther Toxicol. 1992 Sep;30(9):342-62.
23. Haahtela T, Jarvinen M, Kava T, Kiviranta K, Koskinen S, Lehtonen K, Nikander K, Persson T, Reinikainen K, Selroos O, et al.: Comparison of a beta 2-agonist, terbutaline, with an inhaled corticosteroid, budesonide, in newly detected asthma. N Engl J Med. 1991 Aug 8;325(6):388-92.
24. Rhodes MC, Seidler FJ, Abdel-Rahman A, Tate CA, Nyska A, Rincavage HL, Slotkin TA: Terbutaline is a developmental neurotoxicant: effects on neuroproteins and morphology in cerebellum, hippocampus, and somatosensory cortex. J Pharmacol Exp Ther. 2004 Feb;308(2):529-37. Epub 2003 Nov 10.