Midodrine (CED0005277)

Record Information
Version1.0
Creation Date2016-05-25 18:19:00 UTC
Update Date2026-08-18 19:41:12 UTC
Accession NumberCHEM022066
Identification
Common NameMidodrine
ClassSmall Molecule
Description
Midodrine is an organic compound with the chemical formula C12H18N2O4 and an average molecular weight of 254.28 g/mol. Midodrine belongs to the methoxybenzenes, a subclass of benzene and substituted derivatives within the organic compounds. The compound is recorded as being found in or released from 17 different sources across several categories. Within healthcare, pharmaceuticals, and veterinary products, it is identified as a cardiac stimulant, excluding cardiac glycosides. In the category of food, food processing, and cookware, it is associated with food preservation and the processing of fish. Its presence is also noted in building and construction materials, including floors, fencing, and tents or canopies. Additionally, it is found in household cleaning and consumer products, specifically pipe accessories, tobacco smoke filters, perfumes within soaps and detergents, and non-electric simulated smoking devices. It is further recorded in electrical and electronic equipment, including antennas, auxiliary devices, electrodes, electric switches, and electrically stimulated smoking devices. At the molecular level, midodrine interacts with three recorded protein targets. It functions as an agonist of the Alpha-1A adrenergic receptor (ADRA1A), the Alpha-1B adrenergic receptor (ADRA1B), and the Alpha-1D adrenergic receptor (ADRA1D). The recorded route of exposure for this compound is oral.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
(+-)-2-Amino-N-(beta-hydroxy-2,5-dimethoxyphenethyl)acetamideChEBI
1-(2',5'-Dimethoxyphenyl)-2-glycinamidoethanolChEBI
2-Amino-N-(2,5-dimethoxy-beta-hydroxyphenethyl)acetamideChEBI
DL-N1-(beta-Hydroxy-2,5-dimethoxyphenethyl)glycinamidChEBI
MidodrinaChEBI
MidodrinumChEBI
(+-)-2-Amino-N-(b-hydroxy-2,5-dimethoxyphenethyl)acetamideGenerator
(+-)-2-Amino-N-(β-hydroxy-2,5-dimethoxyphenethyl)acetamideGenerator
2-Amino-N-(2,5-dimethoxy-b-hydroxyphenethyl)acetamideGenerator
2-Amino-N-(2,5-dimethoxy-β-hydroxyphenethyl)acetamideGenerator
DL-N1-(b-Hydroxy-2,5-dimethoxyphenethyl)glycinamidGenerator
DL-N1-(Β-hydroxy-2,5-dimethoxyphenethyl)glycinamidGenerator
MidodrinHMDB
Midodrine HCLHMDB
Midodrine hydrochlorideHMDB
AmatineHMDB
Cahill may roberts brand OF midodrine monohydrochlorideHMDB
Nycomed brand OF midodrine monohydrochlorideHMDB
Christiaens brand OF midodrine monohydrochlorideHMDB
Monohydrochloride, midodrineHMDB
ProAmatineHMDB
Shire brand OF midodrine monohydrochlorideHMDB
Midodrine monohydrochlorideHMDB
GutronHMDB
MidonHMDB
Chemical FormulaC12H18N2O4
Average Molecular Mass254.282 g/mol
Monoisotopic Mass254.127 g/mol
CAS Registry Number133163-28-7
IUPAC Name2-amino-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide
Traditional Namemidodrine
SMILESCOC1=CC(C(O)CNC(=O)CN)=C(OC)C=C1
InChI IdentifierInChI=1S/C12H18N2O4/c1-17-8-3-4-11(18-2)9(5-8)10(15)7-14-12(16)6-13/h3-5,10,15H,6-7,13H2,1-2H3,(H,14,16)
InChI KeyPTKSEFOSCHHMPD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassMethoxybenzenes
Direct ParentDimethoxybenzenes
Alternative Parents
Substituents
  • P-dimethoxybenzene
  • Dimethoxybenzene
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Alkyl aryl ether
  • Secondary alcohol
  • Carboximidic acid
  • Carboximidic acid derivative
  • Ether
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Organic nitrogen compound
  • Alcohol
  • Primary amine
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organic oxygen compound
  • 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 Solubility4.45 g/LALOGPS
logP-0.49ALOGPS
logP-0.95ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)13.77ChemAxon
pKa (Strongest Basic)8.14ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area93.81 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity66.22 m³·mol⁻¹ChemAxon
Polarizability26.65 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0019-9420000000-7d9c097f5836b8a5fae7Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0udi-2901000000-dca22bfb649bee6445c3Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a59-5590000000-c1d7a0986ff760045ce1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000t-3900000000-e616153c52e6dab85f03Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05o0-6900000000-90bdd17739520c368242Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-2290000000-2b1a688c778f1a3b4f73Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fki-9780000000-3ec6e31d870a13fc1277Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0596-9510000000-f2530e4ed2f894325b44Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0290000000-be85220bae16e2ca879fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-1910000000-846cb5ab8c2f374a839aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0540-9600000000-457f0b777313d983dbcdNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-3290000000-bba27a0b4e7c20b0735eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-9600000000-75c1caa8420dbc10acecNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0pi3-5920000000-8736da98df9e10c5809cNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR13C 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
546.0Log mg/kg[310:970]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
233BrushesPersonal care & cosmeticsNot Available
286Cardiac stimulants excl. cardiac glycosidesHealthcare, pharmaceuticals & veterinary productsNot Available
496FencingBuilding & ConstructionNot Available
497FloorsBuilding & ConstructionNot Available
503Tents Or CanopiesBuilding & ConstructionNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
535Superconducting Magnets And Superconducting CoilsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
551Processing FishFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)134.835
Alpha-1A adrenergic receptor structureClick to view 3D structureAlpha-1A adrenergic receptorP35348HumansPredicted (SEA)158.267
Click to view 3D structureAlpha-1A adrenergic receptorP43140Rattus norvegicusPredicted (SEA)126.194
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)259.471
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)218.756
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP08909RatPredicted (SEA)147.602
Click to view 3D structureAlpha-1D adrenergic receptorP23944Rattus norvegicusPredicted (SEA)51.7697
Prostaglandin G/H synthase 1 structureClick to view 3D structureProstaglandin G/H synthase 1P23219HumansPredicted (SEA)62.8243
Aldo-keto reductase family 1 member C3 structureClick to view 3D structureAldo-keto reductase family 1 member C3P42330HumansPredicted (SEA)37.2898
Melatonin receptor type 1A structureClick to view 3D structureMelatonin receptor type 1AP48039HumansPredicted (SEA)13.7015
Click to view 3D structureMelatonin receptor type 1BP51050Gallus gallusPredicted (SEA)6.46149
Click to view 3D structureAlpha-2B adrenergic receptorP19328Rattus norvegicusPredicted (SEA)7.94062
Click to view 3D structureAlpha-1B adrenergic receptorP18841Mesocricetus auratusPredicted (SEA)5.13805
Aldo-keto reductase family 1 member C2 structureClick to view 3D structureAldo-keto reductase family 1 member C2P52895HumansPredicted (SEA)38.8468
Glycogen synthase kinase-3 beta structureClick to view 3D structureGlycogen synthase kinase-3 betaP49841HumansPredicted (SEA)1055.17
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)631.046
Serine/threonine-protein kinase PLK1 structureClick to view 3D structureSerine/threonine-protein kinase PLK1P53350HumansPredicted (SEA)702.511
Click to view 3D structureRas-related C3 botulinum toxin substrate 1P63001Mus musculusPredicted (SEA)11.8331
Serine/threonine-protein kinase PAK 4 structureClick to view 3D structureSerine/threonine-protein kinase PAK 4O96013HumansPredicted (SEA)749.143
cAMP-dependent protein kinase catalytic subunit alpha structureClick to view 3D structurecAMP-dependent protein kinase catalytic subunit alphaP17612HumansPredicted (SEA)748.365
Serine/threonine-protein kinase pim-1 structureClick to view 3D structureSerine/threonine-protein kinase pim-1P11309HumansPredicted (SEA)906.788
Ribosomal protein S6 kinase alpha-3 structureClick to view 3D structureRibosomal protein S6 kinase alpha-3P51812HumansPredicted (SEA)747.119
Serine/threonine-protein kinase Chk1 structureClick to view 3D structureSerine/threonine-protein kinase Chk1O14757HumansPredicted (SEA)789.625
Cyclin-dependent kinase 2 structureClick to view 3D structureCyclin-dependent kinase 2P24941HumansPredicted (SEA)975.606
Protein kinase C delta type structureClick to view 3D structureProtein kinase C delta typeQ05655HumansPredicted (SEA)673.162
Concentrations
Not Available
External Links
DrugBank IDDB00211
HMDB IDHMDB0014356
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMidodrine
Chemspider ID4050
ChEBI ID6933
PubChem Compound ID4195
Kegg Compound IDC07890
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11096750
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15273244
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=16676655
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=17901021
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=18410283
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=18840368
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=19522958
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=20376815
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=20844343
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21343575
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=21801220
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22436941
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=23051063
14. Hebenstreit G: [Treatment of hypotension caused by psychopharmacological drugs (author's transl)]. Wien Med Wochenschr. 1981 Feb 28;131(4):109-12.
15. Tsuda M, Terada T, Irie M, Katsura T, Niida A, Tomita K, Fujii N, Inui K: Transport characteristics of a novel peptide transporter 1 substrate, antihypotensive drug midodrine, and its amino acid derivatives. J Pharmacol Exp Ther. 2006 Jul;318(1):455-60. Epub 2006 Apr 5.