Midodrine (CHEM022066)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:19:00 UTC
Update Date2026-04-13 20:29:25 UTC
Accession NumberCHEM022066
Identification
Common NameMidodrine
ClassSmall Molecule
DescriptionAn aromatic ether that is 1,4-dimethoxybenzene which is substituted at position 2 by a 2-(glycylamino)-1-hydroxyethyl group. A direct-acting sympathomimetic with selective alpha-adrenergic agonist activity, it is used (generally as its hydrochloride salt) as a peripheral vasoconstrictor in the treatment of certain hypotensive states. The main active moiety is its major metabolite, deglymidodrine.
Contaminant Sources
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0019-9420000000-7d9c097f5836b8a5fae7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0udi-2901000000-dca22bfb649bee6445c3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a59-5590000000-c1d7a0986ff760045ce1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-3900000000-e616153c52e6dab85f03Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05o0-6900000000-90bdd17739520c368242Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-2290000000-2b1a688c778f1a3b4f73Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fki-9780000000-3ec6e31d870a13fc1277Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-9510000000-f2530e4ed2f894325b44Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0290000000-be85220bae16e2ca879fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-1910000000-846cb5ab8c2f374a839aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0540-9600000000-457f0b777313d983dbcdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3290000000-bba27a0b4e7c20b0735eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9600000000-75c1caa8420dbc10acecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pi3-5920000000-8736da98df9e10c5809cSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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.