Alpha-hydroxymidazolam (CHEM022646)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:44:40 UTC
Update Date2026-03-31 19:09:03 UTC
Accession NumberCHEM022646
Identification
Common NameAlpha-hydroxymidazolam
ClassSmall Molecule
DescriptionAlpha-hydroxymidazolam is a metabolite of midazolam. Midazolam, marketed in English-speaking countries under the trade names Dormicum, Hypnovel, and Versed, is a short-acting drug in the benzodiazepine class developed by Hoffmann-La Roche in the 1970s. The drug is used for treatment of acute seizures, moderate to severe insomnia, and for inducing sedation and amnesia before medical procedures. It possesses profoundly potent anxiolytic, amnestic, hypnotic, anticonvulsant, skeletal muscle relaxant, and sedative properties. (Wikipedia)
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
1'-HydroxymidazolamChEBI
1-HydroxymethylmidazolamChEBI
1-OH-MDZChEBI
8-Chloro-6-(2-fluorophenyl)-1-hydroxymethyl-4H-imidazo[1,5-a][1,4]benzodiazepineChEBI
8-Chloro-6-(2-fluorophenyl)-4H-imidazo[1,5-a][1,4]benzodiazepine-1-methanolChEBI
Ro 21-6347ChEBI
a-HydroxymidazolamGenerator
Α-hydroxymidazolamGenerator
1-HydroxymidazolamHMDB
alpha-HydroxymidazolamMeSH
Chemical FormulaC18H13ClFN3O
Average Molecular Mass341.767 g/mol
Monoisotopic Mass341.073 g/mol
CAS Registry Number59468-90-5
IUPAC Name[12-chloro-9-(2-fluorophenyl)-2,4,8-triazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),3,5,8,11,13-hexaen-3-yl]methanol
Traditional Name[12-chloro-9-(2-fluorophenyl)-2,4,8-triazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),3,5,8,11,13-hexaen-3-yl]methanol
SMILESOCC1=NC=C2CN=C(C3=CC=CC=C3F)C3=C(C=CC(Cl)=C3)N12
InChI IdentifierInChI=1S/C18H13ClFN3O/c19-11-5-6-16-14(7-11)18(13-3-1-2-4-15(13)20)22-9-12-8-21-17(10-24)23(12)16/h1-8,24H,9-10H2
InChI KeyQHSMEGADRFZVNE-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as imidazo[1,5-a][1,4]benzodiazepines. Imidazo[1,5-a][1,4]benzodiazepines are compounds containing an imidazole ring and a 1,4-benzodiazepine ring system, both sharing one nitrogen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodiazepines
Sub Class1,4-benzodiazepines
Direct ParentImidazo[1,5-a][1,4]benzodiazepines
Alternative Parents
Substituents
  • Imidazo[1,5-a][1,4]benzodiazepine
  • Para-diazepine
  • Fluorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl fluoride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • N-substituted imidazole
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Ketimine
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organonitrogen compound
  • Organooxygen compound
  • Imine
  • Primary alcohol
  • Aromatic alcohol
  • Alcohol
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organohalogen compound
  • Organochloride
  • Organofluoride
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility0.025 g/LALOGPS
logP3.09ALOGPS
logP2.48ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)13.95ChemAxon
pKa (Strongest Basic)4.99ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.41 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity101.13 m³·mol⁻¹ChemAxon
Polarizability33.74 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056r-5095000000-e86a4f5a0a71a34e350bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9223000000-3f514c7a0258e49e1f65Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-00di-0049000000-d895e6063cea9b7a09f0Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-014i-0990000000-77bb23f06e802e59ccd0Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0v6s-0492000000-63c05208d4d7c9ff0b8eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-014i-0890000000-77bb23f06e802e59ccd0Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-1c56560c62733c03b222Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-0009000000-8c1db0e6fec0c5c5a135Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0v6s-0492000000-7c15b332e0c6a3e8fe39Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-00di-0049000000-30f3b10d1ecd517c40a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0019000000-66ccd38bae3483f32c1cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0029000000-93fa3c07dc10a1af479dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gk9-2691000000-e01f5df13f0f7059a2c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-31e0874067a2b92c0d0aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-0029000000-ff9099b2ad85a8e30147Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-7091000000-c5de935b2501a445dbe7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dl-0089000000-3044806924cd101e751fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dl-1029000000-77d2ad85be5f7638949eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-8091000000-9820c5ea13f2c191818cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-90d80e8b23a2763d7125Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-0009000000-aa6995ead1e625eff164Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fs-0494000000-d7daea83a7f8e9b0ccdaSpectrum
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 IDNot Available
HMDB IDHMDB0061089
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID97043
ChEBI ID145330
PubChem Compound ID107917
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15914101
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17452028
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=20850770
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21204116
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21531182
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21993197
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23674377
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=28615640
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=28978489
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=31469454
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=6691561
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=7199324
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=7603229
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=8924728
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=9187388
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=9725490