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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:45:08 UTC
Update Date2023-02-21 17:29:00 UTC
HMDB IDHMDB0041872
Secondary Accession Numbers
  • HMDB41872
Metabolite Identification
Common NameDetomidine
DescriptionA profound lethargy and characteristic lowering of the head with reduced sensitivity to environmental stimuli (sound, pain, etc.) are seen with detomidine. A short period of reduced coordination is characteristically followed by immobility and a firm stance with front legs spread. Following administration there is an initial increase in blood pressure, followed by bradycardia and second degree atrioventricular block (this is not pathologic in horses). The horse commonly sweats to excess, especially on the flanks and neck. Other side effects reported include pilo erection (hair standing erect), ataxia, salivation, slight muscle tremors, and (rarely) penile prolapse. An agonist of receptors, adrenergic alpha-2 that is used in veterinary medicine for its analgesic and sedative properties. It is the racemate of dexmedetomidine. [PubChem]; As detomidine is an arrhythmogenic agent, extreme care should be exercised in horses with cardiac disease, and in the concurrent administration of other arrhythmogenics. The concurrent use of potentiated sulfonamide antibiotics is considered particularly dangerous. Detomidine is a poor premedication when using Ketamine as an anesthetic in horses. Detomidine is a sedative with analgesic properties. 2-adrenergic agonists produce dose-dependent sedative and analgesic effects, mediatated by activation of catecholamine receptors, thus inducing a negative feedback response, reducing production of excitatory neurotransmitters. Due to inhibition of the sympathetic nervous system, detomidine also has cardiac and respiratory effects and an antidiuretic action. Detomidine is an imidazole derivative and I-adrenergic agonist, used as a large animal sedative, primarily used in horses. It is usually available as the salt detomidine hydrochloride. It is a prescription medication available to veterinarians sold under the trade name Dormosedan.
Structure
Data?1677000540
Synonyms
ValueSource
(+)-4-((S)-alpha,2,3-Trimethylbenzyl)imidazoleHMDB
4-[(1S)-1-(2,3-Dimethylphenyl)ethyl]-1H-imidazoleHMDB
Dexdor (T)HMDB
DexmedetomidinaHMDB
DexmedetomidineHMDB
DexmedetomidinumHMDB
MedetomidineHMDB
MPV 1440HMDB
Detomidine hydrochlorideHMDB
Detomidine monohydrochlorideHMDB
Chemical FormulaC12H14N2
Average Molecular Weight186.253
Monoisotopic Molecular Weight186.115698458
IUPAC Name5-[(2,3-dimethylphenyl)methyl]-1H-imidazole
Traditional Namedetomidine
CAS Registry Number76631-46-4
SMILES
CC1=C(C)C(CC2=CN=CN2)=CC=C1
InChI Identifier
InChI=1S/C12H14N2/c1-9-4-3-5-11(10(9)2)6-12-7-13-8-14-12/h3-5,7-8H,6H2,1-2H3,(H,13,14)
InChI KeyRHDJRPPFURBGLQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as o-xylenes. These are aromatic compounds that contain a o-xylene moiety, which is a monocyclic benzene carrying exactly two methyl groups at the 1- and 2-positions.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassXylenes
Direct Parento-Xylenes
Alternative Parents
Substituents
  • O-xylene
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM146.830932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.66 g/LALOGPS
logP2.52ALOGPS
logP2.74ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)13.26ChemAxon
pKa (Strongest Basic)7.15ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area28.68 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity58.86 m³·mol⁻¹ChemAxon
Polarizability21.17 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+142.54831661259
DarkChem[M-H]-142.71531661259
DeepCCS[M+H]+142.60630932474
DeepCCS[M-H]-140.2130932474
DeepCCS[M-2H]-175.09830932474
DeepCCS[M+Na]+149.99130932474
AllCCS[M+H]+139.232859911
AllCCS[M+H-H2O]+134.632859911
AllCCS[M+NH4]+143.432859911
AllCCS[M+Na]+144.632859911
AllCCS[M-H]-144.532859911
AllCCS[M+Na-2H]-144.832859911
AllCCS[M+HCOO]-145.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DetomidineCC1=C(C)C(CC2=CN=CN2)=CC=C12603.9Standard polar33892256
DetomidineCC1=C(C)C(CC2=CN=CN2)=CC=C11810.5Standard non polar33892256
DetomidineCC1=C(C)C(CC2=CN=CN2)=CC=C11942.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Detomidine,1TMS,isomer #1CC1=CC=CC(CC2=CN=CN2[Si](C)(C)C)=C1C1918.8Semi standard non polar33892256
Detomidine,1TMS,isomer #1CC1=CC=CC(CC2=CN=CN2[Si](C)(C)C)=C1C1906.6Standard non polar33892256
Detomidine,1TBDMS,isomer #1CC1=CC=CC(CC2=CN=CN2[Si](C)(C)C(C)(C)C)=C1C2174.5Semi standard non polar33892256
Detomidine,1TBDMS,isomer #1CC1=CC=CC(CC2=CN=CN2[Si](C)(C)C(C)(C)C)=C1C2102.4Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Detomidine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0670-2900000000-8ba524c959b883c9ecda2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Detomidine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Detomidine 10V, Positive-QTOFsplash10-000i-0900000000-0f8f38c05df0f8c98d312017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Detomidine 20V, Positive-QTOFsplash10-000i-0900000000-39f1a801ba925643f5102017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Detomidine 40V, Positive-QTOFsplash10-05mo-4900000000-657907c5462aa1a1cadc2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Detomidine 10V, Negative-QTOFsplash10-000i-0900000000-de51e91769533f1baf232017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Detomidine 20V, Negative-QTOFsplash10-000i-1900000000-01409404871e24d18c792017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Detomidine 40V, Negative-QTOFsplash10-014l-5900000000-17a9566856eeb1bf13a52017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Detomidine 10V, Positive-QTOFsplash10-000i-0900000000-f6ccc8b16f0705551f962021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Detomidine 20V, Positive-QTOFsplash10-000i-2900000000-67a15cc632a6d93d907a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Detomidine 40V, Positive-QTOFsplash10-0f96-9600000000-33da807a81d06a9565ad2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Detomidine 10V, Negative-QTOFsplash10-000i-0900000000-518da453fd1641c125492021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Detomidine 20V, Negative-QTOFsplash10-0aor-4900000000-66acc658a98a9d0d12482021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Detomidine 40V, Negative-QTOFsplash10-0693-3900000000-43595eaaac431de8ef3c2021-09-22Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB11556
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID50586
KEGG Compound IDC07450
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDetomidine
METLIN IDNot Available
PubChem Compound56032
PDB IDNot Available
ChEBI ID4466
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available