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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:45:08 UTC

Update Date

2023-02-21 17:29:00 UTC

HMDB ID

HMDB0041872

Secondary Accession Numbers

HMDB41872

Metabolite Identification

Common Name

Detomidine

Description

A 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 09131211452D          

 14 15  0  0  0  0            999 V2000
    0.8212    6.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078    6.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5356    4.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5356    5.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8212    4.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078    4.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0597    3.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0203    2.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8212    6.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1067    5.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1067    4.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1953    2.2581    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2752    3.0428    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  9  1  1  0  0  0  0
  9  4  1  0  0  0  0
 10  2  1  0  0  0  0
 10  9  2  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 11 10  1  0  0  0  0
 12  6  1  0  0  0  0
 12  7  2  0  0  0  0
 13  7  1  0  0  0  0
 13  8  2  0  0  0  0
 14  8  1  0  0  0  0
 14 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041872

> <DATABASE_NAME>
hmdb

> <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_KEY>
RHDJRPPFURBGLQ-UHFFFAOYSA-N

> <FORMULA>
C12H14N2

> <MOLECULAR_WEIGHT>
186.253

> <EXACT_MASS>
186.115698458

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
21.167011644219404

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(2,3-dimethylphenyl)methyl]-1H-imidazole

> <ALOGPS_LOGP>
2.52

> <JCHEM_LOGP>
2.7375062623333335

> <ALOGPS_LOGS>
-2.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.261831991098738

> <JCHEM_PKA_STRONGEST_BASIC>
7.14565089708393

> <JCHEM_POLAR_SURFACE_AREA>
28.68

> <JCHEM_REFRACTIVITY>
58.863899999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.55e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
detomidine

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         0                                  
HETATM    1  C   UNK     0       1.533  12.745   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.135  11.205   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.866   8.895   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.866  10.435   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.533   8.125   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.135   8.125   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.111   5.680   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.905   4.215   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.533  11.205   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.199  10.435   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.199   8.895   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.135   6.585   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -0.365   4.215   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0      -2.380   5.680   0.000  0.00  0.00           N+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3    4    5                                                       
CONECT    4    3    9                                                       
CONECT    5    3   11                                                       
CONECT    6   11   12                                                       
CONECT    7   12   13                                                       
CONECT    8   13   14                                                       
CONECT    9    1    4   10                                                  
CONECT   10    2    9   11                                                  
CONECT   11    5    6   10                                                  
CONECT   12    6    7   14                                                  
CONECT   13    7    8                                                       
CONECT   14    8   12                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

COMPND    HMDB0041872
HETATM    1  C1  UNL     1       3.743  -0.350  -0.080  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.347   0.143   0.193  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.131   1.174   1.090  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.838   1.605   1.321  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.219   1.011   0.661  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.011  -0.019  -0.237  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.099  -0.693  -0.972  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.432  -0.152  -0.648  1.00  0.00           C  
HETATM    9  C9  UNL     1      -3.221  -0.639   0.373  1.00  0.00           C  
HETATM   10  N1  UNL     1      -4.342   0.106   0.346  1.00  0.00           N  
HETATM   11  C10 UNL     1      -4.298   1.027  -0.629  1.00  0.00           C  
HETATM   12  N2  UNL     1      -3.110   0.852  -1.233  1.00  0.00           N  
HETATM   13  C11 UNL     1       1.275  -0.444  -0.463  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.590  -1.556  -1.421  1.00  0.00           C  
HETATM   15  H1  UNL     1       3.865  -1.407   0.205  1.00  0.00           H  
HETATM   16  H2  UNL     1       3.895  -0.256  -1.186  1.00  0.00           H  
HETATM   17  H3  UNL     1       4.443   0.287   0.468  1.00  0.00           H  
HETATM   18  H4  UNL     1       2.984   1.623   1.595  1.00  0.00           H  
HETATM   19  H5  UNL     1       0.696   2.422   2.036  1.00  0.00           H  
HETATM   20  H6  UNL     1      -1.227   1.357   0.849  1.00  0.00           H  
HETATM   21  H7  UNL     1      -1.085  -1.778  -0.747  1.00  0.00           H  
HETATM   22  H8  UNL     1      -0.923  -0.565  -2.070  1.00  0.00           H  
HETATM   23  H9  UNL     1      -3.012  -1.456   1.074  1.00  0.00           H  
HETATM   24  H10 UNL     1      -5.078   1.763  -0.871  1.00  0.00           H  
HETATM   25  H11 UNL     1      -2.797   1.435  -2.039  1.00  0.00           H  
HETATM   26  H12 UNL     1       1.833  -1.085  -2.400  1.00  0.00           H  
HETATM   27  H13 UNL     1       0.747  -2.256  -1.513  1.00  0.00           H  
HETATM   28  H14 UNL     1       2.467  -2.147  -1.084  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3    3   13
CONECT    3    4   18
CONECT    4    5    5   19
CONECT    5    6   20
CONECT    6    7   13   13
CONECT    7    8   21   22
CONECT    8    9    9   12
CONECT    9   10   23
CONECT   10   11   11
CONECT   11   12   24
CONECT   12   25
CONECT   13   14
CONECT   14   26   27   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-4-((S)-alpha,2,3-Trimethylbenzyl)imidazole	HMDB
4-[(1S)-1-(2,3-Dimethylphenyl)ethyl]-1H-imidazole	HMDB
Dexdor (T)	HMDB
Dexmedetomidina	HMDB
Dexmedetomidine	HMDB
Dexmedetomidinum	HMDB
Medetomidine	HMDB
MPV 1440	HMDB
Detomidine hydrochloride	HMDB
Detomidine monohydrochloride	HMDB

Chemical Formula

C₁₂H₁₄N₂

Average Molecular Weight

186.253

Monoisotopic Molecular Weight

186.115698458

IUPAC Name

5-[(2,3-dimethylphenyl)methyl]-1H-imidazole

Traditional Name

detomidine

CAS Registry Number

76631-46-4

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 Key

RHDJRPPFURBGLQ-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Xylenes

Direct Parent

o-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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0041872)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	146.8	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.66 g/L	ALOGPS
logP	2.52	ALOGPS
logP	2.74	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	13.26	ChemAxon
pKa (Strongest Basic)	7.15	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	28.68 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	58.86 m³·mol⁻¹	ChemAxon
Polarizability	21.17 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	142.548	31661259
DarkChem	[M-H]-	142.715	31661259
DeepCCS	[M+H]+	142.606	30932474
DeepCCS	[M-H]-	140.21	30932474
DeepCCS	[M-2H]-	175.098	30932474
DeepCCS	[M+Na]+	149.991	30932474
AllCCS	[M+H]+	139.2	32859911
AllCCS	[M+H-H2O]+	134.6	32859911
AllCCS	[M+NH4]+	143.4	32859911
AllCCS	[M+Na]+	144.6	32859911
AllCCS	[M-H]-	144.5	32859911
AllCCS	[M+Na-2H]-	144.8	32859911
AllCCS	[M+HCOO]-	145.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Detomidine	CC1=C(C)C(CC2=CN=CN2)=CC=C1	2603.9	Standard polar	33892256
Detomidine	CC1=C(C)C(CC2=CN=CN2)=CC=C1	1810.5	Standard non polar	33892256
Detomidine	CC1=C(C)C(CC2=CN=CN2)=CC=C1	1942.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Detomidine,1TMS,isomer #1	CC1=CC=CC(CC2=CN=CN2[Si](C)(C)C)=C1C	1918.8	Semi standard non polar	33892256
Detomidine,1TMS,isomer #1	CC1=CC=CC(CC2=CN=CN2[Si](C)(C)C)=C1C	1906.6	Standard non polar	33892256
Detomidine,1TBDMS,isomer #1	CC1=CC=CC(CC2=CN=CN2[Si](C)(C)C(C)(C)C)=C1C	2174.5	Semi standard non polar	33892256
Detomidine,1TBDMS,isomer #1	CC1=CC=CC(CC2=CN=CN2[Si](C)(C)C(C)(C)C)=C1C	2102.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Detomidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0670-2900000000-8ba524c959b883c9ecda	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Detomidine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Detomidine 10V, Positive-QTOF	splash10-000i-0900000000-0f8f38c05df0f8c98d31	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Detomidine 20V, Positive-QTOF	splash10-000i-0900000000-39f1a801ba925643f510	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Detomidine 40V, Positive-QTOF	splash10-05mo-4900000000-657907c5462aa1a1cadc	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Detomidine 10V, Negative-QTOF	splash10-000i-0900000000-de51e91769533f1baf23	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Detomidine 20V, Negative-QTOF	splash10-000i-1900000000-01409404871e24d18c79	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Detomidine 40V, Negative-QTOF	splash10-014l-5900000000-17a9566856eeb1bf13a5	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Detomidine 10V, Positive-QTOF	splash10-000i-0900000000-f6ccc8b16f0705551f96	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Detomidine 20V, Positive-QTOF	splash10-000i-2900000000-67a15cc632a6d93d907a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Detomidine 40V, Positive-QTOF	splash10-0f96-9600000000-33da807a81d06a9565ad	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Detomidine 10V, Negative-QTOF	splash10-000i-0900000000-518da453fd1641c12549	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Detomidine 20V, Negative-QTOF	splash10-0aor-4900000000-66acc658a98a9d0d1248	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Detomidine 40V, Negative-QTOF	splash10-0693-3900000000-43595eaaac431de8ef3c	2021-09-22	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB11556

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

50586

KEGG Compound ID

C07450

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Detomidine

METLIN ID

Not Available

PubChem Compound

56032

PDB ID

Not Available

ChEBI ID

4466

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Detomidine (HMDB0041872)

MOL for HMDB0041872 (Detomidine)

3D MOL for HMDB0041872 (Detomidine)

3D SDF for HMDB0041872 (Detomidine)

3D-SDF for HMDB0041872 (Detomidine)

PDB for HMDB0041872 (Detomidine)

3D PDB for HMDB0041872 (Detomidine)

SMILES for HMDB0041872 (Detomidine)

INCHI for HMDB0041872 (Detomidine)

Structure for HMDB0041872 (Detomidine)

3D Structure for HMDB0041872 (Detomidine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra