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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 22:55:59 UTC
Update Date2021-09-26 23:17:47 UTC
HMDB IDHMDB0259938
Secondary Accession NumbersNone
Metabolite Identification
Common NameXylazine
DescriptionXylazine, also known as chanazine or bay 1470, belongs to the class of organic compounds known as m-xylenes. These are aromatic compounds that contain a m-xylene moiety, which is a monocyclic benzene carrying exactly two methyl groups at the 1- and 3-positions. Based on a literature review a significant number of articles have been published on Xylazine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Xylazine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Xylazine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
2-(2,6-Dimethylanilino)-5,6-dihydro-4H-1,3-thiazineChEBI
2-(2,6-Dimethylphenylamino)-4H-5,6-dihydro-1,3-thiazineChEBI
5,6-Dihydro-2-(2,6-xylidino)-4H-1,3-thiazineChEBI
BAY 1470ChEBI
ChanazineChEBI
N-(5,6-Dihydro-4H-1,3-thiazinyl)-2,6-xylidineChEBI
RompunChEBI
WH 7286ChEBI
XilazinaChEBI
XilazineChEBI
XylazinumChEBI
BAY va 1470MeSH
BAY-va 1470MeSH
BAYVa 1470MeSH
XylaxineMeSH
XylazinMeSH
XylazineMeSH
Xylazine hydrochlorideMeSH
Xylazine monohydrochlorideMeSH
Xylazine phosphate (1:1)MeSH
Chemical FormulaC12H16N2S
Average Molecular Weight220.33
Monoisotopic Molecular Weight220.103419697
IUPAC NameN-(2,6-dimethylphenyl)-5,6-dihydro-4H-1,3-thiazin-2-amine
Traditional Namexylazine
CAS Registry NumberNot Available
SMILES
CC1=CC=CC(C)=C1NC1=NCCCS1
InChI Identifier
InChI=1S/C12H16N2S/c1-9-5-3-6-10(2)11(9)14-12-13-7-4-8-15-12/h3,5-6H,4,7-8H2,1-2H3,(H,13,14)
InChI KeyBPICBUSOMSTKRF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as m-xylenes. These are aromatic compounds that contain a m-xylene moiety, which is a monocyclic benzene carrying exactly two methyl groups at the 1- and 3-positions.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassXylenes
Direct Parentm-Xylenes
Alternative Parents
Substituents
  • M-xylene
  • Aniline or substituted anilines
  • Meta-thiazine
  • Isothiourea
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic 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 PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP3.23ALOGPS
logP3.63ChemAxon
logS-2.9ALOGPS
pKa (Strongest Basic)6.94ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area24.39 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity68.82 m³·mol⁻¹ChemAxon
Polarizability24.76 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
AllCCS[M+H]+147.33832859911
AllCCS[M+H-H2O]+143.2632859911
AllCCS[M+Na]+152.22532859911
AllCCS[M+NH4]+151.13232859911
AllCCS[M-H]-152.59432859911
AllCCS[M+Na-2H]-152.8832859911
AllCCS[M+HCOO]-153.28832859911
DeepCCS[M+H]+149.86530932474
DeepCCS[M-H]-147.50730932474
DeepCCS[M-2H]-182.31630932474
DeepCCS[M+Na]+156.95830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
XylazineCC1=CC=CC(C)=C1NC1=NCCCS12639.3Standard polar33892256
XylazineCC1=CC=CC(C)=C1NC1=NCCCS12027.8Standard non polar33892256
XylazineCC1=CC=CC(C)=C1NC1=NCCCS11979.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Xylazine,1TMS,isomer #1CC1=CC=CC(C)=C1N(C1=NCCCS1)[Si](C)(C)C1964.1Semi standard non polar33892256
Xylazine,1TMS,isomer #1CC1=CC=CC(C)=C1N(C1=NCCCS1)[Si](C)(C)C1899.9Standard non polar33892256
Xylazine,1TMS,isomer #1CC1=CC=CC(C)=C1N(C1=NCCCS1)[Si](C)(C)C2860.8Standard polar33892256
Xylazine,1TBDMS,isomer #1CC1=CC=CC(C)=C1N(C1=NCCCS1)[Si](C)(C)C(C)(C)C2143.6Semi standard non polar33892256
Xylazine,1TBDMS,isomer #1CC1=CC=CC(C)=C1N(C1=NCCCS1)[Si](C)(C)C(C)(C)C2151.9Standard non polar33892256
Xylazine,1TBDMS,isomer #1CC1=CC=CC(C)=C1N(C1=NCCCS1)[Si](C)(C)C(C)(C)C2952.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Xylazine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-2920000000-828d7051a7615e6674a12021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xylazine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Xylazine LC-ESI-qTof , Positive-QTOFsplash10-0229-3920000000-b822873abe0cc77b65002017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xylazine , positive-QTOFsplash10-0229-3920000000-b822873abe0cc77b65002017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xylazine 10V, Positive-QTOFsplash10-00di-5190000000-4a2426f255239ce7000f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xylazine 20V, Positive-QTOFsplash10-00di-2890000000-e9d742e119aa7bebbf652016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xylazine 40V, Positive-QTOFsplash10-0006-9100000000-874da3019fe4c2a17d312016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xylazine 10V, Negative-QTOFsplash10-0159-1940000000-9ca9274ae36bfc2ed7402016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xylazine 20V, Negative-QTOFsplash10-03ka-2900000000-ab30d3e7c0d334cfbb332016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xylazine 40V, Negative-QTOFsplash10-0c0c-9700000000-d509da0c01ee84ed9b7f2016-08-03Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB11477
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5505
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkXylazine
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID92386
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 References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]