Hmdb loader
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-13 10:35:54 UTC
Update Date2021-09-14 15:00:09 UTC
HMDB IDHMDB0004087
Secondary Accession Numbers
  • HMDB04087
Metabolite Identification
Common Name1-Benzyl-1,2,3,4-tetrahydroisoquinoline
Description1-benzyl-1,2,3,4-tetrahydroisoquinoline (1BnTIQ) as a possible PD-eliciting neurotoxin and evaluated its characteristics relevant to Parkinson disease (PD). 1BnTIQ exist in mammals and is proposed as possible PD-eliciting neurotoxin. PD is believed to be induced by the interaction of genetic predisposition and environmental factors, and a type of neurotoxin is proposed to be one of the environmental factors. 1BnTIQ inhibits [3H] dopamine uptake in HEK293 cells which stably express dopamine transporter. 1BnTIQ also inhibits NADH-ubiquinone oxidoreductase (complex I) in the mitochondrial respiratory chain. 1BnTIQ decreases the dopamine content in the mesencephalon in both dose- and time-dependent manners and it irreversibly reduced the dopamine content. Furthermore, it causes morphological changes in tyrosine hydroxylase-positive cells in the mesencephalon and reduced the number of cells. (PMID 12440154 ).
Structure
Data?1582752298
Synonyms
ValueSource
(R,S)-TetrahydrobenzylisoquinolineChEBI
1,2,3,4-Tetrahydro-1-(phenylmethyl)isoquinolineChEBI
1BnTIQChEBI
(RS)-1-Benzyl-1,2,3,4-tetrahydroisoquinolineKegg
1,2,3,4-tetrahydro-1-(Phenylmethyl)isoquinoline, (+-)-isomerMeSH, HMDB
1,2,3,4-tetrahydro-1-(Phenylmethyl)isoquinoline, (R)-isomerMeSH, HMDB
1,2,3,4-tetrahydro-1-(Phenylmethyl)isoquinoline, (S)-isomerMeSH, HMDB
1,2,3,4-tetrahydro-1-(Phenylmethyl)isoquinoline hydrochlorideMeSH, HMDB
S49 IsoquinolineMeSH, HMDB
1-Benzyl-1,2,3,4-tetrahydroisoquinolineMeSH
Chemical FormulaC16H17N
Average Molecular Weight223.3129
Monoisotopic Molecular Weight223.136099549
IUPAC Name1-benzyl-1,2,3,4-tetrahydroisoquinoline
Traditional Name1BnTIQ
CAS Registry Number19716-56-4
SMILES
C(C1NCCC2=CC=CC=C12)C1=CC=CC=C1
InChI Identifier
InChI=1S/C16H17N/c1-2-6-13(7-3-1)12-16-15-9-5-4-8-14(15)10-11-17-16/h1-9,16-17H,10-12H2
InChI KeyYRYCIFUZSUMAAY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIsoquinolines and derivatives
Sub ClassBenzylisoquinolines
Direct ParentBenzylisoquinolines
Alternative Parents
Substituents
  • Benzylisoquinoline
  • Tetrahydroisoquinoline
  • Aralkylamine
  • Benzenoid
  • Monocyclic benzene moiety
  • Azacycle
  • Secondary amine
  • Secondary aliphatic amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
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
Water Solubility0.0035 g/LALOGPS
logP3.48ALOGPS
logP3.64ChemAxon
logS-4.8ALOGPS
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity71.65 m³·mol⁻¹ChemAxon
Polarizability26.2 ųChemAxon
Number of Rings3ChemAxon
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]+150.27431661259
DarkChem[M-H]-151.2731661259
DeepCCS[M-2H]-183.23330932474
DeepCCS[M+Na]+158.54730932474
AllCCS[M+H]+153.732859911
AllCCS[M+H-H2O]+149.632859911
AllCCS[M+NH4]+157.632859911
AllCCS[M+Na]+158.732859911
AllCCS[M-H]-159.532859911
AllCCS[M+Na-2H]-159.132859911
AllCCS[M+HCOO]-158.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1-Benzyl-1,2,3,4-tetrahydroisoquinolineC(C1NCCC2=CC=CC=C12)C1=CC=CC=C12741.7Standard polar33892256
1-Benzyl-1,2,3,4-tetrahydroisoquinolineC(C1NCCC2=CC=CC=C12)C1=CC=CC=C11944.0Standard non polar33892256
1-Benzyl-1,2,3,4-tetrahydroisoquinolineC(C1NCCC2=CC=CC=C12)C1=CC=CC=C11976.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1-Benzyl-1,2,3,4-tetrahydroisoquinoline,1TMS,isomer #1C[Si](C)(C)N1CCC2=CC=CC=C2C1CC1=CC=CC=C12045.4Semi standard non polar33892256
1-Benzyl-1,2,3,4-tetrahydroisoquinoline,1TMS,isomer #1C[Si](C)(C)N1CCC2=CC=CC=C2C1CC1=CC=CC=C12106.2Standard non polar33892256
1-Benzyl-1,2,3,4-tetrahydroisoquinoline,1TMS,isomer #1C[Si](C)(C)N1CCC2=CC=CC=C2C1CC1=CC=CC=C12589.9Standard polar33892256
1-Benzyl-1,2,3,4-tetrahydroisoquinoline,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCC2=CC=CC=C2C1CC1=CC=CC=C12264.9Semi standard non polar33892256
1-Benzyl-1,2,3,4-tetrahydroisoquinoline,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCC2=CC=CC=C2C1CC1=CC=CC=C12359.7Standard non polar33892256
1-Benzyl-1,2,3,4-tetrahydroisoquinoline,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCC2=CC=CC=C2C1CC1=CC=CC=C12743.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1-Benzyl-1,2,3,4-tetrahydroisoquinoline GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-2900000000-69767d6f6a91a5c24bd12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Benzyl-1,2,3,4-tetrahydroisoquinoline 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 - 1-Benzyl-1,2,3,4-tetrahydroisoquinoline 10V, Negative-QTOFsplash10-00di-0090000000-672b95459dab89c79e3c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Benzyl-1,2,3,4-tetrahydroisoquinoline 20V, Negative-QTOFsplash10-00di-0090000000-87a0dda1779b4676ba7c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Benzyl-1,2,3,4-tetrahydroisoquinoline 40V, Negative-QTOFsplash10-0059-1910000000-d2ecf13f470a7ba9cb0e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Benzyl-1,2,3,4-tetrahydroisoquinoline 10V, Negative-QTOFsplash10-00di-0090000000-279452a29859034561fa2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Benzyl-1,2,3,4-tetrahydroisoquinoline 20V, Negative-QTOFsplash10-00di-0090000000-939f38e3140d9ca30df62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Benzyl-1,2,3,4-tetrahydroisoquinoline 40V, Negative-QTOFsplash10-005c-2900000000-ed789626d72de391b6642021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Benzyl-1,2,3,4-tetrahydroisoquinoline 10V, Positive-QTOFsplash10-00di-0090000000-75679a6f444b9bd42db42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Benzyl-1,2,3,4-tetrahydroisoquinoline 20V, Positive-QTOFsplash10-05gl-3890000000-5df7dde54dbe0fe2b4fa2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Benzyl-1,2,3,4-tetrahydroisoquinoline 40V, Positive-QTOFsplash10-0006-9700000000-3f687e462c9cd0cc1ff22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Benzyl-1,2,3,4-tetrahydroisoquinoline 10V, Positive-QTOFsplash10-00di-0090000000-0e93eae718d771100a692021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Benzyl-1,2,3,4-tetrahydroisoquinoline 20V, Positive-QTOFsplash10-05fr-2960000000-a0da7d0090f88d3059992021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Benzyl-1,2,3,4-tetrahydroisoquinoline 40V, Positive-QTOFsplash10-0a4m-4900000000-148ae7c1169e2d0c08f02021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Cerebrospinal Fluid (CSF)
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.0017 (0.0013 - 0.0022) uMAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.0052 (0.0036-0.0068) uMAdult (>18 years old)Not SpecifiedParkinson's disease details
Associated Disorders and Diseases
Disease References
Parkinson's disease
  1. Kotake Y, Tasaki Y, Makino Y, Ohta S, Hirobe M: 1-Benzyl-1,2,3,4-tetrahydroisoquinoline as a parkinsonism-inducing agent: a novel endogenous amine in mouse brain and parkinsonian CSF. J Neurochem. 1995 Dec;65(6):2633-8. [PubMed:7595560 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023308
KNApSAcK IDNot Available
Chemspider ID88923
KEGG Compound IDC05201
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound98468
PDB IDNot Available
ChEBI ID16804
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000440
Good Scents IDNot Available
References
Synthesis ReferenceShinohara, Tatsumi; Takeda, Akira; Toda, Jun; Terasawa, Noriyo; Sano, Takehiro. A highly efficient synthesis of 1-methyl-, 1-benzyl-, and 1-phenyl-1,2,3,4-tetrahydroisoquinolines by a modified Pummerer reaction. Heterocycles (1997), 46 555-566.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kotake Y, Tasaki Y, Makino Y, Ohta S, Hirobe M: 1-Benzyl-1,2,3,4-tetrahydroisoquinoline as a parkinsonism-inducing agent: a novel endogenous amine in mouse brain and parkinsonian CSF. J Neurochem. 1995 Dec;65(6):2633-8. [PubMed:7595560 ]
  2. Kotake Y: [Tetrahydroisoquinoline derivatives as possible Parkinson's disease-inducing substances]. Yakugaku Zasshi. 2002 Nov;122(11):975-82. [PubMed:12440154 ]