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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-07-25 00:01:34 UTC

Update Date

2023-02-21 17:17:49 UTC

HMDB ID

HMDB0012489

Secondary Accession Numbers

HMDB12489

Metabolite Identification

Common Name

1,2,3,4-Tetrahydroisoquinoline

Description

Tetrahydroisoquinoline is a secondary amine with the chemical formula C9H11N.Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide.The tetrahydroisoquinoline skeleton is commonly encountered in pharmaceutical drugs, notably quaternary ammonium muscle relaxants. Tetrahydroisoquinoline derivatives may be formed in the body as metabolites of some drugs, and this was once thought to be involved in the development of alcoholism.This theory has now been discredited and is no longer generally accepted by the scientific community, but endogenous production of neurotoxic tetrahydroisoquinoline derivatives such as norsalsolinol continue to be investigated as possible causes for some conditions such as Parkinson's disease.{from wiki).

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1234-Tetrahydroisoquinoline	ChEMBL, HMDB
1234-tetrahydro-Isoquinoline	ChEMBL, HMDB
Tetrahydroisoquinoline	HMDB, MeSH
1,2,3,4-tetrahydro-2-Azanaphthalene	HMDB, MeSH
1,2,3,4-tetrahydro-2-Isoquinoline	HMDB
1,2,3,4-Tetrahydroleucoline	HMDB
HCL OF 1,2,3,4-Tetrahydroisoquinoline	MeSH, HMDB
3,4-Dihydro-1H-isoquinoline	MeSH

Chemical Formula

C₉H₁₁N

Average Molecular Weight

133.1903

Monoisotopic Molecular Weight

133.089149357

IUPAC Name

1,2,3,4-tetrahydroisoquinoline

Traditional Name

tetrahydroisoquinoline

CAS Registry Number

14099-81-1

SMILES

C1CC2=C(CN1)C=CC=C2

InChI Identifier

InChI=1S/C9H11N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-4,10H,5-7H2

InChI Key

UWYZHKAOTLEWKK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrahydroisoquinolines

Sub Class

Not Available

Direct Parent

Tetrahydroisoquinolines

Alternative Parents

Substituents

Tetrahydroisoquinoline
Aralkylamine
Benzenoid
Azacycle
Secondary amine
Secondary aliphatic amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Endogenous (HMDB: HMDB0012489)

Process

Not Available

Role

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	< -15 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.81 g/L	ALOGPS
logP	1.31	ALOGPS
logP	1.57	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Basic)	9.36	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	12.03 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	42.62 m³·mol⁻¹	ChemAxon
Polarizability	15.33 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	126.779	31661259
DarkChem	[M-H]-	123.78	31661259
DeepCCS	[M+H]+	130.2	30932474
DeepCCS	[M-H]-	126.768	30932474
DeepCCS	[M-2H]-	164.097	30932474
DeepCCS	[M+Na]+	139.177	30932474
AllCCS	[M+H]+	126.9	32859911
AllCCS	[M+H-H2O]+	122.0	32859911
AllCCS	[M+NH4]+	131.4	32859911
AllCCS	[M+Na]+	132.8	32859911
AllCCS	[M-H]-	128.5	32859911
AllCCS	[M+Na-2H]-	129.8	32859911
AllCCS	[M+HCOO]-	131.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,2,3,4-Tetrahydroisoquinoline	C1CC2=C(CN1)C=CC=C2	1838.9	Standard polar	33892256
1,2,3,4-Tetrahydroisoquinoline	C1CC2=C(CN1)C=CC=C2	1233.4	Standard non polar	33892256
1,2,3,4-Tetrahydroisoquinoline	C1CC2=C(CN1)C=CC=C2	1264.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1,2,3,4-Tetrahydroisoquinoline,1TMS,isomer #1	C[Si](C)(C)N1CCC2=CC=CC=C2C1	1428.5	Semi standard non polar	33892256
1,2,3,4-Tetrahydroisoquinoline,1TMS,isomer #1	C[Si](C)(C)N1CCC2=CC=CC=C2C1	1385.5	Standard non polar	33892256
1,2,3,4-Tetrahydroisoquinoline,1TMS,isomer #1	C[Si](C)(C)N1CCC2=CC=CC=C2C1	1736.3	Standard polar	33892256
1,2,3,4-Tetrahydroisoquinoline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCC2=CC=CC=C2C1	1670.3	Semi standard non polar	33892256
1,2,3,4-Tetrahydroisoquinoline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCC2=CC=CC=C2C1	1654.2	Standard non polar	33892256
1,2,3,4-Tetrahydroisoquinoline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCC2=CC=CC=C2C1	1941.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline EI-B (Non-derivatized)	splash10-001i-7900000000-880ecb945a866c58a869	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline EI-B (Non-derivatized)	splash10-001i-7900000000-880ecb945a866c58a869	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline GC-MS (Non-derivatized) - 70eV, Positive	splash10-100r-2900000000-241c80cb6dc81b9b83e0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline 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 - 1,2,3,4-Tetrahydroisoquinoline 10V, Positive-QTOF	splash10-001i-0900000000-9cda6a8e29a836be071a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline 20V, Positive-QTOF	splash10-00lr-1900000000-0fffb087a6b9e5f092fa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline 40V, Positive-QTOF	splash10-066u-9800000000-ed1397065d659994d996	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline 10V, Negative-QTOF	splash10-001i-0900000000-8b124bc9800fbbc9a3c2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline 20V, Negative-QTOF	splash10-001i-0900000000-7c43cb3e6b9cef43d221	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline 40V, Negative-QTOF	splash10-0uyi-3900000000-58d4ecc958f729594d6b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline 10V, Positive-QTOF	splash10-001i-1900000000-750b3fc0ed1857cd3d2e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline 20V, Positive-QTOF	splash10-001l-4900000000-c1118a9a9962f041fb34	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline 40V, Positive-QTOF	splash10-0006-9100000000-2ee9aad24737bda77796	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline 10V, Negative-QTOF	splash10-001i-0900000000-163cef49a8efd2ca85d5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline 20V, Negative-QTOF	splash10-001i-0900000000-7cb157b4702fa57056e6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline 40V, Negative-QTOF	splash10-0ge9-2900000000-53cc67b7ef90d1c880f4	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029096

KNApSAcK ID

Not Available

Chemspider ID

6779

KEGG Compound ID

Not Available

BioCyc ID

DIHYDRO-DIOH-BENZOATE

BiGG ID

Not Available

Wikipedia Link

Tetrahydroisoquinoline

METLIN ID

Not Available

PubChem Compound

7046

PDB ID

Not Available

ChEBI ID

114116

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 1,2,3,4-Tetrahydroisoquinoline (HMDB0012489)

MOL for HMDB0012489 (1,2,3,4-Tetrahydroisoquinoline)

3D MOL for HMDB0012489 (1,2,3,4-Tetrahydroisoquinoline)

3D SDF for HMDB0012489 (1,2,3,4-Tetrahydroisoquinoline)

3D-SDF for HMDB0012489 (1,2,3,4-Tetrahydroisoquinoline)

PDB for HMDB0012489 (1,2,3,4-Tetrahydroisoquinoline)

3D PDB for HMDB0012489 (1,2,3,4-Tetrahydroisoquinoline)

SMILES for HMDB0012489 (1,2,3,4-Tetrahydroisoquinoline)

INCHI for HMDB0012489 (1,2,3,4-Tetrahydroisoquinoline)

Structure for HMDB0012489 (1,2,3,4-Tetrahydroisoquinoline)

3D Structure for HMDB0012489 (1,2,3,4-Tetrahydroisoquinoline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra