Human Metabolome Database Version 3.5

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Showing metabocard for 1,2,3,4-tetrahydroisoquinoline (HMDB12489)

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Urine

Record Information

Version

3.5

Creation Date

2009-07-24 18:01:34 -0600

Update Date

2013-02-08 17:29:14 -0700

HMDB ID

HMDB12489

Secondary Accession Numbers

None

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

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Tetrahydroisoquinoline
1,2,3,4-Tetrahydro-2-azanaphthalene
1,2,3,4-Tetrahydro-2-isoquinoline
1,2,3,4-Tetrahydroisoquinoline
1,2,3,4-Tetrahydroleucoline

Chemical Formula

C₉H₁₁N

Average Molecular Weight

133.1903

Monoisotopic Molecular Weight

133.089149357

IUPAC Name

1,2,3,4-tetrahydroisoquinoline

Traditional IUPAC 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

Kingdom

Organic Compounds

Super Class

Aromatic Heteropolycyclic Compounds

Class

Isoquinolines

Sub Class

N/A

Other Descriptors

Aromatic Heteropolycyclic Compounds

Substituents

Secondary Aliphatic Amine (Dialkylamine)

Direct Parent

Isoquinolines

Ontology

Status

Expected and Not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Solid

Experimental 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

Predicted Properties

Property	Value	Source
LogP	1.31	ALOGPS
LogP	1.57	ChemAxon
LogS	-1.44	ALOGPS
pKa (strongest basic)	9.36	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	12.03 A²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	42.62	ChemAxon
Polarizability	15.33	ChemAxon
Formal Charge	0	ChemAxon
Physiological Charge	1	ChemAxon