TETRAHYDROISOQUINOLINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H11N
Molecular Weight	133.1903
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C1CC2=C(CN1)C=CC=C2

InChI

InChIKey=UWYZHKAOTLEWKK-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C9H11N
Molecular Weight	133.1903
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22110343 | https://www.ncbi.nlm.nih.gov/pubmed/5460776

The tetrahydroisoquinoline nucleus is present in a number of compounds and drugs. Tetrahydroisoquinolines (THIQs), which belong to a group of cyclized condensation adducts of biogenic amines with aldehydes, are referred to as mammalian alkaloids. They include salsolinol (1-methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline; SAL) and tetrahydropapaveroline (6,7-dihydroxy-1-(3',4'-dihydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline; THP) that are derived from dopamine through condensation with acetaldehyde and dopaldehyde (3,4-dihydroxyphenylacetaldehyde), respectively. THP is a putative dopaminergic neurotoxin that is implicated in the pathology of Parkinson's disease. It is known that THP is detected at a high level in the brain and the urine of parkinsonian patients under 3,4-dihydroxyphenylalanine (L-DOPA) therapy. In addition, significant levels of THP have also been detected in the brain after ethanol uptake and/or L-DOPA treatment, and this endogenous alkaloid is considered to account for the neurobehavioral abnormalities associated with alcoholism and may act as a neurotransmitter

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Phenylethanolamine N-methyltransferase 3 Target ID: CHEMBL2331 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10354406 \| https://www.ncbi.nlm.nih.gov/pubmed/17126018	Inhibitor 8504		5.8 µM [Ki]
Monoamine oxidase B 75 Target ID: CHEMBL2039 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2296014	Inhibitor 8504		15.0 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Effect of acute administration of 1,2,3,4-tetrahydroisoquinoline on the levels of glutathione and reactive oxygen species, and on the enzymatic activity of gamma-glutamyl transpeptidase in dopaminergic structures of rat brain.	2001	11738255
Chromatographic separation and spectrometric identification of the oxidation products from a tetrahydro-isoquinoline alkaloid.	2001 May	11275426
Enantioselective synthesis of the AB-ring system of the antitumor antibiotic tetrazomine.	2001 May 4	11325279
Evaluation of neurotoxicity of TIQ and MPTP and of parkinsonism-preventing effect of 1-MeTIQ by in vivo measurement of pre-synaptic dopamine transporters and post-synaptic dopamine D(2) receptors in the mouse striatum.	2001 Nov	11723179
Synthesis of isoquinolines and pyridines by the palladium-catalyzed iminoannulation of internal alkynes.	2001 Nov 30	11722203
Synthesis, biological activity and molecular modeling studies of 1,2,3,4-tetrahydroisoquinoline derivatives as conformationally constrained analogues of KN62, a potent antagonist of the P2X7-receptor containing a tyrosine moiety.	2002	12040970
Two optically active isoquinoline derivatives.	2002 Aug	12154312
The influence of substitution at aromatic part of 1,2,3,4-tetrahydroisoquinoline on in vitro and in vivo 5-HT(1A)/5-HT(2A) receptor activities of its 1-adamantoyloaminoalkyl derivatives.	2002 Jan	11738610
Comparison of the inhibition of human and Trypanosoma cruzi prolyl endopeptidases.	2002 Jun	11937331
Selective dopaminergic neurotoxicity of isoquinoline derivatives related to Parkinson's disease: studies using heterologous expression systems of the dopamine transporter.	2002 Mar 1	11911843
Further characterization of the stimulus properties of 5,6,7,8-tetrahydro-1,3-dioxolo[4,5-g]isoquinoline.	2002 May	11900809
Tetrahydroisoquinoline derivatives of enkephalins: synthesis and properties.	2002 May 15	12034373
In vitro interaction between ecteinascidin 743 (ET-743) and radiation, in relation to its cell cycle effects.	2003 Dec 15	14676811
Synthetic studies on ecteinascidin 743: rapid access to the fully functionalized tetrahydroisoquinoline with a bridged 10-membered sulfur containing macrocycle.	2003 Dec 7	14680229
Specific nonpeptide inhibitors of puromycin-sensitive aminopeptidase with a 2,4(1H,3H)-quinazolinedione skeleton.	2003 Nov	14600372
Intermolecular, markovnikov hydroamination of vinylarenes with alkylamines.	2003 Nov 26	14624571
Organolathanide-catalyzed regioselective intermolecular hydroamination of alkenes, alkynes, vinylarenes, di- and trivinylarenes, and methylenecyclopropanes. Scope and mechanistic comparison to intramolecular cyclohydroaminations.	2003 Oct 15	14531704
Synthesis and pharmacological evaluation of 1-oxo-2-(3-piperidyl)-1,2,3,4- tetrahydroisoquinolines and related analogues as a new class of specific bradycardic agents possessing I(f) channel inhibitory activity.	2003 Oct 23	14561092
Comparison of four modulators of drug metabolism as protectants against the hepatotoxicity of the novel antitumor drug yondelis (ET-743) in the female rat and in hepatocytes in vitro.	2004 Apr	14669039
Carbazates as potent inhibitors of hormone-sensitive lipase.	2004 Apr 5	15026062
Tetrahydroisoquinoline derivatives as melatonin MT2 receptor antagonists.	2004 Dec 6	15501061
Potential roles of NF-kappaB and ERK1/2 in cytoprotection against oxidative cell death induced by tetrahydropapaveroline.	2004 May 1	15082072
Discovery of novel tetrahydroisoquinoline derivatives as potent and selective factor Xa inhibitors.	2005 Jan 3	15582437

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Other

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:36:11 GMT 2025` Edited by `admin` on `Mon Mar 31 17:36:11 GMT 2025`
Record UNII	56W89FBX3E
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TETRAHYDROISOQUINOLINE

Systematic Name

English

NSC-15312

Preferred Name

English

1,2,3,4-TETRAHYDROISOQUINOLINE

Systematic Name

English

ISOQUINOLINE, 1,2,3,4-TETRAHYDRO-

Systematic Name

English

3,4-DIHYDRO-1H-ISOQUINOLINE

Systematic Name

English

1,2,3,4-TETRAHYDRO-2-AZANAPHTHALENE

Systematic Name

English

Code System Code Type Description

ECHA (EC/EINECS)

202-050-0