Page last updated: 2024-12-07

1,2,3,4-tetrahydro-1-(phenylmethyl)isoquinoline

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

1,2,3,4-tetrahydro-1-(phenylmethyl)isoquinoline, also known as **1-benzyltetrahydroisoquinoline (1-BnTIQ)**, is a **synthetic alkaloid** that holds significance in several areas of research.

**Structure and Properties:**

* 1-BnTIQ is a **heterocyclic compound** with a fused isoquinoline ring system.
* It consists of a tetrahydroisoquinoline core with a benzyl group attached at the 1-position.
* It is a **colorless oil** that is soluble in organic solvents.

**Importance in Research:**

1. **Pharmacology and Neuroscience:**
* **Dopamine Receptor Agonist:** 1-BnTIQ is known to be a **partial agonist at dopamine receptors**, particularly D1 and D2 receptors. This property makes it a valuable tool for studying dopamine signaling in the brain and its implications in diseases like Parkinson's disease and schizophrenia.
* **Neuroprotective Effects:** 1-BnTIQ has shown **neuroprotective activity in animal models**, suggesting its potential for treating neurodegenerative disorders.
* **Antidepressant Activity:** Some studies have indicated that 1-BnTIQ might possess **antidepressant properties**, although further research is needed.

2. **Chemical Synthesis and Drug Development:**
* **Scaffold for New Drugs:** The tetrahydroisoquinoline structure is a common motif found in several pharmaceutical compounds. 1-BnTIQ serves as a **synthetic precursor and building block** for developing novel drugs targeting various therapeutic areas.
* **Analogue Studies:** Researchers synthesize and investigate analogues of 1-BnTIQ to explore structure-activity relationships and identify compounds with enhanced pharmacological properties.

3. **Analytical Chemistry:**
* **Synthetic Standards:** 1-BnTIQ is used as a **reference standard** in analytical techniques such as chromatography and mass spectrometry for the identification and quantification of related compounds.

**Limitations and Safety:**

* 1-BnTIQ has **limited clinical use** due to its potential side effects, including central nervous system effects and cardiovascular complications.
* **Extensive research is needed** to fully understand its therapeutic potential and develop safe and effective clinical applications.

**Overall:**

1,2,3,4-tetrahydro-1-(phenylmethyl)isoquinoline (1-BnTIQ) is an important research compound with potential applications in pharmacology, neuroscience, and drug development. Its unique chemical structure and biological activity make it a valuable tool for exploring dopamine signaling, neuroprotection, and the development of novel drugs targeting various therapeutic areas. However, further research is crucial to address its safety concerns and optimize its therapeutic potential for clinical use.

1,2,3,4-tetrahydro-1-(phenylmethyl)isoquinoline: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID98468
CHEMBL ID21640
CHEBI ID16804
SCHEMBL ID4160731
MeSH IDM0225551

Synonyms (43)

Synonym
nsc-140739
nsc140739
19716-56-4
rac-(1r)-1-benzyl-1,2,3,4-tetrahydroisoquinoline
1,2,3,4-tetrahydro-1-(phenylmethyl)isoquinoline
1bntiq
CHEBI:16804 ,
1-benzyl-1,2,3,4-tetrahydroisoquinoline
isoquinoline, 1-benzyl-1,2,3,4-tetrahydro-,
(r,s)-tetrahydrobenzylisoquinoline
(rs)-1-benzyl-1,2,3,4-tetrahydroisoquinoline
C05201
CHEMBL21640 ,
s49 isoquinoline
F0909-0437
bdbm50017041
A4312
1-benzyl-1,2,3,4-tetrahydro-isoquinoline
1-benzyl-1,2,3,4-tetrahydroisoqu-inoline
AKOS005208313
x4s06gk4kn ,
ai3-61894
unii-x4s06gk4kn
isoquinoline, 1,2,3,4-tetrahydro-1-(phenylmethyl)-
nsc 140739
FT-0682358
J-504243
SCHEMBL4160731
1-benzyl-1,2,3,4-tetrahydroisoquinoline #
ar-r 15209
isoquinoline, 1-benzyl-1,2,3,4-tetrahydro-
J432.285A ,
mfcd00024130
benzyltetrahydroisoquinoline
SR-01000009857-1
sr-01000009857
DTXSID70864898
Q27102081
AMY36471
EN300-120055
isoquinoline,1,2,3,4-tetrahydro-1-(phenylmethyl)-
HY-W029659
CS-0073683

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" We suggest that 1-benzyl-1,2,3,4-tetrahydroisoquinoline is toxic to tyrosine hydroxylase-positive cells in the ventral mesencephalon and that it is correlated with the integral of the concentration by time of exposure."( Neurotoxicity of an endogenous brain amine, 1-benzyl-1,2,3,4-tetrahydroisoquinoline, in organotypic slice co-culture of mesencephalon and striatum.
Kanazawa, I; Kotake, Y; Ohta, S; Sakurai, M, 2003
)
0.32
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
benzyltetrahydroisoquinoline
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Solute carrier family 22 member 1 Homo sapiens (human)IC50 (µMol)82.10000.21005.553710.0000AID1442001
Lysosomal Pro-X carboxypeptidaseHomo sapiens (human)IC50 (µMol)1.00000.00530.60331.9000AID157589
Sigma non-opioid intracellular receptor 1Rattus norvegicus (Norway rat)IC50 (µMol)0.43000.00030.55704.2000AID204608
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (38)

Processvia Protein(s)Taxonomy
xenobiotic metabolic processSolute carrier family 22 member 1 Homo sapiens (human)
neurotransmitter transportSolute carrier family 22 member 1 Homo sapiens (human)
serotonin transportSolute carrier family 22 member 1 Homo sapiens (human)
establishment or maintenance of transmembrane electrochemical gradientSolute carrier family 22 member 1 Homo sapiens (human)
organic cation transportSolute carrier family 22 member 1 Homo sapiens (human)
quaternary ammonium group transportSolute carrier family 22 member 1 Homo sapiens (human)
prostaglandin transportSolute carrier family 22 member 1 Homo sapiens (human)
monoamine transportSolute carrier family 22 member 1 Homo sapiens (human)
putrescine transportSolute carrier family 22 member 1 Homo sapiens (human)
spermidine transportSolute carrier family 22 member 1 Homo sapiens (human)
acetylcholine transportSolute carrier family 22 member 1 Homo sapiens (human)
dopamine transportSolute carrier family 22 member 1 Homo sapiens (human)
norepinephrine transportSolute carrier family 22 member 1 Homo sapiens (human)
thiamine transportSolute carrier family 22 member 1 Homo sapiens (human)
xenobiotic transportSolute carrier family 22 member 1 Homo sapiens (human)
epinephrine transportSolute carrier family 22 member 1 Homo sapiens (human)
serotonin uptakeSolute carrier family 22 member 1 Homo sapiens (human)
norepinephrine uptakeSolute carrier family 22 member 1 Homo sapiens (human)
thiamine transmembrane transportSolute carrier family 22 member 1 Homo sapiens (human)
metanephric proximal tubule developmentSolute carrier family 22 member 1 Homo sapiens (human)
purine-containing compound transmembrane transportSolute carrier family 22 member 1 Homo sapiens (human)
dopamine uptakeSolute carrier family 22 member 1 Homo sapiens (human)
monoatomic cation transmembrane transportSolute carrier family 22 member 1 Homo sapiens (human)
transport across blood-brain barrierSolute carrier family 22 member 1 Homo sapiens (human)
(R)-carnitine transmembrane transportSolute carrier family 22 member 1 Homo sapiens (human)
acyl carnitine transmembrane transportSolute carrier family 22 member 1 Homo sapiens (human)
spermidine transmembrane transportSolute carrier family 22 member 1 Homo sapiens (human)
cellular detoxificationSolute carrier family 22 member 1 Homo sapiens (human)
xenobiotic transport across blood-brain barrierSolute carrier family 22 member 1 Homo sapiens (human)
regulation of thyroid hormone mediated signaling pathwayLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
plasma kallikrein-kinin cascadeLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
proteolysisLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
glucose homeostasisLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
energy homeostasisLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
regulation of reactive oxygen species metabolic processLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
angiogenesis involved in wound healingLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
negative regulation of systemic arterial blood pressureLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
regulation of blood vessel endothelial cell migrationLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (21)

Processvia Protein(s)Taxonomy
acetylcholine transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
neurotransmitter transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
dopamine:sodium symporter activitySolute carrier family 22 member 1 Homo sapiens (human)
norepinephrine:sodium symporter activitySolute carrier family 22 member 1 Homo sapiens (human)
protein bindingSolute carrier family 22 member 1 Homo sapiens (human)
monoamine transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
secondary active organic cation transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
organic anion transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
organic cation transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
prostaglandin transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
pyrimidine nucleoside transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
thiamine transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
putrescine transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
spermidine transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
quaternary ammonium group transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
toxin transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
identical protein bindingSolute carrier family 22 member 1 Homo sapiens (human)
xenobiotic transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
(R)-carnitine transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
serine-type carboxypeptidase activityLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
protein bindingLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
dipeptidyl-peptidase activityLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (12)

Processvia Protein(s)Taxonomy
plasma membraneSolute carrier family 22 member 1 Homo sapiens (human)
basal plasma membraneSolute carrier family 22 member 1 Homo sapiens (human)
membraneSolute carrier family 22 member 1 Homo sapiens (human)
basolateral plasma membraneSolute carrier family 22 member 1 Homo sapiens (human)
apical plasma membraneSolute carrier family 22 member 1 Homo sapiens (human)
lateral plasma membraneSolute carrier family 22 member 1 Homo sapiens (human)
presynapseSolute carrier family 22 member 1 Homo sapiens (human)
plasma membraneLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
azurophil granule membraneLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
intracellular membrane-bounded organelleLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
basal part of cellLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
extracellular exosomeLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
ficolin-1-rich granule membraneLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (12)

Assay IDTitleYearJournalArticle
AID65904The compound has been evaluated for its binding affinity towards Dopamine receptor D2 by displacing the radioligand [3H]YM-09151-2 (0.5 nM) in rat striatal synaptosomes.2000Bioorganic & medicinal chemistry letters, Aug-07, Volume: 10, Issue:15
Inhibition of dopamine receptors by endogenous amines: binding to striatal receptors and pharmacological effects on locomotor activity.
AID1442004Competitive inhibition of human OCT1 expressed in HEK293 cells assessed as decrease in uptake of ASP+ after 2 mins by Lineweaver-Burk plot analysis2017Journal of medicinal chemistry, 04-13, Volume: 60, Issue:7
Discovery of Competitive and Noncompetitive Ligands of the Organic Cation Transporter 1 (OCT1; SLC22A1).
AID17273Dissociation constant was reported2000Bioorganic & medicinal chemistry letters, Aug-07, Volume: 10, Issue:15
Inhibition of dopamine receptors by endogenous amines: binding to striatal receptors and pharmacological effects on locomotor activity.
AID157587Compound was tested for induction of phencyclidine (PCP) like stereotyped behavior1989Journal of medicinal chemistry, Jun, Volume: 32, Issue:6
Phencyclidine-like effects of tetrahydroisoquinolines and related compounds.
AID1442001Inhibition of human OCT1 expressed in HEK293 cells assessed as decrease in uptake of ASP+ after 2 mins by fluorescence assay2017Journal of medicinal chemistry, 04-13, Volume: 60, Issue:7
Discovery of Competitive and Noncompetitive Ligands of the Organic Cation Transporter 1 (OCT1; SLC22A1).
AID65499The compound has been evaluated for its binding affinity towards Dopamine transporter by displacing the radioligand [3H]GBR-12935 (1.0 nM) in rat striatal synaptosomes.2000Bioorganic & medicinal chemistry letters, Aug-07, Volume: 10, Issue:15
Inhibition of dopamine receptors by endogenous amines: binding to striatal receptors and pharmacological effects on locomotor activity.
AID157589Inhibition of [3H]1-[1-(2-thienyl) piperidine ([3H]TCP) binding to phencyclidine receptor1989Journal of medicinal chemistry, Jun, Volume: 32, Issue:6
Phencyclidine-like effects of tetrahydroisoquinolines and related compounds.
AID157586Compound was tested for induction of phencyclidine (PCP) like ataxia behavior1989Journal of medicinal chemistry, Jun, Volume: 32, Issue:6
Phencyclidine-like effects of tetrahydroisoquinolines and related compounds.
AID1442006Ratio of Kii for human OCT1-ASP+-inhibitor complex to Kis for human OCT1-inhibitor complex by Lineweaver-Burk plot analysis2017Journal of medicinal chemistry, 04-13, Volume: 60, Issue:7
Discovery of Competitive and Noncompetitive Ligands of the Organic Cation Transporter 1 (OCT1; SLC22A1).
AID204608Inhibition of [3H]- N-allylnormetazocine ([3H]NANM) binding to sigma receptor1989Journal of medicinal chemistry, Jun, Volume: 32, Issue:6
Phencyclidine-like effects of tetrahydroisoquinolines and related compounds.
AID61650The compound has been evaluated for its binding affinity towards Dopamine receptor D1 by displacing the radioligand [3H]SCH-23390 (1.5 nM) in rat striatal synaptosomes.2000Bioorganic & medicinal chemistry letters, Aug-07, Volume: 10, Issue:15
Inhibition of dopamine receptors by endogenous amines: binding to striatal receptors and pharmacological effects on locomotor activity.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (29)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (3.45)18.7374
1990's6 (20.69)18.2507
2000's12 (41.38)29.6817
2010's9 (31.03)24.3611
2020's1 (3.45)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.80

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.80 (24.57)
Research Supply Index3.43 (2.92)
Research Growth Index5.24 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.80)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (3.33%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other29 (96.67%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]