Page last updated: 2024-12-05

n-methylquipazine

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

Description

N-methylquipazine (NMQ) is a synthetic derivative of the natural alkaloid quipazine. It acts as a potent, non-selective 5-HT receptor agonist, exhibiting high affinity for 5-HT1A, 5-HT2A, and 5-HT2C receptors. NMQ has been studied extensively for its anxiolytic, antidepressant, and procognitive properties in animal models. Its unique pharmacological profile, including its ability to modulate both serotonergic and dopaminergic systems, has made it a valuable tool in understanding the role of serotonin in various neurological and psychiatric conditions. NMQ has also been investigated for its potential therapeutic applications in treating conditions such as anxiety, depression, and cognitive impairment. Its synthesis involves a series of chemical reactions starting from readily available starting materials.'

N-methylquipazine: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

N-methylquipazine : An aminoquinoline that consists of quinoline in which the hydrogen at position 2 is substituted by a 4-methylpiperazin-1-yl group. A 5-HT3 agonist. Has almost the same affinity for 5-HT3 sites as quipazine but unlike the latter, does not bind to 5-HT1B sites. [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]

Cross-References

ID SourceID
PubMed CID5013
CHEMBL ID288591
CHEBI ID64164
SCHEMBL ID606721
MeSH IDM0284438

Synonyms (39)

Synonym
2-(4-methyl-piperazin-1-yl)-quinoline
bdbm50053631
BRD-K62056274-001-01-9
LOPAC0_001000
lopac-q-107
tocris-0566
NCGC00015867-01
NCGC00024653-01
BIOMOL-NT_000084
BPBIO1_001081
OPREA1_654246
STK362919
2-(4-methylpiperazin-1-yl)quinoline
NCGC00024653-03
NCGC00024653-02
CHEMBL288591 ,
chebi:64164 ,
AKOS005453926
CCG-205080
NCGC00015867-03
NCGC00015867-02
NCGC00015867-04
quinoline, 2-(4-methyl-1-piperazinyl)-
28614-26-8
SCHEMBL606721
2-(4-methylpiperazinyl)-quinoline
HOMWNUXPSJQSSU-UHFFFAOYSA-N
DTXSID8043731
2-(1-(4-methyl)-piperazinyl)quinoline
j366.838j ,
1-(2-quinolyl)-4-methylpiperazine
0YV1ZIR6S0 ,
n-methylquipazine
unii-0yv1zir6s0
Q27133086
n methylquipazine
nmethylquipazine
Z31193883
EN300-14327696
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
serotonergic agonistAn agent that has an affinity for serotonin receptors and is able to mimic the effects of serotonin by stimulating the physiologic activity at the cell receptors. Serotonin agonists are used as antidepressants, anxiolytics, and in the treatment of migraine disorders.
[role 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]

Drug Classes (3)

ClassDescription
N-alkylpiperazine
N-arylpiperazine
aminoquinolineAny member of the class of quinolines in which the quinoline skeleton is substituted by one or more amino or substituted-amino groups.
[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 (14)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency25.11890.177814.390939.8107AID2147
TDP1 proteinHomo sapiens (human)Potency24.84460.000811.382244.6684AID686978; AID686979
ThrombopoietinHomo sapiens (human)Potency10.00000.02517.304831.6228AID917; AID918
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency35.48130.011212.4002100.0000AID1030
muscarinic acetylcholine receptor M1Rattus norvegicus (Norway rat)Potency19.95260.00106.000935.4813AID943; AID944
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
5-hydroxytryptamine receptor 3EHomo sapiens (human)IC50 (µMol)0.00470.00042.08059.0000AID1855132
5-hydroxytryptamine receptor 3EHomo sapiens (human)Ki0.00300.00100.88359.9000AID6343
5-hydroxytryptamine receptor 3BHomo sapiens (human)IC50 (µMol)0.00470.00041.95059.0000AID1855132
5-hydroxytryptamine receptor 3BHomo sapiens (human)Ki0.00300.00100.87119.9000AID6343
5-hydroxytryptamine receptor 3ARattus norvegicus (Norway rat)Ki0.00300.00020.484110.0000AID5893; AID6132; AID6295
5-hydroxytryptamine receptor 3AHomo sapiens (human)IC50 (µMol)0.00470.00011.07899.0000AID1855132
5-hydroxytryptamine receptor 3AHomo sapiens (human)Ki0.00220.00000.74119.9000AID6343; AID703982
5-hydroxytryptamine receptor 3DHomo sapiens (human)IC50 (µMol)0.00470.00042.08059.0000AID1855132
5-hydroxytryptamine receptor 3DHomo sapiens (human)Ki0.00300.00100.88359.9000AID6343
5-hydroxytryptamine receptor 3CHomo sapiens (human)IC50 (µMol)0.00470.00042.08059.0000AID1855132
5-hydroxytryptamine receptor 3CHomo sapiens (human)Ki0.00300.00100.88359.9000AID6343
Histamine H4 receptorHomo sapiens (human)Ki6.91830.00060.478710.0000AID327691
5-hydroxytryptamine receptor 3BRattus norvegicus (Norway rat)Ki0.00300.00020.502310.0000AID5893; AID6132; AID6295
Histamine H3 receptorHomo sapiens (human)Ki0.41000.00010.33998.5110AID238933
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (15)

Processvia Protein(s)Taxonomy
serotonin receptor signaling pathway5-hydroxytryptamine receptor 3EHomo sapiens (human)
monoatomic ion transmembrane transport5-hydroxytryptamine receptor 3EHomo sapiens (human)
excitatory postsynaptic potential5-hydroxytryptamine receptor 3EHomo sapiens (human)
inorganic cation transmembrane transport5-hydroxytryptamine receptor 3EHomo sapiens (human)
regulation of membrane potential5-hydroxytryptamine receptor 3EHomo sapiens (human)
chemical synaptic transmission5-hydroxytryptamine receptor 3EHomo sapiens (human)
serotonin receptor signaling pathway5-hydroxytryptamine receptor 3BHomo sapiens (human)
monoatomic ion transmembrane transport5-hydroxytryptamine receptor 3BHomo sapiens (human)
excitatory postsynaptic potential5-hydroxytryptamine receptor 3BHomo sapiens (human)
inorganic cation transmembrane transport5-hydroxytryptamine receptor 3BHomo sapiens (human)
chemical synaptic transmission5-hydroxytryptamine receptor 3BHomo sapiens (human)
regulation of membrane potential5-hydroxytryptamine receptor 3BHomo sapiens (human)
serotonin receptor signaling pathway5-hydroxytryptamine receptor 3AHomo sapiens (human)
monoatomic ion transmembrane transport5-hydroxytryptamine receptor 3AHomo sapiens (human)
excitatory postsynaptic potential5-hydroxytryptamine receptor 3AHomo sapiens (human)
inorganic cation transmembrane transport5-hydroxytryptamine receptor 3AHomo sapiens (human)
regulation of presynaptic membrane potential5-hydroxytryptamine receptor 3AHomo sapiens (human)
chemical synaptic transmission5-hydroxytryptamine receptor 3AHomo sapiens (human)
regulation of membrane potential5-hydroxytryptamine receptor 3AHomo sapiens (human)
serotonin receptor signaling pathway5-hydroxytryptamine receptor 3DHomo sapiens (human)
monoatomic ion transmembrane transport5-hydroxytryptamine receptor 3DHomo sapiens (human)
excitatory postsynaptic potential5-hydroxytryptamine receptor 3DHomo sapiens (human)
inorganic cation transmembrane transport5-hydroxytryptamine receptor 3DHomo sapiens (human)
chemical synaptic transmission5-hydroxytryptamine receptor 3DHomo sapiens (human)
regulation of membrane potential5-hydroxytryptamine receptor 3DHomo sapiens (human)
serotonin receptor signaling pathway5-hydroxytryptamine receptor 3CHomo sapiens (human)
monoatomic ion transmembrane transport5-hydroxytryptamine receptor 3CHomo sapiens (human)
excitatory postsynaptic potential5-hydroxytryptamine receptor 3CHomo sapiens (human)
inorganic cation transmembrane transport5-hydroxytryptamine receptor 3CHomo sapiens (human)
regulation of membrane potential5-hydroxytryptamine receptor 3CHomo sapiens (human)
chemical synaptic transmission5-hydroxytryptamine receptor 3CHomo sapiens (human)
inflammatory responseHistamine H4 receptorHomo sapiens (human)
positive regulation of cytosolic calcium ion concentrationHistamine H4 receptorHomo sapiens (human)
biological_processHistamine H4 receptorHomo sapiens (human)
regulation of MAPK cascadeHistamine H4 receptorHomo sapiens (human)
G protein-coupled serotonin receptor signaling pathwayHistamine H4 receptorHomo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled acetylcholine receptor signaling pathwayHistamine H4 receptorHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerHistamine H4 receptorHomo sapiens (human)
chemical synaptic transmissionHistamine H4 receptorHomo sapiens (human)
neurotransmitter secretionHistamine H3 receptorHomo sapiens (human)
G protein-coupled serotonin receptor signaling pathwayHistamine H3 receptorHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerHistamine H3 receptorHomo sapiens (human)
chemical synaptic transmissionHistamine H3 receptorHomo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled acetylcholine receptor signaling pathwayHistamine H3 receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
serotonin-gated monoatomic cation channel activity5-hydroxytryptamine receptor 3EHomo sapiens (human)
excitatory extracellular ligand-gated monoatomic ion channel activity5-hydroxytryptamine receptor 3EHomo sapiens (human)
transmitter-gated monoatomic ion channel activity involved in regulation of postsynaptic membrane potential5-hydroxytryptamine receptor 3EHomo sapiens (human)
serotonin-gated monoatomic cation channel activity5-hydroxytryptamine receptor 3BHomo sapiens (human)
transmitter-gated monoatomic ion channel activity involved in regulation of postsynaptic membrane potential5-hydroxytryptamine receptor 3BHomo sapiens (human)
excitatory extracellular ligand-gated monoatomic ion channel activity5-hydroxytryptamine receptor 3BHomo sapiens (human)
protein binding5-hydroxytryptamine receptor 3AHomo sapiens (human)
serotonin-gated monoatomic cation channel activity5-hydroxytryptamine receptor 3AHomo sapiens (human)
identical protein binding5-hydroxytryptamine receptor 3AHomo sapiens (human)
serotonin binding5-hydroxytryptamine receptor 3AHomo sapiens (human)
ligand-gated monoatomic ion channel activity involved in regulation of presynaptic membrane potential5-hydroxytryptamine receptor 3AHomo sapiens (human)
transmitter-gated monoatomic ion channel activity involved in regulation of postsynaptic membrane potential5-hydroxytryptamine receptor 3AHomo sapiens (human)
excitatory extracellular ligand-gated monoatomic ion channel activity5-hydroxytryptamine receptor 3AHomo sapiens (human)
protein binding5-hydroxytryptamine receptor 3DHomo sapiens (human)
serotonin-gated monoatomic cation channel activity5-hydroxytryptamine receptor 3DHomo sapiens (human)
excitatory extracellular ligand-gated monoatomic ion channel activity5-hydroxytryptamine receptor 3DHomo sapiens (human)
transmitter-gated monoatomic ion channel activity involved in regulation of postsynaptic membrane potential5-hydroxytryptamine receptor 3DHomo sapiens (human)
protein binding5-hydroxytryptamine receptor 3CHomo sapiens (human)
serotonin-gated monoatomic cation channel activity5-hydroxytryptamine receptor 3CHomo sapiens (human)
excitatory extracellular ligand-gated monoatomic ion channel activity5-hydroxytryptamine receptor 3CHomo sapiens (human)
transmitter-gated monoatomic ion channel activity involved in regulation of postsynaptic membrane potential5-hydroxytryptamine receptor 3CHomo sapiens (human)
histamine receptor activityHistamine H4 receptorHomo sapiens (human)
G protein-coupled serotonin receptor activityHistamine H4 receptorHomo sapiens (human)
G protein-coupled acetylcholine receptor activityHistamine H4 receptorHomo sapiens (human)
histamine receptor activityHistamine H3 receptorHomo sapiens (human)
G protein-coupled acetylcholine receptor activityHistamine H3 receptorHomo sapiens (human)
G protein-coupled serotonin receptor activityHistamine H3 receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (10)

Processvia Protein(s)Taxonomy
plasma membrane5-hydroxytryptamine receptor 3EHomo sapiens (human)
postsynaptic membrane5-hydroxytryptamine receptor 3EHomo sapiens (human)
serotonin-activated cation-selective channel complex5-hydroxytryptamine receptor 3EHomo sapiens (human)
neuron projection5-hydroxytryptamine receptor 3EHomo sapiens (human)
transmembrane transporter complex5-hydroxytryptamine receptor 3EHomo sapiens (human)
synapse5-hydroxytryptamine receptor 3EHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 3EHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 3BHomo sapiens (human)
postsynaptic membrane5-hydroxytryptamine receptor 3BHomo sapiens (human)
serotonin-activated cation-selective channel complex5-hydroxytryptamine receptor 3BHomo sapiens (human)
cell surface5-hydroxytryptamine receptor 3BHomo sapiens (human)
transmembrane transporter complex5-hydroxytryptamine receptor 3BHomo sapiens (human)
synapse5-hydroxytryptamine receptor 3BHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 3BHomo sapiens (human)
neuron projection5-hydroxytryptamine receptor 3BHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 3AHomo sapiens (human)
cleavage furrow5-hydroxytryptamine receptor 3AHomo sapiens (human)
postsynaptic membrane5-hydroxytryptamine receptor 3AHomo sapiens (human)
serotonin-activated cation-selective channel complex5-hydroxytryptamine receptor 3AHomo sapiens (human)
synapse5-hydroxytryptamine receptor 3AHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 3AHomo sapiens (human)
transmembrane transporter complex5-hydroxytryptamine receptor 3AHomo sapiens (human)
neuron projection5-hydroxytryptamine receptor 3AHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 3DHomo sapiens (human)
postsynaptic membrane5-hydroxytryptamine receptor 3DHomo sapiens (human)
serotonin-activated cation-selective channel complex5-hydroxytryptamine receptor 3DHomo sapiens (human)
synapse5-hydroxytryptamine receptor 3DHomo sapiens (human)
transmembrane transporter complex5-hydroxytryptamine receptor 3DHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 3DHomo sapiens (human)
neuron projection5-hydroxytryptamine receptor 3DHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 3CHomo sapiens (human)
postsynaptic membrane5-hydroxytryptamine receptor 3CHomo sapiens (human)
serotonin-activated cation-selective channel complex5-hydroxytryptamine receptor 3CHomo sapiens (human)
synapse5-hydroxytryptamine receptor 3CHomo sapiens (human)
transmembrane transporter complex5-hydroxytryptamine receptor 3CHomo sapiens (human)
neuron projection5-hydroxytryptamine receptor 3CHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 3CHomo sapiens (human)
plasma membraneHistamine H4 receptorHomo sapiens (human)
plasma membraneHistamine H4 receptorHomo sapiens (human)
dendriteHistamine H4 receptorHomo sapiens (human)
synapseHistamine H4 receptorHomo sapiens (human)
plasma membraneHistamine H3 receptorHomo sapiens (human)
presynapseHistamine H3 receptorHomo sapiens (human)
plasma membraneHistamine H3 receptorHomo sapiens (human)
synapseHistamine H3 receptorHomo sapiens (human)
dendriteHistamine H3 receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (14)

Assay IDTitleYearJournalArticle
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1508627Counterscreen qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: GLuc-NoTag assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1508629Cell Viability qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1508628Confirmatory qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID327691Displacement of [3H]histamine from human histamine H4 receptor expressed in HEK293T cells2008Journal of medicinal chemistry, Apr-24, Volume: 51, Issue:8
Fragment based design of new H4 receptor-ligands with anti-inflammatory properties in vivo.
AID703982Displacement of [3H]granisetron from 5HT3A receptor expressed in HEK293 cells after 24 hrs by scintillation counting in presence of quipazine2012Journal of medicinal chemistry, Oct-25, Volume: 55, Issue:20
Design, synthesis, and structure-activity relationships of highly potent 5-HT₃ receptor ligands.
AID6132Inhibition of [3H]granisetron binding to 5-hydroxytryptamine 3 receptor of rat cortical membrane1999Journal of medicinal chemistry, May-06, Volume: 42, Issue:9
Novel potent and selective central 5-HT3 receptor ligands provided with different intrinsic efficacy. 2. Molecular basis of the intrinsic efficacy of arylpiperazine derivatives at the central 5-HT3 receptors.
AID1855132Inhibition of 5HT3 receptor (unknown origin)2022Journal of medicinal chemistry, 08-25, Volume: 65, Issue:16
Positron Emission Tomography (PET) Imaging Tracers for Serotonin Receptors.
AID238933Antagonist potency against human H3 receptor in GTPgamma-S-Assay2005Journal of medicinal chemistry, Jan-13, Volume: 48, Issue:1
2-(4-alkylpiperazin-1-yl)quinolines as a new class of imidazole-free histamine H3 receptor antagonists.
AID6343Compound was tested for the inhibition of [3H]GR-65630 binding to 5-hydroxytryptamine 3 receptor expressed in NG 108-15 cells1996Journal of medicinal chemistry, Sep-27, Volume: 39, Issue:20
Structure-activity relationships for the binding of arylpiperazines and arylbiguanides at 5-HT3 serotonin receptors.
AID6295Binding affinity at 5-hydroxytryptamine 3 receptor in rat cortical membrane by [3H]graniestron displacement.1998Journal of medicinal chemistry, Feb-26, Volume: 41, Issue:5
Novel potent and selective central 5-HT3 receptor ligands provided with different intrinsic efficacy. 1. Mapping the central 5-HT3 receptor binding site by arylpiperazine derivatives.
AID5893Ability to displace [3H]granisetron specifically bound to 5-hydroxytryptamine 3 receptor in rat cortical membrane1998Journal of medicinal chemistry, Feb-26, Volume: 41, Issue:5
Novel potent and selective central 5-HT3 receptor ligands provided with different intrinsic efficacy. 1. Mapping the central 5-HT3 receptor binding site by arylpiperazine derivatives.
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 (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's5 (41.67)18.2507
2000's2 (16.67)29.6817
2010's2 (16.67)24.3611
2020's3 (25.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.17

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 Index12.17 (24.57)
Research Supply Index2.56 (2.92)
Research Growth Index4.73 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.17)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (8.33%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other11 (91.67%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]