Page last updated: 2024-12-05

tetrapropylammonium

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Description

Tetrapropylammonium is a quaternary ammonium cation with the formula (CH3CH2CH2)4N+. It is typically encountered as a salt, such as tetrapropylammonium bromide or tetrapropylammonium chloride. It is a colorless, hygroscopic solid. Tetrapropylammonium salts are often used as phase-transfer catalysts, particularly in organic synthesis. They can also be used as electrolytes in batteries and fuel cells. The compound is prepared by the reaction of tripropylamine with 1-bromopropane.'

tetrapropylammonium: more than 12 salts of above cpd in Chemline [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

tetrapropylammonium : A quarternary ammonium cation with four propyl substituents around the central nitrogen. [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 CID9559
CHEMBL ID2074857
CHEBI ID55319
SCHEMBL ID59838
MeSH IDM0148699

Synonyms (17)

Synonym
13010-31-6
tetrapropylammonium
inchi=1/c12h28n/c1-5-9-13(10-6-2,11-7-3)12-8-4/h5-12h2,1-4h3/q+
tetrapropylamine
tetrapropylazanium
n,n,n-tripropylpropan-1-aminium
n,n,n-tripropyl-1-propanaminium
CHEBI:55319 ,
1-propanaminium, n,n,n-tripropyl-
CHEMBL2074857 ,
bdbm50420179
SCHEMBL59838
tetrapropyl ammonium
OSBSFAARYOCBHB-UHFFFAOYSA-N
DTXSID6047026
taa3
Q27124225
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
quaternary ammonium ionA derivative of ammonium, NH4(+), in which all four of the hydrogens bonded to nitrogen have been replaced with univalent (usually organyl) 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 (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Solute carrier family 22 member 1Mus musculus (house mouse)Ki19.80003.60005.45007.3000AID682044
Solute carrier family 22 member 2Homo sapiens (human)IC50 (µMol)128.00000.40003.10009.7000AID679160
Solute carrier family 22 member 1 Homo sapiens (human)IC50 (µMol)90.00000.21005.553710.0000AID679154
Solute carrier family 22 member 1 Homo sapiens (human)Ki102.00000.55004.26507.4600AID679156
Solute carrier family 22 member 1Rattus norvegicus (Norway rat)IC50 (µMol)17.15000.18003.68578.8000AID681159; AID681348
Solute carrier family 22 member 1Rattus norvegicus (Norway rat)Ki21.00000.13002.37856.9000AID678997
Solute carrier family 22 member 2Rattus norvegicus (Norway rat)IC50 (µMol)22.60001.00004.446710.0000AID681158; AID681345
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Solute carrier family 22 member 1 Homo sapiens (human)Activity22.00000.71005.30179.7000AID681117
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (42)

Processvia Protein(s)Taxonomy
activation of cysteine-type endopeptidase activity involved in apoptotic processSolute carrier family 22 member 2Homo sapiens (human)
positive regulation of gene expressionSolute carrier family 22 member 2Homo sapiens (human)
organic cation transportSolute carrier family 22 member 2Homo sapiens (human)
monoatomic cation transportSolute carrier family 22 member 2Homo sapiens (human)
neurotransmitter transportSolute carrier family 22 member 2Homo sapiens (human)
serotonin transportSolute carrier family 22 member 2Homo sapiens (human)
body fluid secretionSolute carrier family 22 member 2Homo sapiens (human)
organic cation transportSolute carrier family 22 member 2Homo sapiens (human)
quaternary ammonium group transportSolute carrier family 22 member 2Homo sapiens (human)
prostaglandin transportSolute carrier family 22 member 2Homo sapiens (human)
amine transportSolute carrier family 22 member 2Homo sapiens (human)
putrescine transportSolute carrier family 22 member 2Homo sapiens (human)
spermidine transportSolute carrier family 22 member 2Homo sapiens (human)
acetylcholine transportSolute carrier family 22 member 2Homo sapiens (human)
choline transportSolute carrier family 22 member 2Homo sapiens (human)
dopamine transportSolute carrier family 22 member 2Homo sapiens (human)
norepinephrine transportSolute carrier family 22 member 2Homo sapiens (human)
xenobiotic transportSolute carrier family 22 member 2Homo sapiens (human)
epinephrine transportSolute carrier family 22 member 2Homo sapiens (human)
histamine transportSolute carrier family 22 member 2Homo sapiens (human)
serotonin uptakeSolute carrier family 22 member 2Homo sapiens (human)
histamine uptakeSolute carrier family 22 member 2Homo sapiens (human)
norepinephrine uptakeSolute carrier family 22 member 2Homo sapiens (human)
thiamine transmembrane transportSolute carrier family 22 member 2Homo sapiens (human)
purine-containing compound transmembrane transportSolute carrier family 22 member 2Homo sapiens (human)
amino acid import across plasma membraneSolute carrier family 22 member 2Homo sapiens (human)
dopamine uptakeSolute carrier family 22 member 2Homo sapiens (human)
L-arginine import across plasma membraneSolute carrier family 22 member 2Homo sapiens (human)
export across plasma membraneSolute carrier family 22 member 2Homo sapiens (human)
transport across blood-brain barrierSolute carrier family 22 member 2Homo sapiens (human)
L-alpha-amino acid transmembrane transportSolute carrier family 22 member 2Homo sapiens (human)
spermidine transmembrane transportSolute carrier family 22 member 2Homo sapiens (human)
L-arginine transmembrane transportSolute carrier family 22 member 2Homo sapiens (human)
cellular detoxificationSolute carrier family 22 member 2Homo sapiens (human)
xenobiotic transport across blood-brain barrierSolute carrier family 22 member 2Homo sapiens (human)
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)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (24)

Processvia Protein(s)Taxonomy
amine transmembrane transporter activitySolute carrier family 22 member 2Homo sapiens (human)
acetylcholine transmembrane transporter activitySolute carrier family 22 member 2Homo sapiens (human)
neurotransmitter transmembrane transporter activitySolute carrier family 22 member 2Homo sapiens (human)
monoamine transmembrane transporter activitySolute carrier family 22 member 2Homo sapiens (human)
organic anion transmembrane transporter activitySolute carrier family 22 member 2Homo sapiens (human)
organic cation transmembrane transporter activitySolute carrier family 22 member 2Homo sapiens (human)
prostaglandin transmembrane transporter activitySolute carrier family 22 member 2Homo sapiens (human)
L-amino acid transmembrane transporter activitySolute carrier family 22 member 2Homo sapiens (human)
pyrimidine nucleoside transmembrane transporter activitySolute carrier family 22 member 2Homo sapiens (human)
choline transmembrane transporter activitySolute carrier family 22 member 2Homo sapiens (human)
thiamine transmembrane transporter activitySolute carrier family 22 member 2Homo sapiens (human)
putrescine transmembrane transporter activitySolute carrier family 22 member 2Homo sapiens (human)
efflux transmembrane transporter activitySolute carrier family 22 member 2Homo sapiens (human)
spermidine transmembrane transporter activitySolute carrier family 22 member 2Homo sapiens (human)
quaternary ammonium group transmembrane transporter activitySolute carrier family 22 member 2Homo sapiens (human)
toxin transmembrane transporter activitySolute carrier family 22 member 2Homo sapiens (human)
xenobiotic transmembrane transporter activitySolute carrier family 22 member 2Homo sapiens (human)
L-arginine transmembrane transporter activitySolute carrier family 22 member 2Homo sapiens (human)
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)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (8)

Processvia Protein(s)Taxonomy
plasma membraneSolute carrier family 22 member 2Homo sapiens (human)
basal plasma membraneSolute carrier family 22 member 2Homo sapiens (human)
membraneSolute carrier family 22 member 2Homo sapiens (human)
basolateral plasma membraneSolute carrier family 22 member 2Homo sapiens (human)
apical plasma membraneSolute carrier family 22 member 2Homo sapiens (human)
extracellular exosomeSolute carrier family 22 member 2Homo sapiens (human)
presynapseSolute carrier family 22 member 2Homo sapiens (human)
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)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (10)

Assay IDTitleYearJournalArticle
AID678997TP_TRANSPORTER: inhibition of MPP+ uptake in Xenopus laevis oocytes2000The Journal of pharmacology and experimental therapeutics, Mar, Volume: 292, Issue:3
Kinetic and selectivity differences between rodent, rabbit, and human organic cation transporters (OCT1).
AID681117TP_TRANSPORTER: inhibition of TEA uptake in OCT1-expressing HeLa cells2003Molecular pharmacology, Mar, Volume: 63, Issue:3
Influence of molecular structure on substrate binding to the human organic cation transporter, hOCT1.
AID681159TP_TRANSPORTER: inhibition of TEA uptake (TEA: 10 uM) in Xenopus laevis oocytes2001American journal of physiology. Renal physiology, Sep, Volume: 281, Issue:3
Interaction of cations, anions, and weak base quinine with rat renal cation transporter rOCT2 compared with rOCT1.
AID681158TP_TRANSPORTER: inhibition of TEA uptake (TEA: 10 uM) in Xenopus laevis oocytes2001American journal of physiology. Renal physiology, Sep, Volume: 281, Issue:3
Interaction of cations, anions, and weak base quinine with rat renal cation transporter rOCT2 compared with rOCT1.
AID681348TP_TRANSPORTER: inhibition of TEA uptake (TEA: 50 uM) in OCT1-expressing MDCK cells2001Pharmaceutical research, Nov, Volume: 18, Issue:11
Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules.
AID679156TP_TRANSPORTER: inhibition of MPP+ uptake in Xenopus laevis oocytes2000The Journal of pharmacology and experimental therapeutics, Mar, Volume: 292, Issue:3
Kinetic and selectivity differences between rodent, rabbit, and human organic cation transporters (OCT1).
AID679160TP_TRANSPORTER: inhibition of MPP+ uptake (MPP+: 1 uM) in Xenopus laevis oocytes2002Pharmaceutical research, Aug, Volume: 19, Issue:8
Interactions of n-tetraalkylammonium compounds and biguanides with a human renal organic cation transporter (hOCT2).
AID679154TP_TRANSPORTER: inhibition of TEA uptake (TEA: 10 uM) in OCT1-expressing HeLa cells1999The Journal of pharmacology and experimental therapeutics, Mar, Volume: 288, Issue:3
The interaction of n-tetraalkylammonium compounds with a human organic cation transporter, hOCT1.
AID682044TP_TRANSPORTER: inhibition of MPP+ uptake in Xenopus laevis oocytes2000The Journal of pharmacology and experimental therapeutics, Mar, Volume: 292, Issue:3
Kinetic and selectivity differences between rodent, rabbit, and human organic cation transporters (OCT1).
AID681345TP_TRANSPORTER: inhibition of TEA uptake (TEA: 50 uM) in OCT2-expressing MDCK cells2001Pharmaceutical research, Nov, Volume: 18, Issue:11
Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (48)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (4.17)18.7374
1990's9 (18.75)18.2507
2000's22 (45.83)29.6817
2010's14 (29.17)24.3611
2020's1 (2.08)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 40.41

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 strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index40.41 (24.57)
Research Supply Index3.89 (2.92)
Research Growth Index5.10 (4.65)
Search Engine Demand Index56.07 (26.88)
Search Engine Supply Index2.04 (0.95)

This Compound (40.41)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other48 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]