Page last updated: 2024-12-07

1,8-bis(dimethylamino)naphthalene

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

1,8-bis(dimethylamino)naphthalene, also known as Proton Sponge, is a highly basic organic compound. It is characterized by its exceptional ability to abstract protons due to the steric strain induced by the two bulky dimethylamino groups located at the 1 and 8 positions of the naphthalene ring. The strain forces the lone pairs of the nitrogen atoms to interact, resulting in a strong basicity. Proton Sponge exhibits a pKa value of approximately 12.1 in acetonitrile, making it one of the strongest organic bases known. Its synthesis typically involves the reaction of 1,8-diaminonaphthalene with formaldehyde and dimethylamine. Proton Sponge has been extensively studied for its unique properties, particularly its exceptional basicity, which has led to its use as a base in various chemical reactions. For example, it can be used to deprotonate weak acids, activate catalytic processes, and facilitate the formation of reactive intermediates. Researchers also study Proton Sponge to gain a deeper understanding of the factors that influence basicity and the impact of steric effects on molecular properties. Its unusual structure and remarkable basicity make it an intriguing target for both theoretical and experimental studies.'

Cross-References

ID SourceID
PubMed CID88675
CHEMBL ID1574733
CHEBI ID194986
SCHEMBL ID28279
MeSH IDM0377349

Synonyms (78)

Synonym
AC-3025
1,8-bis(dimethylamino)naphtalene
AKOS009031579
1,8-bis(dimethylamino)naphthalene
inchi=1/c14h18n2/c1-15(2)12-9-5-7-11-8-6-10-13(14(11)12)16(3)4/h5-10h,1-4h
n,n,n',n'-tetramethylnaphthalene-1,8-diamine
1,8-naphthalenediamine, n,n,n',n'-tetramethyl-
SR-01000638069-1
MLS000851090
smr000457333
n1,n1,n8,n8-tetramethylnaphthalene-1,8-diamine
proton-sponge(r), 99%
MAYBRIDGE1_002116
B1018
20734-58-1
n,n,n',n'-tetramethyl-1,8-diaminonaphthalene
HMS547I04
n,n,n',n'-tetramethyl-1,8-naphthalenediamine
1,8-bis-(dimethylamino)naphthalene
CHEBI:194986
1-n,1-n,8-n,8-n-tetramethylnaphthalene-1,8-diamine
NCGC00246659-01
(8-dimethylamino-1-naphthyl)-dimethyl-amine
n,n,n',n'-tetramethyl-1,8-naphthalene diamine
n1,n1,n8,n8-tetramethylnaphthalene-1,8-diamine;1,8-bis(dimethylamino)naphthalene
A814845
dman cpd
einecs 244-001-6
ai3-62472
6s79d2p9h8 ,
unii-6s79d2p9h8
CCG-48535
proton sponge
proton-sponge
HMS2812C12
FT-0607031
CS-002/03850003
n-[8-(dimethylamino)-1-naphthyl]-n,n-dimethylamine
AM84721
n1,n1,n8,n8-tetramethyl-1,8-naphthalenediamine
dman [mi]
1,8-bis-(dimethylamino)-naphthalene
n, n, n', n'-tetra-methylnaphthalene-1,8-diamine
1.8-bis(dimethylamino)naphthalene
n, n, n', n'-tetra-methyinaphthalene-1,8-diamine
1,8-bis(dimethylamino)-naphtalene
1,8-bis (dimethylamino)naphthalene
1,8-bis(n,n-dimethylamino)naphthalene
1,8-bis(dimethylamino)-naphthalene
1,8-bis-dimethylaminonaphthalene
n,n,n',n'-tetramethyl-naphthalene-1,8-diamine
1,8-bis(dimethylamino) naphthalene
n,n,n',n'-tetramethyl-1,8-naphthalendiamine
n,n, n',n'-tetramethylnaphthalene-1,8-diamine
n,n,n',n'-tetramethyl-1,8-napthalenediamine
1,8-bis(dimethylamino)naphthalin
n,n, n',n'-tetra-methylnaphthalene-1,8-diamine
SCHEMBL28279
n,n,n inverted exclamation mark ,n inverted exclamation mark -tetramethyl-1,8-naphthalenediamine
mfcd00003920
SY003598
CHEMBL1574733
A1-01181
W-107597
STR04798
CS-W020522
DTXSID10174807
F0001-0738
n,n,n',n'-tetramethyl-1,8-naphthalenediamine, purum, >=99.0% (nt)
n,n,n`,n`-tetramethyl-1,8-naphthalenediamine
Q161564
BRD-K27772377-001-09-4
1,8-naphthalenediamine, n1,n1,n8,n8-tetramethyl-
methyl?imidazo[1,2-a]pyridine-7-carboxylate
1,8-bis(dimethylamino)naphthalene [for dehydrohalogenation]
EN300-20665
u1e ,
SB78955
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
naphthalenesAny benzenoid aromatic compound having a skeleton composed of two ortho-fused benzene rings.
[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 (7)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Putative fructose-1,6-bisphosphate aldolaseGiardia intestinalisPotency3.15480.140911.194039.8107AID2451
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency22.38720.177814.390939.8107AID2147
Microtubule-associated protein tauHomo sapiens (human)Potency37.64600.180013.557439.8107AID1460; AID1468
lysosomal alpha-glucosidase preproproteinHomo sapiens (human)Potency0.89130.036619.637650.1187AID1466; AID2242
DNA polymerase iota isoform a (long)Homo sapiens (human)Potency89.12510.050127.073689.1251AID588590
Neuronal acetylcholine receptor subunit alpha-4Rattus norvegicus (Norway rat)Potency0.89133.548118.039535.4813AID1466
Neuronal acetylcholine receptor subunit beta-2Rattus norvegicus (Norway rat)Potency0.89133.548118.039535.4813AID1466
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (7)

Assay IDTitleYearJournalArticle
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).2014Journal of biomolecular screening, Jul, Volume: 19, Issue:6
A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
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 (26)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's7 (26.92)29.6817
2010's16 (61.54)24.3611
2020's3 (11.54)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 45.05

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 Index45.05 (24.57)
Research Supply Index3.30 (2.92)
Research Growth Index5.46 (4.65)
Search Engine Demand Index65.76 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (45.05)

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%
Other26 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]