Compounds > 1,8-bis(dimethylamino)naphthalene
Page last updated: 2024-12-07

1,8-bis(dimethylamino)naphthalene

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]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
acetic acid
Acetic Acid: Product of the oxidation of ethanol and of the destructive distillation of wood. It is used locally, occasionally internally, as a counterirritant and also as a reagent. (Stedman, 26th ed). acetic acid : A simple monocarboxylic acid containing two carbons.		2.0510monocarboxylic acidantimicrobial food preservative;
Daphnia magna metabolite;
food acidity regulator;
protic solvent
formic acid
formic acid: RN given refers to parent cpd. formic acid : The simplest carboxylic acid, containing a single carbon. Occurs naturally in various sources including the venom of bee and ant stings, and is a useful organic synthetic reagent. Principally used as a preservative and antibacterial agent in livestock feed. Induces severe metabolic acidosis and ocular injury in human subjects.		2.0510monocarboxylic acidantibacterial agent;
astringent;
metabolite;
protic solvent;
solvent
hydrogen
Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.		2.7730elemental hydrogen;
elemental molecule;
gas molecular entity		antioxidant;
electron donor;
food packaging gas;
fuel;
human metabolite
2,5-dihydroxybenzoic acid
2,5-dihydroxybenzoic acid: RN given refers to parent cpd; a oxidative product of saligenin. 2,5-dihydroxybenzoic acid : A dihydroxybenzoic acid having the two hydroxy groups at the 2- and 5-positions.		2.110dihydroxybenzoic acidEC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor;
fungal metabolite;
human metabolite;
MALDI matrix material;
mouse metabolite
acetonitrile
acetonitrile: RN given refers to unlabeled cpd. acetonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a methyl group.		2.0210aliphatic nitrile;
volatile organic compound		EC 3.5.1.4 (amidase) inhibitor;
NMR chemical shift reference compound;
polar aprotic solvent
trifluoroacetic acid
Trifluoroacetic Acid: A very strong halogenated derivative of acetic acid. It is used in acid catalyzed reactions, especially those where an ester is cleaved in peptide synthesis.. trifluoroacetic acid : A monocarboxylic acid that is the trifluoro derivative of acetic acid.		2.0510fluoroalkanoic acidhuman xenobiotic metabolite;
NMR chemical shift reference compound;
reagent
aminacrine
Aminacrine: A highly fluorescent anti-infective dye used clinically as a topical antiseptic and experimentally as a mutagen, due to its interaction with DNA. It is also used as an intracellular pH indicator.. 9-aminoacridine : An aminoacridine that is acridine in which the hydrogen at position 9 is replaced by an amino group. A fluorescent dyd and topical antiseptic agent, it is used (usually as the hydrochloride salt) in eye drops for the treatment of superficial eye infections.		2.0810aminoacridines;
primary amino compound		acid-base indicator;
antiinfective agent;
antiseptic drug;
fluorescent dye;
MALDI matrix material;
mutagen
maleic anhydride
Maleic Anhydrides: Used in copolymerization reactions, in the Diels-Alder(diene)synthesis, in the preparation of resins, pharmaceuticals and agricultural chemicals. It is a powerful irritant and causes burns.. maleic anhydride : A cyclic dicarboxylic anhydride that is the cyclic anhydride of maleic acid.		2.0510cyclic dicarboxylic anhydride;
furans		allergen
1-naphthylamine
1-Naphthylamine: A suspected industrial carcinogen (and listed as such by OSHA). Its N-hydroxy metabolite is strongly carcinogenic and mutagenic.. naphthylamine : A primary arylamine that is naphthalene substituted by an amino group at unspecified position.. 1-naphthylamine : A naphthylamine that is naphthalene substituted by an amino group at position 1.		4.46210naphthylaminehuman xenobiotic metabolite
deuterium
Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.		210dihydrogen
fluorides
[no description available]		2.0610halide anion;
monoatomic fluorine
chromotropic acid
chromotropic acid: RN given refers to parent cpd. chromotropic acid : A naphthalenesulfonic acid that is naphthalene-2,7-disulfonic acid substituted by hydroxy groups at positions 4 and 5.		2.2510naphthalenediols;
naphthalenesulfonic acid		indicator
cobalt
Cobalt: A trace element that is a component of vitamin B12. It has the atomic symbol Co, atomic number 27, and atomic weight 58.93. It is used in nuclear weapons, alloys, and pigments. Deficiency in animals leads to anemia; its excess in humans can lead to erythrocytosis.. cobalt(1+) : A monovalent inorganic cation obtained from cobalt.. cobalt atom : A cobalt group element atom that has atomic number 27.		2.110cobalt group element atom;
metal allergen		micronutrient
porphycene
porphycene: photodynamic therapy agent; structure given in first source		2.0510
urocanic acid
Urocanic Acid: 4-Imidazoleacrylic acid.. urocanic acid : An alpha,beta-unsaturated monocarboxylic acid that is prop-2-enoic acid substituted by a 1H-imidazol-4-yl group at position 3. It is a metabolite of hidtidine.. trans-urocanic acid : A urocanic acid in which the double bond of the carboxyethene moiety has E configuration.		2.2510urocanic acidhuman metabolite
phosphatidylcholines
Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.		2.1101,2-diacyl-sn-glycero-3-phosphocholine
glycolipids
[no description available]		2.0610
ConditionIndicatedRelationship StrengthStudiesTrials
Plasmodium falciparum Malaria
[description not available]		02.110
Malaria, Falciparum
Malaria caused by PLASMODIUM FALCIPARUM. This is the severest form of malaria and is associated with the highest levels of parasites in the blood. This disease is characterized by irregularly recurring febrile paroxysms that in extreme cases occur with acute cerebral, renal, or gastrointestinal manifestations.		02.110
Anemia, Fanconi
[description not available]		02.1310
Fanconi Anemia
Congenital disorder affecting all bone marrow elements, resulting in ANEMIA; LEUKOPENIA; and THROMBOPENIA, and associated with cardiac, renal, and limb malformations as well as dermal pigmentary changes. Spontaneous CHROMOSOME BREAKAGE is a feature of this disease along with predisposition to LEUKEMIA. There are at least 7 complementation groups in Fanconi anemia: FANCA, FANCB, FANCC, FANCD1, FANCD2, FANCE, FANCF, FANCG, and FANCL. (from Online Mendelian Inheritance in Man, http://www.ncbi.nlm.nih.gov/entrez/dispomim.cgi?id=227650, August 20, 2004)		02.1310
Benign Neoplasms
[description not available]		02.110
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		02.110
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		02.4620
chemdatabank.com