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.'
| ID Source | ID |
|---|---|
| PubMed CID | 88675 |
| CHEMBL ID | 1574733 |
| CHEBI ID | 194986 |
| SCHEMBL ID | 28279 |
| MeSH ID | M0377349 |
| 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 |
| Class | Description |
|---|---|
| naphthalenes | Any 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 | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Chain A, Putative fructose-1,6-bisphosphate aldolase | Giardia intestinalis | Potency | 3.1548 | 0.1409 | 11.1940 | 39.8107 | AID2451 |
| Chain A, 2-oxoglutarate Oxygenase | Homo sapiens (human) | Potency | 22.3872 | 0.1778 | 14.3909 | 39.8107 | AID2147 |
| Microtubule-associated protein tau | Homo sapiens (human) | Potency | 37.6460 | 0.1800 | 13.5574 | 39.8107 | AID1460; AID1468 |
| lysosomal alpha-glucosidase preproprotein | Homo sapiens (human) | Potency | 0.8913 | 0.0366 | 19.6376 | 50.1187 | AID1466; AID2242 |
| DNA polymerase iota isoform a (long) | Homo sapiens (human) | Potency | 89.1251 | 0.0501 | 27.0736 | 89.1251 | AID588590 |
| Neuronal acetylcholine receptor subunit alpha-4 | Rattus norvegicus (Norway rat) | Potency | 0.8913 | 3.5481 | 18.0395 | 35.4813 | AID1466 |
| Neuronal acetylcholine receptor subunit beta-2 | Rattus norvegicus (Norway rat) | Potency | 0.8913 | 3.5481 | 18.0395 | 35.4813 | AID1466 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1745845 | Primary qHTS for Inhibitors of ATXN expression | |||
| AID504810 | Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
| AID651635 | Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression | |||
| AID504812 | Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
| AID1794808 | Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL). | 2014 | Journal of biomolecular screening, Jul, Volume: 19, Issue:6 | A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum. |
| AID1794808 | Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL). | |||
| AID1159607 | Screen for inhibitors of RMI FANCM (MM2) intereaction | 2016 | Journal 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] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 7 (26.92) | 29.6817 |
| 2010's | 16 (61.54) | 24.3611 |
| 2020's | 3 (11.54) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
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.
| This Compound (45.05) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 26 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||