4-Dimethylaminophenol
Chemical compound
From Wikipedia, the free encyclopedia
4-Dimethylaminophenol (DMAP) is an aromatic compound containing both phenol and amine functional groups. It has the molecular formula C8H11NO.
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| Names | |
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| Preferred IUPAC name
4-(Dimethylamino)phenol | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.009.642 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C8H11NO | |
| Molar mass | 137.179 g/mol |
| Boiling point | 165 °C (329 °F; 438 K) (0.040 bar) |
| Pharmacology | |
| V03AB27 (WHO) | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis
Heating dimethylaniline N-oxide in concentrated sulfuric acid causes a Bamberger rearrangement to 2- and 4-dimethylaminophenols.[1]
Uses
4-Dimethylaminophenol has been used as an antidote for cyanide poisoning.[2] It has also been shown to be effective in treating hydrogen sulfide toxicity.[3]
It works by generating methemoglobin.[4]
This is suitable as an emergency treatment only; treatment must be followed up with sodium thiosulfate or cobalamin.
In an animal model, it has shown effectiveness when given intramuscularly.[5] Though, intramuscular injection should be avoid due to the probability of muscular necrosis after injection. Intravenous injection is recommended in a dose of 250 mg.[6]