4-Dimethylaminophenol

4-Dimethylaminophenol (DMAP) is an aromatic compound containing both phenol and amine functional groups. It has the molecular formula C8H11NO.

Not to be confused with 4-Dimethylaminopyridine.
4-Dimethylaminophenol
Names
Preferred IUPAC name
4-(Dimethylamino)phenol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.009.642
UNII
  • InChI=1S/C8H11NO/c1-9(2)7-3-5-8(10)6-4-7/h3-6,10H,1-2H3 checkY
    Key: JVVRCYWZTJLJSG-UHFFFAOYSA-N checkY
  • InChI=1/C8H11NO/c1-9(2)7-3-5-8(10)6-4-7/h3-6,10H,1-2H3
    Key: JVVRCYWZTJLJSG-UHFFFAOYAU
  • Oc1ccc(N(C)C)cc1
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).
☒N verify (what is checkY☒N ?)
Infobox references

Uses

4-Dimethylaminophenol has been used as an antidote for cyanide poisoning.[1] It has also been shown to be effective in treating hydrogen sulfide toxicity.[2]

It works by generating methemoglobin.[3]

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.[4] 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.[5]

See also

References
  1. Kampe, S.; Iffland, R.; Korenkov, M.; Diefenbach, Ch. (December 2000). "Survival from a lethal blood concentration of cyanide with associated alcohol intoxication: Case report". Anaesthesia. 55 (12): 1189–1191. doi:10.1046/j.1365-2044.2000.01628.x. PMID 11121929. S2CID 32892580.
  2. Lindenmann, Joerg; Matzi, Veronika; Neuboeck, Nicole; Ratzenhofer-Komenda, Beatrice; Maier, Alfred; Smolle-Juettner, Freyja-Maria (December 2010). "Severe hydrogen sulphide poisoning treated with 4-dimethylaminophenol and hyperbaric oxygen". Diving and Hyperbaric Medicine. 40 (4): 213–217. ISSN 1833-3516. PMID 23111938. Retrieved 2023-10-08.
  3. Vick JA, Von Bredow JD (1996). "Effectiveness of intramuscularly administered cyanide antidotes on methemoglobin formation and survival". J Appl Toxicol. 16 (6): 509–16. doi:10.1002/(SICI)1099-1263(199611)16:6<509::AID-JAT382>3.0.CO;2-V. PMID 8956097. S2CID 36140034.
  4. Vick JA, Froehlich H (July 1991). "Treatment of cyanide poisoning". Mil Med. 156 (7): 330–9. doi:10.1093/milmed/156.7.330. PMID 1922842.
  5. Federation of American Scientists (1 February 1996). NATO HANDBOOK ON THE MEDICAL ASPECTS OF NBC DEFENSIVE OPERATIONS (PDF). p. 334.
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