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4-Dimethylaminophenol

Names
Preferred IUPAC name 4-(Dimethylamino)phenol
Identifiers
CAS Number	619-60-3
3D model (JSmol)	Interactive image
ChemSpider	20816
ECHA InfoCard	100.009.642
PubChem CID	22174
UNII	X387L5559O
CompTox Dashboard (EPA)	DTXSID70210932
InChI InChI=1S/C8H11NO/c1-9(2)7-3-5-8(10)6-4-7/h3-6,10H,1-2H3Key: JVVRCYWZTJLJSG-UHFFFAOYSA-N InChI=1/C8H11NO/c1-9(2)7-3-5-8(10)6-4-7/h3-6,10H,1-2H3Key: JVVRCYWZTJLJSG-UHFFFAOYAU
SMILES Oc1ccc(N(C)C)cc1
Properties
Chemical formula	C8H11NO
Molar mass	137.179 g/mol
Boiling point	165 °C (329 °F; 438 K) (0.040 bar)
Pharmacology
ATC code	V03AB27 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is  ?) Infobox references

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

Uses

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

It works by generating methemoglobin.

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. 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.

See also

• Metol

References

1. Kampe S, Iffland R, Korenkov M, Diefenbach C (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 J, Matzi V, Neuboeck N, Ratzenhofer-Komenda B, Maier A, Smolle-Juettner FM (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.

• Antidotes
• Anilines
• 4-Hydroxyphenyl compounds