4-Dimethylaminophenol

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,1-2H3 Key: JVVRCYWZTJLJSG-UHFFFAOYSA-N ; InChI=1/C8H11NO/c1-9(2)7-3-5-8(10)6-4-7/h3-6,10H,1-2H3 Key: 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 [77 °F], 100 kPa). 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.^[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]

References

^ 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.
^ 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.
^ 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.
^ 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.
^ Federation of American Scientists (1 February 1996). NATO HANDBOOK ON THE MEDICAL ASPECTS OF NBC DEFENSIVE OPERATIONS (PDF). p. 334.

[pmid11121929-1] 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.

[pmid23111938-2] 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.

[pmid8956097-3] 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.

[pmid1922842-4] 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.

[NATO_HANDBOOK_ON_THE_MEDICAL_ASPECTS_OF_NBC_DEFENSIVE_OPERATIONS-5] Federation of American Scientists (1 February 1996). NATO HANDBOOK ON THE MEDICAL ASPECTS OF NBC DEFENSIVE OPERATIONS (PDF). p. 334.

[1]

[2]

[3]

[4]

[5]

Uses

See also

References