4-Dimethylaminophenol
{{cs1 config|name-list-style=vanc}}
{{Distinguish|4-Dimethylaminopyridine}}
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477221522
| ImageFile = 4-Dimethylaminophenol.svg
| ImageSize = 75px
| PIN = 4-(Dimethylamino)phenol
| OtherNames =
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 20816
| InChI = 1/C8H11NO/c1-9(2)7-3-5-8(10)6-4-7/h3-6,10H,1-2H3
| InChIKey = JVVRCYWZTJLJSG-UHFFFAOYAU
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C8H11NO/c1-9(2)7-3-5-8(10)6-4-7/h3-6,10H,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = JVVRCYWZTJLJSG-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|changed|??}}
| CASNo = 619-60-3
| PubChem = 22174
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = X387L5559O
| SMILES = Oc1ccc(N(C)C)cc1
}}
|Section2={{Chembox Properties
| Formula = C8H11NO
| MolarMass = 137.179 g/mol
| Appearance =
| Density =
| MeltingPt =
| BoilingPtC = 165
| BoilingPt_notes = (0.040 bar)
| Solubility =
}}
|Section6={{Chembox Pharmacology
| ATCCode_prefix = V03
| ATCCode_suffix = AB27
}}
|Section7={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
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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.{{cite journal |last1=Kampe |first1=S. |last2=Iffland |first2=R. |last3=Korenkov |first3=M. |last4=Diefenbach |first4=Ch. |date=December 2000 |title=Survival from a lethal blood concentration of cyanide with associated alcohol intoxication: Case report |journal=Anaesthesia |language=en |volume=55 |issue=12 |pages=1189–1191 |doi=10.1046/j.1365-2044.2000.01628.x |pmid=11121929 |s2cid=32892580|doi-access=free }} It has also been shown to be effective in treating hydrogen sulfide toxicity.{{cite journal |last1=Lindenmann |first1=Joerg |last2=Matzi |first2=Veronika |last3=Neuboeck |first3=Nicole |last4=Ratzenhofer-Komenda |first4=Beatrice |last5=Maier |first5=Alfred |last6=Smolle-Juettner |first6=Freyja-Maria |date=December 2010 |title=Severe hydrogen sulphide poisoning treated with 4-dimethylaminophenol and hyperbaric oxygen |url=https://pubmed.ncbi.nlm.nih.gov/23111938/ |journal=Diving and Hyperbaric Medicine |volume=40 |issue=4 |pages=213–217 |issn=1833-3516 |pmid=23111938 |access-date=2023-10-08}}
It works by generating methemoglobin.{{cite journal |vauthors=Vick JA, Von Bredow JD |year=1996 |title=Effectiveness of intramuscularly administered cyanide antidotes on methemoglobin formation and survival |url=https://zenodo.org/record/1235518 |journal=J Appl Toxicol |volume=16 |issue=6 |pages=509–16 |doi=10.1002/(SICI)1099-1263(199611)16:6<509::AID-JAT382>3.0.CO;2-V |pmid=8956097 |s2cid=36140034|doi-access=free }}
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.{{cite journal |vauthors=Vick JA, Froehlich H |date=July 1991 |title=Treatment of cyanide poisoning |journal=Mil Med |volume=156 |issue=7 |pages=330–9 |doi=10.1093/milmed/156.7.330 |pmid=1922842 |doi-access=free}} 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.{{cite book |last=Federation of American Scientists |url=https://fas.org/irp/doddir/army/fm8-9.pdf |title=NATO HANDBOOK ON THE MEDICAL ASPECTS OF NBC DEFENSIVE OPERATIONS |date=1 February 1996 |pages=334}}
See also
References
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{{Antidotes}}
{{DEFAULTSORT:Dimethylaminophenol, 4-}}