4-DIMETHYLAMINOPHENOL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H11NO
Molecular Weight	137.179
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN(C)C1=CC=C(O)C=C1

InChI

InChIKey=JVVRCYWZTJLJSG-UHFFFAOYSA-N

InChI=1S/C8H11NO/c1-9(2)7-3-5-8(10)6-4-7/h3-6,10H,1-2H3

HIDE SMILES / InChI

Molecular Formula	C8H11NO
Molecular Weight	137.179
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23111938 | https://www.ncbi.nlm.nih.gov/pubmed/8956097

4-dimethylaminophenol (or DMAP) is an effective intramuscular antidote for acute cyanide poisoning that works as a methemoglobin former.

Approval Year

PubMed

Title	Date	PubMed
Stability of 4-DMAP in solution.	2001 Oct	11763479
Glutathione-dependent reduction of arsenate in human erythrocytes--a process independent of purine nucleoside phosphorylase.	2004 Dec	15470234
Hyperoxia in lethal methemoglobinemia: effects on oxygen transport, tissue oxygenation, and survival in pigs.	2005 Jul	16003066
Life-threatening intoxication with methylene bis(thiocyanate): clinical picture and pitfalls. A case report.	2006 Apr 11	16608508
Mechanistic studies of the photocatalytic degradation of methyl green: an investigation of products of the decomposition processes.	2007 Jun 15	17626441
Biodegradation of crystal violet by a Shewanella sp. NTOU1.	2008 Aug	18582917
Determination of 4-dimethylaminophenol concentrations in dog blood using LC-ESI/MS/MS combined with precolumn derivatization.	2008 Dec 1	18993119
Clinical outcomes and kinetics of propanil following acute self-poisoning: a prospective case series.	2009 Feb 16	19220887
Severe hydrogen sulphide poisoning treated with 4-dimethylaminophenol and hyperbaric oxygen.	2010 Dec	23111938
Chemical warfare agents.	2010 Jul	21829312
Electrochemical degradation of crystal violet with BDD electrodes: effect of electrochemical parameters and identification of organic by-products.	2010 Sep	20709357

Sample Use Guides

In Vivo Use Guide

dimethylaminophenol (DMAP) is able to prevent the lethal effect of cyanide following intramuscular injections in dose sufficient to induce 20% methemoglobin (DMAP = 2 mg kg-1).

Route of Administration: Intramuscular

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:30:02 GMT 2023` Edited by `admin` on `Fri Dec 15 17:30:02 GMT 2023`
Record UNII	X387L5559O
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

4-DIMETHYLAMINOPHENOL

Systematic Name

English

4-(Dimethylamino)phenol [WHO-DD]

Common Name

English

PHENOL, P-(DIMETHYLAMINO)-

Common Name

English

P-DIMETHYLAMINOPHENOL

Common Name

English

N,N-DIMETHYL-P-HYDROXYANILINE

Common Name

English

4-(DIMETHYLAMINO)PHENOL

Systematic Name

English

N,N-DIMETHYL-4-AMINOPHENOL

Systematic Name

English

PARA-DIMETHYLAMINOPHENOL

Systematic Name

English

PHENOL, 4-(DIMETHYLAMINO)-

Systematic Name

English

Classification Tree Code System Code

WHO-ATC

V03AB27