Contents

4-Aminophenylmercuric acetate

4-Aminophenylmercuric acetate

Names
IUPAC name Acetyloxy-(4-aminophenyl)mercury
Identifiers
CAS Number	6283-24-5
3D model (JSmol)	Interactive image
Beilstein Reference	3664749
ChemSpider	8082118
ECHA InfoCard	100.025.907
EC Number	228-497-1
PubChem CID	16682983
CompTox Dashboard (EPA)	DTXSID8064197
InChI InChI=1S/C6H6N.C2H4O2.Hg/c7-6-4-2-1-3-5-6;1-2(3)4;/h2-5H,7H2;1H3,(H,3,4);/q;;+1/p-1 Key: RXSUFCOOZSGWSW-UHFFFAOYSA-M
SMILES CC(=O)O[Hg]C1=CC=C(C=C1)N
Properties
Chemical formula	C8H9HgNO2
Molar mass	351.757 g·mol−1
Appearance	off-white powder
Solubility in water	5 mM
Solubility	DMSO
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H300, H310, H330, H373, H410
Precautionary statements	P260, P262, P264, P270, P271, P273, P280, P284, P301+P310, P302+P350, P304+P340, P310, P314, P320, P321, P322, P330, P361, P363, P391, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

4-Aminophenylmercuric acetate (CH₃CO₂HgC₆H₄NH₂, also known as 4-(Acetoxymercurio)anilineorAPMA), is an organomercurial compound and thiol-blocking reagent used in experimental biology and chemistry to activate matrix metalloproteinases and collagenase proteolytic enzymes.^[1][2] The material is highly toxic.

Properties[edit]

APMA has a molecular weight of 351.8 g/mol and appears as a white powder with a slight yellowish cast. Its melting temperature is 163–165 °C.^[3] APMA is soluble in water to concentrations as high as 5 mM, and in DMSO to concentrations of 10 M or more. In 100% acetic acid, an APMA solution of 50 mg/mL is a light translucent yellow.^[3]

Protein modification[edit]

APMA is known to activate matrix metalloproteinase enzymes and collagenase.^[4] APMA activates proteolytic enzymes by reacting with cysteines at the amino terminal domains that bind zinc, near the location of the enzyme active site.^[4]

Toxicity[edit]

APMA and APMA vapors are highly toxic or fatal in contact with skin, or if inhaled or swallowed.^[3]

See also[edit]

• 4-Chloromercuribenzoic acid - an organomercury compound that is used as a protease inhibitor
• Phenylmercury acetate - a structurally related organomercury compound historically used as a preservative in paints

References[edit]