4-Aminophenylmercuric acetate

4-Aminophenylmercuric acetate (CH₃CO₂HgC₆H₄NH₂, also known as 4-(Acetoxymercurio)aniline or APMA), 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.

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 pictograms
GHS Signal word	Danger
GHS hazard statements	H300, H310, H330, H373, H400, H410
GHS precautionary statements	P260, P262, P264, P270, P271, P273, P280, P284, P301+310, P302+350, P304+340, P310, P314, P320, P321, P322, P330, P361, P363, P391, P403+233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Properties

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

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

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

See also

• 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

1. Rosenfeldt, Mathias (2005). "The organomercurial 4-aminophenylmercuric acetate, independent of matrix metalloproteinases, induces dose-dependent activation/ inhibition of platelet aggregation". Thromb Haemost. 93 (2): 326. doi:10.1160/th04-08-0541. PMID 15711750.
2. Sellers, Anthony; Cartwright, Elizabeth; Murphy, Gillian; Reynolds, John (1977). "Evidence that Latent Collagenases are Enzyme-Inhibitor Complexes". Biochemical Journal. 163: 303–307. doi:10.1042/bj1630303. PMC 1164697. PMID 194584.
3. "p-Aminotophenylmercuric acetate material safety data sheet" (PDF). sigmaaldrich.com. Sigma Aldrich. Retrieved 7 June 2018.
4. Lundblad, Roger (2014). Chemical reagents for protein modification (Fourth ed.). CRC Press. p. 234. Retrieved 7 June 2018.

Acetyl halides and salts of the acetate ion
AcOH																		He
LiOAc	Be(OAc)2 BeAcOH												B(OAc)3	AcOAc ROAc	NH4OAc	AcOOH	FAc	Ne
NaOAc	Mg(OAc)2												Al(OAc)3 ALSOL Al(OAc)2OH Al2SO4(OAc)4	Si	P	S	ClAc	Ar
KOAc	Ca(OAc)2		Sc(OAc)3	Ti(OAc)4	VO(OAc)3	Cr(OAc)2 Cr(OAc)3	Mn(OAc)2 Mn(OAc)3	Fe(OAc)2 Fe(OAc)3	Co(OAc)2, Co(OAc)3	Ni(OAc)2	Cu(OAc)2	Zn(OAc)2	Ga(OAc)3	Ge	As(OAc)3	Se	BrAc	Kr
RbOAc	Sr(OAc)2		Y(OAc)3	Zr(OAc)4	Nb	Mo(OAc)2	Tc	Ru(OAc)2 Ru(OAc)3 Ru(OAc)4	Rh2(OAc)4	Pd(OAc)2	AgOAc	Cd(OAc)2	In	Sn(OAc)2 Sn(OAc)4	Sb(OAc)3	Te	IAc	Xe
CsOAc	Ba(OAc)2	*	Lu(OAc)3	Hf	Ta	W	Re	Os	Ir	Pt(OAc)2	Au	Hg2(OAc)2, Hg(OAc)2	TlOAc Tl(OAc)3	Pb(OAc)2 Pb(OAc)4	Bi(OAc)3	Po	At	Rn
Fr	Ra	**	Lr	Rf	Db	Sg	Bh	Hs	Mt	Ds	Rg	Cn	Nh	Fl	Mc	Lv	Ts	Og
		*	La(OAc)3	Ce(OAc)x	Pr	Nd	Pm	Sm(OAc)3	Eu(OAc)3	Gd(OAc)3	Tb	Dy(OAc)3	Ho(OAc)3	Er	Tm	Yb(OAc)3
		**	Ac	Th	Pa	UO2(OAc)2	Np	Pu	Am	Cm	Bk	Cf	Es	Fm	Md	No