Pamoic acid

Pamoic acid

Names
IUPAC name 4-[(3-Carboxy-2-hydroxynaphthalen-1-yl)methyl]-3-hydroxynaphthalene-2-carboxylic acid
Other names Embonic acid
Identifiers
CAS Number	130-85-8 Y
Beilstein Reference	901319
ChEBI	CHEBI:50186
ChEMBL	ChEMBL177880 Y
ChemSpider	8228 Y
EC Number	204-998-0
IUPHAR/BPS	2920
Jmol 3D model	Interactive image Interactive image
MeSH	Pamoic+acid
PubChem	8546
RTECS number	QL2180000
UNII	7RRQ8QZ38N Y
InChI InChI=1S/C23H16O6/c24-20-16(14-7-3-1-5-12(14)9-18(20)22(26)27)11-17-15-8-4-2-6-13(15)10-19(21(17)25)23(28)29/h1-10,24-25H,11H2,(H,26,27)(H,28,29) Y Key: WLJNZVDCPSBLRP-UHFFFAOYSA-N Y
SMILES OC(=O)C1=CC2=CC=CC=C2C(CC2=C(O)C(=CC3=CC=CC=C23)C(O)=O)=C1O C1=CC=C2C(=C1)C=C(C(=C2CC3=C(C(=CC4=CC=CC=C43)C(=O)O)O)O)C(=O)O
Properties
Chemical formula	C23H16O6
Molar mass	388.38 g·mol−1
Melting point	≥300 °C
log P	6.169
Acidity (pKa)	2.675
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Pamoic acid, also called embonic acid, is a naphthoic acid derivative. Salts and esters of pamoic acid are known as pamoates or embonates. It can be prepared by the reaction of 2-hydroxy-3-naphthoic acid with formaldehyde.

In pharmacology, the salt form of pamoic acid (pamoate ion) can be used as a counter ion of a drug compound to increase the solubility of the drug in water. The presence of multiple oxygen atoms enables significant hydrogen bonding to occur. Hydrogen bonds facilitate the dissolution of compounds in water.

Pamoic acid has agonist activity for the orphan G protein-coupled receptor GPR35 by which it activates ERK and beta-arrestin2, and causes antinociceptive activity. Although (like other drug salts) it has been considered an inactive compound by the FDA, these recent data suggest that its permitted uses may need to be reexamined.