2-Aminoethoxydiphenyl borate

2-Aminoethoxydiphenyl borate

Names
IUPAC name 2-Diphenylboranyloxyethanamine
Other names 2-Aminoethyl diphenyl borate Diphenylborinic acid 2-aminoethyl ester 2-Aminoethyl diphenylborinate
Identifiers
CAS Number	524-95-8
Abbreviations	2-APB
ChEBI	CHEBI:131184
ChEMBL	ChEMBL169233
ChemSpider	1540
IUPHAR/BPS	2433
Jmol interactive 3D	Image Image
PubChem	1598
InChI InChI=1S/C14H16BNO/c16-11-12-17-15(13-7-3-1-4-8-13)14-9-5-2-6-10-14/h1-10H,11-12,16H2 Key: BLZVCIGGICSWIG-UHFFFAOYSA-N InChI=1/C14H16BNO/c16-11-12-17-15(13-7-3-1-4-8-13)14-9-5-2-6-10-14/h1-10H,11-12,16H2 Key: BLZVCIGGICSWIG-UHFFFAOYAJ
SMILES B(C1=CC=CC=C1)(C2=CC=CC=C2)OCCN O(B(c1ccccc1)c2ccccc2)CCN
Properties
Chemical formula	C14H16BNO
Molar mass	225.10 g·mol^−1
Appearance	white
Density	1.04g/cm3
Melting point	192 to 194 °C (378 to 381 °F; 465 to 467 K)
Boiling point	325.3 °C (617.5 °F; 598.5 K) at 760mmHg
Hazards
S-phrases	S22 S24/25
Flash point	150.6 °C (303.1 °F; 423.8 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

2-Aminoethoxydiphenyl borate (2-APB) is a chemical that acts to inhibit both IP₃ receptors^[1] and TRP channels (although it activates TRPV1, TRPV2, & TRPV3 at higher concentrations).^[2][3] In research it is used to manipulate intracellular release of calcium ions (Ca²⁺) and modify TRP channel activity, although there its lack of specific effects make it less than ideal under some circumstances. Additionally, there is evidence that 2-APB acts directly to inhibit gap junctions made of connexin26 or connexin32.^[4] Increasing evidence showed that 2-APB is a powerful modifier of store-operated calcium channels (SOC) function, low concentration of 2-APB can enhance SOC while high concentration induces a transient increase followed by complete inhibition.^[5][6][7]

References

1. Diver JM, Sage SO, Rosado JA (2001). The inositol trisphosphate receptor antagonist 2-aminoethoxydiphenylborate (2-APB) blocks Ca2+ entry channels in human platelets: cautions for its use in studying Ca2+ influx. Cell Calcium, 30(5), 323-329.
2. Xu SZ, Zeng F, Boulay G, Grimm C, Harteneck C, Beech DJ (2005). Block of TRPC5 channels by 2-aminoethoxydiphenyl borate: a differential, extracellular and voltage-dependent effect. British Journal of Pharmacology, 145(4), 320-328.
3. Bootman, MD, Collins, TJ, Makenzie, L, Roderick, HL, Berridge, MJ, & Peppiatt, CM (2002). 2-Aminoethoxydiphenyl borate (2-APB) is a reliable blocker of store-operated Ca²⁺ entry but an inconsistent inhibitor of InsP3-induced Ca²⁺ release. The FASEB Journal, 16(10), 1145-1150.
4. Tao, L, & Harris, AL (2007). 2-aminoethoxydiphenyl borate directly inhibits channels composed of connexin26 and/or connexin32. Molecular Pharmacology, 71(2), 570-579.
5. Ma HT, et al. (2000) Requirement of the inositol trisphosphate receptor for activation of store-operated Ca2+ channels. Science 287:1647–1651.
6. Prakriya M, Lewis RS (2001) Potentiation and inhibition of Ca2+ release-activated Ca2+ channels by 2-aminoethyldiphenyl borate (2-APB) occurs independently of IP 3 receptors. J Physiol 536:3–19.
7. Ma HT, Venkatachalam K, Parys JB, Gill DL (2002) Modification of store-operated channel coupling and inositol trisphosphate receptor function by 2-aminoethoxydiphenyl borate in DT40 lymphocytes. J Biol Chem 277:6915–6922.