2-Aminoethoxydiphenyl borate

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 the 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 connexin.^[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]

2-Aminoethoxydiphenyl borate

Names
Preferred IUPAC name 2-[(Diphenylboranyl)oxy]ethan-1-amine
Other names 2-Aminoethyl diphenyl borate Diphenylborinic acid 2-aminoethyl ester 2-Aminoethyl diphenylborinate
Identifiers
CAS Number	524-95-8 N
3D model (JSmol)	Interactive image Interactive image
Abbreviations	2-APB
ChEBI	CHEBI:131184 N
ChEMBL	ChEMBL169233 Y
ChemSpider	1540 Y
ECHA InfoCard	100.007.607
EC Number	208-366-5
IUPHAR/BPS	2433
KEGG	C20698
PubChem CID	1598
UNII	E4ES684O93
CompTox Dashboard (EPA)	DTXSID0040389
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 Y Key: BLZVCIGGICSWIG-UHFFFAOYSA-N Y 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
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H315, H319, H335
Precautionary statements	P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
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). N verify (what is YN ?) Infobox references

References

1. Diver, J. M.; Sage, S. O.; Rosado, J. A. (2001-11-01). "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. doi:10.1054/ceca.2001.0239. ISSN 0143-4160. PMID 11733938.
2. Xu, Shang-Zhong; Zeng, Fanning; Boulay, Guylain; Grimm, Christian; Harteneck, Christian; Beech, David J. (2005-06-01). "Block of TRPC5 channels by 2-aminoethoxydiphenyl borate: a differential, extracellular and voltage-dependent effect". British Journal of Pharmacology. 145 (4): 405–414. doi:10.1038/sj.bjp.0706197. ISSN 0007-1188. PMC 1576154. PMID 15806115.
3. Bootman, Martin D.; Collins, Tony J.; Mackenzie, Lauren; Roderick, H. Llewelyn; Berridge, Michael J.; Peppiatt, Claire M. (2002-08-01). "2-aminoethoxydiphenyl borate (2-APB) is a reliable blocker of store-operated Ca2+ entry but an inconsistent inhibitor of InsP3-induced Ca2+ release". FASEB Journal. 16 (10): 1145–1150. doi:10.1096/fj.02-0037rev. ISSN 1530-6860. PMID 12153982. S2CID 43766251.
4. Bai, Donglin; del Corsso, Cristiane; Srinivas, Miduturu; Spray, David C. (2006-12-01). "Block of specific gap junction channel subtypes by 2-aminoethoxydiphenyl borate (2-APB)". The Journal of Pharmacology and Experimental Therapeutics. 319 (3): 1452–1458. doi:10.1124/jpet.106.112045. ISSN 0022-3565. PMID 16985167. S2CID 2375567.
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.