2-Aminoethyl diphenylborinate (2-APB) - Moligand™, ≥98% , Channel blocker of TRPC1;Channel blocker of TRPC3;Channel blocker of TRPC4;Channel blocker of TRPC5;Channel blocker of TRPC6;Channel blocker of TRPC7;Channel blocker of TRPM2;Gating inhibitor of TR, Channel blocker of TRPC1;Channel blocker of TRPC3;Channel blocker of TRPC4;Channel blocker of TRPC5;Channel blocker of TRPC6;Channel blocker of TRPC7;Channel blocker of TRPM2;Gating inhibitor of TRPM3;Activator of TRPM6;Activator of TRPM7;Channel blocker

CAS: 524-95-8 Cat. No.: A106408 Molecular Weight: 225.09 Beilstein Registry Number: 2942273 EC Number: 208-366-5

GRADE & PURITY Moligand™, ≥98%

Synonyms

MFCD00014823 | SB79870 | BORINIC ACID, B,B-DIPHENYL-, 2-AMINOETHYL ESTER | 2-Aminoethyl diphenylborinate | C14H16BNO | UNII-E4ES684O93 | 2-aminoethoxydephenylborate | STL481977 | HB1208 | 2-((Diphenylboryl)oxy)ethanamine | 2-(Diphenylboryloxy)Ethanamine |

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

2-APB is a transient receptor potential (TRP) activator. The compound also directly blocks the mitochondrial permeability transition pore, sarco/endoplasmic reticulum Ca2+-ATPase pumps, and native store operated channels, as well as other ion channels. 

2-APB does not activate the subfamily transient receptor potential vanilloids (TRPVs) TRPV4, TRPV5, and TRPV6, but can activate VR1 (TRPV1), VRL-1 (TRPV2), and TRPV3. 2-ABP was first used as an inhibitor of IP3R (inositol 1,4,5-triphosphate receptor) with the ability to permeate the membrane. 

2-ABP can induce Ca2+entry without activating exocytosis. In pancreatic acinar cells 2-ABP can inhibit calcium mobilization. 2-APB is an activator of Orai3.

Specifications

Synonyms

MFCD00014823 | SB79870 | BORINIC ACID, B, B-DIPHENYL-, 2-AMINOETHYL ESTER | 2-Aminoethyl diphenylborinate | C14H16BNO | UNII-E4ES684O93 | 2-aminoethoxydephenylborate | STL481977 | HB1208 | 2-((Diphenylboryl)oxy)ethanamine | 2-(Diphenylboryloxy)Ethanamine |

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Cell-permeable, allosteric inhibitor of D- myo -inositol 1, 4, 5-trisphosphate (IP3) -induced Ca 2+ release . Inhibits IP3-induced Ca 2+ release without affecting IP3 receptor binding. Blocks store operated Ca 2+ entry.

Storage

Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

ACTIVATOR, CHANNEL BLOCKER, GATING INHIBITOR

Mechanism of action

Channel blocker of TRPC1;Channel blocker of TRPC3;Channel blocker of TRPC4;Channel blocker of TRPC5;Channel blocker of TRPC6;Channel blocker of TRPC7;Channel blocker of TRPM2;Gating inhibitor of TRPM3;Activator of TRPM6;Activator of TRPM7;Channel blocker

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488179629
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488179629
• Canonical Smiles: B(C1=CC=CC=C1)(C2=CC=CC=C2)OCCN
• IUPAC Name: 2-diphenylboranyloxyethanamine
• InChIKey: BLZVCIGGICSWIG-UHFFFAOYSA-N
• 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
• Isomeric SMILES: B(C1=CC=CC=C1)(C2=CC=CC=C2)OCCN
• WGK Germany: 3
• RTECS: ED6150000
• Molecular Weight: 225.09
• Beilstein: 2942273
• Reaxy-Rn: 2942273
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2942273&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzene and substituted derivatives
• Alternative Parents: Borinic acid esters Organic metalloid salts Organopnictogen compounds Organooxygen compounds Organoboron compounds Monoalkylamines Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Monocyclic benzene moiety - Borinic acid ester - Borinic acid derivative - Organic metalloid salt - Amine - Hydrocarbon derivative - Organic salt - Organopnictogen compound - Organic oxygen compound - Primary amine - Organooxygen compound - Organonitrogen compound - Organoboron compound - Primary aliphatic amine - Organic nitrogen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

TRPM2 Tchem Transient receptor potential cation channel subfamily M member 2 (6 Activities)

Discover Target: TRPM2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

TRPM3 Tchem Transient receptor potential cation channel subfamily M member 3 (1 Activities)

Discover Target: TRPM3

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

TRPM6 Tchem Transient receptor potential cation channel subfamily M member 6 (0 Activities)

Discover Target: TRPM6

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

TRPM7 Tchem Transient receptor potential cation channel subfamily M member 7 (1 Activities)

Discover Target: TRPM7

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

TRPV3 Tchem Transient receptor potential cation channel subfamily V member 3 (1 Activities)

Discover Target: TRPV3

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

TRPV6 Tchem Transient receptor potential cation channel subfamily V member 6 (0 Activities)

Discover Target: TRPV6

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

TRPC3 Tchem Short transient receptor potential channel 3 (1 Activities)

Discover Target: TRPC3

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

TRPC4 Tchem Short transient receptor potential channel 4 (0 Activities)

Discover Target: TRPC4

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

TRPC5 Tchem Short transient receptor potential channel 5 (1 Activities)

Discover Target: TRPC5

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

TRPC6 Tchem Short transient receptor potential channel 6 (0 Activities)

Discover Target: TRPC6

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

TRPV1 Tclin Transient receptor potential cation channel subfamily V member 1 (0 Activities)

Discover Target: TRPV1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

TRPC7 Tchem Short transient receptor potential channel 7 (0 Activities)

Discover Target: TRPC7

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

TRPC1 Tbio Short transient receptor potential channel 1 (0 Activities)

Discover Target: TRPC1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

TRPV2 Tchem Transient receptor potential cation channel subfamily V member 2 (1 Activities)

Discover Target: TRPV2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

TRPM8 Tclin Transient receptor potential cation channel subfamily M member 8 (0 Activities)

Discover Target: TRPM8

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

VDR Tclin Vitamin D receptor (26531 Activities)

Discover Target: VDR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TSHR Tclin Thyroid stimulating hormone receptor (29986 Activities)

Discover Target: TSHR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

THRB Tclin Thyroid hormone receptor beta-1 (7926 Activities)

Discover Target: THRB

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TRPV1 Tclin Vanilloid receptor (8273 Activities)

Discover Target: TRPV1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALOX15B Tchem Arachidonate 15-lipoxygenase, type II (7244 Activities)

Discover Target: ALOX15B

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

Discover Target: ALDH1A1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALOX12 Tchem Arachidonate 12-lipoxygenase (3262 Activities)

Discover Target: ALOX12

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)

Discover Target: CYP2D6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALOX15 Tchem Arachidonate 15-lipoxygenase (7108 Activities)

Discover Target: ALOX15

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)

Discover Target: CYP1A2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)

Discover Target: CYP2C9

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)

Discover Target: CYP2C19

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

Discover Target: CYP3A4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SH-SY5Y (11521 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TRPV3 Tchem Transient receptor potential cation channel subfamily V member 3 (542 Activities)

Discover Target: TRPV3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

Discover Target: TDP1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TRPM2 Tchem Transient receptor potential cation channel subfamily M member 2 (348 Activities)

Discover Target: TRPM2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TRPM7 Tchem Transient receptor potential cation channel subfamily M member 7 (19 Activities)

Discover Target: TRPM7

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

KDM4E Tchem Lysine-specific demethylase 4D-like (40243 Activities)

Discover Target: KDM4E

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HPGD Tchem 15-hydroxyprostaglandin dehydrogenase [NAD+] (24926 Activities)

Discover Target: HPGD

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

USP1 Tchem Ubiquitin carboxyl-terminal hydrolase 1 (22556 Activities)

Discover Target: USP1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)

Discover Target: MEN1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ORAI1 Tchem Calcium release-activated calcium channel protein 1 (150 Activities)

Discover Target: ORAI1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SMAD2 Tbio Mothers against decapentaplegic homolog 2 (9 Activities)

Discover Target: SMAD2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Cruzipain (33337 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mapk1 MAP kinase ERK2 (650 Activities)

Discover Target: Mapk1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Trpv2 Transient receptor potential cation channel subfamily V member 2 (148 Activities)

Discover Target: Trpv2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mycobacterium tuberculosis (203094 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

lef Anthrax lethal factor (7585 Activities)

Discover Target: lef

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ATP2A1 Sarcoplasmic/endoplasmic reticulum calcium ATP-ase (121 Activities)

Discover Target: ATP2A1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GCN5 Histone acetyltransferase GCN5 (89 Activities)

Discover Target: GCN5

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Trpm8 Transient receptor potential cation channel subfamily M member 8 (889 Activities)

Discover Target: Trpm8

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Rorc Nuclear receptor ROR-gamma (89407 Activities)

Discover Target: Rorc

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ffp 4'-phosphopantetheinyl transferase ffp (24982 Activities)

Discover Target: ffp

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in Methanol
• Sensitivity: Light and Moisture Sensitive
• Melt Point(°C): 190-194°C
• Molecular Weight: 225.100 g/mol
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 225.132 Da
• Monoisotopic Mass: 225.132 Da
• Topological Polar Surface Area: 35.300 Ų
• Heavy Atom Count: 17
• Formal Charge: 0
• Complexity: 182.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

XLogP3

References

1. Kong Yuanyuan, Hu Xiaoli, Zhong Yingqun, Xu Ke, Wu Buling, Zheng Jianmao.  (2019)  Magnesium-enriched microenvironment promotes odontogenic differentiation in human dental pulp stem cells by activating ERK/BMP2/Smads signaling.  Stem Cell Research & Therapy,  10  (1): (1-11).  [PMID:31823825] [10.1186/s13287-019-1493-5]

2. Zhihui Yu, Yating Gao, Huiling Duan, Dan Zheng, Ziqi Shang, Lixin Zhang, Yisheng Chen.  (2024)  Ultrasound-assisted germination of red kidney beans: Enhancements in physicochemical and nutritional profiles.  FOOD CHEMISTRY,      [PMID:38810443] [10.1016/j.foodchem.2024.139829]

3. Mingzhi Luo, Peili Yu, Kai Ni, Yang Jin, Lei Liu, Jingjing Li, Yan Pan, Linhong Deng.  (2020)  Sanguinarine Rapidly Relaxes Rat Airway Smooth Muscle Cells Dependent on TAS2R Signaling.  BIOLOGICAL & PHARMACEUTICAL BULLETIN,  43  (7): (1027-1034).  [PMID:32404582] [10.1248/bpb.b19-00825]

4. Liu Tao, Zhu Yuzhang, Wang Jiahui, Hong Xiangyu, Liu Mi, Kong Chaonan, Zhou Rui, Li Xianke, Yang Lifang.  (2024)  Antibacterial effects and mechanisms of quercetin-β-cyclodextrin complex mediated photodynamic on Escherichia coli O157:H7.  ARCHIVES OF MICROBIOLOGY,  206  (11): (1-18).  [PMID:39443369] [10.1007/s00203-024-04175-1]