Cimaterol(CL 263780) - Moligand™, ≥98% , Agonist of β 1-adrenoceptor;Agonist of β 2-adrenoceptor, CAS No.54239-37-1, Agonist of β 1-adrenoceptor;Agonist of β 2-adrenoceptor

CAS: 54239-37-1 Cat. No.: C140718 Molecular Weight: 219.28 Beilstein Registry Number: 2418129 EC Number: 632-644-9

GRADE & PURITY Moligand™, ≥98%

Synonyms

Cimater | Cimaterolum | 2-amino-5-[1-hydroxy-2-[(1-methylethyl)amino]ethyl]-benzonitrile | CL 263780 | CL 263780 | (±)-2-Amino-5-[1-hydroxy-2-[(1-methylethyl)amino]ethyl]benzonitrile

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Cimaterol (CL 263780) is a β-adrenergic agonist on energy metabolism in ob/ob mice. The Kd for Cimaterol binding to the L6 β-receptor is 26 nM which is compatible with its EC50 for the stimulation of protein synthesis (approx 5 nM).

Specifications

Synonyms

Cimater | Cimaterolum | 2-amino-5-[1-hydroxy-2-[(1-methylethyl)amino]ethyl]-benzonitrile | CL 263780 | CL 263780 | (±)-2-Amino-5-[1-hydroxy-2-[(1-methylethyl)amino]ethyl]benzonitrile

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

β adrenoceptor agonist (K i = 2.32 μM). Active in vivo .

Storage

Protected from light, Store at -20°C

Shipped In

Ice chest + Ice pads

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

Grade

Moligand™

Action Type

AGONIST

Mechanism of action

Agonist of β 1-adrenoceptor;Agonist of β 2-adrenoceptor

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

• Canonical Smiles: CC(C)NCC(C1=CC(=C(C=C1)N)C#N)O
• IUPAC Name: 2-amino-5-[1-hydroxy-2-(propan-2-ylamino)ethyl]benzonitrile
• InChIKey: BUXRLJCGHZZYNE-UHFFFAOYSA-N
• INCHI: 1S/C12H17N3O/c1-8(2)15-7-12(16)9-3-4-11(14)10(5-9)6-13/h3-5,8,12,15-16H,7,14H2,1-2H3
• Isomeric SMILES: CC(C)NCC(C1=CC(=C(C=C1)N)C#N)O
• WGK Germany: 3
• RTECS: DI2457930
• Alternate CAS: 54239-37-1
• MeSH Entry Terms: 5-(1-hydroxy-2-(isopropylamino)ethyl)anthranilonitrile;cimaterol;cimatrol;CL 263,780;CL-263,780
• Molecular Weight: 219.28
• Beilstein: 2418129
• Reaxy-Rn: 2418129
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2418129&ln=

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Benzonitriles
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzonitriles
• Alternative Parents: Aniline and substituted anilines Aralkylamines Secondary alcohols 1,2-aminoalcohols Nitriles Dialkylamines Primary amines Organopnictogen compounds Hydrocarbon derivatives Aromatic alcohols
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Benzonitrile - Aniline or substituted anilines - Aralkylamine - 1,2-aminoalcohol - Secondary alcohol - Secondary aliphatic amine - Carbonitrile - Nitrile - Secondary amine - Primary amine - Organooxygen compound - Organonitrogen compound - Amine - Alcohol - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Aromatic alcohol - Hydrocarbon derivative - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as benzonitriles. These are organic compounds containing a benzene bearing a nitrile substituent.
• 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)

ADRB2 Tclin Beta-2 adrenergic receptor (0 Activities)

Discover Target: ADRB2

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

ADRB1 Tclin Beta-1 adrenergic receptor (1 Activities)

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

ABL1 Tclin Tyrosine-protein kinase ABL (18331 Activities)

Discover Target: ABL1

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

ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)

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

ADRB1 Tclin Beta-1 adrenergic receptor (6630 Activities)

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

ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

Discover Target: ADRA2A

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

AGTR1 Tclin Type-1 angiotensin II receptor (5176 Activities)

Discover Target: AGTR1

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

ADRB3 Tclin Beta-3 adrenergic receptor (5850 Activities)

Discover Target: ADRB3

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GSK3B Tclin Glycogen synthase kinase-3 beta (11785 Activities)

Discover Target: GSK3B

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

CSNK1D Tchem Casein kinase I delta (4546 Activities)

Discover Target: CSNK1D

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

S1PR1 Tclin Sphingosine 1-phosphate receptor Edg-1 (5806 Activities)

Discover Target: S1PR1

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

CDK2 Tchem Cyclin-dependent kinase 2 (9050 Activities)

Discover Target: CDK2

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

GLP1R Tclin Glucagon-like peptide 1 receptor (111429 Activities)

Discover Target: GLP1R

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

C5AR1 Tclin C5a anaphylatoxin chemotactic receptor (2677 Activities)

Discover Target: C5AR1

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AURKA Tchem Serine/threonine-protein kinase Aurora-A (10240 Activities)

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U2OS (164939 Activities)

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CX3CR1 Tchem C-X3-C chemokine receptor 1 (1686 Activities)

Discover Target: CX3CR1

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FPR2 Tchem Lipoxin A4 receptor (3472 Activities)

Discover Target: FPR2

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FFAR4 Tchem G-protein coupled receptor 120 (2999 Activities)

Discover Target: FFAR4

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BRD4 Tchem Bromodomain-containing protein 4 (13122 Activities)

Discover Target: BRD4

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

GPR35 Tchem G-protein coupled receptor 35 (2643 Activities)

Discover Target: GPR35

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

RGS4 Tchem Regulator of G-protein signaling 4 (13867 Activities)

Discover Target: RGS4

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

TRIM24 Tchem Transcription intermediary factor 1-alpha (2087 Activities)

Discover Target: TRIM24

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

BRPF1 Tchem Peregrin (2217 Activities)

Discover Target: BRPF1

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HEK-293T (167025 Activities)

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Associated Targets(non-human)

Aplnr Apelin receptor (201 Activities)

Discover Target: Aplnr

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

Fgfr3 Fibroblast growth factor receptor 3 (21 Activities)

Discover Target: Fgfr3

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

Plasmodium falciparum (966862 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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Gpr119 Glucose-dependent insulinotropic receptor (270 Activities)

Discover Target: Gpr119

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

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SARS-CoV-2 (38078 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water (partly miscible), ethanol (100 mM), DMSO (100 mM), and methanol
• Molecular Weight: 219.280 g/mol
• XLogP3: 1.700
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 219.137 Da
• Monoisotopic Mass: 219.137 Da
• Topological Polar Surface Area: 82.100 Ų
• Heavy Atom Count: 16
• Formal Charge: 0
• Complexity: 258.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Lanteng Wang, Jin Wang, Ang Zhang, Xin-an Huang, Hongtao Lei.  (2021)  Two binding epitopes modulating specificity of immunoassay for β-agonist detection: Quantitative structure–activity relationship.  FOOD CHEMISTRY,      [PMID:34537613] [10.1016/j.foodchem.2021.131071]

2. Yufeng Zhou, Haijiao Zheng, Jiutong Ma, Qiong Jia.  (2017)  Preparation of a polymer monolith modified with delaminated layered double hydroxides for the microextraction of β-agonists.  JOURNAL OF SEPARATION SCIENCE,  40  (7): (1548-1555).  [PMID:28181395] [10.1002/jssc.201601324]

3. Liang Luo, Chaochao Chen, Jincheng Xiong, Yanton Pan, Qiang Li, Xiaonan Wang, Sihan Wang, Jianzhong Shen, Zhanhui Wang.  (2024)  Nanozyme–Enzyme Cascade Reaction-Enhanced Ratiometric Fluorescence Immunosensing Platform for Sensitive and Accurate Detection of Ractopamine.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:39537347] [10.1021/acs.jafc.4c08869]