Phentolamine Mesylate - ≥98% , Adrenergic receptor alpha antagonist, CAS No.65-28-1, Adrenergic receptor alpha antagonist

CAS: 65-28-1 Cat. No.: P123277 Molecular Weight: 377.46 EC Number: 200-604-6

GRADE & PURITY ≥98%

Synonyms

3-[[(4,5-Dihydro-1H-imidazol-2-yl)methyl](4-methylphenyl)amino]phenol methanesulfonate | PHENTOLAMINE MESYLATE (USP-RS) | Regitine methanesulfonate | LP00982 | NSC 220061 | P 7561 | Phentolamine mesilate [INN:BAN] | Phentolamine methanesulfonate salt, >=9

Storage

Protected from light,Room temperature

Shipped In

Normal

Overview

α-Adrenergic receptor antagonist; peripheral vasodilator.

Specifications

Synonyms

3-[[(4, 5-Dihydro-1H-imidazol-2-yl)methyl](4-methylphenyl)amino]phenol methanesulfonate | PHENTOLAMINE MESYLATE (USP-RS) | Regitine methanesulfonate | LP00982 | NSC 220061 | P 7561 | Phentolamine mesilate [INN:BAN] | Phentolamine methanesulfonate salt, >=9

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Potent, competitive and reversible non-selective α-adrenoceptor antagonist. Inhibits agonist-induced smooth muscle contractions (IC 50 = 5-30 nM). Shows vasodilatory, positive inotropic, chronotropic and antihypertensive effects in vivo.

Storage

Protected from light, Room temperature

Shipped In

Normal

Action Type

ANTAGONIST

Mechanism of action

Adrenergic receptor alpha antagonist

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: 488186651
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488186651
• Canonical Smiles: CC1=CC=C(C=C1)N(CC2=NCCN2)C3=CC(=CC=C3)O.CS(=O)(=O)O
• IUPAC Name: 3-[N-(4,5-dihydro-1H-imidazol-2-ylmethyl)-4-methylanilino]phenol;methanesulfonic acid
• InChIKey: OGIYDFVHFQEFKQ-UHFFFAOYSA-N
• INCHI: 1S/C17H19N3O.CH4O3S/c1-13-5-7-14(8-6-13)20(12-17-18-9-10-19-17)15-3-2-4-16(21)11-15;1-5(2,3)4/h2-8,11,21H,9-10,12H2,1H3,(H,18,19);1H3,(H,2,3,4)
• Isomeric SMILES: CC1=CC=C(C=C1)N(CC2=NCCN2)C3=CC(=CC=C3)O.CS(=O)(=O)O
• WGK Germany: 3
• RTECS: SL5430000
• Molecular Weight: 377.46
• Reaxy-Rn: 3826682
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=3826682&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic nitrogen compounds
    • Class Organonitrogen compounds
      • Subclass Amines
        • Level5 Tertiary amines
          • Level6 Tertiary alkylarylamines
            • Level7 Alkyldiarylamines

• Kingdom: Organic compounds
• Superclass: Organic nitrogen compounds
• Class: Organonitrogen compounds
• Subclass: Amines
• Intermediate Tree Nodes: Tertiary amines - Tertiary alkylarylamines
• Direct Parent: Alkyldiarylamines
• Alternative Parents: m-Aminophenols Aminotoluenes Aniline and substituted anilines 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Imidolactams Sulfonyls Alkanesulfonic acids Organosulfonic acids Imidazolines Methanesulfonates Carboximidamides Carboxamidines Azacyclic compounds Propargyl-type 1,3-dipolar organic compounds Hydrocarbon derivatives Organooxygen compounds Organopnictogen compounds Organic oxides
• Molecular Framework: Not available
• Substituents: Alkyldiarylamine - M-aminophenol - Aminophenol - Aminotoluene - Aniline or substituted anilines - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Toluene - Monocyclic benzene moiety - Benzenoid - Imidolactam - 2-imidazoline - Methanesulfonate - Organic sulfonic acid or derivatives - Organosulfonic acid or derivatives - Organosulfonic acid - Sulfonyl - Alkanesulfonic acid - Amidine - Carboxylic acid amidine - Carboximidamide - Azacycle - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Organoheterocyclic compound - Organopnictogen compound - Organic oxide - Organosulfur compound - Organooxygen compound - Hydrocarbon derivative - Organic oxygen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as alkyldiarylamines. These are tertiary alkylarylamines having two aryl and one alkyl groups attached to the amino group.
• 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)

CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

Discover Target: CHRM1

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TSHR Tclin Thyroid stimulating hormone receptor (29986 Activities)

Discover Target: TSHR

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KCNH2 Tclin HERG (29587 Activities)

Discover Target: KCNH2

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CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)

Discover Target: CYP2D6

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NFKB1 Tclin Nuclear factor NF-kappa-B p105 subunit (1459 Activities)

Discover Target: NFKB1

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

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CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)

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CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)

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CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

Discover Target: CYP3A4

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HEK293 (82097 Activities)

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POLH Tchem DNA polymerase eta (21678 Activities)

Discover Target: POLH

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EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)

Discover Target: EHMT2

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

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BLM Tchem Bloom syndrome protein (4248 Activities)

Discover Target: BLM

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SMAD3 Tchem Mothers against decapentaplegic homolog 3 (68039 Activities)

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GMNN Tbio Geminin (128009 Activities)

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PMP22 Tbio Peripheral myelin protein 22 (699 Activities)

Discover Target: PMP22

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ATAD5 Tbio ATPase family AAA domain-containing protein 5 (122566 Activities)

Discover Target: ATAD5

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MPHOSPH8 Tbio M-phase phosphoprotein 8 (656 Activities)

Discover Target: MPHOSPH8

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BAZ2B Tchem Bromodomain adjacent to zinc finger domain protein 2B (56204 Activities)

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TARDBP Tchem TAR DNA-binding protein 43 (40113 Activities)

Discover Target: TARDBP

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Associated Targets(non-human)

Plasmodium falciparum (966862 Activities)

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Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)

Discover Target: Nfe2l2

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ffp 4'-phosphopantetheinyl transferase ffp (24982 Activities)

Discover Target: ffp

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NS1 Nonstructural protein 1 (33327 Activities)

Discover Target: NS1

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: ethanol: soluble26 mg/mL H2O: soluble50 mg/mL
• Sensitivity: light sensitive
• Melt Point(°C): 178.0°C-182.0°C
• Molecular Weight: 377.500 g/mol
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 377.141 Da
• Monoisotopic Mass: 377.141 Da
• Topological Polar Surface Area: 111.000 Ų
• Heavy Atom Count: 26
• Formal Charge: 0
• Complexity: 456.000
• 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: 2

XLogP3

References

1. Xinyi Yuan, Aerduosi Shayiranbieke, Ru Xu, Hongmei Jiang, Yushan Yang, Yajun Zhang, Guowei Yin, Xinfeng Zhao.  (2022)  Site-selective covalently immobilized alpha 1A adrenergic receptor for thermodynamic and extra-thermodynamic study of four ligands binding to the receptor by chromatographic methods.  JOURNAL OF CHROMATOGRAPHY A,      [PMID:35078002] [10.1016/j.chroma.2022.462827]