Phentolamine Mesylate

Alias: Phentolamine mesilate; Phentolamine methanesulfonate; OraVerse; Regitine mesylate; Regitine; Regityn; Rogitine; Z-Max; Phentolamine Mesylate

Cat No.:V1140 Purity: ≥98%

COA Product Data Instructions for use SDS

Phentolamine Mesylate Chemical Structure CAS No.: 65-28-1
Product category: Adrenergic Receptor

This product is for research use only, not for human use. We do not sell to patients.

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Other Forms of Phentolamine Mesylate:

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Top Publications Citing lnvivochem Products

Nature 2021, 597(7874):119-125.

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J Am Chem Soc 2022,144:21831-21836.

Cell 2020,183:1202-1218.e25.

Science Adv 2022:8,eabm9427.

Nature 2021,597(7874):119-125.

Cell 2020,183:1202-1218.e25.

PNAS Nexus 2022,1(3):pgac063.

ACS Nano 2023,17(10):9110-9125.

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Purity & Quality Control Documentation

Current batch：

Purity: ≥98%

COA

MSDS

NMR

Instructions

Product Description
Bioactivity & Protocols
Physicochemical Properties
Solubility Data
Calculators
Clinical Trial Information
Biological Data

Product Description

Phentolamine Mesylate (OraVerse, Regitine mesylate, Regitine, Regityn, Rogitine, Z-Max), the mesylate/mesilate/methanesulfonate salt of Phentolamine, is a reversible and nonselective alpha-adrenergic receptor antagonist with antihypertensive effects. It has been applied to stop or manage episodes of hypertension. In corpus cavernosum membranes, phentolamine mesylate selectively displaces the binding of alpha 1 receptor antagonists [125I]HEAT and [3H]prazosin, as well as alpha 2 receptor antagonists [3H]rauwolscine and [3H]RX 821002 with a relatively high affinity.

Biological Activity I Assay Protocols (From Reference)

Targets

α-adrenergic receptor

ln Vitro

In vitro activity: Phentolamine mesylate breaks the binding of the alpha 2 receptor antagonists [³H]rauwolscine and [³H]RX 821002 with a comparatively high affinity in corpus cavernosum membranes, as well as the selective alpha 1 receptor antagonists [¹²⁵I]HEAT and [³H]prazosin. When phentolamine mesylate is combined with non-adrenergic contractile agents like endothelin and KCl, as well as adrenergic agonists like phenylephrine, norepinephrine, oxymetazoline, and UK 14,304, it results in concentration-dependent relaxation in erectile tissue strips. The erectile tissue in the corpus cavernosum relaxes when phenolamine mesylate is present because it directly binds to alpha 1 and 2 adrenergic receptors and indirectly through an endothelium-mediated, non-adrenergic mechanism that may activate nitric oxide synthase.[1] Phentolamine is an alpha-adrenergic antagonist that improves the systemic absorption of the local anesthetic from the injection site by blocking the vasoconstriction linked to the epinephrine used in dental anesthetic formulations.[2]

ln Vivo

Phentolamine is a competitive alpha-adrenergic antagonist that is reversible and has comparable affinity for alpha2 and alpha1 receptors. By lowering peripheral vascular resistance, phentolamine mesylate induces vasodilatation and consequently hypotension.[4] Electrical field stimulation-induced relaxation of the rabbit corpus cavernosum is dose-dependently enhanced by phenolamine mesylate (30 and 100 nM). Alpha-adrenergic receptor blockade is not necessary for phentolamine to relax the rabbit corpus cavernosum. Through the activation of NO synthase, phentolamine mesylate relaxes nonadrenergic noncholinergic neurons in the rabbit corpus cavernosum without the need for alpha-adrenergic receptor blockade.[5]

Animal Protocol

References

[1]. Int J Impot Res . 1998 Dec;10(4):215-23.

[2]. Anesth Prog . 2008 Summer;55(2):40-8.

[3]. J Pharm Pharmacol . 1995 Oct;47(10):837-45.

[4]. Fundam Clin Pharmacol . 2001 Feb;15(1):1-7.

These protocols are for reference only. InvivoChem does not independently validate these methods.

Physicochemical Properties

Molecular Formula

C18H23N3O4S

Molecular Weight

377.46

Exact Mass

377.14

Elemental Analysis

C, 57.28; H, 6.14; N, 11.13; O, 16.95; S, 8.49

CAS #

65-28-1

Related CAS #

Phentolamine; 50-60-2; Phentolamine hydrochloride; 73-05-2; Phentolamine-d4 hydrochloride; 1346599-65-2

Appearance

White to off-white solid powder

SMILES

CC1=CC=C(C=C1)N(CC2=NCCN2)C3=CC(=CC=C3)O.CS(=O)(=O)O

InChi Key

OGIYDFVHFQEFKQ-UHFFFAOYSA-N

InChi Code

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)

Chemical Name

3-[N-(4,5-dihydro-1H-imidazol-2-ylmethyl)-4-methylanilino]phenol;methanesulfonic acid

Synonyms

Phentolamine mesilate; Phentolamine methanesulfonate; OraVerse; Regitine mesylate; Regitine; Regityn; Rogitine; Z-Max; Phentolamine Mesylate

HS Tariff Code

2934.99.9001

Storage

Powder -20°C 3 years

4°C 2 years

In solvent -80°C 6 months

-20°C 1 month

Shipping Condition

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Solubility Data

Solubility (In Vitro)

DMSO: ~76 mg/mL ( ~201.3 mM)

Water: ~76 mg/mL (~201.3 mM)

Ethanol: ~76 mg/mL (~201.3 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (6.62 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

Solubility in Formulation 2: 100 mg/mL (264.93 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.

(Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.6493 mL	13.2464 mL	26.4929 mL
	5 mM	0.5299 mL	2.6493 mL	5.2986 mL
	10 mM	0.2649 mL	1.3246 mL	2.6493 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Mass

Concentration

Volume

Molecular Weight*

Calculate Reset

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

Calculate the Mass of a compound required to prepare a solution of known volume and concentration
Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume

See Example

An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?

Enter 350.26 in the Molecular Weight (MW) box
Enter 10 in the Concentration box and choose the correct unit (mM)
Enter 5 in the Volume box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Concentration (Start)

Volume (Start)

Concentration (End)

Volume (End)

Calculate Reset

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:

Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
Enter 25 into the Concentration (End) box and select the correct unit (mM)
Enter 25 into the Volume (End) box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box

Molecular formula

Total molecular weight

g/mol

Calculate Reset

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4 c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:

To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.

Definitions of molecular mass, molecular weight, molar mass and molar weight:

Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.

Volume (to add to vial)

Mass (in vial)

Desired Reconstitution Concentration

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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
Click the “Calculate” button
The answer appears in the Volume (to add to vial) box

In vivo Formulation Calculator (Clear solution)

Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)

Dosage mg/kg

Average weight of animals g

Dosing volume per animal μL

Number of animals

Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)

% DMSO

% Tween 80

% ddH₂O

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Calculation results

Working concentration： mg/mL；

Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH₂O，mix and clarify.

Note： (1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.

Clinical Trial Information

NCT Number	Recruitment	interventions	Conditions	Sponsor/Collaborators	Start Date	Phases
NCT03079921	Active Recruiting	Drug: Phentolamine Drug: Propranolol	Type1diabetes Hypoglycemia	University of Pennsylvania	January 20, 2017	Early Phase 1
NCT03318094	Recruiting	Drug: Phentolamine Other: Saline	Insulin Resistance Healthy	Vanderbilt University Medical Center	October 24, 2017	Phase 1
NCT06172998	Recruiting	Drug: Phentolamine Injection	Obstructive Sleep Apnea	Xu J	April 1, 2022	Early Phase 1
NCT05219799	Recruiting	Drug: Phentolamine Mesylate Drug: Isoproterenol	Obesity Vasodilation	University of Missouri-Columbia	March 14, 2023	Early Phase 1
NCT05448807	Not yet recruiting	Drug: OraVerse	Soft Tissue Injuries	Cairo University	October 2022	Phase 3

Biological Data

The plasma concentration–time curves for phentolamine following the administration of phentolamine 0.4 mg intravenously (1Piv; closed triangle), phentolamine 0.4 mg submucosally (1L1P; closed circle), and phentolamine 0.8 mg submucosally (4L2P; open square). Anesth Prog . 2008 Summer;55(2):40-8.

The plasma concentration–time curves for lidocaine following the administration of 1 cartridge of 2% lidocaine 1 : 100,000 epinephrine followed after 30 minutes with 1 cartridge of phentolamine (1L1P; open circle); 4 cartridges of 2% lidocaine 1 : 100,000 epinephrine followed after 30 minutes with 2 cartridges of phentolamine (4L2P; open square); and 4 cartridges of 2% lidocaine 1 : 100,000 epinephrine followed by no phentolamine (4L; closed square). Anesth Prog . 2008 Summer;55(2):40-8.