Benztropine mesylate

Alias:
Cat No.:V1248 Purity: ≥98%
Benztropine mesylate (NSC-42199; ST-50997629; NSC 42199; ST 50997629; Cogentin; MLS000737056), the mesilate salt of Benztropine, is a highly potent dopamine transporter (DAT) inhibitor used for the treatment of symptoms of Parkinson's disease such as involuntary tremor and dystonia.
Benztropine mesylate Chemical Structure CAS No.: 132-17-2
Product category: Dopamine Receptor
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
500mg
1g
2g
5g
Other Sizes

Other Forms of Benztropine mesylate:

  • Benzatropine
  • Benztropine-d3 mesylate (benzatropine mesylate-d3; benztropine mesylate-d3)
Official Supplier of:
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Benztropine mesylate (NSC-42199; ST-50997629; NSC 42199; ST 50997629; Cogentin; MLS000737056), the mesilate salt of Benztropine, is a highly potent dopamine transporter (DAT) inhibitor used for the treatment of symptoms of Parkinson's disease such as involuntary tremor and dystonia. It suppresses the dopamine transporter with an IC50 of 118 nM. Benztropine is a synthetic substance that acts centrally to sabotage M1 muscarinic acetylcholine receptors. It is derived from the combination of atropine and diphenhydramine.

Biological Activity I Assay Protocols (From Reference)
Targets
Human D2 Receptor
ln Vitro

In vitro activity: Benztropine has a concentration-dependent effect on the inhibition of [3H]WIN binding to the Wild-type dopamine transporter caused by MTSET, with an EC50 of 28 μM. By shielding Cys-342 from reaction, bentropine has a protective ratio (EC50/inhibiting [3H]WIN (4 nm) binding with IC50) of 32 in the X-A342C DAT construct. [2] In HEK-293 cells incubated with [3H]CFT, the apparent equilibrium dissociation constant of W84L DAT for benztropine is far higher than that of WT in the absence of sodium; however, this difference becomes smaller in the presence of 130 mM sodium. In HEK-293 cells incubated with [3H]CFT, the apparent equilibrium dissociation constant of D313N DAT for benztropine shows a slight increase in the presence of 130 mM sodium. In general, one of the single mutants' apparent equilibrium dissociation constant values and that of the double mutant (W84L D313N DAT) are quite similar.[3]

ln Vivo
Benztropine (3.0 mg/day) is successful in reducing tremor and the United Parkinson's Disease Rating Scale's motor score without causing side effects like leukopenia.[4] In the rat striatum, bentropine (5 mg/kg and 25 mg/kg) causes dose-dependent increases in extracellular dopamine.[5]
Cell Assay
Cell Line: MDA-MB-231 cells
Concentration: 0.1 μM, 0.625 μM, 1.25 μM, 2.5 μM, 5 μM, 10 μM
Incubation Time: 72 hours
Result: Inhibited the cell growth of MDA-MB-231 cells with an IC50 of ~5 μM.
Animal Protocol
Balb/c mice bearing 4T1 breast tumors
1.5 mg/kg
Injection; 3 weeks
References

[1]. J Med Chem . 2005 May 5;48(9):3337-43.

[2]. J Biol Chem . 2001 Aug 3;276(31):29012-8.

[3]. J Neurochem . 2004 May;89(4):853-64.

[4]. Neurology . 1997 Apr;48(4):1077-81.

[5]. Eur J Pharmacol . 1987 Jul 23;139(3):345-8.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C22H29NO4S
Molecular Weight
403.53
Exact Mass
403.18
Elemental Analysis
C, 65.81; H, 6.78; N, 3.49; O, 15.94; S, 7.99
CAS #
132-17-2
Related CAS #
Benztropine; 86-13-5; Benztropine-13C,d3 mesylate; Benztropine-d3 mesylate; 202529-16-6
Appearance
White to light yellow crystalline powder
SMILES
CN1[C@@H]2CC[C@H]1CC(C2)OC(C3=CC=CC=C3)C4=CC=CC=C4.CS(=O)(=O)O
InChi Key
CPFJLLXFNPCTDW-IIPFOPBBSA-N
InChi Code
InChI=1S/C21H25NO.CH4O3S/c1-22-18-12-13-19(22)15-20(14-18)23-21(16-8-4-2-5-9-16)17-10-6-3-7-11-17;1-5(2,3)4/h2-11,18-21H,12-15H2,1H3;1H3,(H,2,3,4)/t18-,19+,20?;
Chemical Name
(1R,5S)-3-benzhydryloxy-8-methyl-8-azabicyclo[3.2.1]octane;methanesulfonic acid
Synonyms

NSC42199; ST50997629; NSC-42199; ST-50997629; NSC 42199; ST 50997629; Benzatropine mesylate; Benzotropine mesylate; Benztropine methanesulfonate; Benztropine Mesylate; Cogentin; Cogentin mesylate; MLS000737056

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: 50~100 mg/mL (123.9~247.8 mM)
Water: ~81 mg/mL (200.7 mM)
Ethanol: ~81 mg/mL (~200.7 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.20 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (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 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (6.20 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.

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Solubility in Formulation 3: 100 mg/mL (247.81 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 2.4781 mL 12.3907 mL 24.7813 mL
5 mM 0.4956 mL 2.4781 mL 4.9563 mL
10 mM 0.2478 mL 1.2391 mL 2.4781 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

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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?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

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:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

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
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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.)
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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.

(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
NCT00000333 Completed Drug: Benztropine Cocaine-Related Disorders National Institute on Drug
Abuse (NIDA)
May 2001 Phase 2
NCT00000793 Completed Drug: Benztropine mesylate
Drug: Mexiletine hydrochloride
HIV Infections
Peripheral Nervous System Disease
National Institute of Allergy
and Infectious Diseases
(NIAID)
October 1997 Phase 2
NCT00018200 Completed Drug: Benztropine
Drug: Fluoxetine
Back Pain
Sciatica
US Department of Veterans Affairs April 1999 Phase 2
NCT00066937 Completed Behavioral: Disease MGT
Behavioral: CBT
Temporomandibular Joint
Disorders
Johns Hopkins University November 2002 Phase 2
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