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Benztropine mesylate

CAS# 132-17-2

Benztropine mesylate

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Chemical structure

Benztropine mesylate

3D structure

Chemical Properties of Benztropine mesylate

Cas No. 132-17-2 SDF Download SDF
PubChem ID 8584 Appearance Powder
Formula C22H29NO4S M.Wt 403.53
Type of Compound N/A Storage Desiccate at -20°C
Synonyms Benzatropine mesylate; Benzotropine mesylate; Benztropine methanesulfonate
Solubility H2O : ≥ 200 mg/mL (495.61 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name (1R,5R)-3-benzhydryloxy-8-methyl-8-azabicyclo[3.2.1]octane;methanesulfonic acid
SMILES CN1C2CCC1CC(C2)OC(C3=CC=CC=C3)C4=CC=CC=C4.CS(=O)(=O)O
Standard InChIKey CPFJLLXFNPCTDW-STYNFMPRSA-N
Standard InChI 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-;/m1./s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Benztropine mesylate

DescriptionBenzotropine is a centrally-acting, antimuscarinic agent used as an adjunct in the treatment of Parkinson's disease. Target: mAChR Benzotropine is a centrally-acting, antimuscarinic agent used as an adjunct in the treatment of Parkinson's disease. It may also be used to treat extrapyramidal reactions, such as dystonia and Parkinsonism, caused by antipsychotics. Symptoms of Parkinson's disease and extrapyramidal reactions arise from decreases in dopaminergic activity which creates an imbalance between dopaminergic and cholinergic activity. Anticholinergic therapy is thought to aid in restoring this balance leading to relief of symptoms. In addition to its anticholinergic effects, benztropine also inhibits the reuptake of dopamine at nerve terminals via the dopamine transporter. Benzotropine also produces antagonistic effects at the histamine H1 receptor [1, 2]. Benztropine (BZT) and its analogues inhibit dopamine uptake and bind with moderate to high affinity to the dopamine transporter (DAT). BZT analogues also exhibit varied binding affinities for muscarinic M(1) and histamine H(1) receptors. The BZT analogues showed a wide range of histamine H(1) receptor (K(i)=16-37,600 nM) and DAT (K(i)=8.5-6370 nM) binding affinities [3].

References:
[1]. Wszola, B.A., K.M. Newell, and R.L. Sprague, Risk factors for tardive dyskinesia in a large population of youths and adults. Exp Clin Psychopharmacol, 2001. 9(3): p. 285-96. [2]. van Harten, P.N., et al., Intermittent neuroleptic treatment and risk for tardive dyskinesia: Curacao Extrapyramidal Syndromes Study III. Am J Psychiatry, 1998. 155(4): p. 565-7. [3]. Kulkarni, S.S., et al., Comparative structure-activity relationships of benztropine analogues at the dopamine transporter and histamine H(1) receptors. Bioorg Med Chem, 2006. 14(11): p. 3625-34.

Benztropine mesylate Dilution Calculator

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Benztropine mesylate Molarity Calculator

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Preparing Stock Solutions of Benztropine mesylate

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.4781 mL 12.3907 mL 24.7813 mL 49.5626 mL 61.9533 mL
5 mM 0.4956 mL 2.4781 mL 4.9563 mL 9.9125 mL 12.3907 mL
10 mM 0.2478 mL 1.2391 mL 2.4781 mL 4.9563 mL 6.1953 mL
50 mM 0.0496 mL 0.2478 mL 0.4956 mL 0.9913 mL 1.2391 mL
100 mM 0.0248 mL 0.1239 mL 0.2478 mL 0.4956 mL 0.6195 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Benztropine mesylate

Benztropine is a dopamine transporter (DAT) inhibitor with IC50 of 118 nM.

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References on Benztropine mesylate

New use of an old drug: inhibition of breast cancer stem cells by benztropine mesylate.[Pubmed:27894093]

Oncotarget. 2017 Jan 3;8(1):1007-1022.

Cancer stem cells (CSCs) play major roles in cancer initiation, metastasis, recurrence and therapeutic resistance. Targeting CSCs represents a promising strategy for cancer treatment. The purpose of this study was to identify selective inhibitors of breast CSCs (BCSCs). We carried out a cell-based phenotypic screening with cell viability as a primary endpoint, using a collection of 2,546 FDA-approved drugs and drug-like molecules in spheres formed by malignant human breast gland-derived cells (HMLER-shEcad cells, representing BCSCs) and control immortalized non-tumorigenic human mammary cells (HMLE cells, representing normal stem cells). 19 compounds were identified from screening. The chemically related molecules Benztropine mesylate and deptropine citrate were selected for further validation and both potently inhibited sphere formation and self-renewal of BCSCs in vitro. Benztropine mesylate treatment decreased cell subpopulations with high ALDH activity and with a CD44+/CD24- phenotype. In vivo, Benztropine mesylate inhibited tumor-initiating potential in a 4T1 mouse model. Functional studies indicated that Benztropine mesylate inhibits functions of CSCs via the acetylcholine receptors, dopamine transporters/receptors, and/or histamine receptors. In summary, our findings identify Benztropine mesylate as an inhibitor of BCSCs in vitro and in vivo. This study also provides a screening platform for identification of additional anti-CSC agents.

Description

Benzatropine mesylate is a centrally-acting, antimuscarinic agent used as an adjunct in the treatment of Parkinson's disease.

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