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Benztropine mesylate

Benztropine mesylate Structure
Benztropine mesylate
  • CAS No.132-17-2
  • Chemical Name:Benztropine mesylate
  • CBNumber:CB2742553
  • Molecular Formula:C22H29NO4S
  • Formula Weight:403.53
  • MOL File:132-17-2.mol
Benztropine mesylate Property
  • Melting point 135 °C(lit.)
  • storage temp. Inert atmosphere,2-8°C
  • solubility H2O: soluble20mg/mL, clear
  • form powder
  • color white to beige
  • Water Solubility Soluble in water (81 mg/ml at 25°C), DMSO (50 mg/ml at 25°C), ethanol (81 mg/ml at 25°C), and ether (very slightly).
  • Stability Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
  • LogP 4.962 (est)
  • CAS DataBase Reference 132-17-2(CAS DataBase Reference)
  • FDA UNII WMJ8TL7510
  • UNSPSC Code 12352200
  • NACRES NA.77
Safety
  • Hazard Codes  :T
  • Risk Statements  :23/24/25
  • Safety Statements  :36/37/39-45
  • RIDADR  :UN 2811 6.1/PG 3
  • WGK Germany  :3
  • RTECS  :YM3150000
  • HazardClass  :6.1
  • HS Code  :2939800000
  • NFPA 704:
    0
    4 0
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal wordDanger
  • Hazard statements H302-H311+H331
  • Precautionary statements P261-P264-P280-P301+P312-P302+P352+P312-P304+P340+P311
Benztropine mesylate Price More Price(4)
  • Brand: Sigma-Aldrich(India)
  • Product number: SML0847
  • Product name : Benztropine mesylate
  • Purity: ≥98% (HPLC)
  • Packaging: 500MG
  • Price: ₹4232.58
  • Updated: 2022/06/14
  • Buy: Buy
  • Brand: Sigma-Aldrich(India)
  • Product number: 5.09890
  • Product name : Benztropine - CAS 132-17-2 - Calbiochem
  • Purity: An antagonist of muscarinic M1 and M3 receptors that induces robust differentiation of oligodendrocytes precursor cell differentiation (EC?? = 500 nM)
  • Packaging: 50MG
  • Price: ₹10970.01
  • Updated: 2022/06/14
  • Buy: Buy
  • Brand: TCI Chemicals (India)
  • Product number: B5592
  • Product name : Benztropine Mesylate
  • Purity: 
  • Packaging: 5G
  • Price: ₹8300
  • Updated: 2022/05/26
  • Buy: Buy
  • Brand: TCI Chemicals (India)
  • Product number: B5592
  • Product name : Benztropine Mesylate
  • Purity: 
  • Packaging: 25G
  • Price: ₹26300
  • Updated: 2022/05/26
  • Buy: Buy

Benztropine mesylate Chemical Properties,Usage,Production

  • Description Benztropine mesylate (132-17-2) is a centrally acting M1?muscarinic acetylcholine receptor antagonist (Ki=0.59 nM, rat).1?Also inhibits the dopamine transporter (Ki=160 nM).2?Benztropine mesylate enhances remyelination and significantly decreases clinical severity in the experimental autoimmune encephalomyelitis model of relapsing-remitting multiple sclerosis alone or in combination with immunosuppressive agents.3?Inhibits hepatitis C virus infection.4
  • Chemical Properties Benztropine mesylate is a synthetic compound containing structural features found in atropine and diphenhydramine.
    Benztropine mesylate is a crystalline white powder, very soluble in water, and has a molecular weight of 403.54. COGENTIN (benztropine mesylate) is supplied as a sterile injection for intravenous and intramuscular use.
  • Originator Cogentin,Merck Sharp and Dohme,US,1954
  • Uses Benzotropine methanesulfonate is used to treat the symptoms of Parkinson?s disease and is currently in clincial trials for chronic back pain. It shows anti-muscarinic effects comparable to Atropine, and also demonstrates competitive anti-nicotinic action at the nAChR (nicotinic acetylcholine receptor).
  • Uses Used as an antiparkinsonian.
  • Uses Benztropine mesylate is an anti-histamine and dopamine re-uptake inhibitor. It has been used to study its target identification and mode of action against ebolavirus infection. It has also been used in pharmacological animal studies to evaluate its effect on SLC6A19 (solute carrier family 6 member 19; B0AT1).
  • Definition ChEBI: The methanesulfonate salt of benzatropine. An acetylcholine receptor antagonist, it is used in the treatment of Parkinson's disease, and to reduce parkinsonism and akathisia side effects of antipsychotic treatments.
  • Manufacturing Process Diphenyldiazomethane was prepared by shaking 7.9 grams of benzophenone hydrazone and 8.8 grams of yellow mercuric oxide in petroleum ether, filtering and evaporating off the petroleum ether from the filtrate under reduced pressure. To the residual diphenyldiazomethane 2.83 grams of tropine and 4.5 ml of benzene were added. The mixture was warmed in a pan of hot water at about 85°C under reflux for 24 hours after which time the original purple color had been largely discharged. The reaction mixture was dissolved by adding benzene and water containing hydrochloric acid in excess of the quantity theoretically required to form a salt. A rather large amount of water was required since the tropine benzohydryl ether hydrochloride was not very soluble and tended to separate as a third phase. The aqueous layer was separated, washed with benzene and with ether and made alkaline with an excess of sodium hydroxide. The resulting insoluble oil was extracted with benzene.
    The benzene extracts were dried over potassium carbonate and evaporated under reduced pressure, leaving a residue of 4.1 grams. The residue (tropine benzohydryl ether) was dissolved in ether and treated with hydrogen bromide gas until an acidic reaction was obtained. The precipitate soon became crystalline and was collected on a filter and dried. The tropine benzohydryl ether hydrobromide weighed 4.1 grams. Recrystallization from absolute ethanol gave 3.3 grams of first crop melting at 247°-248°C (dec.). Twelve grains of tropine benzohydryl ether hydrobromide was converted to the free base by warming with dilute aqueous sodium hydroxide. The oily base was extracted with toluene. The toluene extract was washed with water and then extracted with about 100 ml of water containing 28.1 ml of 1.10 N methanesulfonic acid, (an equimolecular quantity). The toluene solution was extracted twice more with fresh portions of water. The combined water extracts were evaporated under reduced pressure. Residual water was removed by dissolving the residue in absolute ethanol and evaporating under reduced pressure several times. Residual alcohol was then removed by dissolving the residue in acetone and evaporating under reduced pressure several times. The resulting residue was recrystallized by dissolving in acetone and adding ether. The crystalline precipitate was collected on a filter, washed with ether and dried at 56°C in vacuo. The tropine benzohydryl ether methanesulfonate weighed 10.2 grams, MP 138°-140°C.
  • brand name Cogentin (Merck).
  • Therapeutic Function Antiparkinsonian
  • General Description Benztropine mesylate,3α-(diphenylmethoxy)-1αH,5αH-tropane methanesulfonate(Cogentin), has anticholinergic, antihistaminic, and localanesthetic properties. Its anticholinergic effect makes it applicableas an antiparkinsonian agent. It is about as potent ananticholinergic as atropine and shares some of the side effectsof this drug, such as mydriasis and dryness of mouth.Importantly, however, it does not produce central stimulationbut instead exerts the characteristic sedative effect ofthe antihistamines.
  • Biological Activity Benztropine mesylate is a centrally acting muscarinic acetylcholine receptor antagonist and dopamine transporter (DAT) inhibitor (IC50 = 118 nM). Benztropine mesylate has been used to treat the symptoms of Parkinson′s disease and is currently in clincial trials for chronic back pain.
    Benztropine mesylate serves as an inhibitor of breast cancer stem cells (BCSCs) in vitro and in vivo. It can help in improving the efficacy of chemotherapy in vitro. It is considered as an anti-cancer stem cell (CSC) drug, which can modify tumorigenic properties.
  • Clinical Use The tremor and rigidity characteristic of parkinsonismare relieved by benztropine mesylate, and it is particularlyvaluable for those patients who cannot tolerate central excitation(e.g., aged patients). It may also have a useful effectin minimizing drooling, sialorrhea, masklike facies, oculogyriccrises, and muscular cramps.
    The usual caution exercised with any anticholinergic inglaucoma and prostatic hypertrophy is observed with thisdrug.
  • Safety Profile Poison by ingestion, intravenous, subcutaneous, and intraperitoneal routes. Human systemic effects by ingestion: psychotropic effects. Mutation data reported. When heated to decomposition it emits very toxic fumes of NOx and SOx. See also ETHERS.
  • References 1) Zhang et al. (2001),?Synthesis and biological evaluation of tropane-like 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine (GBR 12909) analogues; J. Med. Chem.,?44?3937 2) Schmitt?et al. (2008),?Interaction of cocaine-, benztropine-, and GBR12909-like compounds with wild-type and mutant human dopamine transporters: molecular features that differentially determine antagonist binding properties; J. Neurochem.,?107?928 3) Deshmukh?et al. (2013),?A regenerative approach to the treatment of multiple sclerosis; Nature,?502?327 4) Mingorance?et al. (2014),?Selective inhibition of hepatitis C virus infection by hydroxyzine and benztropine: Agents Chemother.,?58?3451
Benztropine mesylate Preparation Products And Raw materials
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Benztropine mesylate Spectrum
132-17-2, Benztropine mesylateRelated Search:
  • Heterocycles
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  • 化学试剂
  • 抑制剂
  • 试剂
  • 药靶配体
  • 原料药
  • 医药原料药
  • 医药原料
  • 中枢性抗胆碱药
  • 医用原料
  • 小分子抑制剂
  • 中间体
  • 神经信号
  • AMINE
  • C22H29NO4S
  • C22H28NOHSO3
  • C22H28NOSO3H
  • C21H25NOCH3SO3H
  • C21H25NOCH4SO3
  • C21H25NOCH4O3S
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  • 132-17-2
  • 2-Methyl-197-nitrobenzyl&chloride
  • Benztropine Mesylate (1061005)
  • BENZTROPINE MESYLATE USP/EP/BP
  • endo-3-(Diphenylmethoxy)-8-methyl-8-Azabicyclo[3.2.1]octane methanesulfonate
  • (1R,3R,5S)-3-(diphenylmethoxy)-8-methyl-8-azabi cyclo[3.2.1]octane
  • Benzo bracket methanesulfonate
  • Diphenhydramine Impurity 4
  • Benzoate methanesulfonate
  • 3-(DIPHENYLMETHOXY)-8-METHYL-8-AZABICYCLO[3.2.1]OCTANE METHANE SULFONATE
  • Benzatropine mesilate
  • Benzatropine mesylate
  • Cogentin,Cogentinol
  • BENZTROPINE MESYLATE 95%
  • 5-alpha-h-tropane,3-alpha-(diphenylmethoxy)-1-alpha-methanesulfonate
  • 3-diphenylmethoxytropanemethanesulfonate
  • 3-diphenylmethoxytropanemesylate
  • 3-alpha-(diphenylmethoxy)-1-alpha-h,5-alpha-h-tropanemethanesulfonate
  • 3-(diphenylmethoxy)-8-azabicyclo(3.2.1)octanendo-8-azabicyclo(3.2.1)octanmethanesulfonate
  • BENZTROPINE METHANESULFONATE
  • BENZTROPINE MESYLATE
  • BENZOTROPINE MESYLATE

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