endo-3-(Diphenylmethoxy)-8-methyl-8-azoniabicyclo[3.2.1]octanmethansulfonat

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Achtung

• Gefahrenhinweise

  H302：Gesundheitsschädlich bei Verschlucken.

• Sicherheit

  P261：Einatmen von Staub vermeiden.

  P264：Nach Gebrauch gründlich waschen.

  P264：Nach Gebrauch gründlich waschen.

  P280：Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.

  P301+P312：BEI VERSCHLUCKEN: Bei Unwohlsein GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.

Benztropine mesylate Chemische Eigenschaften,Einsatz,Produktion Methoden

• R-Sätze Betriebsanweisung:

  R23/24/25:Giftig beim Einatmen, Verschlucken und Berührung mit der Haut.

• S-Sätze Betriebsanweisung:

  S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
  S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).

• Beschreibung

  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

• Chemische Eigenschaften

  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

• Verwenden

  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).

• Verwenden

  Used as an antiparkinsonian.

• Verwenden

  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.

• Trademarks

  Cogentin (Merck).

• Therapeutic Function

  Antiparkinsonian

• Allgemeine Beschreibung

  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.

• Biologische Aktivität

  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.

• Sicherheitsprofil

  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.

• Einzelnachweise

  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 Upstream-Materialien And Downstream Produkte

endo-3-(Diphenylmethoxy)-8-methyl-8-azoniabicyclo[3.2.1]octanmethansulfonat Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global(228)Suppliers

132-17-2, Benztropine mesylate Verwandte Suche: