alpha-Bicyclo(2.2.1)hept-5-en-2-yl-alphaphenyl)-1-piperidin-propanol-hydrochlorid

Bezeichnung:alpha-Bicyclo(2.2.1)hept-5-en-2-yl-alphaphenyl)-1-piperidin-propanol-hydrochlorid

CAS-Nr1235-82-1

Englisch Name:Biperiden hydrochloride

CBNumberCB2726050

SummenformelC21H30ClNO

Molgewicht347.92

MOL-Datei1235-82-1.mol

Synonyma

Biperidenhydrochlorid

alpha-Bicyclo(2.2.1)hept-5-en-2-yl-alphaphenyl)-1-piperidin-propanol-hydrochlorid

alpha-Bicyclo(2.2.1)hept-5-en-2-yl-alphaphenyl)-1-piperidin-propanol-hydrochlorid physikalisch-chemischer Eigenschaften

Schmelzpunkt	238°
storage temp.	2-8°C
Löslichkeit	DMSO: >20mg/mL
Aggregatzustand	powder
Farbe	off-white
BCS Class	3/1
NIST chemische Informationen	Akineton, hydrochloride(1235-82-1)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	22-R22
WGK Germany	3
RTECS-Nr.	TN3706000
Toxizität	LD50 in rats, dogs (mg/kg): 750, 340 orally (Hanna)

Gefahreninformationscode (GHS)

Biperiden hydrochloride Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
Chemische Eigenschaften
White Solid
Originator
Akineton HCl,Knoll,US,1959
Verwenden
A muscarinic receptor antagonist
Verwenden
Antiparkinsonian;Anticholinergic
Verwenden
Biperiden hydrochloride is antiparkinsonian; non-selective muscarinic receptor antagonist. Biperiden is used for the adjunctive treatment of all forms of Parkinson′s Disease (postencephalitic, idiopathic, and arteriosclerotic); also commonly used to improve parkinsonian signs and symptoms related to antipsychotic drug therapy.
Definition
ChEBI: The hydrochloride salt of biperiden. A muscarinic antagonist affecting both the central and peripheral nervous systems, it is used in the treatment of all forms of Parkinson's disease.
Manufacturing Process
65 grams of 3-piperidino-1-phenyl propanone-1 of the summary formula C14H29ON, produced according to Mannich's reaction by reacting acetophenone with formaldehyde and piperidine hydrochloride are dissolved in 300 cc of benzene. The resulting solution is added to an organo-magnesium solution prepared from 96 grams of [δ5-bicyclo-(2,2,1)-heptenyl-2]-chloride (also known as 5-chloro-2-norbomene) 18.5 grams of magnesium shavings, and 300 cc of ether.
The reaction mixture is boiled for half an hour under reflux. Thereafter the ether is removed by distillation, until the inside temperature reaches 65°- 70°C. The resulting benzene solution is added to 95 cc concentrated hydrochloric acid containing ice for further processing. Thereby, 3-piperidino- 1-phenyl-1-[δ5-bicyclo-(2,2,1)-heptenyl-2]-propanol-1 of the summary formula C21H29ON is obtained. The compound melts at 101°C and its chlorohydrate has a melting point of about 238°C. The compound is difficultly soluble in water, slightly soluble in ethanol, and readily soluble in methanol.
Trademarks
Akineton (Abbott).
Therapeutic Function
Antiparkinsonian
Allgemeine Beschreibung
Biperiden hydrochloride,α-5-norbornen-2-yl- -phenyl-1-piperidinepropanolhydrochloride (Akineton hydrochloride), is a white, opticallyinactive, crystalline, odorless powder that is slightlysoluble in water, ether, alcohol, and chloroform and sparinglysoluble in methanol.
Biologische Aktivität
Muscarinic receptor antagonist that displays some selectivity for the M 1 subtype (K i values are 0.48, 2.4, 3.9, 6.3 and 6.3 nM for M 1 , M 4 , M 3 , M 2 and M 5 receptors respectively). Alleviates extrapyramidal symptoms associated with antipsychotic drugs. Displays antiparkinsonian activity.
Biochem/physiol Actions
Biperiden hydrochloride is antiparkinsonian; non-selective muscarinic receptor antagonist. It is used for the adjunctive treatment of all forms of Parkinson′s Disease (postencephalitic, idiopathic, and arteriosclerotic); also commonly used to improve parkinsonian signs and symptoms related to antipsychotic drug therapy. LD50 in rats 750 mg/kg; in dogs 340 mg/kg.
Clinical Use
Biperiden hydrochloride has all of the actions describedfor biperiden. The hydrochloride is used for tablets becauseit is better suited to this dosage form than is the lactate salt.As with the free base and the lactate salt, xerostomia (drynessof the mouth) and blurred vision may occur.
Sicherheitsprofil
Poison by ingestion andintravenous routes. When heated to decomposition itemits very toxic fumes of NOx and HCl.
Lager
Desiccate at +4°C
Einzelnachweise
[1] brocks d r. anticholinergic drugs used in parkinson’s disease: an overlooked class of drugs from a pharmacokinetic perspective. j pharm pharm sci, 1999, 2(2): 39-46.
[2] espi martinez f, espi forcen f, shapov a, et al. biperiden dependence: case report and literature review. case reports in psychiatry, 2012, 2012.

Biperiden hydrochloride Upstream-Materialien And Downstream Produkte

alpha-Bicyclo(2.2.1)hept-5-en-2-yl-alphaphenyl)-1-piperidin-propanol-hydrochlorid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

1235-82-1, Biperiden hydrochloride Verwandte Suche:

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