Biperiden hydrochloride

Biperiden hydrochloride Basic information
Product Name:Biperiden hydrochloride
Synonyms:1-Piperidinepropanol, α-bicyclo[2.2.1]hept-5-en-2-yl-α-phenyl-, hydrochloride;NSC 170950;NSC 84989;α-(Bicyclo[2.2.1]hept-5-en-2-yl)-α-phenyl-1-piperidinepropanol hydrochloride;1-(5-Bicyclo[2.2.1]hept-2-enyl)-1-phenyl-3-(1-piperidinyl)propan-1-ol hydrochloride;1-bicycloheptenyl-1-phenyl-3-piperidinopropanol-1hydrochloride;Akineton, Akinophyl, 1-(5-Bicyclo[2.2.1]hept-2-enyl)-1-phenyl-3-(1-piperidinyl)propan-1-ol hydrochloride;1-(Bicyclo[2.2.1]hept-5-en-2alpha-yl)-1-phenyl-3-piperidinopropanol hydrochloride
CAS:1235-82-1
MF:C21H30ClNO
MW:347.92
EINECS:214-976-2
Product Categories:Amines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Acetylcholine receptor;Inhibitors;Akineton
Mol File:1235-82-1.mol
Biperiden hydrochloride Structure
Biperiden hydrochloride Chemical Properties
Melting point 238°
storage temp. 2-8°C
solubility DMSO: >20mg/mL
form powder
color off-white
BCS Class3/1
NIST Chemistry ReferenceAkineton, hydrochloride(1235-82-1)
Safety Information
Hazard Codes Xn
Risk Statements 22-R22
WGK Germany 3
RTECS TN3706000
ToxicityLD50 in rats, dogs (mg/kg): 750, 340 orally (Hanna)
MSDS Information
Biperiden hydrochloride Usage And Synthesis
Chemical PropertiesWhite Solid
OriginatorAkineton HCl,Knoll,US,1959
UsesA muscarinic receptor antagonist
UsesAntiparkinsonian;Anticholinergic
UsesBiperiden 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.
DefinitionChEBI: 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 Process65 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.
Brand nameAkineton (Abbott).
Therapeutic FunctionAntiparkinsonian
General DescriptionBiperiden 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.
Biological ActivityMuscarinic 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 ActionsBiperiden 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 UseBiperiden 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.
Safety ProfilePoison by ingestion andintravenous routes. When heated to decomposition itemits very toxic fumes of NOx and HCl.
storageDesiccate at +4°C
references[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 Preparation Products And Raw materials
Raw materialsHydrochloric acid-->Magnesium-->Piperidine hydrochloride-->Acetophenone-->Formaldehyde
Buflomedil hydrochloride 1-Piperidinepropanol Propane Biperiden hydrochloride Diphenoxylate Topotecan hydrochloride Sibutramine hydrochloride Tramadol hydrochloride 1,3-BIS(2-ACETYL-3-HYDROXYPHENOXY)-2-PROPANOL CYCLOPENTYLPHENYLMETHANOL PHENCYCLIDINE-D5 HYDROCHLORIDE 1-AdaMantanethylaMine Bipariden Haloperidol Hydroxylamine hydrochloride 2,2,6,6-Tetramethyl-4-piperidinol cycrimine DROPERIDOL

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