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Bipariden

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Bipariden Basic information
Bipariden Chemical Properties
  • Melting point:114°C
  • Boiling point:451.49°C (rough estimate)
  • Density 1.0202 (rough estimate)
  • refractive index 1.5614 (estimate)
  • pka14.05±0.29(Predicted)
  • Water Solubility 25.1 mg/L
  • NIST Chemistry ReferenceBiperiden(514-65-8)
Safety Information
Bipariden Usage And Synthesis
  • OriginatorAkineton HCl,Knoll,US,1959
  • Usesamoebicide
  • DefinitionChEBI: N-Propylpiperidine in which the methyl hydrogens are substituted by hydroxy, phenyl, and 5-norbornen-2-yl groups. A muscarinic antagonist affecting both the central and peripheral nervous systems, it is used in the treatment of all form 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,α-5-norbornen-2-yl- -phenyl-1-piperidinepropanol (Akineton), introduced in 1959,has a relatively weak visceral anticholinergic, but a strongnicotinolytic, action in terms of its ability to block nicotineinducedconvulsions. Therefore, its neurotropic action israther low on intestinal musculature and blood vessels. It hasa relatively strong musculotropic action, which is aboutequal to that of papaverine, in comparison with most syntheticanticholinergic drugs. Its action on the eye, althoughmydriatic, is much lower than that of atropine. These weakanticholinergic effects add to its usefulness in Parkinson syndromeby minimizing side effects.
  • Clinical UseBiperiden is used in all types of Parkinson disease (postencephalitic,idiopathic, arteriosclerotic) and helps toeliminate akinesia, rigidity, and tremor. It is also usedin drug-induced extrapyramidal disorders to eliminatesymptoms and permit continued use of tranquilizers.Biperiden is also of value in spastic disorders not related toparkinsonism, such as multiple sclerosis, spinal cord injury,and cerebral palsy. It is contraindicated in all formsof epilepsy.
  • Safety ProfilePoison by ingestion,subcutaneous, intraperitoneal, and intravenous routes.When heated to decomposition, it emits toxic fumes ofNOx.
  • Chemical SynthesisBiperiden, 1-(5-norbornen-2-yl)-1-phenyl-3-piperidinopropan-1-ol (10.2.4), is also synthesized according to the method of making trihexyphenidyl, except by reacting 2-(1-piperidino)propiophenone (10.2.1) with 5-norbornen-2-ylmagnesiumbromide [33,34].
Bipariden Preparation Products And Raw materials
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