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| Bipariden Basic information |
| Product Name: | Bipariden | | Synonyms: | alpha-(bicyclo(2.2.1)hept-5-en-2-yl)-alpha-phenyl-1-piperidinopropanol;alpha-5-norbornen-2-yl-alpha-phenyl-1-piperidinepropano;alpha-5-Norbornen-2-yl-alpha-phenyl-1-piperidinepropanol;alpha-bicyclo(2.2.1)hept-5-en-2-yl-alpha-phenyl-1-piperidinepropano;alpha-phenyl-alpha-(2-piperidinoethyl)-5-norbornene-2-methano;Beperiden;-Bicyclo[2,2,1]hept-5-en-2yl-phenyl-1-piperidinepropanol;Bicyclo[2.2.1]hept-5-ene-2-methanol, alpha-phenyl-alpha-[2-(1-piperidinyl)ethyl]- | | CAS: | 514-65-8 | | MF: | C21H29NO | | MW: | 311.46106 | | EINECS: | 2081846 | | Product Categories: | | Mol File: | 514-65-8.mol |
| Bipariden Chemical Properties |
| Melting point | 114°C | | Boiling point | 451.49°C (rough estimate) | | density | 1.0202 (rough estimate) | | refractive index | 1.5614 (estimate) | | storage temp. | 2-8°C | | solubility | Chloroform (Slightly), DMSO (Slightly,Sonicated), Methanol (Slightly, Sonicated) | | form | Solid | | pka | 14.05±0.29(Predicted) | | color | White to Off-White | | Water Solubility | 25.1 mg/L | | NIST Chemistry Reference | Biperiden(514-65-8) |
| Bipariden Usage And Synthesis |
| Originator | Akineton HCl,Knoll,US,1959 | | Uses | amoebicide | | Definition | ChEBI: 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 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. | | Brand name | Akineton
(Abbott). | | Therapeutic Function | Antiparkinsonian | | General Description | Biperiden,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 Use | Biperiden 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 Profile | Poison by ingestion,subcutaneous, intraperitoneal, and intravenous routes.When heated to decomposition, it emits toxic fumes ofNOx. | | Synthesis | Biperiden, 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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