144-11-6 Usage
Description
Trihexylphenidyl, also known as Artane or Tremin, is an antiparkinsonian drug that exhibits central and peripheral anticholinergic actions, as well as a direct relaxant effect on smooth muscle. It is effective in reducing muscle rigidity and general stiffness, with a relatively minor impact on tremors.
Uses
Used in Pharmaceutical Industry:
Trihexylphenidyl is used as an antiparkinsonian agent for the treatment of Parkinson's disease and other movement disorders. It helps alleviate muscle rigidity and general stiffness, providing relief to patients suffering from these conditions.
Used in Parkinsonism Treatment:
Trihexylphenidyl is used as a monotherapy or in combination with levodopa for the treatment of Parkinsonism. It is particularly effective in reducing muscle rigidity and general stiffness, making it a valuable addition to the treatment regimen for patients with this condition.
Used as an Anticholinergic:
Trihexylphenidyl is used as an anticholinergic agent, which helps to block the action of acetylcholine, a neurotransmitter responsible for muscle contractions. This action contributes to its effectiveness in reducing muscle rigidity and stiffness associated with Parkinson's disease and other movement disorders.
Brand Names:
Trihexylphenidyl is available under the brand names Artane (Lederle) and Tremin (Schering), making it accessible to patients in need of treatment for Parkinsonism and related conditions.
Originator
Artane,Lederle,US,1949
Manufacturing Process
Acetophenone, paraformaldehyde and piperidine are first reacted to give ω-(1-
piperidyl)propiophenone.
To an absolute ethyl ether solution of cyclohexylmagnesium bromide
(prepared from 261 parts of cyclohexyl bromide, 38.8 parts magnesium
turnings and 700 parts by volume absolute ethyl ether) a dry solution of 174
parts omega-(1-piperidyl)-propiophenonein 600 parts by volume of ether is
added, with stirring, at such a rate that gentle reflux is maintained with no
external cooling or heating. The reaction mixture is stirred for about 5 hours
and then allowed to stand at room temperature until reaction appears
complete. While being cooled the reaction mixture is then decomposed by the
dropwise addition of 500 parts by volume of 2.5 N hydrochloric acid, and
finally is made strongly acidic to Congo red by the addition of concentrated
hydrochloric acid.
The resulting white solid is collected on a filter, air dried, redissolved in 2,500
parts water at 95°C and the resulting solution treated with decolorizing
charcoal and clarified by filtration. The cooled filtrate is made alkaline with
ammonia and the product, crude 3-(1-piperidyl)-1-cyclohexyl-1-phenyl-1-
propanol is collected. The hydrochloride melts with decomposition in ten
seconds in a bath held at 258.5°C. The alcohol melts at 114.3° to 115.0°C,
according to US Patent 2,716,121.
Therapeutic Function
Antiparkinsonian
Safety Profile
Poison by intraperitoneal, subcutaneous, and intravenous routes. When heated to decomposition it emits toxic fumes of NOx.
Synthesis
Trihexyphenidyl, 1-cyclohexyl-1-phenyl-3-piperidineopropan-1-ol
(10.2.2), is synthesized by the reaction of 2-(1-piperidino)propiophenone (10.2.1) with cyclohexylmagnesiumbromide. The initial 2-(1-piperidino)propiophenone is synthesized in turn
by the aminomethylation of benzophenone using paraformaldehyde and piperidine [24–27].
Check Digit Verification of cas no
The CAS Registry Mumber 144-11-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,4 and 4 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 144-11:
(5*1)+(4*4)+(3*4)+(2*1)+(1*1)=36
36 % 10 = 6
So 144-11-6 is a valid CAS Registry Number.
InChI:InChI=1/C20H31NO/c22-20(18-10-4-1-5-11-18,19-12-6-2-7-13-19)14-17-21-15-8-3-9-16-21/h1,4-5,10-11,19,22H,2-3,6-9,12-17H2
144-11-6Relevant articles and documents
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Baltzly,Billinghurst
, p. 4330 (1965)
-
Aryl-cycloalkyl-alkanolamines for treatment of cholinergic neurotoxins
-
, (2008/06/13)
A compound and method are disclosed for reducing neurotoxic effects (such as seizures and brain damage) caused by cholinergic agents such as soman (a nerve gas) and pilocarpine (a convulsant drug used to study the mechanisms of epilepsy). Effective treatment can be provided by administering an aryl-cycloalkylalkanolamine substance having the general formula: STR1 The compoudns procyclidine, biperiden, and trihexyphenidyl fall within this class of compounds. Although not previously recognized to be effective against soman or other cholinergic neurotoxins, all three representative compounds have been discovered to be highly effective against all cholinergic neurotoxins tested to data, even when administered after actual seizures begin.