144-11-6 Usage
Originator
Artane,Lederle,US,1949
Uses
Different sources of media describe the Uses of 144-11-6 differently. You can refer to the following data:
1. Trihexyphenidyl, an antiparkinsonian drug, possesses central and peripheral anticholinergic actions, as well as a direct relaxant effect on smooth muscle. It reduces muscle rigidity and general stiffness, and has a relatively minor effect on tremors. It is used in
Parkinsonism in the form of monotherapy as well as in combination with levodopa.
2. Anticholinergic; antiparkinsonian.
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.
Brand name
Artane (Lederle); Tremin (Schering).
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
-
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.
