23047-25-8 Usage
Description
Lofepramine is a first generation tricyclic antidepressant that is extensively metabolized to desipramine. It potently inhibits serotonin and norepinephrine transporters (Kds = 70 and 5.4 nM, respectively) and less potently antagonizes serotonin, histamine, and muscarinic receptors.
Chemical Properties
Light Yellow Solid
Originator
Gamonil,E. Merck
Uses
Different sources of media describe the Uses of 23047-25-8 differently. You can refer to the following data:
1. Psychotropic drug related to imipramine. Antidepressant.
2. Psychotropic drug related to imipramine. Antidepressant
Manufacturing Process
9.8 parts of 10,11-dihydro-5H-dibenzo[b,f]azepine are dissolved in 10 parts of
dry toluene and 3.1 parts of sodium amide are added and the mixture is
refluxed and stirred for four hours. A solution of 13.5 parts of 1-(4-
chlorophenyl)-2-[(3-chloropropyl)methylamino]ethanone in 20 parts of dry
toluene is added dropwise and the mixture is stirred and refluxed for eight
hours.After cooling to room temperature water is carefully added to the reaction
mixture and the toluene solution is extracted with water to which hydrochloric
acid is added so that the aqueous phase obtains the pH-value of 5. The
aqueous extract is discarded and the toluene phase is evaporated to dryness
in vacuum. The residue is dissolved in 50 parts of methanol. Hydrogen gas is
introduced to give the crystalline hydrochloride 1-(4-chlorophenyl)-2-((3-
(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl)methylamino)ethanone;
MP: 154°-156°C. The hydrochloride may be removed by adding an equivalent
of any base (triethyl amine, sodium hydroxide and so on).
Therapeutic Function
Antidepressant
Biological Activity
Serotonin and noradrenalin re-uptake inhibitor (SNRI) that is metabolized to desipramine. Produces inhibition of liver tryptophan pyrollase activity in vitro and displays antidepressant properties in vivo .
Mechanism of action
Lofepramine differs from imipramine by the attachment of a p-chlorophenacyl moiety to the N-aminopropyl
side chain. This change confers enhanced lipophilicity and the potential of more rapid
distribution into the CNS with greater in vitro affinity and selectivity for NET. Its mechanism of antidepressant
action is attributed to its rapid metabolism to the secondary amine metabolite, desipramine, which selectively
inhibits the neuronal uptake of NE.
Check Digit Verification of cas no
The CAS Registry Mumber 23047-25-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,3,0,4 and 7 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 23047-25:
(7*2)+(6*3)+(5*0)+(4*4)+(3*7)+(2*2)+(1*5)=78
78 % 10 = 8
So 23047-25-8 is a valid CAS Registry Number.
InChI:InChI=1/C26H27ClN2O/c1-28(19-26(30)22-13-15-23(27)16-14-22)17-6-18-29-24-9-4-2-7-20(24)11-12-21-8-3-5-10-25(21)29/h2-5,7-10,13-16H,6,11-12,17-19H2,1H3
23047-25-8Relevant articles and documents
NEW PROCESS FOR THE SYNTHESIS OF LOFERPRAMINE MALEATE: A STABLE SALT OF LOFERPRAMINE
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Page/Page column 5,6, (2009/01/20)
This invention relates to a stable salt of Lofepramine and A process for the synthesis of stable Lofepramine maleate comprising; dissolving maleic acid in ethyl acetate by warming and the solution is then filtered hot; adding purified Lofepramine base to the said clear solution of maleic acid and heated upto about 40-60°C; filtering the precipitates of Lofepramine maleate; drying the said precipitates at 45 to 55°C to obtain Lofepramine maleate.
