14611-52-0 Usage
Description
Selegiline hydrochloride, also known as Deprenyl, is a potent inhibitor of monoamine oxidase B (MAO-B) and a crystalline solid. It has been used for the treatment of Parkinson's disease and displays neuroprotective effects by rescuing nigral dopaminergic neurons after systemic MPTP treatment and protecting PC12 cells from trophic withdrawal-induced apoptosis. Glyceraldehyde-3-phosphate dehydrogenase has been identified as the putative target responsible for its neuroprotective effects. Selegiline hydrochloride is available under the brand names Eldepryl (Somerset) and Zelapar (Valeant).
Uses
1. Used in Pharmaceutical Industry:
Selegiline hydrochloride is used as an antidepressant for its neuroprotective effects and ability to rescue neurons from apoptosis, making it a valuable compound in the treatment of mood disorders.
2. Used in Neurological Applications:
Selegiline hydrochloride is used as an antiparkinsonian agent for alleviating the symptoms of Parkinson's disease by inhibiting monoamine oxidase B (MAO-B) and providing neuroprotection to dopaminergic neurons.
3. Used in Antimicrobial Applications:
Selegiline hydrochloride is used as an antibacterial agent, leveraging its ability to inhibit certain enzymes and potentially disrupt bacterial cell function.
4. Used in Parkinson's Disease Treatment:
Selegiline hydrochloride is used as a therapeutic agent for Parkinson's disease, where it helps manage the symptoms by inhibiting MAO-B and providing neuroprotection to the affected neurons.
Biological Activity
Selective inhibitor of monoamine oxidase B (MAO-B).
Clinical Use
Monoamine-oxidase-B inhibitor:
Treatment of Parkinson’s disease
Veterinary Drugs and Treatments
Selegiline is approved for use in dogs for the treatment of Cushing’s
disease and for Canine Cognitive Dysfunction (so-called “old dog
dementia”). Its use for Cushing’s disease is somewhat controversial
as clinical studies evaluating its efficacy have shown disappointing
results. In humans, selegiline’s primary indication is for the adjunctive
treatment of Parkinson’s disease.
Drug interactions
Potentially hazardous interactions with other drugs
Analgesics: hyperpyrexia and CNS toxicity reported
with pethidine - avoid; avoid with opioid analgesics.
Antidepressants: avoid with citalopram and
escitalopram; increased risk of hypertension and
CNS excitation with fluvoxamine, sertraline or
venlafaxine, do not start selegiline until 1 week after
stopping them, avoid for 2 weeks after stopping
selegiline; increased risk of hypertension and CNS
excitation with paroxetine, do not start selegiline
until 2 weeks after stopping paroxetine, avoid for 2
weeks after stopping selegiline avoid concomitant
use with other MAOIs and moclobemide (can
lead to hypertensive crisis) - allow at least 14 days
before starting a MAOI; avoid concomitant use with
fluoxetine, allow 5 weeks between stopping fluoxetine
and starting selegiline; allow 14 days between
stopping selegiline and starting fluoxetine; increased
CNS toxicity with tricyclics and vortioxetine.
Oestrogens and progestogens: concentration of
selegiline increased - avoid.
Sympathomimetics: concomitant use is not
recommended; risk of hypertensive crisis with
dopamine.
Metabolism
Extensive first-pass metabolism in the liver to produce
at least 5 metabolites, including desmethylselegiline
(norselegiline), N-methylamfetamine, and amfetamine.
Plasma concentrations of selegiline metabolites are greatly
reduced after doses of the oral lyophilisate preparation,
the majority of which undergoes absorption through the
buccal mucosa.
Selegiline is excreted as metabolites mainly in the urine
and about 15% appears in the faeces.
References
Gerlach et al. (1992), The molecular pharmacology of L-deprenyl; Eur. J. Pharmacol., 226 97
Tetrud and Langston (1989), The effect of deprenyl (selegiline) on the natural history of Parkinson’s disease; Science, 245 519
Tatton and Greenwood (1991), Rescue of dying neurons: a new action of deprenyl in MPTP parkinsonism; J. Neurosci Res., 30 666
Tatton et al. (1994), (-)-Deprenyl reduces PC12 cell apoptosis by inducing new protein synthesis; J. Neurochem, 63 1572
Kargten et al. (1998), Glyceraldehyde-3-phosphate dehydrogenase, the putative target of the antiapoptotic compounds CGP 3466 and R-(-)-deprenyl; J. Biol. Chem., 273 5821
Check Digit Verification of cas no
The CAS Registry Mumber 14611-52-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,6,1 and 1 respectively; the second part has 2 digits, 5 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 14611-52:
(7*1)+(6*4)+(5*6)+(4*1)+(3*1)+(2*5)+(1*2)=80
80 % 10 = 0
So 14611-52-0 is a valid CAS Registry Number.
InChI:InChI=1/C12H15N.ClH/c1-4-13(3)11(2)10-12-8-6-5-7-9-12;/h1,5-9,11H,10H2,2-3H3;1H
14611-52-0Relevant articles and documents
Selegiline hydrochloride synthesis process
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Paragraph 0135-0141, (2020/01/25)
The invention relates to the field of chemical pharmacy, particularly to a selegiline hydrochloride preparation method. According to the invention, the method avoids the use of ephedrine, pseudoephedrine, deoxyephedrine and other management and control products, has characteristics of inexpensive and easily-available raw materials, short synthesis route, safe and environmentally-friendly production and synthesis cost reducing, can obtain the high-purity target compound at high yield, and is suitable for industrial large-scale production.
Improved process for the preparation of propargyl ammonium-chloride derivatives
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, (2008/06/13)
The present invention relates to a process for the preparation of L-isomer of propargyl-ammonium-chloride derivatives of the general formula (I) by decomposing D-tartarate of L-isomer of the amine of the general formula (II) and by reacting the obtained L-isomer amine of the general formula (II) in the presence of a base with a halide of the general formula (V), and by reacting the so-obtained L-isomer of the general formula (III) with hydrogen-chloride in an organic solvent, wherein, ???- x stands for a halogen atom,???- y stands for a hydrogen or fluorine atom, ???which comprises releasing the amine base from the D-tartarate of the L-isomer of the amine of the general formula (II), wherein y is as given above, in aqueous suspension with ammonium hydroxide or basic alkaline salt and/or ammonium salt, and reacting same with 1-1.5 mole equivalent of a halide of the general formula (V), wherein, ???- x is as defined above -, ???at 0-50 °C in a buffer system of the pH of 8-12 directly formed in the course of the base release and after separating the aqueous layer extracting the mixture containing L-isomer amines of the general formulae (II) and (III) in the organic layer with water and with a mixture of ammonium hydroxide and water and/or with a solution of aqueous phosphate salt of a pH of 5.5-7.5 and dissolving the L-isomer amine of the general formula (II) or salts thereof into the aqueous layer and selectively separating it from the L-isomer amine of the general formula (III) and converting the L-isomer amine of the general formula (III) after distillation to L-isomer salt of the general formula (I) by a method known per se.
