14611-51-9

Basic information

• Product Name: SELEGILINE
• Synonyms: SELEGILINE BASE;dl-Depreny;N-(Methyl-d3),a-methyl-N-2-propyn-1-yl-benzeneethanamine;N-(Methyl-d3),a-methyl-N-2-propynyl Phenethylamine;SELEGILINEHYDROCHLORDE;(R)-(-)-Deprenyl;Benzeneethanamine, N,a-dimethyl-N-2-propynyl-, (aR)- (9CI);Benzeneethanamine, N,a-dimethyl-N-2-propynyl-, (R)-
• CAS NO: 14611-51-9
• Molecular Formula: C₁₃H₁₇N
• Molecular Weight: 187.28
• EINECS: 200-659-6
• Mol File: 14611-51-9.mol
• Article Data: 14

Chemical Properties

• Melting Point: 137.5-139 °C
• Boiling Point: 273℃
• Flash Point: 108℃
• Appearance: /
• Density: 0.954
• Vapor Pressure: 0.00606mmHg at 25°C
• Refractive Index: nD20 1.5180
• Storage Temp.: ?20°C
• PKA: 7.53±0.50(Predicted)
• CAS DataBase Reference: SELEGILINE(CAS DataBase Reference)
• NIST Chemistry Reference: SELEGILINE(14611-51-9)
• EPA Substance Registry System: SELEGILINE(14611-51-9)

Safety Data

• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 7-16-36/37-45
• RIDADR: 1851
• WGK Germany: 1
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 14611-51-9(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 14611-51-9 differently. You can refer to the following data:
1. Antidyskinetic; antiparkinsonian (in combination with levodopa/carbidopa).
2. This drug is a selective inhibitor of monoaminooxidase B, which suppresses dopamineinactivation processes and facilitates an increase of its level in the brain. In treating Parkinsonism, selegiline is usually used in combination with levodopa.

Brand name

Emsam (Somerset).

World Health Organization (WHO)

Selegiline was introduced in the early 1990s. It is a monoamine oxidase inhibitor and is used in the management of Parkinson's disease. A symptomatic effect of selegiline in Parkinson's disease has been shown, but longer follow-up failed to provide any definitive evidence of ability to retard the loss of dopaminergic neurons (Parkinson's Study Group, 1993).

Biological Functions

Another drug used in the treatment of Parkinson’s disease is selegiline (also known as deprenyl, or Eldepryl). It is an irreversible inhibitor of MAO-B, an important enzyme in the metabolism of dopamine (Fig. 33.2). Blockade of dopamine metabolism makes more dopamine available for stimulation of its receptors. Selegiline, as monotherapy, may be effective in the newly diagnosed patient with parkinsonism because its pharmacological effect enhances the actions of endogenous dopamine. Selegiline is also used in conjunction with levodopa– carbidopa in later-stage parkinsonism to reduce levodopa dosage requirements and to minimize or delay the onset of dyskinesias and motor fluctuations that usually accompany long-term treatment with levodopa. It has also been proposed that selegiline may slow the progression of the disease by reducing the formation of toxic free radicals produced during the metabolism of dopamine. However, any neuroprotective effect of selegiline in parkinsonian patients remains to be established. Most of the adverse reactions to selegiline are related to actions of increased levels of dopamine, as discussed earlier. At recommended doses, and unlike the nonselective MAO inhibitors used in the treatment of depression, selegiline has little effect on MAO-A and therefore generally does not cause the hypertension associated with the ingestion of tyramine-enriched foods. However, at doses higher than those usually recommended, MAO-A may be inhibited, which increases the risk of a tyramine reaction. Selegiline should not be coadministered with tricyclic antidepressants or selective serotonin uptake inhibitors because of the possibility of a severe adverse drug reaction (e.g., hyperpyrexia, agitation, delirium, coma).

Synthesis

Selegiline, N-methyl-N-(2-propinyl)-2-methyl-1-phenylethylamine (10.1.14), is synthesized by the alkylation of (-)methyamphetamine (8.1.2.3) using propargylbromide [20–23].

InChI:InChI=1/C13H17N/c1-4-10-14(3)12(2)11-13-8-6-5-7-9-13/h1,5-9,12H,10-11H2,2-3H3/t12-/m1/s1

Upstream product

• 56862-28-3 (-)-Desmethylselegiline 
• 74-88-4 methyl iodide 
• 33817-09-3 (R)-2-methylamino-1-phenylpropane 
• 106-96-7 propargyl bromide 
• 7632-10-2 methamphetamin 
• 111525-66-7 (3(2S),4S)-3-(2-azido-3-phenyl-1-oxopropyl)-4-(phenylmethyl)-2-oxazolidinone 
• 439694-28-7 (S)-2-azido-3-phenyl-propan-1-ol 
• 501-52-0 3-Phenylpropionic acid 
• 136159-65-4 (S)-4-benzyl-3-(3-phenylpropanoyl)oxazolidin-2-one 
• 826-10-8 (R)-2-N-methylamino-1-phenylpropane hydrochloride 
• 624-65-7 2-propynyl chloride 
• 2323-36-6 deprenyl 
• 73058-30-7 (2S)-2-benzylazacyclopropane 
• 63-91-2 L-phenylalanine 

Downstream Products

• 2323-36-6 (-)-N,1-dimethyl-N-propargylphenylethylamine 
• 14611-52-0 (R)-(-)-deprenyl hydrochloride 
• 1354052-20-2 C₁₉H₂₆N₄O₄ 

Relevant articles and documents

Selegiline-functionalized, PEGylated poly(alkyl cyanoacrylate) nanoparticles: Investigation of interaction with amyloid-β peptide and surface reorganization

Alzheimer's disease (AD) is a neurodegenerative disorder for which the research of new treatments is highly challenging. Since the fibrillogenesis of amyloid-β peptide 1-42 (Aβ1-42) peptide is considered as a major cause of neuronal degeneration, specific interest has been focused on aromatic molecules for targeting this peptide. In this paper, the synthesis of selegiline-functionalized and fluorescent poly(alkyl cyanoacrylate) nanoparticles (NPs) and their evaluation for the targeting of the Aβ1-42 peptide are reported. The synthetic strategy relied on the design of amphiphilic copolymers by tandem Knoevenagel-Michael addition of cyanoacetate derivatives, followed by their self-assembly in aqueous solutions to give the corresponding NPs. Different cyanoacetates were used: (i) hexadecyl cyanoacetate (HDCA) to form the hydrophobic core of the NPs; (ii) rhodamine B cyanoacetate (RCA) for fluorescent purposes; (iii) methoxypoly(ethylene glycol) cyanoacetate (MePEGCA) for stealth properties and (iv) selegiline-poly(ethylene glycol) cyanoacetate (SelPEGCA) to obtain the desired functionality. Two different amphiphilic copolymers were synthesized, a selegiline-containing copolymer, P(MePEGCA-co-SelPEGCA-co-HDCA), and a rhodamine-labelled counterpart, P(MePEGCA-co-RCA-co-HDCA), further blended at variable ratios to tune the amount of selegiline moieties displayed at the surface of the NPs. Optimal formulations involving the different amphiphilic copolymers were determined by the study of the NP colloidal characteristics. Interestingly, it was shown that the zeta potential value of the selegiline-functionalized nanoparticles dramatically decreased, thus emphasizing a significant modification in the surface charge of the nanoparticles. Capillary electrophoresis has then been used to test the ability of the selegiline-functionalized NPs to interact with the Aβ1-42 peptide. In comparison with non functionalized NPs, no increase of the interaction between these functionalized NPs and the monomeric form of the Aβ1-42 peptide was observed, thus highlighting the lack of availability of the ligand at the surface of the nanoparticles. A mechanism explaining this result has been proposed and was mainly based on the burial of the hydrophobic selegiline ligand within the nanoparticles core.

Selegiline hydrochloride synthesis process

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.

METHOD FOR PREPARING SELEGILINE BASE

The present invention relates to a process for the preparation of selegiline base, an irreversible and selective inhibitor of the MAO-B enzymes and which is used in the treatment of Parkinson's Disease.