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(+-)-Selegiline

HCID 5195
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
14611-51-9
Standard SMILES
C#CCN(C)C(C)Cc1ccccc1
InChIKey
MEZLKOACVSPNER-UHFFFAOYSA-N
Molecular formula
C13H17N
Average molar mass
187.28 g/mol
Monoisotopic mass
187.13609955

Overview

Selegiline is a tertiary amine, a phenethylamine alkaloid and a terminal acetylenic compound. It is a conjugate base of a selegiline(1+).

Names & identifiers

Preferred name
(+-)-Selegiline
IUPAC
N-methyl-1-phenyl-N-prop-2-ynylpropan-2-amine
English name
Deprenyl
Molecular formula
C13H17N
Molecular weight
187.284

Names & synonyms

DeprenylDeprenil2323-36-6DPF682Q08VPHENETHYLAMINE, N,alpha-DIMETHYL-N-2-PROPYNYL-(+-)-SelegilineRefChem:905515(+/-)-DeprenylN,alpha-Dimethyl-N-2-propynylphenethylamineN-methyl-1-phenyl-N-prop-2-ynylpropan-2-amine(+/-)-Deprenyl-d3Phenethylamine, N,.alpha.-dimethyl-N-2-propynyl-
Show more names
seleglineSelegiline oxalate salt2H5]-Selegiline oxalate saltR(-SELEGILINE,1.0MG/MLINMETHANOLN,α-Dimethyl-N-(2-propynyl)benzeneethanaminemethyl-(1-methyl-2-phenyl-ethyl)-propargyl-amineBenzeneethanamine, N,a-dimethyl-N-2-propyn-1-yl-Benzeneethanamine, N,α-dimethyl-N-2-propyn-1-yl-
(RS)-Selegiline hydrochloride CRS(+-)-DeprenylSelegilinum [INN-Latin]Selegilina [INN-Spanish]dl-Deprenyl(.+/-.)-DeprenylN,alpha-Dimethyl-N-2-propynylbenzeneethanamineCHEMBL8663

Database identifiers

CAS

Properties

Computed structural properties

XLogP
2.8
Topological polar surface area
3.2 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
4
Heavy atoms
14
Formal charge
0
Complexity
195

Experimental & physicochemical properties

DrugsPharmaceuticals
LogP2.7
Solubility2.54e-02 g/L
Melting Point141 - 142 °C
Physical DescriptionSolid

Physicochemical properties

Boiling point
5 · bp5 103-110°
Density
0.954 · 0.954±0.06 g/cm3(Predicted)
refractive index
20 · nD20 1.5224
pka
7.53 · 7.53±0.50(Predicted)
FDA UNII
682 Q08V · DPF682Q08V
RIDADR
1851 · 1851
HazardClass
6.1 · 6.1(b)
PackingGroup
III

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Toxicology

Treatment · 1 item

Treatment of overdose with non-selective MAOIs is symptomatic and supportive. Induction of emesis or gastric lavage with instillation of charcoal slurry may be helpful in early poisoning, provided the airway has been protected against aspiration. Signs and symptoms of central nervous system stimulation, including convulsions, should be treated with diazepam, given slowly intravenously. Phenothiazine derivatives and central nervous system stimulants should be avoided. Hypotension and vascular collapse should be treated with intravenous fluids and, if necessary, blood pressure titration with an intravenous infusion of a dilute pressor agent. It should be noted that adrenergic agents may produce a markedly increased pressor response. Respiration should be supported by appropriate measures, including management of the airway, use of supplemental oxygen, and mechanical ventilatory assistance, as required. Body temperature should be monitored closely. Intensive management of hyperpyrexia may be required. Maintenance of fluid and electrolyte balance is essential. (L1712)

Exposure RoutesOral. Rapidly absorbed from the gastrointestinal tract.
Toxicity Summary · 1 item

Although the mechanisms for selegiline's beneficial action in the treatment of Parkinson's disease are not fully understood, the selective, irreversible inhibition of monoamine oxidase type B (MAO-B) is thought to be of primary importance. MAO-B is involved in the oxidative deamination of dopamine in the brain. Selegiline binds to MAO-B within the nigrostriatal pathways in the central nervous system, thus blocking microsomal metabolism of dopamine and enhancing the dopaminergic activity in the substantial nigra. Selegiline may also increase dopaminergic activity through mechanisms other than inhibition of MAO-B. At higher doses, selegiline can also inhibit monozmine oxidase type A (MAO-A), allowing it to be used for the treatment of depression. MAO's activity is inhibited when selegiline binds to the isoalloxazine flavin adenine dinucleotide (FAD) at its active center

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Chemistry & industry

Pharmacology

Metabolism/MetabolitesHalf Life: 1.2-2 hours
MeSH Pharmacological Classification · 4 items

Mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. Several MONOAMINE OXIDASE INHIBITORS are useful as antidepressants apparently as a long-term consequence of their modulation of catecholamine levels. The tricyclic compounds useful as antidepressive agents (ANTIDEPRESSIVE AGENTS, TRICYCLIC) also appear to act through brain catecholamine systems. A third group (ANTIDEPRESSIVE AGENTS, SECOND-GENERATION) is a diverse group of drugs including some that act specifically on serotonergic systems.

Agents used in the treatment of Parkinson's disease. The most commonly used drugs act on the dopaminergic system in the striatum and basal ganglia or are centrally acting muscarinic antagonists.

A chemically heterogeneous group of drugs that have in common the ability to block oxidative deamination of naturally occurring monoamines. (From Gilman, et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed, p414)

Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids.

Cellular LocationsCytoplasm

Uses & manufacturing

Uses · 1 item

Monotherapy for initial treatment of Parkinson's disease, as well as an adjunct therapy in patients with a decreased response to levodopa/carbadopa. Also used for the palliative treatment of mild to moderate Alzheimer's disease and at higher doses, for the treatment of depression.

Suppliers2 total

上海陶术生物科技股份有限公司

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
14611-51-9、2323-36-6
PubChem CID
5195
DTXSID
DTXSID60860142
ChEMBL
CHEMBL8663
ChEBI
CHEBI:50217
UNII
DPF682Q08V
Nikkaji
J21.365I
Toxicity DataLD50: 63 mg/kg (Intravenous, Rat) (A308)

Safety data

ridadr
1851
hazard_class
6.1(b)
packing_group
III
13564774135 · [email protected]
杭州洁汉化工有限公司+86-571-86217390; +8618058761490 · [email protected]

Additional notes

DefinitionChEBI: Selegiline is a phenethylamine alkaloid, a tertiary amine and a terminal acetylenic compound. It is a conjugate base of a selegiline(1+).