methyl[(2R)-1-phenylpropan-2-yl](prop-2-yn-1-yl)amine

• ChemBase ID: 909
• Molecular Formular: C13H17N
• Molecular Mass: 187.28078
• Monoisotopic Mass: 187.13609955
• SMILES: N([C@@H](Cc1ccccc1)C)(CC#C)C
• Canonical SMILES: C[C@@H](N(CC#C)C)Cc1ccccc1
• InChI: InChI=1S/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
• InChIKey: MEZLKOACVSPNER-GFCCVEGCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl[(2R)-1-phenylpropan-2-yl](prop-2-yn-1-yl)amine
• IUPAC Traditional name: selegiline
• Brand Name: Apo-Selegiline; Carbex; Eldepryl; Gen-Selegiline; Jumex; Novo-Selegiline; Nu-Selegiline; Sd Deprenyl; Zelapar; Emsam
• Synonyms: L-Deprenalin; Selegeline Hcl; Selegilina [INN-Spanish]; Selegilinum [INN-Latin]; selegiline; Selegiline

Database IDs

• CAS Number: 14611-51-9
• PubChem SID: 160964372
• PubChem CID: 26757

CALCULATED PROPERTIES

JChem

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): -0.15821154
• LogD (pH = 7.4): 1.5548966
• Log P: 2.847962
• Molar Refractivity: 61.3547 cm^3
• Polarizability: 23.641752 Å^3
• Polar Surface Area: 3.24 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.08
• LOG S: -3.87
• Solubility (Water): 2.54e-02 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 2.7

DETAILS

DrugBank - DB01037

• Drug Groups: approved; investigational
• Description: A selective, irreversible inhibitor of Type B monoamine oxidase. It is used in newly diagnosed patients with Parkinson's disease. It may slow progression of the clinical disease and delay the requirement for levodopa therapy. It also may be given with levodopa upon onset of disability. (From AMA Drug Evaluations Annual, 1994, p385) The compound without isomeric designation is Deprenyl. [PubChem]
• Indication: 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.
• Pharmacology: Dopamine is an essential chemical that occurs in many parts of the body. It is the premature degradation of dopamine that results in the symptoms of Parkinson's disease. Monoamine oxidase (MAO) is an enzyme which accelerates the breakdown of dopamine. Selegiline can prolong the effects of dopamine in the brain by preventing its breakdown through seletively blocking MAO-B. It also may prevent the removal of dopamine between nerve endings and enhance release of dopamine from nerve cells.
• Toxicity: LD₅₀=63 mg/kg (rats, IV)
• Affected Organisms: Humans and other mammals
• Absorption: Rapidly absorbed from the gastrointestinal tract.
• Half Life: 1.2-2 hours
• Protein Binding: > 99.5%
• References: Engberg G, Elebring T, Nissbrandt H: Deprenyl (selegiline), a selective MAO-B inhibitor with active metabolites; effects on locomotor activity, dopaminergic neurotransmission and firing rate of nigral dopamine neurons. J Pharmacol Exp Ther. 1991 Nov;259(2):841-7. [Pubmed] ; Macleod AD, Counsell CE, Ives N, Stowe R: Monoamine oxidase B inhibitors for early Parkinson's disease. Cochrane Database Syst Rev. 2005 Jul 20;(3):CD004898. [Pubmed] ; Magyar K, Tothfalusi L: Pharmacokinetic aspects of deprenyl effects. Pol J Pharmacol Pharm. 1984 Jul-Aug;36(4):373-84. [Pubmed] ; Heinonen EH, Anttila MI, Lammintausta RA: Pharmacokinetic aspects of l-deprenyl (selegiline) and its metabolites. Clin Pharmacol Ther. 1994 Dec;56(6 Pt 2):742-9. [Pubmed] ; Deleu D, Northway MG, Hanssens Y: Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinson's disease. Clin Pharmacokinet. 2002;41(4):261-309. [Pubmed] ; Culpepper L, Kovalick LJ: A review of the literature on the selegiline transdermal system: an effective and well-tolerated monoamine oxidase inhibitor for the treatment of depression. Prim Care Companion J Clin Psychiatry. 2008;10(1):25-30. [Pubmed] ; Lee KC, Chen JJ: Transdermal selegiline for the treatment of major depressive disorder. Neuropsychiatr Dis Treat. 2007;3(5):527-37. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• Engberg G, Elebring T, Nissbrandt H: Deprenyl (selegiline), a selective MAO-B inhibitor with active metabolites; effects on locomotor activity, dopaminergic neurotransmission and firing rate of nigral dopamine neurons. J Pharmacol Exp Ther. 1991 Nov;259(2):841-7. Pubmed
• Macleod AD, Counsell CE, Ives N, Stowe R: Monoamine oxidase B inhibitors for early Parkinson's disease. Cochrane Database Syst Rev. 2005 Jul 20;(3):CD004898. Pubmed
• Magyar K, Tothfalusi L: Pharmacokinetic aspects of deprenyl effects. Pol J Pharmacol Pharm. 1984 Jul-Aug;36(4):373-84. Pubmed
• Heinonen EH, Anttila MI, Lammintausta RA: Pharmacokinetic aspects of l-deprenyl (selegiline) and its metabolites. Clin Pharmacol Ther. 1994 Dec;56(6 Pt 2):742-9. Pubmed
• Deleu D, Northway MG, Hanssens Y: Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinson's disease. Clin Pharmacokinet. 2002;41(4):261-309. Pubmed
• Culpepper L, Kovalick LJ: A review of the literature on the selegiline transdermal system: an effective and well-tolerated monoamine oxidase inhibitor for the treatment of depression. Prim Care Companion J Clin Psychiatry. 2008;10(1):25-30. Pubmed
• Lee KC, Chen JJ: Transdermal selegiline for the treatment of major depressive disorder. Neuropsychiatr Dis Treat. 2007;3(5):527-37. Pubmed