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Selegiline hydrochloride

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Name

Selegiline hydrochloride

EINECS 604-508-9
CAS No. 14611-52-0 Density 0.954g/cm3
PSA 3.24000 LogP 2.98460
Solubility water: >10 mg/mL Melting Point 141-142 °C
Formula C13H18ClN Boiling Point 272.5 °C at 760mmHg
Molecular Weight 223.746 Flash Point 108.4 °C
Transport Information N/A Appearance white Crystalline Solid
Safety 22-26 Risk Codes N/A
Molecular Structure Molecular Structure of 14611-52-0 (Selegiline hydrochloride) Hazard Symbols N/A
Synonyms

Benzeneethanamine, N,a-dimethyl-N-2-propynyl-, hydrochloride, (aR)- (9CI);(-)-Deprenyl hydrochloride;Eldeprine;Eldepryl;Jumex;Movergan;Plurimen;l-Deprenyl hydrochloride;Selegiline HCl;

Article Data 4

Selegiline hydrochloride Synthetic route

1336-21-6

ammonium hydroxide

L-methyl-anara-D-tartarate

L-methyl-anara-D-tartarate

106-96-7

propargyl bromide

14611-52-0

(R)-(-)-deprenyl hydrochloride

Conditions
ConditionsYield
In water
In water
L-methyl-anara-D-tartarate

L-methyl-anara-D-tartarate

584-08-7

potassium carbonate

106-96-7

propargyl bromide

14611-52-0

(R)-(-)-deprenyl hydrochloride

Conditions
ConditionsYield
In water
3182-95-4

L-Phenylalaninol

14611-52-0

(R)-(-)-deprenyl hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: sulfuric acid / toluene / 0.5 h / 20 °C
1.2: 20 h / 80 °C
2.1: ammonium hydroxide / 3 h / 30 - 35 °C
3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 5 h / 80 - 85 °C
3.2: 1 h / 25 - 30 °C
4.1: methanol / 3 h / 0 - 10 °C
4.2: 3 h / 0 - 10 °C
4.3: 0 - 10 °C / pH 4-6
5.1: hydrogenchloride / isopropyl alcohol / 2 h / 20 °C
View Scheme
63-91-2

L-phenylalanine

14611-52-0

(R)-(-)-deprenyl hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: sodium tetrahydroborate / 1,4-dioxane / 0.5 h / 20 °C
1.2: 20 h / 20 °C
2.1: sulfuric acid / toluene / 0.5 h / 20 °C
2.2: 20 h / 80 °C
3.1: ammonium hydroxide / 3 h / 30 - 35 °C
4.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 5 h / 80 - 85 °C
4.2: 1 h / 25 - 30 °C
5.1: methanol / 3 h / 0 - 10 °C
5.2: 3 h / 0 - 10 °C
5.3: 0 - 10 °C / pH 4-6
6.1: hydrogenchloride / isopropyl alcohol / 2 h / 20 °C
View Scheme
73058-30-7

(2S)-2-benzylazacyclopropane

14611-52-0

(R)-(-)-deprenyl hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: ammonium hydroxide / 3 h / 30 - 35 °C
2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 5 h / 80 - 85 °C
2.2: 1 h / 25 - 30 °C
3.1: methanol / 3 h / 0 - 10 °C
3.2: 3 h / 0 - 10 °C
3.3: 0 - 10 °C / pH 4-6
4.1: hydrogenchloride / isopropyl alcohol / 2 h / 20 °C
View Scheme

C12H13N

14611-52-0

(R)-(-)-deprenyl hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 5 h / 80 - 85 °C
1.2: 1 h / 25 - 30 °C
2.1: methanol / 3 h / 0 - 10 °C
2.2: 3 h / 0 - 10 °C
2.3: 0 - 10 °C / pH 4-6
3.1: hydrogenchloride / isopropyl alcohol / 2 h / 20 °C
View Scheme
14611-52-0

(R)-(-)-deprenyl hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In isopropyl alcohol at 20℃; for 2h;145 g
14611-52-0

(R)-(-)-deprenyl hydrochloride

Conditions
ConditionsYield
With sodium carbonate for 1h;100%
14611-52-0

(R)-(-)-deprenyl hydrochloride

108-88-3

toluene

(R)-N-methyl-N-(1-phenylpropan-2-yl)-3-(p-tolyl)prop-2-yn-1-amine

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 23℃; for 16h; Sonogashira Cross-Coupling; Schlenk technique; Inert atmosphere;84%
14611-52-0

(R)-(-)-deprenyl hydrochloride

826-10-8

(R)-2-N-methylamino-1-phenylpropane hydrochloride

Conditions
ConditionsYield
With phosphate buffer at 105℃; Thermodynamic data; Rate constant; Kinetics; ΔE(excit.); other reagent; other temperature;

Selegiline hydrochloride Specification

Selegiline hydrochloride, with CAS number of 14611-52-0, can be called Benzeneethanamine,N,a-dimethyl-N-2-propynyl-,hydrochloride, (R)-; Benzeneethanamine, N,a-dimethyl-N-2-propynyl-, hydrochloride, (aR)- (9CI); (-)-Deprenilhydrochloride; (-)-Deprenyl hydrochloride; l-Deprenyl hydrochloride; Selegilinehydrochloride; R-Selegiline hydrochloride. Selegiline hydrochloride is a levorotatory acetylenic derivative of phenethylamine.  It is commonly referred to in the clinical and pharmacological literature as l-deprenyl. It is used in newly diagnosed patients with Parkinson's disease.

Physical properties about Selegiline hydrochloride are: (1)ACD/LogP: 2.954; (2)ACD/LogD (pH 5.5): 0.95; (3)ACD/LogD (pH 7.4): 2.58; (4)ACD/BCF (pH 5.5): 1.03; (5)ACD/BCF (pH 7.4): 43.99; (6)ACD/KOC (pH 5.5): 9.62; (7)ACD/KOC (pH 7.4): 409.51; (8)#H bond acceptors: 1; (9)#Freely Rotating Bonds: 4; (10)Flash Point: 108.4 °C; (11)Enthalpy of Vaporization: 51.08 kJ/mol; (12)Boiling Point: 272.5 °C at 760 mmHg; (13)Vapour Pressure: 0.00606 mmHg at 25°C

You can still convert the following datas into molecular structure:
(1)InChI=1S/C13H17N.ClH/c1-4-10-14(3)12(2)11-13-8-6-5-7-9-13;/h1,5-9,12H,10-11H2,2-3H3;1H/t12-;/m1./s1;
(2)InChIKey=IYETZZCWLLUHIJ-UTONKHPSSA-N;
(3)SmilesCl.c1(C[C@H](N(CC#C)C)C)ccccc1

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 unreported 121mg/kg (121mg/kg)   Acta Physiologica Academiae Scientiarum Hungaricae. Vol. 32, Pg. 377, 1967.
rat LD50 intravenous 81mg/kg (81mg/kg)   Acta Physiologica Academiae Scientiarum Hungaricae. Vol. 32, Pg. 377, 1967.
rat LD50 subcutaneous 280mg/kg (280mg/kg)   Acta Physiologica Academiae Scientiarum Hungaricae. Vol. 32, Pg. 377, 1967.

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