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Memantine hydrochloride

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Name

Memantine hydrochloride

EINECS 255-219-6
CAS No. 41100-52-1 Density N/A
PSA 26.02000 LogP 4.19640
Solubility N/A Melting Point 292 °C
Formula C12H21N.HCl Boiling Point 239.8 °C at 760 mmHg
Molecular Weight 215.766 Flash Point 92.3 °C
Transport Information N/A Appearance Crystalline solid
Safety 24/25 Risk Codes N/A
Molecular Structure Molecular Structure of 41100-52-1 (Memantine HCl) Hazard Symbols N/A
Synonyms

Akatinol;Memantine hydrochloride [USAN];Axura;Namenda;Ebixza;Tricyclo(3.3.1.1(3,7))decan-1-amine, 3,5-dimethyl-, hydrochloride;3,5-Dimethyltricyclo(3.3.1.13,7)decan-1-amine hydrochloride;3,5-dimethyladamantan-1-amine hydrochloride;Memantine HCl;1,3-Dimethyl-5-aminoadamantane hydrochloride;Fructus Mume P.E.;3,5-dimethyltricyclo[3.3.1.13,7]decan-1-amine hydrochloride;

Article Data 53

Memantine hydrochloride Synthetic route

1058345-42-8

2,2,2-trichloroethyl 3,5-dimethyladamantylcarbamate

41100-52-1

memantine hydrochloride

Conditions
ConditionsYield
Stage #1: 2,2,2-trichloroethyl 3,5-dimethyladamantylcarbamate With acetic acid; zinc at 20℃; for 2h;
Stage #2: With acetyl chloride In methanol at 40℃; for 16h; Heating;
100%
19982-07-1

1-acetamido-3,5-dimethyladamantane

41100-52-1

memantine hydrochloride

Conditions
ConditionsYield
Stage #1: 1-acetamido-3,5-dimethyladamantane With sodium hydroxide In diethylene glycol for 6h; Reflux;
Stage #2: With water In dichloromethane; diethylene glycol at 20℃; for 0.25h;
Stage #3: With hydrogenchloride In ethyl acetate at 0 - 30℃; for 6h;
99.3%
Stage #1: 1-acetamido-3,5-dimethyladamantane With potassium hydroxide; butan-1-ol at 20 - 132℃; for 10.33 - 10.5h;
Stage #2: With hydrogenchloride In water at 20 - 25℃; for 0.666667h;
95%
Stage #1: 1-acetamido-3,5-dimethyladamantane With sodium hydroxide In ethylene glycol at 150 - 160℃; for 0.5h; Large scale;
Stage #2: With hydrogenchloride In ethyl acetate Large scale;
82.78%
941-37-7

3,5-dimethyl-1-bromoadamantane

41100-52-1

memantine hydrochloride

Conditions
ConditionsYield
Stage #1: 3,5-dimethyl-1-bromoadamantane; urea In 1-methyl-pyrrolidin-2-one at 120℃; for 4h;
Stage #2: With sodium hydroxide In 1-methyl-pyrrolidin-2-one at 120℃; for 6h;
Stage #3: With hydrogenchloride In 1-methyl-pyrrolidin-2-one; water at 25℃; for 16h; Solvent; Temperature;
97%
351329-88-9

1-formamido-3,5-dimethyltricyclo[3.3.1.13,7]decane

41100-52-1

memantine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water at 100℃; for 5h;94%
Stage #1: 1-formamido-3,5-dimethyltricyclo[3.3.1.13,7]decane With water; sodium hydroxide In methanol for 12h; Reflux;
Stage #2: With hydrogenchloride In methanol; n-heptane at 60 - 65℃; Product distribution / selectivity;
86%
With hydrogenchloride In hexane; water for 2.5h; Reflux;84.65%
1309688-17-2

N-((1,3,5,7)-3,5-dimethyladamantan-1-yl)-1,1,1-trifluoromethanesulfonamide

41100-52-1

memantine hydrochloride

Conditions
ConditionsYield
Stage #1: N-((1,3,5,7)-3,5-dimethyladamantan-1-yl)-1,1,1-trifluoromethanesulfonamide With potassium carbonate; 1-bromomethyl-4-nitro-benzene In acetone at 20℃;
Stage #2: With caesium carbonate In tetrahydrofuran at 50℃; for 14h;
Stage #3: With hydrogenchloride In tetrahydrofuran; water
92%
19982-08-2

memantine*

41100-52-1

memantine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water; acetone at -5 - 30℃; for 5h;91.9%
With hydrogenchloride pH=6; Gas phase;88%
With hydrogenchloride In water; acetone at 0 - 10℃; Solvent;88%
6588-68-7

1-nitro-3,5-dimethyl-adamantane

41100-52-1

memantine hydrochloride

Conditions
ConditionsYield
Stage #1: 1-nitro-3,5-dimethyl-adamantane With iron; acetic acid at 20℃; for 4.5h;
Stage #2: With hydrogenchloride In ethyl acetate for 0.5h;
449.2 g

1-acetamido-3,5-dimethyladamantane p-toluenesulfonate

41100-52-1

memantine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: ammonia / dichloromethane; water / 0.5 h / 25 - 30 °C / pH 9.5 - 10.0
2.1: sodium hydroxide / diethylene glycol / 10 h / Heating / reflux
2.2: 2 h / 10 - 15 °C
View Scheme
40430-57-7

3, 5-dimethyl-1-adamantyl methyl ketone

41100-52-1

memantine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: methanol; O-benzenesulfonyl-acetohydroxamic acid ethyl ester; toluene-4-sulfonic acid / 12 h / Inert atmosphere; Reflux
2: hydrogenchloride / acetone / 3 h / 23 °C / Inert atmosphere
View Scheme
10160-24-4

7-bromoheptyl alcohol

41100-52-1

memantine hydrochloride

1402933-70-3

7-((3,5-dimethyladamantan-1-yl)amino)heptan-1-ol

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 48h;92%

Memantine hydrochloride Chemical Properties

Molecular Structure of Memantine hydrochloride (CAS NO.41100-52-1):

IUPAC Name: 3,5-dimethyladamantan-1-amine hydrochloride
Molecular formula:C12H22ClN
Molecular Weight:215.76
H bond acceptors: 1
H bond donors: 2
Freely Rotating Bonds: 1
Flash Point: 92.3 °C
Enthalpy of Vaporization: 47.67 kJ/mol
Boiling Point: 239.8 °C at 760 mmHg
Vapour Pressure: 0.0393 mmHg at 25°C
EINECS: 255-219-6
Melting point: 292 °C
Appearance:Crystalline Solid
InChI
InChI=1/C12H21N.ClH/c1-10-3-9-4-11(2,6-10)8-12(13,5-9)7-10;/h9H,3-8,13H2,1-2H3;1H
Smiles
C1[C@@]2(CC3(CC(C2)C[C@@]1(C3)C)N)C.Cl
Product Categories: Adamantane derivatives; Antispasmodic; Antiparkinsonian; Adamantanes; Intermediates & Fine Chemicals; Pharmaceuticals; Glutamate receptor; Glutamate

Memantine hydrochloride Uses

  Memantine hydrochloride is used as an antiparkinsonian and antispasmodic.

Memantine hydrochloride Safety Profile

The Safety Statements information of  Memantine hydrochloride (CAS NO.41100-52-1):
24/25: Avoid contact with skin and eyes 
WGK Germany: 3

Memantine hydrochloride Specification

  Memantine hydrochloride , with CAS number of 41100-52-1, can be called Memantine HCl ; 1,3-Dimethyl-5-aminoadamantane hydrochloride ; 1,3-Dimethylaminoadamantane hydrochloride ; 1-amino-3,5-dimethyladamantane hcl ; 1-amino-3,5-dimethyladamantane hydrochloride ; 1-amino-3,4-dimethyladamantane hydrochloride . It is a crystalline solid, Memantine hydrochloride (CAS NO.41100-52-1) can be used as an antiparkinsonian and antispasmodic.

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