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41100-52-1

Basic Information
CAS No.: 41100-52-1
Name: Memantine hydrochloride
Molecular Structure:
Molecular Structure of 41100-52-1 (Memantine hydrochloride)
Formula: C12H21N.HCl
Molecular Weight: 215.76
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;
EINECS: 255-219-6
Density:
Melting Point: 292 °C
Boiling Point: 239.8 °C at 760 mmHg
Flash Point: 92.3 °C
Solubility:
Appearance: Crystalline solid
Hazard Symbols:
Risk Codes:
Safety: 24/25
Transport Information:
PSA: 26.02000
LogP: 4.19640
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%
1575-61-7

5-Chlorovaleroyl chloride

41100-52-1

memantine hydrochloride

1402933-98-5

5-chloro-N-(3,5-dimethyladamantan-1-yl)pentanamide

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃; for 4h;91%

(R)-2-((1S,4S)-4-(6-fluoroquinolin-4-yl)cyclohexyl) propanoic acid

41100-52-1

memantine hydrochloride

(cis)-(2R)-N-(3,5-dimethyladamantan-1-yl)-2-(4-(6-fluoroquinolin-4-yl)cyclohexyl)propanamide

Conditions
ConditionsYield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 1h;91%
75-36-5

acetyl chloride

41100-52-1

memantine hydrochloride

19982-07-1

1-acetamido-3,5-dimethyladamantane

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 3h; Solvent;91%
55362-80-6

9-bromononan-1-ol

41100-52-1

memantine hydrochloride

1402933-72-5

9-((3,5-dimethyladamantan-1-yl)amino)nonan-1-ol

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 48h;90%
64-18-6

formic acid

41100-52-1

memantine hydrochloride

351329-88-9

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

Conditions
ConditionsYield
With titanium sulfate at 80℃; for 5h; Reagent/catalyst; Temperature;90%
68-12-2, 33513-42-7

N,N-dimethyl-formamide

41100-52-1

memantine hydrochloride

351329-88-9

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

Conditions
ConditionsYield
With titanium(IV) oxide at 105℃; for 3h; Reagent/catalyst;90%
108-24-7

acetic anhydride

41100-52-1

memantine hydrochloride

19982-07-1

1-acetamido-3,5-dimethyladamantane

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 2.5h; Solvent;90%
4286-55-9

1-bromo-6-hexanol

41100-52-1

memantine hydrochloride

1402933-69-0

6-((3,5-dimethyladamantan-1-yl)amino)hexan-1-ol

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 48h;89%
24066-82-8

ethyl 2-isothiocyanatoacetate

41100-52-1

memantine hydrochloride

ethyl {[(3,5-dimethyladamantan-1-yl)carbamothioyl]amino}acetate

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 80℃; for 12h;89%
118591-58-5

5-tosyloxy-3-oxapentanol

41100-52-1

memantine hydrochloride

1402934-02-4

2-(2-((3,5-dimethyladamantan-1-yl)amino)ethoxy)ethanol

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 48h;88%
1402934-00-2

2-((2-hydroxyethyl)thio)ethyl 4-methylbenzenesulfonate

41100-52-1

memantine hydrochloride

2-((2-((3,5-dimethyladamantan-1-yl)amino)ethyl)thio)ethanol

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 48h;87%
41100-52-1

memantine hydrochloride

2949-22-6

Glycine ethyl ester isocyanate

ethyl {[(3,5-dimethyladamantan-1-yl)carbamoyl]amino}acetate

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 12h;87%
41100-52-1

memantine hydrochloride

180851-50-7

toluene-4-sulfonic acid 4-tert-butoxycarbonylaminobutyl ester

tert-butyl (4-((3,5-dimethyladamantan-1-yl)amino)butyl)carbamate

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide under 12929 Torr; for 1h; Microwave irradiation;87%
50816-19-8

8-bromooctanol

41100-52-1

memantine hydrochloride

1402933-71-4

8-((3,5-dimethyladamantan-1-yl)amino)octan-1-ol

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 48h;86%
41100-52-1

memantine hydrochloride

4635-59-0

4-Chlorobutanoyl chloride

1402933-97-4

4-chloro-N-(3,5-dimethyladamantan-1-yl)butanamide

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃; for 4h;86%
41100-52-1

memantine hydrochloride

351329-88-9

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

Conditions
ConditionsYield
With copper(II) choride dihydrate at 40℃; for 4h;86%
19347-73-0

6-chlorohexanoyl chloride

41100-52-1

memantine hydrochloride

1402933-99-6

6-chloro-N-(3,5-dimethyladamantan-1-yl)hexanamide

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃; for 4h;85%
41059-02-3

9-bromononanoic acid

41100-52-1

memantine hydrochloride

9-bromo-N-(3,5-dimethyladamantyl)nonamide

Conditions
ConditionsYield
With 2-chloro-1,3-dimethyl-4,5-dihydro-1H-imidazolium chloride; triethylamine In dichloromethane at 0 - 20℃; for 18h;85%
619-65-8

4-cyanobenzoic Acid

41100-52-1

memantine hydrochloride

C20H24N2O

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; Inert atmosphere; Cooling with ice;81%
805983-04-4

3-(prop-2-en-1-yldisulfanyl)propanoic acid

41100-52-1

memantine hydrochloride

1215295-30-9

3-(prop-2-en-1-yldisulfanyl)-N-((1r,3R,5S,7r)-3,5-dimethyladamantan-1-yl)propanamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; Inert atmosphere; Cooling with ice;79%
41100-52-1

memantine hydrochloride

86536-92-7

6-((tert-butoxycarbonyl)amino)hexyl 4-methylbenzenesulfonate

tert-butyl (6-((3,5-dimethyladamantan-1-yl)amino)hexyl)carbamate

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide under 12929 Torr; for 1h; Microwave irradiation;79%
Downstream Products
19982-08-2
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    41100-52-1

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    41100-52-1

    Memantine HCl 41100-52-1

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    white powder Molecular formula:C12H21NHCL Molecular weight:215.81 Cas:41100-52-1 Appearance:White crystal or powder Melting range:290οC-295οC Loss on drying:≤0.5% Content:≥98.5%(HPLC) Appearance:White or almost

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    Memantine HCl

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    41100-52-1

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    Memantine hydrochloride

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    Memantine hydrochloride

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    Memantine HCl Basic information Description References Product Name: Memantine HCl Synonyms: MEMANTINE HCL;LABOTEST-BB LT00233220;1,3-Dimethyl-5-aminoadamantane hydrochloride;1,3-DIMETHYLAMINOADAMANTANE HYDROCHLORIDE;1-AMINO-3,5-DIMETHYLADAMA

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  • TIANFU-CHEM CAS:41100-52-1 Memantine HCl

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    41100-52-1

    TIANFU-CHEM CAS:41100-52-1 Memantine HCl

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    Memantine HCl Basic information Product Name: Memantine HCl Synonyms: MEMANTINE HCL;LABOTEST-BB LT00233220;D-145;1,3-Dimethyl-5-aminoadamantane hydrochloride;1,3-DIMETHYLAMINOADAMANTANE

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Chemistry

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

Uses

  Memantine hydrochloride is used as an antiparkinsonian and antispasmodic.

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

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.