6284-40-8

Basic information

• Product Name: Meglumine
• Synonyms: 1-deoxy-1-(methylamino)-d-glucito;1-Deoxy-1-(methylamino)hexitol;Glucitol, 1-deoxy-1-(methylamino)-, D-;Meglumin;Methylglucamin;Methylglucamine;D-GLUCITOL, 1-DEOXY-1-(METHYLAMINO)-;D(-)-N-METHYLGLUCAMINE
• CAS NO: 6284-40-8
• Molecular Formula: C₇H₁₇NO₅
• Molecular Weight: 195.21
• EINECS: 228-506-9
• Product Categories: Anilines, Aromatic Amines and Nitro Compounds;Aminosugars;Biochemistry;Sugars;PREDEF;Diagnostic agents;API
• Mol File: 6284-40-8.mol
• Article Data: 29

Chemical Properties

• Melting Point: 129-131.5 °C(lit.)
• Boiling Point: 331.88°C (rough estimate)
• Flash Point: 251.6 °C
• Appearance: White to almost white/Crystalline Powder
• Density: 1.2669 (rough estimate)
• Vapor Pressure: 1.12E-11mmHg at 25°C
• Refractive Index: -16.5 ° (C=2, H2O)
• Storage Temp.: Store below +30°C.
• Solubility: H2O: 0.1 g/mL, clear, colorless
• PKA: pKa 9.39(H2O,t =30.0,I=0.05N2)(Approximate)
• Water Solubility: 100 g/100 mL (25 ºC)
• Sensitive: Air Sensitive & Hygroscopic
• Merck: 14,6078
• BRN: 385906
• CAS DataBase Reference: Meglumine(CAS DataBase Reference)
• NIST Chemistry Reference: Meglumine(6284-40-8)
• EPA Substance Registry System: Meglumine(6284-40-8)

Safety Data

• Statements: 36/37/38
• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: LZ4295770
• F: 3-10-23
• TSCA: Yes
• Hazardous Substances Data: 6284-40-8(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 6284-40-8 differently. You can refer to the following data:
1. white to almost white crystalline powder
2. Meglumine occurs as a white to slightly yellow-colored crystalline powder; it is odorless or with a slight odor.

Uses

Different sources of media describe the Uses of 6284-40-8 differently. You can refer to the following data:
1. antiinflammatory
2. excipient in cosmetics and X-ray contrast media
3. N-Methyl-D-glucamine is used in conjunction with iodinated organic compounds in contrast media viz. diatrizoate meglumine and iodipamide meglumine. It is useful in ion-exchange resins to chelate boron ions selectively. It is also used as an excipient in pharmaceuticals, in cosmetics and X-ray contrast media. It is also employed in the synthesis of surface active agents, pharmaceuticals and dyes.

Production Methods

Meglumine is prepared by the imination of glucose and monomethylamine, in an alcoholic solution, followed by catalytic hydrogenation.

Definition

ChEBI: A hexosamine that is D-glucitol in which the hydroxy group at position 1 is substituted by the nitrogen of a methylamino group. A crystalline base, it is used in preparing salts of certain acids for use as diagnostic radiopaque media, whi e its antimonate is used as an antiprotozoal in the treatment of leishmaniasis.

General Description

Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.Meglumine is a glucose-derived secondary amine which is widely used as an excipient in pharmaceutical formulations.

Pharmaceutical Applications

Meglumine is an organic base used as a pH-adjusting agent and solubilizing agent, primarily in the preparation of soluble salts of iodinated organic acids used as X-ray contrast media.

Safety

Meglumine is widely used in parenteral pharmaceutical formulations and is generally regarded as a nontoxic material at the levels usually employed as an excipient. LD50 (mouse, IP): 1.68 g/kg

storage

Meglumine does not polymerize or dehydrate unless heated above 150°C for prolonged periods. The bulk material should be stored in a well-closed container in a cool, dry place. Meglumine should not be stored in aluminum containers since it reacts to evolve hydrogen gas; it discolors if stored in containers made from copper or copper alloys. Stainless steel containers are recommended.

Purification Methods

Crystallise N-methyl-D(-)-glucamine from MeOH. Its solubility in H2O is 10%. [Karrer & Herkenrath Helv Chim Acta 20 83 1957 also for other N-alkyl derivatives, Beilstein 4 IV 1914.]

Incompatibilities

Incompatible with aluminum, copper, mineral acids, and oxidizing materials. Differential scanning calorimetry studies suggest meglumine is incompatible with glipizide.

Regulatory Status

Included in the FDA Inactive Ingredients Database (injections; oral tablets). Included in parenteral medicines licensed in the UK.

InChI:InChI=1/C7H17NO5/c1-8-2-4(10)6(12)7(13)5(11)3-9/h4-13H,2-3H2,1H3/p+1/t4-,5-,6+,7-/m1/s1

Synthetic route

N-methyl-D-gluconamide (24758-59-6) → 1-deoxy-1-(methylamino)-D-glucitol (6284-40-8)

Conditions	Yield
With ammonia borane; palladium/alumina at 78℃; under 975.098 - 48004.8 Torr; for 2h; Temperature; Pressure; Reagent/catalyst; Inert atmosphere; Large scale;	69.3%

D-glucose (50-99-7) + methylamine (74-89-5) → 1-deoxy-1-(methylamino)-D-glucitol (6284-40-8)

Conditions	Yield
With hydrogen In water at 10 - 100℃; under 5171.62 - 25858.1 Torr; for 21.5h;	62.5%
With nickel kieselguhr; water at 95 - 120℃; under 36775.4 - 102971 Torr; Hydrogenation;
With ethanol Hydrierung des Reaktionsprodukts an Palladium-Kohle in Methanol bei 60grad/20-25at;

D-glucose (50-99-7) → 1-deoxy-1-(methylamino)-D-glucitol (6284-40-8)

Conditions	Yield
With methylamine

D-glucose (50-99-7) + methylaminomethanol (3400-38-2) → 1-deoxy-1-(methylamino)-D-glucitol (6284-40-8)

magnesium stearate (557-04-0) → poloxamer + 1-deoxy-1-(methylamino)-D-glucitol (6284-40-8)

D-glucose (50-99-7) + methylamine (74-89-5) → 1-deoxy-1-(methylamino)-D-glucitol (6284-40-8) + N,N`-dimethylethylenediamine (110-70-3)

Conditions	Yield
With 5 wt% ruthenium/carbon; hydrogen In water at 124.84℃; under 56255.6 Torr; for 1h;

5-({4-[(4-butylphenyl)ethynyl]benzyl}{[2-(ethoxycarbonyl)cyclopropyl]methyl}amino)-2-fluorobenzoic acid + 1-deoxy-1-(methylamino)-D-glucitol (6284-40-8) → 5-({4-[(4-butylphenyl)ethynyl]benzyl}{[2-(ethoxycarbonyl)cyclopropyl]methyl}amino)-2-fluorobenzoic acid N-methyl-D-glucamine salt

Conditions	Yield
In methanol; water	100%

gadolinium(III) oxide + 2-[1,4,7,10-tetraaza-4,7-di(1-carboxy-2-benzyloxy-ethyl)-10-carboxymethyl-cyclododecane-1-yl]-3-benzyloxypropionic acid (124628-06-4) + 1-deoxy-1-(methylamino)-D-glucitol (6284-40-8) → {gadolinium(C8H17N4(CH2COO)(CH(COO)CH2OCH2C6H5)3)(D(-)-N-methylglucamine)}

Conditions	Yield
In water heating to 70°C until a clear soln. was obtained; evapn. (vac.) and isolation after drying to const. weight; elem. anal.;	100%

gadolinium(III) oxide + 2-[1,4,7,10-tetraaza-4-(1-carboxy-2-benzyloxy-ethyl)-7,10-di(carboxymethyl)-cyclododecane-1-yl]-3-benzyloxypropionic acid (124628-02-0) + 1-deoxy-1-(methylamino)-D-glucitol (6284-40-8) → {gadolinium(C8H17N4(CH2COO)2(CH(COO)CH2OCH2C6H5)2)(D(-)-N-methylglucamine)}

Conditions	Yield
In water heating to 70°C until a clear soln. was obtained; evapn. (vac.) and isolation after drying to const. weight; elem. anal.;	100%

gadolinium(III) oxide + 2-[1,4,7,10-tetraaza-4,7,10-tri(carboxymethyl)-cyclododecane-1-yl]-3-benzyloxypropionic acid (124628-08-6) + 1-deoxy-1-(methylamino)-D-glucitol (6284-40-8) → {gadolinium(C8H17N4(CH2COO)3CH(COO)CH2OCH2C6H5)(D(-)-N-methylglucamine)}

Conditions	Yield
In water heating to 70°C until a clear soln. was obtained; evapn. (vac.) and isolation after drying to const. weight; elem. anal.;	100%

gadolinium(III) oxide + 2-[1,4,7,10-tetraaza-7-(1-carboxy-2-benzyloxy-ethyl)-4,10-di(carboxymethyl)-cyclododecane-1-yl]-3-benzyloxypropionic acid (124628-04-2) + 1-deoxy-1-(methylamino)-D-glucitol (6284-40-8) → {gadolinium(C8H17N4(CH2COO)2(CH(COO)CH2OCH2C6H5)2)(D(-)-N-methylglucamine)}

Conditions	Yield
In water heating to 70°C until a clear soln. was obtained; evapn. (vac.) and isolation after drying to const. weight; elem. anal.;	100%

D-isoglutamyl-D-tryptophan (186087-26-3) + 1-deoxy-1-(methylamino)-D-glucitol (6284-40-8) → D-isoglutamyl-D-tryptophan mono-N-methyl-D-glucamine salt (1034125-74-0)

Conditions	Yield
In water at 20℃; pH=~ 7;	100%
In water at 20℃; for 168h; pH=Ca. 7;	100%

5-chloro-2-([(2-([3-(furan-3-yl)phenyl]amino)-2-oxoehtoxy)acetyl]amino)benzoic acid (1190221-43-2) + 1-deoxy-1-(methylamino)-D-glucitol (6284-40-8) → 5-chloro-2-([(2-([3-(furan-3-yl)phenyl]amino)-2-oxoethoxy)acethyl]amino)benzoic acid N-methyl-D-glucaminesalt (1190221-63-6)

Conditions	Yield
In methanol for 0.5h;	100%

(S)-2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenamido)-4-methylpentanoic acid + 1-deoxy-1-(methylamino)-D-glucitol (6284-40-8) → C7H17NO5*C26H41NO3

Conditions	Yield
In methanol at 20℃; for 2h;	100%

O-[1-(propofol-O-yl)]cyclobut-1-yl-monoester phosphoric acid + 1-deoxy-1-(methylamino)-D-glucitol (6284-40-8) → O-[1-(propofol-O-yl)]cyclobut-1-yl-monoester dimeglumine phosphate

Conditions	Yield
In water at 20℃; for 1h;	100%

1-deoxy-1-(methylamino)-D-glucitol (6284-40-8) + epichlorohydrin (106-89-8) → C10H22ClNO6

Conditions	Yield
In methanol at 20℃; for 72h;	100%

2-(5-nitrothiazol-2-yl-carbamoyl)phenyl dihydrogen phosphate + 1-deoxy-1-(methylamino)-D-glucitol (6284-40-8) → 2-(5-nitrothiazol-2-ylcarbamoyl)phenyl dihydrogen phosphate methylglucamine salt

Conditions	Yield
In methanol at 20℃; for 0.333333h;	100%

(4S)-4-[5-(2,5-dichloro-4-[[(4R)-4-[(4-cyclopropyl-1,2,3,4-tetrahydroquinoxalin-1-yl)carbonyl]-1,3-thiazolidin-3-yl]methyl]phenyl)pentanamido]-5-methoxy-5-oxopentanoic acid + 1-deoxy-1-(methylamino)-D-glucitol (6284-40-8) → methyl (2S)-2-[5-(2,5-dichloro-4-[[(4R)-4-[(4-cyclopropyl-1,2,3,4-tetrahydroquinoxalin-1-yl)carbonyl]-1,3-thiazolidin-3-yl]methyl]phenyl)pentanamido]-4-[methyl[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]carbamoyl]butanoate

Conditions	Yield
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℃;	100%

3,8-bis(1-methoxyethyl)deuteroporphyrin IX + 1-deoxy-1-(methylamino)-D-glucitol (6284-40-8) → 3,8-bis(1-methoxyethyl)porphyrin IX dimeglumine salt

Conditions	Yield
In ethanol for 1h; Reflux;	100%

(R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridine-5-yl)-3-fluorophenyl)-5-hydroxymethyl oxazolidin-2-one dihydrogen phosphate + 1-deoxy-1-(methylamino)-D-glucitol (6284-40-8) → tedizolid phosphate dimeglumine

Conditions	Yield
In water at 20℃; Concentration;	99.5%

gadolinium(III) oxide + (3β,5β,7α,12α)-3-[[[[[bis[2-[bis(carboxymethyl)amino]ethyl]amino]-acetyl]amino]-acetyl]amino]-7,12-dihydroxycholan-24-oic acid (174267-98-2) + 1-deoxy-1-(methylamino)-D-glucitol (6284-40-8) → gadolinium complex of (3β,5β,7α, 12α)-3-[[[[[bis[2-[bis(carboxymethyl)amino]ethyl]amino]acetyl]amino]acetyl]amino]-7,12-dihydroxycholan-24-oic acid salified with 1-deoxy-1-(methylamino)-D-glucitol (1:2)

Conditions	Yield
In water at 50℃; for 25h; pH=5.0 - 6.8;	99%

2,5-dihydroxy-1,4-dithiane-2,5-dicarboxylic acid (80003-64-1) + 1-deoxy-1-(methylamino)-D-glucitol (6284-40-8) → 2,5-dihydroxy-1,4-dithiane-2,5-dicarboxylic acid, bis-((2R,3R,4R,5S)-6-methylaminohexane-1,2,3,4,5-pentol) salt

Conditions	Yield
In water at 20℃; for 0.166667h;	99%

26-succinate-22-deacetyl-neoboutomellerone (1256465-11-8) + 1-deoxy-1-(methylamino)-D-glucitol (6284-40-8) → 26-succinate-22-deacetyl-neoboutomellerone N-methyl-D-glucamine salt (1256465-12-9)

Conditions	Yield
In ethanol; water for 0.166667h;	99%
In ethanol; water for 0.166667h;	99%

2,5-dioxopyrrolidin-1-yl pent-4-ynoate (132178-37-1) + 1-deoxy-1-(methylamino)-D-glucitol (6284-40-8) → N-methyl-N-(4-pentynoyl)-D-glucamine (1448147-88-3)

Conditions	Yield
With triethylamine In pyridine; N,N-dimethyl-formamide at 20℃; for 1h;	99%

methacryloyl anhydride (760-93-0) + 1-deoxy-1-(methylamino)-D-glucitol (6284-40-8) → N-methacryloyl-N-methyl-1-amino-1-deoxy-D-glucitol

Conditions	Yield
In methanol at 15 - 25℃; for 2h; Solvent;	99%

1-deoxy-1-(methylamino)-D-glucitol (6284-40-8) + 3-(triethoxypropyl) isocyanate (24801-88-5) → N-methyl-N-(2,3,4,5,6-pentahydroxyhexyl)-N'-(3-triethoxysilylpropyl)urea

Conditions	Yield
In tetrahydrofuran at 80 - 90℃; for 2.5h;	99%

1-deoxy-1-(methylamino)-D-glucitol (6284-40-8) + tris(4-hydroxyphenyl)methane triglycidyl ether → 4,4',4''-tris{2-hydroxy-3-[N-methyl-(2',3',4',5',6'-pentahydroxy-D-gluco-hexyl)amino]propoxy}triphenylmethane

Conditions	Yield
In ethanol for 7h; Reflux;	99%

(R)-3-methyl-6-(2-((5-methyl-2-(6-(trifluoromethyl)pyridin-3-yl)-1H-imidazol-1-yl)methyl)phenoxy)hexanoic acid + 1-deoxy-1-(methylamino)-D-glucitol (6284-40-8) → C24H26F3N3O3*C7H17NO5

Conditions	Yield
In tetrahydrofuran; water at 20℃; for 16h; Solvent; Temperature;	98.95%
In isopropyl alcohol at 25 - 50℃; for 1.33333h; Solvent; Sealed tube;
In isopropyl alcohol at 25 - 50℃; for 1.33333h; Solvent; Sealed tube; Sonication;

(R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridine-5-yl)-3-fluorophenyl)-5-hydroxymethyl oxazolidin-2-one dihydrogen phosphate + 1-deoxy-1-(methylamino)-D-glucitol (6284-40-8) → tedizolid phosphate monomeglumine

Conditions	Yield
In water at 20℃; Concentration;	98.9%

1-deoxy-1-(methylamino)-D-glucitol (6284-40-8) + wortmannin (19545-26-7) → WmC20-N-methyl-glucamine

Conditions	Yield
In dimethyl sulfoxide at 20℃; for 0.5h;	98.7%

1-deoxy-1-(methylamino)-D-glucitol (6284-40-8) + 4-ethylbenzylaldehyde (4748-78-1) → (2R,5S)-2-(4-ethylphenyl)-3-methyl-5-(D-arabino-1,2,3,4-tetrahydroxybutyl)oxazolidine (1042065-80-4)

Conditions	Yield
In benzene Heating;	98%

1,10-diisocyanatodecane (4538-39-0) + 1-deoxy-1-(methylamino)-D-glucitol (6284-40-8) → N,N'-decamethylenebis[N''-(1-deoxy-D-glucitol-1-yl)-N''-methylurea] (1056030-07-9)

Conditions	Yield
In 1,4-dioxane; water at 20℃; for 2h;	98%

4-(((1S,2S)-2,3-dihydro-1-hydroxy-2-(1H-inden-2-yl)-1H-inden-2-yl)methyl)benzoic acid (1380445-03-3) + 1-deoxy-1-(methylamino)-D-glucitol (6284-40-8) → (2R,3R,4R,5S)-6-(methylamino)hexane-1,2,3,4,5-pentanol 4-(((1S,2S)-1-hydroxy-2,3-dihydro-1H,1'H-[2,2-biinden]-2-yl)methyl)benzoic acid (1380445-04-4)

Conditions	Yield
In methanol at 55℃;	98%
In water

gadolinium(III) oxide + diethylenetriaminopentaacetic acid (67-43-6) + 1-deoxy-1-(methylamino)-D-glucitol (6284-40-8) → gadopentate dimeglumine

Conditions	Yield
Stage #1: diethylenetriaminopentaacetic acid; 1-deoxy-1-(methylamino)-D-glucitol In water for 0.0333333h; Sonication; Green chemistry; Stage #2: gadolinium(III) oxide In water for 0.3h; Sonication; Green chemistry;	98%

1-deoxy-1-(methylamino)-D-glucitol (6284-40-8) + aprepitant (170729-80-3) → Fosaprepitant dimeglumine

Conditions	Yield
Stage #1: aprepitant With dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate; sodium hexamethyldisilazane In tetrahydrofuran at -3℃; for 2h; Stage #2: 1-deoxy-1-(methylamino)-D-glucitol With palladium 10% on activated carbon; hydrogen In methanol; water for 4h;	98%

1-deoxy-1-(methylamino)-D-glucitol (6284-40-8) + fosaprepitant → fosaprepitant dimeglumine

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol; water for 4h;	98%

Upstream product

• 2280-44-6 D-Glucose 
• 74-89-5 methylamine 
• 24758-59-6 N-methyl-D-gluconamide 
• 50-99-7 D-glucose 
• 557-04-0 magnesium stearate 
• 3400-38-2 methylaminomethanol 

Downstream Products

• 87157-40-2 N-[(2,4-dichloro-phenoxy)-acetyl]-N-methyl-D-glucamine 
• 74-93-1 methylthiol 
• 113224-27-4 C₁₀H₁₇N₅O₅ 
• 121018-33-5 N-<2-<(1-deoxy-D-sorbitolyl)(methyl)carbamoyl>ethyl>2-nitro-3-benzyloxy-4-methylbenzamide 
• 121018-34-6 N-<5-<(1-deoxy-D-sorbitolyl)(methyl)carbamoyl>pentyl>-2-nitro-3-benzyloxy-4-methylbenzamide 
• 87246-72-8 N-dodecanoyl-N-methyl-1-glucamine 
• 85261-20-7 MEGA 10 
• 266363-14-8 N-(2S,3R,4S,5S)-2,3,4,5,6-pentahydroxyhexyl-1-yl-N-methyl-N'-phenylthiourea 
• 265121-04-8 Fosaprepitant dimeglumine 
• 717107-36-3 N-methyl-D-glucamine salt of 4-{3-[4-(3,5-dichloro-pyridin-4-yl-methyl)-7-methoxy-phthalazin-1-yl]-phenoxy}-butyric acid 
• 717107-38-5 N-methyl-D-glucamine salt of 3-{3-[4-(3,5-dichloro-pyridin-4-ylmethyl)-7-methoxy-phthalazin-1-yl]-phenyl}-acrylic acid 

Relevant articles and documents

Method for synthesizing meglumine through catalytic hydrogenation by taking ammonia borane as hydrogen source

The invention discloses a method for synthesizing meglumine through catalytic hydrogenation by taking ammonia borane as a hydrogen source, and belongs to the technical field of chemical drug synthesis. The method comprises the step that on the basis that glucose-methylamine schiff base is synthesized by taking glucose and methylamine as raw materials, and by taking ammonia borane as the hydrogen source for performing catalytic hydrogenation, the meglumine is synthesized. Compared with a method in the past, the method has the advantages of being mild in catalytic hydrogenation reaction, safe and high yield.

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