D(-)-N-Methylglucamine - for resolution of racemates for synthesis , CAS No.6284-40-8

CAS: 6284-40-8 Cat. No.: D433156 Molecular Weight: 195.21 Beilstein Registry Number: 385906 EC Number: 228-506-9

GRADE & PURITY for resolution of racemates for synthesis

Synonyms

Z1255485274 | 6HG8UB2MUY | A834035 | Meglumine 100 microg/mL in Acetonitrile | CAS-6284-40-8 | Meglumine (JP17/USP/INN) | MEGLUMINE [II] | AB00430469-03 | Meglumine, Pharmaceutical Secondary Standard; Certified Reference Material | Megluminum [INN-Latin]

Storage

Room temperature

Shipped In

Normal

Specifications

Synonyms

Z1255485274 | 6HG8UB2MUY | A834035 | Meglumine 100 microg/mL in Acetonitrile | CAS-6284-40-8 | Meglumine (JP17/USP/INN) | MEGLUMINE [II] | AB00430469-03 | Meglumine, Pharmaceutical Secondary Standard; Certified Reference Material | Megluminum [INN-Latin]

Specifications & Purity

for resolution of racemates for synthesis

Storage

Room temperature

Shipped In

Normal

Names and Identifiers

• Canonical Smiles: CNCC(C(C(C(CO)O)O)O)O
• IUPAC Name: (2R,3R,4R,5S)-6-(methylamino)hexane-1,2,3,4,5-pentol
• InChIKey: MBBZMMPHUWSWHV-BDVNFPICSA-N
• INCHI: 1S/C7H17NO5/c1-8-2-4(10)6(12)7(13)5(11)3-9/h4-13H,2-3H2,1H3/t4-,5+,6+,7+/m0/s1
• Isomeric SMILES: CNC[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O
• WGK Germany: 3
• Alternate CAS: 90191-92-7
• Molecular Weight: 195.21
• Beilstein: 385906
• Reaxy-Rn: 2324336
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2324336&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Monosaccharides
          • Level6 Hexoses

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Monosaccharides
• Direct Parent: Hexoses
• Alternative Parents: 1,3-aminoalcohols Secondary alcohols 1,2-aminoalcohols Polyols Dialkylamines Primary alcohols Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Hexose monosaccharide - 1,3-aminoalcohol - Secondary alcohol - 1,2-aminoalcohol - Secondary amine - Polyol - Secondary aliphatic amine - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Primary alcohol - Organonitrogen compound - Amine - Alcohol - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.
• External Descriptors: secondary amino compound - hexosamine

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

ADRB1 Tclin Adrenergic receptor beta (1214 Activities)

Discover Target: ADRB1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: 1000g/L
• Specific Rotation[α]: -16.5 ° (C=2, H2O)
• Boil Point(°C): 210 °C/1013 hPa
• Melt Point(°C): 129-131.5 °C (lit.)
• Molecular Weight: 195.210 g/mol
• XLogP3: -2.800
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 195.111 Da
• Monoisotopic Mass: 195.111 Da
• Topological Polar Surface Area: 113.000 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 134.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Kong Ruiping, Xu Lingwei, Zhu Li, Sun Yongrong.  (2023)  Preparation, characterization and evaluation of cefixime ternary inclusion complexes formated by mechanochemical strategy.  JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY,      [PMID:] [10.1007/s10847-023-01214-0]

2. Tongtong Pan, Xiangmei Cui.  (2023)  Gelatin aerogel with good mechanical properties and adjustable physical properties for boron adsorption from salt lake brines: An optimized process.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:37597634] [10.1016/j.ijbiomac.2023.126403]

3. Guolong Huang, Yifan Qiu, Lei Bi, Huiyi Wei, Guocong Li, Zhijun Li, Peizhen Ye, Min Yang, Yanfang Shen, Hao Liu, Lu Wang, Hongjun Jin.  (2022)  PET Imaging of P2X7 Receptor (P2X7R) for Neuroinflammation with Improved Radiosynthesis of Tracer [18F]4A in Mice and Non-human Primates.  ACS Chemical Neuroscience,      [PMID:36441909] [10.1021/acschemneuro.2c00506]

4. Chun Bai, Kexin Li, Dezhen Fang, Xiushen Ye, Huifang Zhang, Quan Li, Jun Li, Haining Liu, Zhijian Wu.  (2021)  Efficient separation of boron from salt lake brine using a novel flotation agent synthesized from NMDG and 1-bromooctadecane.  COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS,      [PMID:] [10.1016/j.colsurfa.2021.127178]

5. Mei Hong, Die Li, Bingyu Wang, Jingyu Zhang, Bin Peng, Xiaoling Xu, Yan Wang, Chunyang Bao, Jing Chen, Qiang Zhang.  (2021)  Cellulose-derived polyols as high-capacity adsorbents for rapid boron and organic pollutants removal from water.  JOURNAL OF HAZARDOUS MATERIALS,      [PMID:34214857] [10.1016/j.jhazmat.2021.126503]

6. Qihong Zhang, Wei Ren, Alexandr V. Dushkin, Weike Su.  (2020)  Preparation, characterization, in vitro and in vivo studies of olmesartan medoxomil in a ternary solid dispersion with N-methyl-D-glucamine and hydroxypropyl-β-cyclodextrin.  JOURNAL OF DRUG DELIVERY SCIENCE AND TECHNOLOGY,      [PMID:] [10.1016/j.jddst.2020.101546]

7. Yanyun Bai, Jinxing Li, Xiumei Tai, Guoyong Wang.  (2020)  Preparation, characterization, and properties of novel meglumine-based polysiloxane surfactants.  JOURNAL OF INDUSTRIAL AND ENGINEERING CHEMISTRY,      [PMID:] [10.1016/j.jiec.2020.01.003]

8. Ming Zhao, Tianhao Li, Lichao Jia, Huilin Li, Weiyong Yuan, Chang Ming Li.  (2019)  Pristine-Graphene-Supported Nitrogen-Doped Carbon Self-Assembled from Glucaminium-Based Ionic Liquids as Metal-Free Catalyst for Oxygen Evolution.  ChemSusChem,  12  (22): (5041-5050).  [PMID:31589802] [10.1002/cssc.201901961]

9. Lei Hu, Li Gao, Xiaoming Yan, Wenji Zheng, Yan Dai, Ce Hao, Xuemei Wu, Gaohong He.  (2019)  Proton delivery through a dynamic 3D H-bond network constructed from dense hydroxyls for advanced ion-selective membranes.  Journal of Materials Chemistry A,  7  (25): (15137-15144).  [PMID:] [10.1039/C9TA04423J]

10. Jinxing Li, Yanyun Bai, Wanxu Wang, Xiumei Tai, Guoyong Wang.  (2019)  Green Glucamine-Based Trisiloxane Surfactant: Surface Activity, Aggregate Behavior, and Superspreading on Hydrophobic Surfaces.  ACS Sustainable Chemistry & Engineering,      [PMID:] [10.1021/acssuschemeng.8b06282]

11. Xueri Nan, Jing Liu, Xiuli Wang, Xianhui Pan, Xiaomei Wang, Xu Zhang.  (2018)  Preparation of Superhydrophilic Adsorbents with 3DOM Structure by Water-Soluble Colloidal Crystal Templates for Boron Removal from Natural Seawater.  ACS Applied Materials & Interfaces,      [PMID:30289685] [10.1021/acsami.8b11763]

12. Qiang Wu, Mingyan Liu, Xiong Wang.  (2018)  A novel chitosan based adsorbent for boron separation.  SEPARATION AND PURIFICATION TECHNOLOGY,      [PMID:] [10.1016/j.seppur.2018.09.070]

13. Tianhao Li, Daomei Tang, ChangMing Li.  (2017)  A high active hydrogen evolution reaction electrocatalyst from ionic liquids-originated cobalt phosphide/carbon nanotubes.  INTERNATIONAL JOURNAL OF HYDROGEN ENERGY,      [PMID:] [10.1016/j.ijhydene.2017.07.100]

14. Xuefang Ding, Wei Wang, Yazhe Wang, Xiuli Bao, Yu Wang, Cheng Wang, Jian Chen, Fangrong Zhang, Jianping Zhou.  (2014)  Versatile Reticular Polyethylenimine Derivative-Mediated Targeted Drug and Gene Codelivery for Tumor Therapy.  MOLECULAR PHARMACEUTICS,      [PMID:25058017] [10.1021/mp5001263]

15. Xiaoling Xu, Bin Peng, Yanqiu Wang, Yaqi Dong, Hui Wang, Wentong Chen, Yan Liu, Qiang Zhang.  (2024)  Fabrication of POSS-centered polyester network as high anti-chlorine and anti-fouling separation layer of membrane via successive Photo-ATRP and interfacial polymerization for molecular separation.  JOURNAL OF MEMBRANE SCIENCE,      [PMID:] [10.1016/j.memsci.2024.123432]

16. Guo Haikun, Li Xiang, Chai Shengchao, Li Haibin, Li Tingting, Song Shihao, Zuo Peng, Li Haolong.  (2025)  Flexible supramolecular polymer proton conductors with high mechanical-conductive decoupling ability.  Science China-Chemistry,      [PMID:] [10.1007/s11426-024-2549-6]

17. Yanzhi Dong, Gang Shu, Yibo Wei, Jinbin Pan, Dong Li, Shao-Kai Sun.  (2024)  Gram-Scale Synthesis of Renal-Clearable Tantalum Nanodots with High Water Solubility for Computed Tomography Imaging In Vivo.  ACS Nano,      [PMID:39207307] [10.1021/acsnano.4c06705]

18. Ruihao Wang, Qian Li, Xiyan Sun, Xinyu Jia, Shuxian Li, Li Wei, Xitong Sun.  (2025)  High efficiency adsorption of boron by sodium alginate/polyethyleneimine/polysiloxane composite aerogel.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:39805451] [10.1016/j.ijbiomac.2025.139784]

19. Ma Li, Pan Jinbin, Shu Gang, Pan Haiyan, Li Jingang, Li Dong, Sun Shaokai.  (2024)  Non-invasive fast assessment of hepatic injury through computed tomography imaging with renal-clearable Bi-DTPA dimeglumine.  Regenerative Biomaterials,      [PMID:39398283] [10.1093/rb/rbae118]

20. Wenqing Wang, Hao Li, Yongquan Zhou, Jianming Pan.  (2023)  Investigation of the mechanism of establishing a solid–water–oil system by metastable droplets and their application in the fabrication of polyol nanosheets for rapid boron removal.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2023.145930]

21. Yanqin Xu, Jie Liu, Shumin Guan, Yuan Cao, Changguo Chen, Dan Wang.  (2020)  A dual pH and redox-responsive Ag/AgO/carboxymethyl chitosan composite hydrogel for controlled dual drug delivery.  JOURNAL OF BIOMATERIALS SCIENCE-POLYMER EDITION,      [PMID:32614709] [10.1080/09205063.2020.1774118]

22. Lu Zhao, Li Ma, Xuetao Jia, Xiaoxue Wang, Wenjing Hou, Gang Shu, Bing Han, Dianxun Fu, Dong Li, Shao-Kai Sun, Jinbin Pan.  (2025)  Bismuth Chelate-Mediated Computed Tomography Perfusion Imaging of Acute Ischemic Stroke In Vivo.  ACS Applied Materials & Interfaces,      [PMID:40445005] [10.1021/acsami.5c02378]