≥98 atom% D,≥98% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at -20°C Ships Ice chest + Ice pads Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Methotrexate-methyl-d3 is a deuterated form of methotrexate, an antineoplastic and antirheumatic agent. Studies indicate that methotrexate-methyl-d3 can act as a folic acid antagonist. Methotrexate competitively and irreversibly inhibits dihydrofolate reductase (DHFR) which is essential in tetrahydrofolate synthesis. In addition, the reduction in tetrahydrofolate synthesis causes a decrease in purine base synthesis which results in the inhibition of DNA, RNA, thymidylates, and proteins. Alternate studies suggest that methotrexate-methyl-d3 can suppress T cell activation and adhesion molecule expression through IL-1 suppression.
| Canonical Smiles | CN(CC1=CN=C2C(=N1)C(=NC(=N2)N)N)C3=CC=C(C=C3)C(=O)NC(CCC(=O)O)C(=O)O |
|---|---|
| IUPAC Name | (2S)-2-[[4-[(2,4-diaminopteridin-6-yl)methyl-(trideuteriomethyl)amino]benzoyl]amino]pentanedioic acid |
| InChIKey | FBOZXECLQNJBKD-FUPFOCIHSA-N |
| INCHI | 1S/C20H22N8O5/c1-28(9-11-8-23-17-15(24-11)16(21)26-20(22)27-17)12-4-2-10(3-5-12)18(31)25-13(19(32)33)6-7-14(29)30/h2-5,8,13H,6-7,9H2,1H3,(H,25,31)(H,29,30)(H,32,33)(H4,21,22,23,26,27)/t13-/m0/s1/i1D3 |
| Isomeric SMILES | [2H]C([2H])([2H])N(CC1=CN=C2C(=N1)C(=NC(=N2)N)N)C3=CC=C(C=C3)C(=O)N[C@@H](CCC(=O)O)C(=O)O |
| Alternate CAS | 59-05-2(unlabelled) |
| Molecular Weight | 457.46 |
| Reaxy-Rn | 4219876 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=4219876&ln= |
Comprehensive hazard, handling, storage, and regulatory compliance document.
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Look up COA →Full quality attributes and acceptance criteria for this grade.
View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organoheterocyclic compounds |
| Class | Pteridines and derivatives |
| Subclass | Pterins and derivatives |
| Intermediate Tree Nodes | Pteroic acids and derivatives - Folic acids and derivatives |
| Direct Parent | Folic acids |
| Alternative Parents | Glutamic acid and derivatives N-acyl-alpha amino acids Hippuric acids Aminobenzamides Aniline and substituted anilines Benzoyl derivatives Dialkylarylamines Aminopyrimidines and derivatives Aralkylamines Pyrazines Imidolactams Dicarboxylic acids and derivatives Heteroaromatic compounds Secondary carboxylic acid amides Amino acids Carboxylic acids Azacyclic compounds Carbonyl compounds Organic oxides Primary amines Hydrocarbon derivatives |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Folic acid - Glutamic acid or derivatives - Hippuric acid or derivatives - Hippuric acid - N-acyl-alpha-amino acid - N-acyl-alpha amino acid or derivatives - Alpha-amino acid or derivatives - Aminobenzamide - Aminobenzoic acid or derivatives - Benzamide - Benzoic acid or derivatives - Benzoyl - Aniline or substituted anilines - Dialkylarylamine - Tertiary aliphatic/aromatic amine - Aminopyrimidine - Aralkylamine - Pyrazine - Pyrimidine - Monocyclic benzene moiety - Dicarboxylic acid or derivatives - Benzenoid - Imidolactam - Heteroaromatic compound - Secondary carboxylic acid amide - Amino acid or derivatives - Amino acid - Carboxamide group - Tertiary amine - Carboxylic acid derivative - Carboxylic acid - Azacycle - Organic oxygen compound - Carbonyl group - Organonitrogen compound - Hydrocarbon derivative - Organooxygen compound - Primary amine - Organic nitrogen compound - Organic oxide - Amine - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as folic acids. These are heterocyclic compounds based on the 4-[(pteridin-6-ylmethyl)amino]benzoic acid skeleton conjugated with one or more L-glutamate units. |
| External Descriptors | Not available |
| Solubility | Soluble in DMSO |
|---|---|
| Molecular Weight | 457.500 g/mol |
| XLogP3 | -1.800 |
| Hydrogen Bond Donor Count | 5 |
| Hydrogen Bond Acceptor Count | 12 |
| Rotatable Bond Count | 9 |
| Exact Mass | 457.19 Da |
| Monoisotopic Mass | 457.19 Da |
| Topological Polar Surface Area | 211.000 Ų |
| Heavy Atom Count | 33 |
| Formal Charge | 0 |
| Complexity | 704.000 |
| Isotope Atom Count | 3 |
| Defined Atom Stereocenter Count | 1 |
| 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 |
