Altretamine

Base Information

• Chemical Name: Altretamine
• CAS No.: 645-05-6
• Molecular Formula: C9H18N6
• Molecular Weight: 210.282
• Hs Code.: 2933690000
• European Community (EC) Number: 211-428-4
• NSC Number: 758231,13875
• UNII: Q8BIH59O7H
• DSSTox Substance ID: DTXSID4022579
• Nikkaji Number: J7.067J
• Wikipedia: Altretamine
• Wikidata: Q415242
• NCI Thesaurus Code: C544
• Metabolomics Workbench ID: 42833
• ChEMBL ID: CHEMBL1455
• Mol file: 645-05-6.mol

Synonyms:2,4,6-Tris(dimethylamino)-1,3,5-triazine;2,4,6-Tris(dimethylamino)-s-triazine;Hexamethylmelamine;

Chemical Property of Altretamine

Chemical Property:

• Appearance/Colour: Colorless crystalline solid
• Melting Point: 171-175 °C(lit.)
• Refractive Index: 1.569
• Boiling Point: 339.4 °C at 760 mmHg
• PKA: pKa 10.3 (Uncertain)
• Flash Point: 159.1 °C
• PSA: 48.39000
• Density: 1.148 g/cm³
• LogP: 0.06960
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Sparingly), Methanol (Slightly, Heated)
• Water Solubility.: Insoluble
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 210.15929460
• Heavy Atom Count: 15
• Complexity: 148

Purity/Quality:

99% ^*data from raw suppliers

Altretamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antineoplastic Agents, Alkylating Agents
• Canonical SMILES: CN(C)C1=NC(=NC(=N1)N(C)C)N(C)C
• Recent ClinicalTrials: Altretamine and Etoposide in Treating Patients With HIV-Related Cancer
• Uses: An antitumor agent which also acts as a chemosterilant for male houseflies and other insects. Antineoplastic. antimalarial As experimental insect chemosterilant.
• Indications: Although both DNA and RNA synthesis are inhibited in cells exposed to hexamethylmelamine (Hexalen), the molecular mechanisms of these effects are not known.
• Therapeutic Function: Antitumor
• Clinical Use: Hexamethylmelamine is useful for the treatment of ovarian adenocarcinoma and is frequently combined with cyclophosphamide, cisplatin, and doxorubicin in the treatment of this tumor. It also has some activity against small cell lung cancer.

Technology Process of Altretamine

There total 12 articles about Altretamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

2-chloro-4,6-bis(dimethylamino)-1,3,5-triazine (3140-74-7) + dimethyl amine (124-40-3) → Altretamine (645-05-6)

Guidance literature:

With sodium hydroxide; In water; for 2h; Reflux;

DOI:10.1021/acs.joc.6b00355

Reference yield: 94.0%

1,3,5-trichloro-2,4,6-triazine (108-77-0) + dimethyl amine (124-40-3) → Altretamine (645-05-6)

Guidance literature:

HY zeolite; In water; at 180 ℃; for 0.1h; microwave irradiation;

DOI:10.1016/j.bmcl.2007.04.007

Reference yield: 91.0%

NCNMe2 (1467-79-4) → Altretamine (645-05-6)

Guidance literature:

With bis(trimethylsilyl)methyllithium; In hexane; at 20 ℃; for 12h;

DOI:10.1016/S0022-328X(02)01422-5

upstream raw materials:

1,3,5-trichloro-2,4,6-triazine

N,N-dimethylammonium chloride

dimethyl amine

NCNMe₂

Downstream raw materials:

dimethyl amine

isocyanuric acid

Refernces

• 1、 Anisimova, Tatyana B.,Bokach, Nadezhda A.,Dolgushin, Fedor M.,Kukushkin, Vadim Yu.. "Dialkylcyanamides are more reactive substrates toward metal-mediated nucleophilic addition than alkylcyanides". . p. 12460 - 12467. Retrieved 2013/09/02.
• 2、 Dornan, Peter,Rowley, Christopher N.,Priem, Jessica,Barry, Sean T.,Burchell, Tara J.,Woo, Tom K.,Richeson, Darrin S.. "Atom efficient cyclotrimerization of dimethylcyanamide catalyzed by aluminium amide: A combined experimental and theoretical investigation". supporting information; experimental part. p. 3645 - 3647. Retrieved 2009/02/05.