| Identification | More | [Name]
Altretamine | [CAS]
645-05-6 | [Synonyms]
2,4,6-TRIS(DIMETHYLAMINO)-1,3,5-TRIAZINE
ALTRETAMIN
ALTRETAMINE
HEXAMETHYLMELAMINE
N,N,N',N',N'',N''-HEXAMETHYL-1,3,5-TRIAZINE-2,4,6-TRIAMINE
1,3,5-Triazine-2,4,6-triamine, N,N,N',N',N'',N''-hexamethyl-
1,3,5-tris(dimethylamino)-s-triazine
2,4,6-tris(dimethylamino)-s-triazin
2,4,6-Tris(Dimethylamino)-s-triazine
5-triazine-2,4,6-triamine,n,n,n’,n’,n’’,n’’-hexamethyl-3
Aitretamine
ENT 50852
ENT050852
ent50852
Hemel
Hexalen
hexamethyl-melamin
Hexastat
HMM
HTM | [EINECS(EC#)]
211-428-4 | [Molecular Formula]
C9H18N6 | [MDL Number]
MFCD00549245 | [Molecular Weight]
210.28 | [MOL File]
645-05-6.mol |
| Chemical Properties | Back Directory | [Definition]
A hexamethyl-2,4,6-
triamine derivative of 1,3,5-triazine.
| [Melting point ]
171-175 °C (lit.) | [Boiling point ]
339.81°C (rough estimate) | [density ]
1.0441 (rough estimate) | [refractive index ]
1.6100 (estimate) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [solubility ]
Chloroform (Sparingly), Methanol (Slightly, Heated) | [form ]
solid
| [pka]
pKa 10.3 (Uncertain) | [color ]
White to Off-White | [Water Solubility ]
Insoluble | [Merck ]
13,318 | [CAS DataBase Reference]
645-05-6(CAS DataBase Reference) | [NIST Chemistry Reference]
Altretamine(645-05-6) | [EPA Substance Registry System]
645-05-6(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [RTECS ]
OS1050000
| [HS Code ]
2933690000 | [Hazardous Substances Data]
645-05-6(Hazardous Substances Data) | [Toxicity]
LD50 in rats, guinea pigs (mg/kg): 350, 255 orally (Jasper) |
| Hazard Information | Back Directory | [General Description]
Colorless crystalline solid. Insoluble in water. | [Reactivity Profile]
HEXAMETHYLMELAMINE(645-05-6) neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides. | [Air & Water Reactions]
Insoluble in water. | [Hazard]
Toxic. | [Chemical Properties]
White Solid | [Originator]
Hexastat,Roger Bellon,France,1979 | [Uses]
An antitumor agent which also acts as a chemosterilant for male houseflies and other insects. Antineoplastic. | [Uses]
antimalarial | [Uses]
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. | [Manufacturing Process]
50 g of hexamethylolmelamine-hexamethyl ether in 950 cc methanol are
hydrogenated, at 90°C to 100°C, in the presence of 2 g Raney nickel with 100
atmospheres excess pressure of hydrogen in a steel autoclave holding 2 L
until the absorption of hydrogen is terminated. After the catalyst has been
filtered off with suction, the methanol is distilled off. As a result, 23.1 g (86%
of the theoretical) of crude hexamethylmelamine are formed having a melting
point of 158°C to 162°C. After recrystallization from methanol, the pure
product is obtained having a melting point of 168°C. | [Brand name]
Hexalen (Millot Laboratories,
France). | [Therapeutic Function]
Antitumor | [Mechanism of action]
Hexamethylmelamine is readily absorbed after oral
administration, with peak plasma levels achieved after 1
hour.The drug is readily metabolized to form a number
of demethylated metabolites. Urinary elimination is the
primary route of drug excretion. | [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. | [Side effects]
Nausea and vomiting are the major toxicities associated
with hexamethylmelamine administration. Myelosuppression
and a peripheral neuropathy also may
occur. | [Metabolism]
This unique structure is believed to damage tumor cells through the production of the weakly alkylating species formaldehyde, a product of CYP450-mediated N-demethylation. Administered orally, altretamine is extensively metabolized on first pass, producing primarily mono- and didemethylated metabolites. Additional demethylation reactions occur in tumor cells, releasing formaldehyde in situ before the drug is excreted in the urine. |
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