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Altretamine

Product Name
Altretamine
CAS No.
645-05-6
Chemical Name
Altretamine
Synonyms
HMM;HTM;Hemel;NC 195;RB-1515;Hexylen;Hexalen;WR-95704;ent50852;Hexastat
CBNumber
CB9480937
Molecular Formula
C9H18N6
Formula Weight
210.28
MOL File
645-05-6.mol
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Altretamine Property

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)
pka
pKa 10.3 (Uncertain)
form 
solid
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
Altretamine (645-05-6)
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Safety

Hazard Codes 
Xn
Risk Statements 
22-36/37/38
Safety Statements 
26-36
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)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PHR2343
Product name
Altretamine
Purity
Pharmaceutical Secondary Standard; Certified Reference Material
Packaging
1G
Price
$194
Updated
2024/03/01
Sigma-Aldrich
Product number
549835
Product name
2,4,6-Tris(dimethylamino)-1,3,5-triazine
Purity
96%
Packaging
25g
Price
$432
Updated
2024/03/01
Sigma-Aldrich
Product number
1017105
Product name
Altretamine
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
500mg
Price
$174.4
Updated
2024/03/01
Cayman Chemical
Product number
23662
Product name
Altretamine
Purity
≥98%
Packaging
50mg
Price
$44
Updated
2024/03/01
Cayman Chemical
Product number
23662
Product name
Altretamine
Purity
≥98%
Packaging
100mg
Price
$78
Updated
2024/03/01
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Altretamine Chemical Properties,Usage,Production

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.

Definition

A hexamethyl-2,4,6- triamine derivative of 1,3,5-triazine.

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

General Description

Altretamine is available in 50-mg capsules for oraladministration as a second-line treatment for ovarian cancer.The mechanism of action has not been firmly established, althoughthe spectrum of activity is similar to that for otheralkylating agents; however, cross-resistance is not seen.Cytotoxicity has been correlated with metabolism to give thecarbinolamines, which may form imines capable of crosslinking,or decompose to give formaldehyde, which may reactwith nucleophiles on DNA or proteins. The agent is well absorbedupon oral administration, well distributed, and highly(90%) plasma protein bound. The agent is extensively metabolizedin the liver by CYP to give demethylated metabolites via the previously mentioned carbinolamines. Elimination occursprimarily in the urine as mostly demethylated metaboliteswith a terminal elimination half-life of 4 to 10 hours.Myleosuppression and nausea/vomiting are dose-limitingtoxicities. Other adverse effects include lethargy, agitation,hallucinations, skin rash, and elevations in transaminase levels,flulike symptoms, abdominal cramps, and diarrhea.

General Description

Colorless crystalline solid. Insoluble in water.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Altretamine 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.

Hazard

Toxic.

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.

Altretamine Preparation Products And Raw materials

Raw materials

Preparation Products

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Altretamine Suppliers

J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
94657
Advantage
76
Pure Chemistry Scientific Inc.
Tel
001-857-928-2050 or 1-888-588-9418
Fax
001-617-206-9595
Email
sales@chemreagents.com
Country
United States
ProdList
10186
Advantage
62
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2123
Advantage
70
Nanjing Chemlin Chemical Co., Ltd
Tel
025-83697070
Fax
+86-25-83453306
Email
info@chemlin.com.cn
Country
China
ProdList
19172
Advantage
64
Shanghai Hanhong Scientific Co.,Ltd.
Tel
021-54306202 13764082696
Email
info@hanhongsci.com
Country
China
ProdList
42958
Advantage
64
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32321
Advantage
50
Syntechem Co.,Ltd
Tel
Fax
E-Mail Inquiry
Email
info@syntechem.com
Country
China
ProdList
12984
Advantage
57
China Langchem Inc.
Tel
0086-21-58956006
Fax
0086-21-58956100
Country
China
ProdList
7811
Advantage
57
Sinopharm Chemical Reagent Co,Ltd.
Tel
86-21-63210123
Fax
86-21-63290778 86-21-63218885
Email
sj_scrc@sinopharm.com
Country
China
ProdList
9815
Advantage
79
Hangzhou Yuhao Chemical Technology Co., Ltd
Tel
0571-82693216
Fax
+86-571-82880190
Email
info@yuhaochemical.com
Country
China
ProdList
9387
Advantage
52
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View Lastest Price from Altretamine manufacturers

Hebei Weibang Biotechnology Co., Ltd
Product
Altretamine 645-05-6
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2021-08-05
Anhui Ruihan Technology Co., Ltd
Product
Altretamine 645-05-6
Price
US $50.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
10000tons
Release date
2023-09-11
Hebei Mojin Biotechnology Co., Ltd
Product
Altretamine 645-05-6
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
50000KG/month
Release date
2023-08-29

645-05-6, AltretamineRelated Search:


  • RB-1515
  • WR-95704
  • 2,4,6-Tris(dimethylamino)-1,3,5-triazine 96%
  • 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
  • HEXAMETHYLMELAMINE
  • Altretamine, >=99%
  • 2,4,6-TRIS(DIMETHYLAMINO)-1,3,5-TRIAZINE
  • ALTRETAMIN
  • ALTRETAMINE
  • N,N,N',N',N'',N''-HEXAMETHYL-1,3,5-TRIAZINE-2,4,6-TRIAMINE
  • ALTRETAMINE [2,4,6-TRIS(DIMETHYLAMINO)-1,3,5-TRIAZINE]
  • ALTRETAMINE, Hexamethylmelamine
  • [4,6-bis(dimethylamino)-s-triazin-2-yl]-dimethyl-amine
  • 2-N,2-N,4-N,4-N,6-N,6-N-hexamethyl-1,3,5-triazine-2,4,6-triamine
  • N2,N2,N4,N4,N6,N6-hexamethyl-1,3,5-triazine-2,4,6-triamine
  • 6-Tris(diMethylaMino)-1
  • AltretaMine [2
  • AltretaMine, USP
  • Altretamine (500 mg)
  • AltretaMine(Hexalen)
  • Hexylen
  • Altretamine (RB-1515,WR-95704)
  • Aitretamine
  • ENT 50852
  • ENT050852
  • ent50852
  • Hemel
  • Hexalen
  • hexamethyl-melamin
  • Hexastat
  • HMM
  • HTM
  • Melamine, hexamethyl-
  • melamine,hexamethyl-
  • NC 195
  • NCI-C50259
  • NSC 13875
  • nsc13875
  • NSC-13875
  • s-Triazine, 2,4,6-tris(dimethylamino)-
  • 1,3,5-Triazine-2,4,6-triamine, N2,N2,N4,N4,N6,N6-hexamethyl-
  • Altretamine USP/EP/BP
  • Altretamine (ENT-50852)
  • Altretamine (1017105)
  • HSDB 1402
  • Hexamethylmelamine|||NSC13875|||RB-1515|||ENT-50852|||WR-95704
  • 645-05-6
  • C9H18N6
  • C9H24N6
  • Heterocyclic Building Blocks
  • DNA Intercalators and Crosslinkers
  • DNA metabolism
  • Triazines
  • Building Blocks