51-79-6 Usage
Description
Ethyl carbamate occurs as colourless or white columnar crystals or granular powder. It is
very soluble in water. With heat, ethyl carbamate undergoes decomposition and emits toxic
fumes of carbon monoxide, carbon dioxide, and nitrogen oxides. Ethyl carbamate is used
as an intermediate in the synthesis of a number of chemical products, for example, pharmaceuticals,
in biochemical research and medicine, and as a solubiliser and co-solvent for
pesticides and fumigants.
Prior to World War II, ethyl carbamate saw relatively heavy use in the treatment of
multiple myeloma before it was found to be toxic, carcinogenic, and largely ineffective.
However, due to U.S. FDA regulations, ethyl carbamate has been withdrawn from pharmaceutical
use. However, small quantities of ethyl carbamate are also used in laboratories
as an anaesthetic for animals.
Chemical Properties
Different sources of media describe the Chemical Properties of 51-79-6 differently. You can refer to the following data:
1. Colorless crystals or white powder;
odorless, saltpeter-like taste. Solutions neutral to litmus. Soluble in water,
alcohol, ether, glycerol, and chloroform; slightly
soluble in olive oil. Combustible.
2. Urethane is a colorless, almost odorless crystalline
solid or powder.
Occurrence
Urethane (ethyl carbamate) occurs as a natural byproduct in fermented products such as wine, liquors, yogurt, beer, bread, olives, cheeses, and soy sauces. Whereas urethane has a known cancer etiology in experimental animals, no such relationship has yet been proven in humans. Alcohol may act by blocking the metabolism of urethane, and thus exert a protective effect in humans consuming alcoholic beverages.
Uses
Different sources of media describe the Uses of 51-79-6 differently. You can refer to the following data:
1. The primary use of urethane has been as a chemical intermediate in preparation of amino resins (IARC 1974). The process involves a reaction with formaldehyde to give hydroxymethyl derivatives that are used as cross-linking agents in permanent-press textile treatments designed to impart wash-and-wear properties to fabrics. Urethane isalso used as a solubilizer and co-solvent in the manufacture of pesticides, fumigants, and cosmetics, as an intermediate in the manufacture of pharmaceuticals, and in biochemical research (HSDB 2009). Urethane was formerly used as an active ingredient in drugs prescribed for the treatment of neoplastic diseases, as a sclerosing solution for varicose veins, as a hypnotic, and as a topical bactericide. It is also used in veterinary medicine as an anesthetic (IARC 1974). Urethane is produced naturally during many fermentation processes(Zimmerli and Schlatter 1991).
2. Naturally occurring contaminant in fermented foods, particularly wine, stone-fruit brandies, and bread.
This substance is reasonably anticipated to be a human carcinogen.
3. Intermediate in organic synthesis. In the preparation and modification of amino resins. As solvent, solubilizer and cosolvent for various organic materials. Animal anesthetic in laboratory procedures.
Definition
A poisonous flammable
organic compound, used in medicine, as a
solvent, and as an intermediate in the manufacture of polyurethane resins.
World Health Organization (WHO)
Urethane was formerly used as an antineoplastic agent in the
treatment of chronic myeloid leukaemia. It is also a mild hypnotic which has been
used as an anaesthetic for veterinary practice. It has been reported to have both a
carcinogenic and mutagenic potential. Although urethane continues to be used as
an industrial solvent, WHO has no information to suggest that it remains
commercially available in pharmaceutical preparations.
General Description
Odorless colorless crystals or white powder. Sublimes readily at 217°F and 54 mm Hg. Cooling saline taste.
Air & Water Reactions
Water soluble. Aqueous solutions are neutral to litmus .
Reactivity Profile
Urethane is incompatible with alkalis, acids, chloral hydrate, camphor, menthol and thymol. Also incompatible with antipyrine and salol. May react with strong oxidizing agents. Liquefies with benzoic acid, resorcinol and salicylic acid. Reacts with phosphorus pentachloride to form an explosive product .
Hazard
Toxic by ingestion.
Safety Profile
Confirmed carcinogen
with experimental carcinogenic,
neoplastigenic, and tumorigenic data. A
transplacental carcinogen. Moderately toxic
by ingestion, intraperitoneal, subcutaneous,
intramuscular, parenteral, and intravenous
routes. An experimental teratogen.
Experimental reproductive effects. Human
mutation data reported. Causes depression
of bone marrow and occasionally focal
degeneration in the brain. Can also produce
central nervous system depression, nausea
and vomiting. Has been found in over 1000
beverages sold in the United States. The
most heavily contaminated liquors are
bourbons, sherries, and fruit brandies (some had 1000 to 12,000 ppb urethane). Many
whiskeys, table and dessert wines, brandies,
and liqueurs contain potentially hazardous
amounts of urethane. The allowable limit for
urethane in alcoholic beverages is 125 ppb.
It is formed as a side product during
processing.Hot aqueous acids or alkalies decompose
urethane to ethanol, carbon dioxide, and
ammonia. Reacts with phosphorus
pentachloride to form an explosive product.
When heated it emits toxic fumes of NOx.
Used as an intermedate in the manufacture
of pharmaceuticals, pesticides, and
fungicides. See also CARBAMATES.
Potential Exposure
Urethane is used as a chemical intermediate
in manufacture of pharmaceuticals; pesticides, and
fungicides; in the preparation of amino resins. It may be
reacted with formaldehyde to give cross-linking agents
which impart wash-and-wear properties to fabrics. It has
also been used as a solubilizer and cosolvent in the manufacture
of pesticides, fumigants, and cosmetics. It was formerly
used in the treatment of leukemia. It occurs when
diethylpyrocarbonate, a preservative used in wines, fruit
juices, and soft drinks, is added to aqueous solutions.
Carcinogenicity
Urethane is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
Environmental Fate
Urethane may be released to the environment in various waste
streams. If released to the atmosphere, urethane is expected to
exist solely as a vapor in the ambient atmosphere. Vapor-phase
urethane is degraded in the atmosphere by reaction with
photochemically produced hydroxyl radicals with an estimated
half-life of 2.2 days. If released to soil, urethane has very high mobility. Volatilization from moist soil surfaces does not
occur. Biodegradation of urethane in soil may be important. If
released into water, urethane is not adsorbed to suspended
solids and sediment in the water column. Volatilization from
water surfaces does not occur. The potential for bioconcentration
in aquatic organisms is low based on an estimated
bioconcentration factor (BCF) of 0.45. Urethane is
resistant to hydrolysis under environmental conditions;
hydrolysis half-lives of 3300 and 330 years at pH 7 and 8,
respectively, were estimated for urethane. Urethane was judged
easy to biodegrade in river die-away tests. Other biodegradation
studies using activated sludge indicate urethane may
biodegrade slowly.
Purification Methods
Urethane is best purified by fractional distillation, but it can be 20 25 1.4144. sublimed at ~103o/~50mm. It has also been recrystallised from *benzene. Its solubilitiy at room temperature is 2g/mL in H2O, 1.25g/mL in EtOH, 1.1g/mL in CHCl3, 0.67g/mL in Et2O and 0.03g/mL in olive oil. It is a suspected human carcinogen.[Beilstein 3 H 22, 3 IV 40.]
Toxicity evaluation
Urethane is activated in the liver into a carcinogenic metabolite.
The activation of urethane by cytochrome P450 involves two
sequential reactions. First, urethane is dehydrogenated to vinyl
carbamate followed by epoxidation to form vinyl carbamate
epoxide. The former is believed to be the ultimate carcinogenic
metabolite of urethane.
Incompatibilities
Dust may form explosive mixture with
air. Incompatible with oxidizers (chlorates, nitrates, peroxides,
permanganates, perchlorates, chlorine, bromine, fluorine,
etc.); contact may cause fires or explosions. Keep
away from alkaline materials, strong bases, strong acids,
oxoacids, epoxides, gallium, perchlorate.
Waste Disposal
Consult with environmental
regulatory agencies for guidance on acceptable disposal
practices. Generators of waste containing this contaminant
(≥100 kg/mo) must conform to EPA regulations
governing storage, transportation, treatment, and waste
disposal. Controlled incineration (incinerator equipped
with a scrubber or thermal unit to reduce nitrogen oxides
emissions).
Check Digit Verification of cas no
The CAS Registry Mumber 51-79-6 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 1 respectively; the second part has 2 digits, 7 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 51-79:
(4*5)+(3*1)+(2*7)+(1*9)=46
46 % 10 = 6
So 51-79-6 is a valid CAS Registry Number.
InChI:InChI=1/C3H7NO2/c1-2-6-3(4)5/h2H2,1H3,(H2,4,5)
51-79-6Relevant articles and documents
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Fuchigami,Nonaka
, p. 1087,1088,1089 (1977)
-
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Steyermark
, p. 3570 (1963)
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CARBONYLATION OF 2 AND 2; A NEW SELECTIVE METHOD FOR PREPARATION OF
Monica, G. La,Monti, C.,Pizzotti, M.,Cenini, S.
, p. 241 - 244 (1983)
Carbonylation of 2 (COD=1,5-cyclooctadiene) in ethanol gave the rhodium cluster selectively in high yield; when non polar solvents were used, the known 2 and 2 were obtained.Reaction of carbon monoxide with the isocyanato-bridged derivative 2 in ethanol also gave .In both cases the carbonylation reaction also gave NH2COOEt.Carbonylation of the iridium dichloride dimer 2 in the presence of sodium citrate gave .
Discovery of a dual tubulin polymerization and cell division cycle 20 homologue inhibitor via structural modification on apcin
Huang, Pan,Le, Xiangyang,Huang, Fei,Yang, Jie,Yang, Haofeng,Ma, Junlong,Hu, Gaoyun,Li, Qianbin,Chen, Zhuo
, p. 4685 - 4700 (2020/06/08)
Apcin is one of the few compounds that have been previously reported as a Cdc20 specific inhibitor, although Cdc20 is a very promising drug target. We reported here the design, synthesis, and biological evaluations of 2,2,2-trichloro-1-aryl carbamate derivatives as Cdc20 inhibitors. Among these derivatives, compound 9f was much more efficient than the positive compound apcin in inhibiting cancer cell growth, but it had approximately the same binding affinity with apcin in SPR assays. It is possible that another mechanism of action might exist. Further evidence demonstrated that compound 9f also inhibited tubulin polymerization, disorganized the microtubule network, and blocked the cell cycle at the M phase with changes in the expression of cyclins. Thus, it induced apoptosis through the activation of caspase-3 and PARP. In addition, compound 9f inhibited cell migration and invasion in a concentration-dependent manner. These results provide guidance for developing the current series as potential new anticancer therapeutics.
EXON SKIPPING OLIGOMER CONJUGATES FOR MUSCULAR DYSTROPHY
-
, (2019/12/24)
Antisense oligomer conjugates complementary to a selected target site in the human dystrophin gene to induce exon 52 skipping are described.
