Thioacetamide is an
organosulfur compound
Organosulfur compounds are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur derivatives, e.g., saccharin. Nature abounds with organosulfur compounds—sulf ...
with the
formula
In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwe ...
C2 H5 N S. This white crystalline solid is soluble in water and serves as a source of
sulfide
Sulfide (British English also sulphide) is an inorganic anion of sulfur with the chemical formula S2− or a compound containing one or more S2− ions. Solutions of sulfide salts are corrosive. ''Sulfide'' also refers to chemical compounds la ...
ions in the synthesis of organic and inorganic compounds. It is a prototypical
thioamide.
Research
Thioacetamide is known to induce acute or chronic liver disease (fibrosis and cirrhosis) in the experimental animal model. Its administration in rat induces hepatic encephalopathy, metabolic acidosis, increased levels of transaminases, abnormal coagulopathy, and centrilobular necrosis, which are the main features of the clinical chronic liver disease so thioacetamide can precisely replicate the initiation and progression of human liver disease in an experimental animal model.
Coordination chemistry
Thioacetamide is widely used in classical
qualitative inorganic analysis
Classical qualitative inorganic analysis is a method of analytical chemistry which seeks to find the elemental composition of inorganic compounds. It is mainly focused on detecting ions in an aqueous solution, therefore materials in other forms m ...
as an in situ source for sulfide ions. Thus, treatment of aqueous solutions of many metal cations to a solution of thioacetamide affords the corresponding metal sulfide:
:M
2+ + CH
3C(S)NH
2 + H
2O → MS + CH
3C(O)NH
2 + 2 H
+ (M = Ni, Pb, Cd, Hg)
Related precipitations occur for sources of
soft trivalent cations (As
3+, Sb
3+, Bi
3+) and monovalent cations (Ag
+, Cu
+).
Preparation
Thioacetamide is prepared by treating acetamide with
phosphorus pentasulfide as shown in the following idealized reaction:
:CH
3C(O)NH
2 + 1/4 P
4S
10 → CH
3C(S)NH
2 + 1/4 P
4S
6O
4
Structure
The C
2NH
2S portion of the molecule is planar; the C-S, C-N, and C-C distances are 1.68, 1.31, and 1.50 Å, respectively. The short C-S and C-N distances indicate multiple bonding.
Safety
Thioacetamide is
carcinogen
A carcinogen is any substance, radionuclide, or radiation that promotes carcinogenesis (the formation of cancer). This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes. Several radioactive sub ...
class 2B.
It is known to produce marked hepatotoxicity in exposed animals. Toxicity values are 301 mg/kg in rats (LD50, oral administration), 300 mg/kg in mice (LD50, intraperitoneal administration). This is evidenced by enzymatic changes, which include elevation in the levels of serum
alanine transaminase
Alanine transaminase (ALT) is a transaminase enzyme (). It is also called alanine aminotransferase (ALT or ALAT) and was formerly called serum glutamate-pyruvate transaminase or serum glutamic-pyruvic transaminase (SGPT) and was first characte ...
,
aspartate transaminase
Aspartate transaminase (AST) or aspartate aminotransferase, also known as AspAT/ASAT/AAT or (serum) glutamic oxaloacetic transaminase (GOT, SGOT), is a pyridoxal phosphate (PLP)-dependent transaminase enzyme () that was first described by Arthur ...
and
aspartic acid
Aspartic acid (symbol Asp or D; the ionic form is known as aspartate), is an α-amino acid that is used in the biosynthesis of proteins. Like all other amino acids, it contains an amino group and a carboxylic acid. Its α-amino group is in the pro ...
.
References
*
{{Authority control
IARC Group 2B carcinogens
Thioamides
Hepatotoxins