TChem Chapter 11_ Decomposition Products
ThanatoChemistry
Chapter 11: Decomposition Products
Chapter 11 To-Do’s
Differentiate the Structure Amine vs. Amide
Importance of Nitrogen in the Body
Role of Nitrogen in Embalming
Compare/Contrast Primary, Secondary, Tertiary Amines
List and Describe Amine Products Created During Decomposition
Function of Amines as a Base
Creation of Urotropin
Role of Urotropin in Embalming
Characteristics of Quaternary Ammonium Compounds
Characteristics of Heterocyclic Amines
Seven examples given by the chapter
Describe Examples of Amides (3) and their characteristics
Define the "Theory of Vitalism"
Disproof of the Theory of Vitalism
Nitrogen
Occurs naturally in the body
Amino Acids: Building blocks of proteins; components of DNA and RNA.
Product of decomposition:
Breaking down proteins and nitrogenous bases (DNA/RNA).
Creates nitrogen build-up in the body:
Urea
pH changes
Formaldehyde neutralization.
Decomposition discolorations and smells are nitrogenous compounds.
Amines
Compounds and functional groups containing nitrogen with a "lone pair" of electrons.
Classified as Lewis Bases (donate a pair of electrons).
Organized into three sub-categories:
Primary Amine: One hydrogen atom replaced by an alkyl or aromatic group.
Secondary Amine: Two organic substituents bonded to nitrogen.
Tertiary Amine: All three hydrogen atoms replaced with organic substituents.
Amines as Decomposition Products
Ptomaines: Derived from corpses; previously thought to cause food poisoning.
By-products of putrefaction include Putrescine and Cadaverine:
Created from:
Protein breakdown
Other nitrogen-containing substances such as nucleic acids.
Produce strong, disagreeable odors (e.g., Ammonia or "Fishy").
Amines as Bases
Nitrogen has available electrons that bind to H+, forming ammonium ion.
Bulky R-groups make amines less basic due to difficulty accessing nitrogen's electrons.
Urotropin Creation
Natural by-product of decomposition, occurring in pathological states of excess urea.
Increased ammonia and nitrogen levels raise aldehyde neutralization and preservative demand.
Requires higher concentrations of formaldehyde/glutaraldehyde for effective embalming due to free nitrogen levels.
Urotropin is formed during the neutralization process of aldehydes.
Quaternary Ammonium Compound “Quat”
Composed of salts and surfactants.
Nitrogen can bond four substituents due to its free electrons.
Creates a positively charged nitrogen center (ion or salt).
Functions as surfactants: Lower surface tension between fluids (cell membranes and fluids).
Acts as penetrating agents in embalming and topical antiseptics; rendered ineffective when combined with soap.
Heterocycle
“Hetero” refers to the presence of non-carbon atoms in a bonded aromatic ring.
When nitrogen is a component, it forms heterocyclic amines.
May consist of 5 or 6 membered rings and are part of larger biomolecules:
Examples: Hemoglobin, Myoglobin, Nucleic Acids.
Heterocyclic Amines Examples
Pyrrole: 5 member ring, a major building block for heme (in hemoglobin and myoglobin).
Indole: Bicyclic structure leading to neurotransmitters like Tryptophan, a precursor to serotonin.
Skatole: Bicyclic structure, product of decomposition with a distinct smell, also used in perfumes.
Pyridine: 6 membered ring, an industrial chemical used in solvents and pesticides; precursor to Vitamin B3.
Pyrimidine: 6 member ring containing 2 nitrogen atoms, crucial for creating nucleotides which are building blocks for DNA & RNA.
Purine: Composed of 2 rings with 2 nitrogen atoms each, important for DNA & RNA.
Amide
Defined by the presence of a carbonyl group bonded to nitrogen.
Simplest amides derived from ammonia by replacing hydrogen with an acyl group.
Examples include Dimethylformamide (DMF) and peptides (chain of amino acids forming proteins).
Carbamide
A secondary amide characterized by two amine groups bonded to a carbonyl group.
Urea is the main nitrogen-containing substance in urine, formed by combining ammonia with CO2 in the liver.
Challenges with embalming due to nitrogenous compounds related to urea.
Theory of Vitalism
Theory posited that only living organisms could create organic compounds, governed by distinct scientific principles.
Disproved in 1828 when urea was synthesized from inorganic cyanate, showcasing that metabolic products could be produced outside living organisms.