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.