Nitrogen Containing Compounds Nitrogen Containing Compounds • Nitrgen containing compounds are compounds that contain N in their structure with special properties. They includes: • Amines: There are many kinds of amines in nature and in use in medicine. • Amines: are compds that contain one or more organic groups bonded to nitrogen: RNH2, R2NH, or R3N N compds cont… • Primary Amine: An amine that has one organic group bonded to nitrogen: RNH2 • Secondary Amine: an amine that has two organic groups bonded to nitrogen: R2NH • Tertiary Amine: an amine that has three organic groups bonded to nitrogen: R3N • Heterocyclic Nitrogen compds: In many Ncontaining compds, the N atom is in a ring with C-atoms. Exs: piperidine or pyridine. N-Compd cont… • Many amines have strong odors such as : • Putrescine H2NCH2CH2CH2CH2NH2 or cadaverine: H2NCH2CH2CH2CH2CH2NH2 some amine have physiological properties. • Some simpler amines are irritating to the skin, eyes and mucous membranes and are toxic by ingestion. Some heterocyclic amine are carcinogen. N-Compds cont… • Amines in biomolecules: Proteins and amino acids are N-containing compds. They have amino group in their structure. Ex: some amino acids : alanine: • Another major class of biomolecules, the Nucleotides all contain nitrogen heterocyclic rings derived from either purin or pyrimidin. • Nitrogen heterocycles are also part of several vitamins including B vitamins. N-compds cont… • Some neurotransmitters which transmit nerve impulses throughout the body are amines including: serotonin and dopamine. • Amines in Plants: • Alkaloids: A naturally occuring nitrogen containing compound isolated from a plant: usually basic, bitter, and poisonous. Exs: • Atropine: is the toxic substance in the herb known as belladonna (Atropa belladonna). It is act on the CNS, in low dose used to reduce cramping of the digestive tract. N-compd cont… • Solanine: is found in tomatoes and potatoes, when they are exposed to sunlight the production of solanine increased to levels that can be dangerous. • Caffeine: is another compd used worldwide. It is CNS stimulant, not suggested to use during pregnancy. • Amines in drugs: many drugs are amines or nitrogen heterocycles: • Histamine: is the biomolecule responsible for the symptoms of the allergic reaction. It is also chemical that causes an itchy bump when an insect bites you. N-compd cont… • Ephedrine: ephedrine and its salts are used in over the counter medications for asthma and nasal congestion because they dilate bronchial and nasal passage ways. • Other N-compounds in body fluids: • Urea: the principal end product of the metabolism of protein. The precursor is NH3 in urea cycle. • Uric Acid: a product of the metabolism of purins from nucleoprotein. N-Compds cont… • Creatinine: is a product of the breakdown of creatine. • Creatine: is produced in the body from three AAs: arginine, methionine, and glycine. Increased in nephritis, renal destruction and pregnancy. • Another important N-compound is Nitric Oxide (NO). Super Molecule NO NO is an astonishing molecule that has opened up a new era in the field of biomedical/medicine area and soon will change the parities of medicine Chemical Nature of NO • • • • • • NO has a bond length of 1.15 angestrom It is a diatomic (NO) It is a free radical molecule (NO) Chemically it is a highly reactive molecule It is a lipophilic molecule It has short half-life of a few seconds to a few minutes. NO formula Biological nature of NO • • • • • It is a new messenger. It is a new neurotransmitter/hormone. It is a biological mediator. It has cytotoxic/cytostatic function. It has many biological roles among different. Systems. Nitric Oxide’s roles in biological systems • Cardiovascular System:it is a vasodilator, blood pressure control, maintaining • blood flow, inhibition of platelet adhesion & aggregation/clotting. Immune System: Anti-microbial, and anti-tomur. • Respiratory system: broncho-dilator, regulating airways function/ asthma. • CNS/Peripheral system: Neurotransmitter, synaptic plasticity, long-term potentiation/memory formation. • Urogenital system: Regulation of renal function, male penile erection, women’s pregnancy. • Gastrointestinal tract: Gasteric relaxation, ulcer formation. • Wound Healing: Cytotoxic in early phase, regulatory in later phase oh healing. Cell types producing NO • Cells of immune system: – Macrophages/Monocytes – Kupffer cells (liver) – Microgelia – Neutrophils – Mesangial (kidney) – T-lymphocytes: NK cells & Th-1 cells • Non-immune cell types – – – – – – – – – – Epithelial cells Endothelial cells Vascular smooth muscle cells Fibroblasts Osteoblasts Keratinocytes Hepatocytes Pancreatic B cells Asterocytes Neuronal cells