Published on January 14, 2008
Common Recreational Drugs and their Biochemical Processes in the Human Body: Common Recreational Drugs and their Biochemical Processes in the Human Body A Research Presentation by: Jeff Karnes Cory Henson May 3, 2005 CHEM 104-500 Slide2: Alcoholic drinks are among the most common of recreational drugs, dating back into historical antiquity in religion, hygiene, daily consumption, etc. Alcohol is defined as any organic compound with the functional group hydroxyl (-OH) attached to its chemical structure. Some alcohols can be used as fuel in numerous industrial processes, antifreeze, a solvent found in perfumes, paints, and tinctures, etc. The type of alcohol used in the brewing of alcoholic beverages is known as ethyl alcohol, or ethanol. Slide3: Ethanol is a flammable, colorless chemical compound, and is one of the alcohols most commonly found in alcoholic beverages. Its chemical formula is C2H5OH. Molecular weight: 46.069 amu Melting point: 158.5 K (liquid at room temperature) Contains both hydrophilic and hydrophobic properties. This allows for a relatively high miscibility in water while remaining a good solvent for fatty substances and oils. Slide4: The synthesis of alcohol (ethanol) is produced during the natural metabolic breakdown of carbohydrates and sugars during the anaerobic process called fermentation. Fermentation occurs in the absence of oxygen, and occurs in two methods: lactic fermentation or alcoholic fermentation. Lactic fermentation yields lactic acid. Used in production of cheese, etc. Alcoholic fermentation yields ethanol and carbon dioxide. This process is often performed in organisms such as yeast, where they regularly undergo this fermentation process. However, other organisms can be substituted. Fermentation, however, usually generates 3-5% ethanol (15% maximum). Thus, distillation was incorporated to increase concentration. Slide5: C6H12O6 (glucose) →2C2H5OH + 2CO2 In alcoholic fermentation, glucose breaks down into ethanol and carbon dioxide. Distillation is then used to increase the concentration of ethanol for the purpose of brewing. Ethanol makes a good compound to be used in beverage creation due to its dual hydrophobic and hydrophilic properties. The hydroxyl group readily forms intermolecular bonds with water, allowing for quick transport through the blood and solubility in water. The ethyl group (C2H5-) makes a good solvent for the addition of flavoring, coloring, and other chemicals. Slide6: The metabolic breakdown of alcohol occurs primarily in the liver. Effectively, 90% of alcohol is converted to acetic acid in your body. The breakdown of alcohol involves a series of oxidations that take part in two main steps: oxidation by the cytosolic enzyme alcohol dehydrogenase (ADH) yielding acetaldehyde, oxidation of acetaldehyde to acetate by the enzyme acetaldehyde dehydrogenase. CH3CH2OH + NAD+ -> CH3CHO + NADH + H+ CH3CHO + NAD+ -> CH3COOH + NADH + H+ A secondary metabolic process involves the enzyme cytochrome P450IIE1. Due to its small molecular size and hydrophilic/hydrophobic properties, alcohol surpasses the blood-brain barrier and subsequently disperses through the brain. Slide7: When ethanol enters the brain, the brain responds by releasing endorphins, the chemical that results in the feeling of euphoria. Alcohol is a depressant. It facilitates the production of the depressant neurotransmitter GABA and inhibits the production of the excitatory neurotransmitter glutamate. Alcohol is often consumed for its calming, euphoria effects. Prolonged consumption of alcohol can lead to the alteration of GABA receptors, which links it to the withdrawal effects experienced amongst alcoholics. The hangover is the most common after-effect of alcohol, which is essentially the dehydrating properties of ethanol. Harmful effects include: liver damage (fat disposition, alcoholic hepatitis, and alcoholic cirrhosis), cell death in the brain, fluctuation of the acid-base balance of the body, LDL oxidation, endothelial dysfunction, damage to the fetus, inhibition of platelet aggregation, etc. Alcohol, in minor doses, provides beneficial effects to the cardiovascular system. Slide8: Liver damage: Alcoholic hepatitis: occurs 50% in heavy drinkers, inflammation that results in fever, jaundice, and abdominal pain. Alcoholic cirrhosis: occurs 15 to 30% in heavy drinkers. Extensive scar tissue which stiffen blood vessels, etc. Weakens the electrochemical gradient, which is the motive force that operates ion pumps and channels. Can cause an increased concentration of intercellular calcium that activates certain proteases which inhibit the production of cell proteins. Effectively kills brain cells. Alterations to the acid-base balance of the body: Alkalosis: extreme reduction of acidity in the body as a result of intense vomiting and the loss of stomach acids, fluid, and salt. Usually occurs after intense bing drinking. Alternatively, an increase of phosphate may occur as a result of hyperventilation. Slide9: Ecstasy has become a primary fixture in the dance-rave scene since the early 1980’s. Not even made illegal in the US till 1985, it was then approved by the FDA in 2001 for research with patients suffering from post-traumatic stress disorder. Appears in the form of colorful tablets that have been imprinted with a monogram to depict ‘brand’ names. Ecstasy is one of street names for the compound 3,4-methylenedioxymethamphetamine (MDMA). It is also known as Adam, Beans, Disco Biscuits, E, Eccies, Googs, Madman, M&Ms, Mollies, Pills, Rolls, Scoobies, Smarties, Tabs, Vitamin X, Vitamin E, X, XTC and Yokes. Slide10: MDMA is a synthetic entactogen of the phenethylamine family that stimulates the brain into producing increased amounts of the neurotransmitter serotonin. The chemical formula for MDMA is C11H15NO2. Serotonin is a monoamine neurotransmitter that is responsible for mood and pleasure. The chemical name for serotonin is 5-hydroxytryptamine, and its chemical formula is C10H12N2O. Slide11: The production of MDMA is performed by a clandestine synthesis of 3,4-methylenedioxy phenyl-2-propanone during a process called reductive amination. Reductive amination is the process by which ammonia is condensed with aldehydes or ketones to form imines. A summary of the reaction process is as follows: The first step involves a nucleophilic addition to the carbonyl group followed by a rapid proton transfer. Then a secondary reaction occurs involving the elimination of water from the hemiaminal and imine formation. Slide12: With the consumption of MDMA, serotonin stores are released into the synapses of the brain. The release of large amounts of serotonin generate feelings of openness, euphoria, empathy, heightened self-awareness, increased tactile sensations with physical contact, etc. The neurological sections of the brain affected by MDMA include: the monoamine transporters, the SERT (serotonin transporter), DAT (dopamine transporter), and NET (norepinephrine transporter). Other effects of ecstasy include: photosensitivity, pupil dilation, jaw clenching, juddering vision and restlessness, lose of appetite, lack of concentration and focus, tingling sensations, and sweaty palms. A single high can last anywhere from 4 – 6 hours. Slide13: SERT activity in a rat brain under different concentrations of MDMA dosage Slide14: The most immediate risk of ecstasy are dangers concerning the tablet’s purity. Because it’s appearance varies and is easily replicable, drugs that have been advertised as ecstasy may include any number of active ingredients. Potential ‘impurities’ in MDMA may include: MDEA, MDA, and MDBD or even traces of ampthetamines (speed), DXM, etc. MDMA masks the body’s normal thirst and exhaustion responses, making users prone to dehydration. This is particularly common seeing as most users are within the dance-rave circle. “Water intoxication,” or hyponatremia, occurs when the blood becomes increasingly diluted, forcing the brain to swell. Those afraid of dehydration may consume too much water. Slide15: Some scientists project that due to MDMA’s effect on natural serotonin production, long terms effects might include acute or chronic depression. The feeling of depression can result from the synaptic terminals of serotonin neurons becoming damaged or inactive. The metabolic breakdown of ecstasy in the body is said to produce free radicals, or reactive oxygen species. Due to free electrons, they are highly reactive and are known to cause oxidative cell damage. This can damage the synaptic terminals. Allergic reaction Drug coupling: Many ecstasy users will pair alternative drugs with ecstasy to achieve different effects. MDMA + SSRIs: SSRIs are antidepressants (zoloft, prozac, etc.) taken to counteract possible acute depression effects. This may result in serotonin syndrome, a condition that causes headaches, vomiting, and dizziness – or even coma and death. SEXTACY: Coupling of viagra and MDMA. Slide16: Caffeine is the most used and abused drug in the world Caffeine is from the French/Spanish/Portuguese word for coffee (café) The molecule is useless to the normal functions of the plants that produce it; it is made because it is toxic or unpleasant to most animals Found naturally in coffee, tea and cocoa beans and artificially placed in colas and made into caffeine pills Slide17: Caffeine is also known as trimethylxanthine because it is derived from xanthine and has three ethyl groups bonded to its nitrogens At room temperature it is a white solid It is an alkaloid and tastes very bitter Acts as a stimulant, meaning it increases nervous system activity Slide18: Organic solvent extraction: several solvents including benzene, cholorform and trichloroethylene were used because of there ability to pull out caffeine and nothing else, later dichloromethane and ethyl acetate were used, but these chemicals are all moderately toxic (method used until 1990’s) Water extraction: beans are soaked in hot water, the caffeine is pulled out, but so is flavor, which must be replaced in flavor enriched water Supercritical fluid extraction: carbon dioxide at very high temperature and pressure is forced through the beans, the gas properties of the fluid allow it to fill its container while the liquid properties allow it to act as a solvent; very effective and non-toxic Slide19: Caffeine is usually taken orally and once in the blood stream can pass the blood-brain barrier due to its polar and non-polar solubility Caffeine mimics the chemical adenosine in the brain Caffeine blocks the adenosine receptors in the synapses of the neurons of the central nervous system Adenosine receptors think there is ample adenosine available, stops making it, adenosine is reduced in the brain Caffeine is similar enough to adenosine to block receptors, but not enough to perform its functions Slide20: The chemical adenosine is important for sleep (especially REM), it causes cells to slow their function A lowered amount of adenosine as a result of the presence of caffeine causes neurons to fire more rapidly, making the pituitary gland believe an emergency is in progress, so adrenaline is released, this combination of rapid firing and adrenaline is responsible for the pick-me-up effect of caffeine Caffeine can also reduces the re-uptake of dopamine, creating a desire to have more caffeine Slide21: Caffeine’s worst affect on the body is its tendency to create dependence Tolerance to caffeine makes the body more sensitive to adenosine, giving headaches to heavy users in withdrawal In some people caffeine increases the production of stomach acid, making the chance of getting an ulcer greater One would need to drink approximately 160 cups of coffee very quickly to reach a lethal dose Caffeine has a half life of 5 hours, so if it is still present when someone falls asleep it can interfere with REM sleep, making them feel tired; this person will probably return to caffeine to get an energy boost, thus, with the help of dopamine, creating an addictive cycle Slide22: Marijuana is the most used illicit drug in the United States Marijuana is a Schedule I drug in America, meaning it is classified as having no medicinal value Marijuana is from the Cannibus sativa plant native to northern India The earliest known record of marijuana cultivation was in 28 BC in China The Cannibus sativa plant is also used to make hemp, a useful resource for making fibers, fuel and food Slide23: The chemical that gives marijuana its psychoactive properties is delta-9-tetrahydrocannabinol, or THC It is not very water soluble, but it is soluble in organic solvents, such as ethanol In its pure state it is glassy and solid in cold and thick and sticky if warm THC is in the cannabinoid family of drugs; there are no cannabinoids produced naturally in the body Slide24: There are 2 common ways in which THC can enter the body: smoking and ingestion Smoking is typically done using a joint (cigarette), blunt (cigar), bong (water pipe); it is also baked into food and put in drinks Inhalation produces quicker effects, but ingestion gives longer lasting ones When smoked, THC enters the lungs and is passed into the bloodstream through the alveoli Slide25: All drugs work by mimicking a naturally occurring chemical in the nervous system, THC mimics anandamine The role of anandamine in the brain is still not totally known, the receptors for it are concentrated in the pink areas on the right Because anandamine receptors are only concentrated in certain area, only those areas are affected by THC, these areas include: hippocampus (short-term memory), basal ganglia (unconscious muscle movement), cerebellum (muscle coordination), and cerebrum (higher thought) THC replaces endocannibinoids that active hunger signals in the hypothalamus Slide26: The half life of THC is anywhere from 20 hours to 10 days, so it stays in your system a long time Short term effects include distorted perception, difficulty thinking, and loss of coordination A joint has more tar and carcinogens per puff than a cigarette Can damage reproductive system and heart (changes blood pressure and heart rate) LD50 is very high (1000 mg/kg); one would need to smoke 900 joints in one sitting to reach lethal dose Less addictive than caffeine, but studies vary on how addictive Because anandamine is used to communicate between mothers and embryos, the use of marijuana can be very dangerous during pregnancy Slide27: Even though marijuana THC is a schedule I drug, dronabinol, or marinol, is a schedule III drug, which means it can be used for limited medical purposes Dronabinol is pure THC while marijuana is a mixture of several dozen/hundred chemicals One of the most effective uses of THC as medicine is to exploit the “munchies,” THC can be used to cure nausea in chemo patients and to stimulate appetite in AIDS patients THC can reduce ocular pressure, reducing the symptoms of glaucoma, however, it can only relieve the symptoms and only while under the influence, it is not a cure The big debate is whether the positive effects of THC in each case outweigh all the negative effects
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