Organic and Biological Chemistry

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					                                                  1



Drugs, Toxic Substances
         and
  Forensic Chemistry


       Chapter 9

                   Chem 113, Prof. J.T. Spencer
                                        2
www.usdoj.gov/dea/index.htm
www.dea.gov




         Chem 113, Prof. J.T. Spencer
             Drugs and Toxins                                        3

   Drugs - what does the term mean
       » Drugs vs. Medicines

   Drugs - Natural or synthetic compounds used for
    physiological (and possibly psychological ) effects.
     – Medicinal Uses - to correct or help some physiological or
       psychological problem
     – Drug Abuse - chemicals taken for unintended uses or
       uncontrolled use (e.g., alcohol addiction).
        » Cuts across socio-economic levels
        » > 75% of forensic investigations involve drug use
        » Not victimless crimes.



                                      Chem 113, Prof. J.T. Spencer
    Drugs and Toxins                                        4

   Start with Medicinal Chemistry
    – Toxins
    – Poisons
    – Drug Discovery and Development

•   Drug Definitions and Types
•   Drug Laws
•   Drug Dependence
•   Drug Testing and Identification




                             Chem 113, Prof. J.T. Spencer
             Drugs and Toxic Substances                               5

   Dose - amount of substance that enters the body
   LD50 - Dose necessary to kill 1/2 of the population
   Acute Toxicity - effects are immediate
   Chronic Toxicity - effects occur over an extended time
                                        Cl         O         Cl


   Species Specific:                  Cl        O     Cl

   Dioxin - polychlorinated organic compounds (many)
     – From burning chlorinated compounds
     – Agent orange
                                          Species LD50
     – Paper industry                     Guinea Pig   0.0006
     – Toxicity varies with species       Rabbit       0.115
                                             Hamster         3.5
                                             Monkey          0.07


                                       Chem 113, Prof. J.T. Spencer
           Toxic Substances                                            6

LD50 Calculations:                               Substance         LD50
   Cyanide (for 150 lb human - ~ 70 Kg)          Aspirin           1750
      (70Kg)(10mg/Kg) = 700 mg (0.70g)           Ethanol           1000
                                                 Morphine          500
   Nicotine (e.g.; from Cigarettes)              Caffeine          200
      (70Kg)(2 mg/Kg) = 140 mg (0.14g)           Heroin            150
      (note 1 cig. = ~ 2 mg Nicotine)            Lead              20
                                                 Cocaine           17.5
   Ethanol                                       Cyanide           10
      (70Kg)(1000mg/Kg) = 70,000mg (70g)         Nicotine          2
                                                 Strychnine        0.8
                                                 Batrachotoxin     0.002
Effect of Body Weight: Ethanol
  150 lb Human = lethal dose = ~ 70 g
  40 lb Dog = lethal dose = ~ 20 g
                                            Right to Know Laws

                                        Chem 113, Prof. J.T. Spencer
            MSDS Sheets                                             7

   Materials Safety Data Sheets - provide specific
    toxicological, chemical and physical data about a
    compound.
     – Physical Properties and Names
     – Chemical Reactivities
     – Incompatibilities
     – Safe Handling
     – Toxicology (symptoms and means of exposure)
     – Safety and First Aid




                                     Chem 113, Prof. J.T. Spencer
             MSDS Sheets - Example                                                                     8
NICOTINE         (S)-3-(1-Methylpyrrolidin-2-yl)pyridine          CAS # 54-11-5
                   3-(1-Methyl-2-pyrrolidinyl)pyridine            RTECS # QS5250000
                    b-Pyridyl-a-N-methylpyrrolidine               ICSC # 0519
                   1-Methyl-2-(3-pyridyl)pyrrolidine              EC # 614-001-00-4
                         C10H14N2                                 Molecular mass: 162.2

TYPES OF      ACUTE HAZARDS/                         PREVENTION                FIRST AID/
HAZARD        SYMPTOMS                                                         FIRE FIGHTING

FIRE          Combustible. Gives off irritating      NO open flames.           Powder, alcohol-resistant
              or toxic fumes (or gases) in a fire.                             foam, water spray, carbon
                                                                               dioxide.
EXPLOSION     Above 95°C explosive vapour/air           Above 95°C use a closed
              mixtures may be formed.                   system, ventilation.
EXPOSURE      PREVENT GENERATION OF MISTS! AVOID EXPOSURE OF (PREGNANT) WOMEN!
              IN ALL CASES CONSULT A DOCTOR!
INHALATION    Burning sensation. Nausea. Vomiting.
              Convulsions. Abdominal pain. Diarrhoea. Headache.
              Sweating. Weakness. Dizziness. Confusion.
              Ventilation, local exhaust, or breathing protection.
              Fresh air, rest. Refer for medical attention.
SKIN          MAY BE ABSORBED! Redness. Burning sensation
              Protective gloves. Protective clothing. Remove contaminated clothes. Rinse and then wash skin
              with water and soap. Refer for medical attention.



                                                           Chem 113, Prof. J.T. Spencer
             Poisons (and drugs)                                     9

   Intentional or Accidental Poisoning?
   Corrosive Poisons - Substances that actually destroy tissue
    outright
   Metabolic Poisons - Affect biochemical mechanisms




                                      Chem 113, Prof. J.T. Spencer
             Corrosive Poisons                                        10

   Substances that actually destroy tissue outright
     – Acids/Bases (Alkali)
        » Sulfuric Acid (H2SO4)
        » Hydrochloric Acid (HCl)
        » Sodium Hydroxide (NaOH; cleaners)
     – Death can result from a little as 1 oz. H2SO4
        » Works by dehydrating tissues

        » Cells die fast because water is removed AND
          proteins are destroyed by acid-catalyzed hydrolysis
          of peptide bonds.


                                       Chem 113, Prof. J.T. Spencer
             Corrosive Poisons                                       11

   Warning Properties:
     – Corrosive toxins interact with body sensory systems to
       alert of exposure:
         » Ammonia (above 0.01% in air) causes choking
         » Acids interact with nerves to send pain signals upon
           exposure
     – Some lack warnings!
         » HF (very corrosive; used in electronics) - destroys
           both tissue / bone but does not cause pain upon
           tissue exposure . Only sends pain when BONE is
           exposed.
         » Bases (NaOH) slippery


                                      Chem 113, Prof. J.T. Spencer
              Corrosive Poisons                                     12

   Some are toxic because of reactions
     – Phosgene (mustard gas, WWI and in plastics industry) -
       if inhaled it reacts with water in lungs to form HCl.
         » Causes Pulmonary edema (fluid in lungs) because it
           draws water from surrounding tissues - victim
           drowns.
         » Phosgene does not have good warning properties
           (smells like new-mown hay and lung reactions are
           slow.

          O
                   + H2O(l)                       2(g)
                                      2HCl(aq) + CO
          C
     Cl       Cl

                                     Chem 113, Prof. J.T. Spencer
            Metabolic Poisons                                        13

   Affect Biochemical Mechanisms:
     – Carbon Monoxide (Gas) - colorless, odorless, toxic -
       suicide or homocide.
         » Binds to iron in hemoglobin and only very slowly is
           released - displacing oxygen - Carboxyhemoglobin
           is 140 time more stable than oxyhemoglobin
         » Breathing 0.1% CO in air for 4 hours converts 60% of
           hemoglobin to carboxyhemoglobin!
         » CO produced by incomplete combustion - 200
           million tons in US annually
         » Not a cumulative poison (given time, the free
           hemoglobin is released)




                                      Chem 113, Prof. J.T. Spencer
            Hemoglobin Transport                                         14



                                                              Fe site -
                                                              point of
                                                              attachment




                (Heme groups in orange)
            O                                             O
       O                       H2O                        C
                                           CO
     HEME                    HEME                       HEME
                O2
     Red                     Blue                      Red
Oxyhemoglobin                                    Carboxyhemoglobin


                                          Chem 113, Prof. J.T. Spencer
Hemoglobin Transport                              15


          Oxyhemoglobin




                                     Oxyhemoglobin




                   Chem 113, Prof. J.T. Spencer
         Metabolic Poisons                                        16
– Cyanide (suicide or homocide - Tylenol murders)
   » Common industrial agent (plastics formation,
     electroplating, metal-ore processing)
   » NaCN reacts with acids to form HCN (gas) - weak
     odor of almonds (if can be smelled - big problem)
   » Naturally occurs in seeds (protects seeds until they
     germinate).
   » Very fast working (seconds)
   » Causes asphyxiation - similar to CO but different
     mechanism - interferes with enzymes (binds tightly
     with iron) so that, even though lots of oxygen gets to
     cells, they can’t use it to support life.
   » Eventually, cyanide is removed by enzyme.
   » Administer large amts of thiocyanate can be effective
     - ANTIDOTE.

                                   Chem 113, Prof. J.T. Spencer
            Cyanide Poisoning                                          17

Cyanide is commonly thought of as a gas, but you also can be
  poisoned by it if you ingest wild cherry syrup, prussic acid,
  bitter almond oil, or large amounts of apricot pits. Cherry seeds,
  peach and plum pits, corn, chickpeas, cashews, and some other
  fruits and vegetables contain cyanogenic (i.e., cyanide-forming)
  glycosides that release hydrogen cyanide when chewed or
  digested. However, cyanide poisoning from a food source is
  rare.




                                        Chem 113, Prof. J.T. Spencer
            Arsenic Poisoning                                       18

   As commonly occurs in pesticides, shrimp, pressure
    treated wood (Paris green), old wallpaper (green color)
   React with SH groups of enzymes - stopping their normal
    function
   Accumulates in the body (not eliminated)
   Used as a poison gas in WWI - led to search for antidote
    and discovery of chelating reagents (molecules that have
    two or more sites to bind to a single metal center)
           OH                                 OH

           OH    + M 2+
                                             O            + 2 H+
                                                    M
           OH                                O



                                     Chem 113, Prof. J.T. Spencer
             Arsenic Poisoning                                                19
                                                         Napoleon
The wallpaper in his room was dyed with
Scheele's Green, a colouring pigment that
had been used in fabrics and wallpapers
from around 1770. Named after the
Swedish chemist who invented it, the dye
contained copper arsenite. It was
discovered that if wallpaper containing
Scheele’s Green became damp, the mould
converted the copper arsenite to a
poisonous vapor form of arsenic.
Breathing the arsenic on its own might
not have been enough to kill Napoleon,      After Waterloo, Napoleon was exiled
but he was ill already with a stomach       to the remote tiny volcanic island of
ulcer. On the 5 May 1821, the arsenic       St. Helena, south of the Equator.
tipped the scale against "the little        The nearest land is Ascension Island,
corporal."                                  1,120 km (700 miles) to the north.


                                               Chem 113, Prof. J.T. Spencer
             Mercury Poisoning                                  20
   Fluorescent lamps, dental amalgams, fungicides, “blocking of
    hats (“Mad Hatter” syndrome).
   Newton - alchemy (base metals into gold) - Newton’s hair had
    high amounts of mercury.
                   O    OH                   O   OH
   Mechanism:
                  H     C      C    SH    + M2+        H   C       C        S   M     + H+
                               H2                                  H2
                        NH2                                NH2


                                                                   M
                      SH    HS       Active Site               S        S       Blocked
                                                                                Active Site
                                         + M2+
                      Enzyme                                   Enzyme




                                 Antidote- Chelating Agents


                                                   Chem 113, Prof. J.T. Spencer
             Lead Poisoning                                            21

   Romans - Lead Plumbing (downfall of Rome - Pb in Emperor’s
    wine and water lead to mental illness)
   Modern - Leaded Gas, Paint, water pipe joints
     – Plumbing - (joints) EPA allows max 15 ppb, many cities have
       500 ppb.
     – Paint - PbO (white paint) - children ingest (now use TiO2 -
       not-toxic)
     – Wine - correlates with sales of leaded gas
    Leaded Gas    Air      Soil      Grapes      Wine        Humans

                    1978                                  1978
Picograms                            Leaded
Pb/gm wine                           Gas
                                     sales in
                                     France


                                        Chem 113, Prof. J.T. Spencer
            Medicinal Chemistry                                      22

   Chemicals designed for therapeutic uses.
   First drugs - “Miracle Drug”
     – Long known that willow bark could reduce fever,
       pain, etc.
     – Isolated compound from willow trees.
     – Acidic form causes side-effects.          Chemical
       modification could                 greatly reduce
       these side effects.
     – Toxicity 20-30 g/person with
         suggested dose - 325 - 750 mg/4hrs.
     – Aspirin



                                      Chem 113, Prof. J.T. Spencer
Medicinal Chemistry                           23




               Chem 113, Prof. J.T. Spencer
              Drug Discovery - An Aside                                  24
   Finding new drugs
     – Exploring folk remedies (ethnopharmacology)(i.e.,
       aspirin, digitalis, quinine, morphine):
         » Researching traditions (shamans and tribal healers).
         » Isolating active ingredients and determining their
           structures ingredients (very difficult chemical
           investigation).
         » Determining if effects are fact of fiction (i.e., aspirin
           works but rhino horns are without medical validity).
         » Synthesis of compounds.
         » Chemical modification to enhance action (may be
           coupled with information from studies on the mode
           of action of the chemical).



                                          Chem 113, Prof. J.T. Spencer
              Drug Discovery - An Aside                                    25
   Finding New Drugs
     – Fortuitous accidents - the KEY is someone realizing what they have
       stumbled upon (rare!).
         » 1928. Alex. Flemming was curious when he observed that a
           bacteria culture that had accidentally been contaminated with
           mold had no bacteria. Series of chance events;
              Researcher floor below Flemming studing rare strain of
               mold (penicillium Notatum).
              Flemming working on Staphylococcus (very sensitive to
               Penicillin)
              Mold spores drifted into Flemmings lab and contaminated
               some of his Petri dishes which were left unwashed while
               Flemming was on vacation
              Uncommonly cool weather slowed bacteria growth but not
               mold. Then warm weather permitted bacterial growth
               except around mold
              Flemming noticed antibacterial action




                                            Chem 113, Prof. J.T. Spencer
              Drug Discovery - An Aside                                    26
   Finding New Drugs
     – Fortuitous accidents - the KEY is someone realizing what they have
       stumbled upon (rare!).




                                            Chem 113, Prof. J.T. Spencer
              Drug Discovery - An Aside                                    27
   Finding New Drugs
     – Fortuitous accidents - the KEY is someone realizing what they have
       stumbled upon (rare!).




                                            Chem 113, Prof. J.T. Spencer
              Drug Discovery - An Aside                                    28
   Finding New Drugs
     – Fortuitous accidents - the KEY is someone realizing what they have
       stumbled upon (rare!).




                                            Chem 113, Prof. J.T. Spencer
             Drug Discovery - An Aside                                      29

   Even when “break” comes from tradition or chance, much
    very hard scientific work must be done to turn the discovery
    into something productive.
     – Penicillin:
        » Isolate active agent produced by Penicillium notatum
        » Separate, purify, concentrate new compound.
        » Structure and properties of new compound
        » Efficacy studies (is it really effective) and toxicity
        » Human studies
        » Synthesis and production
        » Expansion to new, related families of compounds - effective
          against different strains, allergic effects, etc.
        » Mode of action (Penicillin kills bacteria by interfering with the
          ability to synthesize cell wall.)

                                             Chem 113, Prof. J.T. Spencer
              Drug Development/Approval                                     30
   Drug Development & Approval Process - It costs an average of $500 -
    $800 million and may take nearly fifteen years to develop one new
    drug. Only 1 in 1,000 compounds that enter preclinical testing make it
    to human testing. Only one in five tested in people is approved by the
    Food & Drug Administration (FDA).
      – Synthesis and Extraction
      – Biological Screening and Pharmacological Testing
      – Pharmaceutical Dosage Formulation and Stability Testing
      – Toxicology and Safety Testing
      – Regulatory Review: Investigational New Drug (IND) Application
      – Phase I, II, and III Clinical Evaluations
      – Process Development for Manufacturing and Quality Control
      – Bioavailability Studies
      – Regulatory Review: New Drug Application (NDA)
      – Postapproval Research



                                             Chem 113, Prof. J.T. Spencer
               Targeted Drug Discovery                                       31

   Often, a drug needs only to have the right functional
    groups at the right place - - - determine the active portion
    of a molecule - - - synthesize active portion and manipulate
    the rest (often simpler than natural product)
   Morphine very difficult to synthesize but Demerol easy
    (possibly helps improve side effects?)
                       CH3                      CH3                      CH3
                       N                        N                        N
    Active Area



                                                                             O
       HO         O          OH                               H3 CH2CO


            Morphine              Active Area             Demerol


                                            Chem 113, Prof. J.T. Spencer
           Controlled Substances Act                              32

   CSA, Title II of the Comprehensive
    Drug Abuse Prevention & Control
    Act of 1970.
     – Legal foundation of the
       government’s fight against
       abuse of drugs & other
       substances.
     – A consolidation of numerous
       laws regulating the
       manufacture &
        distribution of narcotics,
       stimulants, depressants &
       hallucinogens
   Classifies Drugs into Classes
    (schedules)


                                   Chem 113, Prof. J.T. Spencer
         Schedule I                                              33



   Substance has a high potential for abuse
   Substance has no currently accepted medical use in
    treatment in the United States
   There is a lack of accepted safety for use of
    the substance under medical supervision
   Heroin, LSD, Marijuana, Methaqualone




                                  Chem 113, Prof. J.T. Spencer
        Schedule II                                             34



   Substance has the highest potential for abuse
   Substance has a currently accepted medical use in
    treatment in the U.S. or a currently accepted
    medical uses with severe restrictions
   Abuse of the substance may lead to severe
    psychological or physical dependence
   Morphine, PCP, cocaine, methadone,
    methamphetamine




                                 Chem 113, Prof. J.T. Spencer
        Schedule III                                            35


   Substance has a potential for abuse less than those
    in Schedules I and II
   Has a currently accepted medical use in treatment
    in the U.S.
   Abuse may lead to moderate or low physical
    dependence or high psychological dependence
   Anabolic steroids, codeine & hydrocodone with
    aspirin or Tylenol, some barbiturates




                                 Chem 113, Prof. J.T. Spencer
         Schedule IV                                            36


   The substance has a low potential for abuse
    relative to those in Schedule III
   Has a currently accepted medical use in
    treatment in the U.S.
   Abuse may lead to limited physical
    dependence or psychological dependence
    relative to those in Schedule III
   Librium, Darvon, Xanax, Valium (tranquilizers)




                                 Chem 113, Prof. J.T. Spencer
        Schedule V                                             37

   The substance has low potential for abuse
    relative those in Schedule IV
   Has a currently accepted medical use in
    treatment in the U.S.
   Abuse may lead to limited physical or
    psychological dependence relative to those
    substances in Schedule IV
   Over-the-counter cough medicines with codeine




                                Chem 113, Prof. J.T. Spencer
            Types of Abused Drugs                                    38

   Narcotics - relief from pain and bring sleep. (now
    generally means a socially unacceptable drug).
     – Narcotics are analgesic - relieve pain by depressing
       nervous system (opium, morphine, heroin, codeine,
       opiates - oxycontin, methadone).
   Hallucinogens - alter normal thoughts, perceptions and
    moods (PCP, LSD, mescaline, MDMA, ecstasy).
   Depressants - depress functions of central nervous system,
    cause calm and bring about sleep (alcohol, barbituates).
    Tranquilizers are depressants.
   Stimulants - increase alertness and activity (cocaine,
    amphetamines).
   Steroids - promote muscle growth (androgen, testosterone,
    anabolic steroids).


                                      Chem 113, Prof. J.T. Spencer
             Types of Abused Drugs                                   39

   Narcotics - relief from pain and bring sleep. (now
    generally means a socially unacceptable drug).
     – Narcotics are analgesic - relieve pain by depressing
       nervous system (opium, morphine, heroin, codeine,
       opiates - oxycontin, methadone).
     – Cocaine (stimulant), Marijuana (hallucinogen), etc are
       Not classified as narcotics even
        though they are frequently called that.
     – Most narcotics are opium derived.
     – Opium from Poppy plants (sap is 4
        - 21% opium).




                                                   Opium Poppy
                                      Chem 113, Prof. J.T. Spencer
           Types of Abused Drugs                          40

   Opium and Poppies




                                        Opium Poppy
                           Chem 113, Prof. J.T. Spencer
Opium Family                                  41

                                 Codeine,
                                 morphine,
                                 heroin, etc all
                                 present in
                                 opium, BUT
                                 morphine is by
                                 far the most
                                 abundant.

                                 Most Heroin,
                                 Codeine made
                                 synthetically
                                 from
                                 Morphine.




               Chem 113, Prof. J.T. Spencer
                  Heroin               CH3                                          42
                                       N

                      Morphine                     Acetic anhydride       CH3
                                                                          N

   Water Soluble - easy
    IV use.
   Rapid onset but short
    term (2-3 hrs) effects.   HO   O         OH
                                                     H 3C
                                                                                     CH3
   Field test uses reagent                                 O         O         O
    called marquis; purple                            O                              O
    color indicative of
    positive test                                               Heroin
   Most common diluent
    (diluting agent) is
    quinine
   Chemical derivative of
    morphine
   Usually street drug 20-
    30% pure (w/ starch,
    quinine, novocain,
    lactose, etc..)



                                                  Chem 113, Prof. J.T. Spencer
Heroin Forms                                        43


                        Black Tar Heroin


                                  Heroin Packages




        Heroin Powder

                    Chem 113, Prof. J.T. Spencer
Heroin Paraphenalia                           44




               Chem 113, Prof. J.T. Spencer
             Hallucinogens                                            45

   Hallucinogens - alter normal thoughts, perceptions and
    moods (PCP, LSD, mescaline, MDMA, ecstasy).
   Marijuana most common (derived from Cannabis or
    “hemp” plant).
     – Derive resin from plant secretions that is extracted with
       organic solvents.
     – In use for 1000’s of years.
     – Brought to the US ca. 1920.




                                       Chem 113, Prof. J.T. Spencer
Marijuana                                             46

         Hallucinogen
         Continued use results in low degree of
          psychological dependence
         Prior to 1970, it was classified as a
          narcotic drug
         Hashish is a concentrated preparation
         Active ingredient is
          tetrahydrocannabinol
         Can tentatively be identified by the
          Duquenois-Levine color test
         Is NOT synthesized from Canniabis
          sativa




                       Chem 113, Prof. J.T. Spencer
Marijuana                                  47




            Chem 113, Prof. J.T. Spencer
               LSD                                                                        48
•Derived from Ergot Fungus (on grasses/grains)
•First described in 1943 after “accidental” lab
ingestion (potent - 25mg for long lsating effects!)




                              QuickTime™ and a


                                                                     lysergic acid
                           Anima tion d ecompressor
                        are neede d to see this picture.




                                                                     diethylamide




                                                           Chem 113, Prof. J.T. Spencer
LSD   Street Form                             49




               Chem 113, Prof. J.T. Spencer
Other Hallucinogens
                                                 50
    Phencyclidine (PCP)-
     (phencyclidine)
     Street Names: Angel
     Dust, Crystal, Hog,
     Supergrass, Killer Joints,
     Ozone, Wack, Embalming
     Fluid, and Rocket Fuel.
     Easily Synthesized.
    Mescaline
    Psilocybin- Street
     Name: Shrooms, Mushies,
     and Mexican Magic
     Mushrooms
    STP
    LSD- Street Names:
     Acid, Boomers, Yellow
     Sunshines, Cid, Doses,
     and Trips
    Ecstacy


                  Chem 113, Prof. J.T. Spencer
            Drug Labs                                                   51

   Often Inexperienced Chemists!




                       Don’t try this at home!




                                         Chem 113, Prof. J.T. Spencer
          Stimulants and Depressants                       52

1.   Caffeine          1.   Labrium
2.   Amphetamine       2.   Valium
3.   Cocaine           3.   Methaqualone
                       4.   Ethyl Alcohol




                            Chem 113, Prof. J.T. Spencer
             Depressants                                               53

   Depressants - depress functions of central nervous system,
    cause calm and bring about sleep (alcohol, barbituates).
    Tranquilizers are depressants.
     – Downers - relax, create feeling of well-being, produce
       sleep.
     – Act on central nervous system.
     – Usually taken orally.
     – Also includes tranquilizers (e.g., librium and Valium)
       and “glue sniffing” (toluene, gasoline, freon, etc.) - all
       effect central nervous system. Major problems -
       chemical eposures cause permanent liver, kidney, heart
       and brain damage.




                                        Chem 113, Prof. J.T. Spencer
Ethanol                                         54

             Depressant, not a
              stimulant.
             Continued use may lead
              to physical dependency.
             Over 1 billion gal.
              Produced annually.
             Even low doses can cause
              impairment (with the
              feeling of no effect).
             Examine effects in more
              detail later.




                 Chem 113, Prof. J.T. Spencer
             Stimulants                                               55

   Stimulants - increase alterness and acivity (cocaine,
    amphetamines).
     – Amphetamines - synthetic drugs that stimulate the
       central nervous system.
     – Once stimulant wears off then severe depression
       usually sets in - requiring more stimulant (speed binge).




                                       Chem 113, Prof. J.T. Spencer
             Stimulants                                                 56
   Cocaine -
     – Powerfully addictive stimulant drug and strong central
       nervous system stimulant - interferes with the reabsorption
       of dopamine, a chemical messenger associated with
       pleasure causing buildup of dopamine and continuous
       stimulation of “receiving” neurons, leads to euphoria
     – The powdered, hydrochloride salt form of cocaine can be
       snorted or dissolved in water and injected.
     – Crack has not been neutralized by an acid to make the HCl
       salt. This form of cocaine comes in a rock crystal that can be
       heated and its vapors smoked. The term “crack” refers to
       the crackling sound heard when it is heated.
     – users can experience acute cardiovascular or
       cerebrovascular emergencies, such as a heart attack or
       stroke. Cocaine-related deaths are often a result of cardiac
       arrest or seizure followed by respiratory arrest.
     – Physical effects of cocaine use include constricted blood
       vessels, dilated pupils, and increased temperature, heart
       rate, and blood pressure.

                                         Chem 113, Prof. J.T. Spencer
Rock Cocaine                                  57




               Chem 113, Prof. J.T. Spencer
Crack Cocaine                                  58




                Chem 113, Prof. J.T. Spencer
Cocaine Paraphenalia                          59




               Chem 113, Prof. J.T. Spencer
Club Drugs/Date Rape Drugs                    60




               Chem 113, Prof. J.T. Spencer
      Date Rape Drugs                                     61




Flunitrazepam   Ketamine          MDMA (Ecstacy)
(Rohypnol)


                                     GHB


                           Chem 113, Prof. J.T. Spencer
              Date Rape Drugs                                             62
   Rohypnot, Ketamine, GHB, Ecstacy.
   GHB (depressant) effects can be felt within 15 minutes after
    ingestion. Mixed with alcohol GHB can cause the central nervous
    system to shut down, lead to loss of consciousness, and possibly
    result in a coma or death.
   Rohypnol (depressant) effects begin within 30 minutes, peak
    within 2 hours, and may persist for up to 8 hours or more,
    depending upon the dosage.
   Ketamine (hallucinogen) causes the person to feel as if their mind
    is “separated” from the body. The drug causes a combination of
    amnesia and hallucinations. Also, it stops the feeling of pain and
    lowers the heart rate leading to oxygen starvation to the brain and
    muscles. Vet Medicnine.
   Ecstatsy (hallucinogen)causes psychological difficulties, including
    confusion, depression, sleep problems, drug craving, severe
    anxiety, and paranoia-during and sometimes weeks after taking
    Ecstatsy.


                                           Chem 113, Prof. J.T. Spencer
           Date Rape Drugs                                  63

   Ketamine




        Ketamine Powder




                             Chem 113, Prof. J.T. Spencer
             Rohypnol (flunitrazepam)                                          64
   Street Names: Roofies, Rophies, Roche, Forget-me Pill, Circles, Mexican
    Valium, Rib, Roach-2, Roopies, Rope, Ropies, Ruffies, and Roaches




                                                Chem 113, Prof. J.T. Spencer
           Rohypnol (flunitrazepam)                                    65
   The "date rape" drug is the common name for Rohypnol,
    generically called flunitrazepam.
   Rohypnol is manufactured by Hoffman-La Roche and
    prescribed as a sleeping pill in countries outside of the US.
   It is used as a short-term treatment for insomnia, as a
    sedative hypnotic and a pre-anesthetic.
   It has physiological effects similar to Valium (diazepam),
    but is approximately ten times more potent.
   Rohypnol is a low-cost drug, less than $5.00 per tablet.
   Misconceptions may explain the drug's popularity :
     – many erroneously believe that the drug is unadulterated
       because it comes in pre-sealed bubble packs -- and therefore
       tamper-proof and safe
     – many mistakenly think its use cannot be detected by
       urinalysis testing.
     – Rohypnol IS addictive (true)
                                        Chem 113, Prof. J.T. Spencer
             Rohypnol (flunitrazepam)                                       66
   Rohypnol (a benzodiazepine), a very potent tranquilizer similar in
    nature to valium (diazepam), but many times stronger.
    The drug produces a sedative effect, amnesia, muscle relaxation, and a
    slowing of psychomotor responses.
   Sedation occurs 20-30 minutes after administration and lasts for hours.
   The drug is not commonly used by physicians in the US.
   The drug has been added to drinks at parties, where it is reportedly
    given to female party participants in hopes of lowered inhibitions.
    Police report that after ingestion of "Roofies" that women have
    reported waking up in frat houses with no clothes on.
   Rohypnol, particularly when mixed with alcohol or other drugs may
    lead to respiratory depression, aspiration, and even death. An amnesia
    producing effect of "Roofies" prevents users from remembering how or
    why they took the drug or even that they were given it by others. This
    makes investigation of sexually related or other offenses very difficult
    and may account for repeated reports of "date rapes" involving the use
    of the drug.

                                             Chem 113, Prof. J.T. Spencer
     Rohypnol (flunitrazepam)                              67

–Rohypnol manufacturer recently reformulated
 the drug to make it more detectable.
   »When put in a light-colored drink, new
    Rohypnol will now turn the beverage bright
    blue.
   »Consumers of darker-colored beverages
    should be tipped off by a cloudy appearance.
   »Proponents claim risks associated with
    Ecstasy can be minimized by drinking lots of
    water.




                            Chem 113, Prof. J.T. Spencer
             Ecstacy                                                  68

   Also known as MDMA and is called “Adam,” “XTC,” “Bean,”
    “E,” “M,” and “Roll” on the street
   Ecstasy comes in a tablet that is often branded, just a few
    are shown below:




                                       Chem 113, Prof. J.T. Spencer
              Date Rape Drugs                                       69

   Instant Testing Market




     DrinkSafe Date Rape Test Pack

                                               Date Rape Coaster



                                     Chem 113, Prof. J.T. Spencer
             Date Rape Drugs                                         70
   What You Can Do to Protect Yourself?
   Don't accept drinks that you did not open yourself.
   Don't exchange or share drinks with anyone.
   Don't drink anything out of a punch bowl.
   Monitor the behavior of friends who seem more
    intoxicated than the amount of alcohol would
    warrant.
   Never consume a drink that you have not mixed
    yourself, or have not watched someone else prepare.
   Never accept a drink from someone you don't know
    and trust.
   At parties or clubs with friends never leave your drink
    unattended.
   Be aware of your surroundings - Listen for the street names
    of the drugs - Trust you instincts
                                      Chem 113, Prof. J.T. Spencer
           Date Rape Drugs                                          71
Spring Breakers Beware!
   – The heaviest concentrations of GHB have been found in
     California, Texas, Georgia, and Florida.
   – Rohypnol has been encountered by U.S. law
     enforcement agencies in Southern States from California
     to Florida.
   – In the United States, Rohypnol is used widely in Texas.
   – Roypnol is reported to be readily available in the Miami
     area, and epidemiologists from that area have stated that
     it is South Florida’s fastest growing drug problem.
   – Two thirds of patients for GHB ingestion are aged 18-25
     years · Ecstasy abuse as increased 500 percent over a
     five-year period.



                                     Chem 113, Prof. J.T. Spencer
Date Rape Drugs                                  72




                  Chem 113, Prof. J.T. Spencer
        Date Rape Drugs                                       73

PHYSICAL SYMPTOMS
•Acting intoxicated.
•Bloodshot or red eyes, droopy eyelids.
•Imprecise eye movement.
•Wearing sunglasses at inappropriate times.
•Abnormally pale complexion.
•Change in speech patterns and vocabulary
patterns.
•Repressed physical development.
•Sudden appetite, especially for sweets.
•Unexplained weight loss or loss of appetite.
•Neglect of personal appearance, grooming.



                               Chem 113, Prof. J.T. Spencer
            Drug Identification                                    74

   Chromatography- used for separating and tentative
    identification
   Spectrometry- IR, MS, NMR, etc…




                                    Chem 113, Prof. J.T. Spencer

				
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