Transcript Organic and Biological Chemistry

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Drugs and
Forensic Chemistry
Chapter 9
Chem 113, Prof. J.T. Spencer
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www.usdoj.gov/dea/index.htm
www.dea.gov
Chem 113, Prof. J.T. Spencer
Drug Dependence
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Drug’s ability to induce dependence due to complex
physiological and social factors
Degrees and patterns of dependency dependent on:
- nature of drug
- administration route
- dose
- frequency
- metabolism
- non-drug factors- characteristics of user,
expectancies, setting of drug use, public attitude
Interaction of drug w/individual & drug’s impact on
society
Chem 113, Prof. J.T. Spencer
Drug Dependence
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 Psychological
Dependence:
the conditioned use of a drug
caused by emotional needs
High degree- alcohol, heroin,
amphetamines,
barbiturates, cocaine
Low degree- marijuana, codeine,
LSD
Chem 113, Prof. J.T. Spencer
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Physical
Dependence: physical need
for drug due to regular use
Withdrawal sickness/ abstinence syndrome
results when user does not adhere to regular
schedule of use:
body chills, vomiting, cramps, convulsions,
insomnia, pain, hallucinations
Drugs - alcohol
- heroin
- barbiturates
Chem 113, Prof. J.T. Spencer
Types of Abused Drugs
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Narcotics – 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, barbiturates).
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
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Narcotics – narkotikos – state of lethargy- relief from pain
and produce sleep (now generally means a socially
unacceptable drug).
– Narcotics are analgesic - relieve pain by depressing
nervous system
– Physical dependence
– Most narcotics are opium derived- morphine, heroin,
codeine (cough suppressant)
– Opium from Poppy plants (sap is 4 - 21% opium)
– Synthetic opiates- oxycodone, methadone (pain relief)
Opium Poppy
Chem 113, Prof. J.T. Spencer
Types of Abused Drugs
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Opium and Poppies
Opium Poppy
Chem 113, Prof. J.T. Spencer
Opium Family
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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
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Morphine + acetic anhydride or acetyl chloride  Heroin
Water Soluble - easy IV use.
Quickly metabolized to morphine in blood
Rapid onset but short term (3-4 hrs) effects.
Field test uses reagent called marquis; purple color
indicative of positive test
Most common diluent (diluting agent) is quinine
Chemical derivative of morphine
Usually street drug 20-30% pure (w/ starch, quinine,
novocain, procaine, lactose, etc..)
Methodone used as “substitute” for recovering heroin
addicts
Chem 113, Prof. J.T. Spencer
Heroin Forms
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Black Tar Heroin
Heroin Packages
Heroin Powder
Chem 113, Prof. J.T. Spencer
Heroin Paraphernalia
Chem 113, Prof. J.T. Spencer
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Hallucinogens
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Hallucinogens - induces change in mood, attitude, thought
or perception, tiredness, impairs reasoning
LSD (lysergic acid diethylamide)
Mescaline
PCP (phencyclidine)
Ecstasy/MDMA (methylenedioxymethamphetamine)
Marijuana
Chem 113, Prof. J.T. Spencer
Marijuana
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most common (derived from Cannabis or “hemp” plant).
– Derive resin from plant secretions that is extracted with
organic solvents (alcohol)
– In use for 1000’s of years.
– Brought to the US ca. 1920.
– Most widely abused illicit drug in U.S.
active ingredient is THC (tetrahydrocannabinol)
Concentration-(Lowest to Highest) stems, roots or seeds 
leaves  flowers  Resin (hashish)
Potency- Loose vegetation  hashish sinsemilla 
hashish oil*
Chem 113, Prof. J.T. Spencer
Marijuana
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Medicinal Uses: antiemetic, pain killer, mild
sedative, muscle relaxant, decreases eye pressure
of glaucoma
Psychological dependence (not physical)
Effects: Inc. heart rate, dryness of mouth, red eyes,
impaired motor skills, and concentration,
frequent hunger (sweets)
Prior to 1970, it was incorrectly classified as a
narcotic drug
Can tentatively be identified by the DuquenoisLevine color test
Chem 113, Prof. J.T. Spencer
Marijuana
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Chem 113, Prof. J.T. Spencer
LSD
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•Derived from Ergot Fungus
(on grasses/grains)
•First described in 1943 after
“accidental” lab ingestion
•(potent - 25mg for long lasting effects!)
lysergic acid
diethylamide
Chem 113, Prof. J.T. Spencer
LSD
Street Form
Chem 113, Prof. J.T. Spencer
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Other Hallucinogens
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Phencyclidine (PCP)(phencyclidine)
Street Names: Angel
Dust, Crystal, Hog,
Supergrass, Killer Joints,
Ozone, Wack, Embalming
Fluid, and Rocket Fuel.
Easily Synthesized in
illegal labs
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
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Drug Labs
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Often Inexperienced Chemists!
Don’t try this at home!
Chem 113, Prof. J.T. Spencer
Depressants
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Depressants - depress functions of central nervous
system, cause calm and bring about sleep
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Barbiturates
Ethanol (Ethyl Alcohol)
Tranquilizers
Glue Sniffing- (volatile solvents) toluene,
gasoline, freon, etc.
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– Major problems - chemical exposures cause
permanent liver, kidney, heart, brain damage and
death
– Exhilaration, euphoria, slurred speech, double vision,
stupor, drowsiness
Chem 113, Prof. J.T. Spencer
Barbiturates
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Barbiturates- “barbs", derivatives of barbituric acid (25)
Downers - relaxation, feeling of well-being, produce sleep
Medical uses (sedatives), socially abused
Usually taken orally, 10-70 mg
Phenobarbital (slow absorption), pentobarbital,
secobarbital, amobarbital, butabarbital
Ex- Nembutal (yellow jackets), Seconal (reds), Tuinal
(christmas trees), Amytal (blues), Quaaludes
Chem 113, Prof. J.T. Spencer
Barbiturates
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Chem 113, Prof. J.T. Spencer
Tranquilizers
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Relaxing tranquility w/o impairment of thinking and sleep
Major tranquilizers (Reserpine, Chlorpromazine)- reduce
anxiety and tension of mental patients
Mild Tranquilizers (Valium, Librium, Miltown) - everyday
tension
Psychological and physical dependency
Chem 113, Prof. J.T. Spencer
Ethanol
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Depressant, not a
stimulant.
most widely used and
abused drug
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).
Chem 113, Prof. J.T. Spencer
Stimulants
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Stimulants- (Uppers, Speed) Stimulate CNS by
interfering with neurotransmitter (dopamine),
increased alertness, activity, well-being,
decreased appetite, 5-20 mg/day
Caffeine (oral)
Amphetamine (oral, injection)
Cocaine (*snort, smoked)
Chem 113, Prof. J.T. Spencer
Amphetamines
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Amphetamines- synthetic stimulant, violent behavior,
paranoia, anxiety, confusion, insomnia, hallucinations,
cause psychological dependence
Methamphetamine- usually injected (500-1000 mg)
Flash” “Rush”- initial high
Once stimulant wears off then severe depression
usually sets in - requiring more stimulant (speed
binge)
“ice”- smokable methamphetamine
Phenmetrazine, phendimetrazine- weight loss
Chem 113, Prof. J.T. Spencer
Stimulants
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Chem 113, Prof. J.T. Spencer
Stimulants- Cocaine
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Cocaine – Powerfully psychological addictive CND stimulant drug 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 (derived
from Erythroxylon coca plant) can be *snorted or dissolved
in water and injected.
– Used by Freud
– Local anesthetic
– Physical effects of cocaine use include constricted blood
vessels, dilated pupils, and increased temperature, heart
rate, and blood pressure.
– 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.
Chem 113, Prof. J.T. Spencer
Crack Cocaine
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• Rock crystal that can be heated and its vapors smoked.
The term “crack” refers to the crackling sound heard
when it is heated.
• Most difficult drug addiction to overcome
Chem 113, Prof. J.T. Spencer
Crack Cocaine
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Chem 113, Prof. J.T. Spencer
Cocaine Paraphenalia
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Club Drugs/Date Rape Drugs
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Club Drugs- Synthetic drugs used at nightclubs, bars, and
raves
Chem 113, Prof. J.T. Spencer
Date Rape Drugs
Flunitrazepam
(Rohypnol)
Ketamine
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MDMA (Ecstacy)
GHB
Chem 113, Prof. J.T. Spencer
Date Rape Drugs
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Rohypnol, Ketamine, GHB, Ecstasy.
GHB (gamma hydroxybutyrate) (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 Medicine.
*Ecstasy (hallucinogen)- causes psychological difficulties,
including confusion, depression, sleep problems, drug craving,
severe anxiety, and paranoia-during and sometimes weeks after
taking Ecstasy.
Chem 113, Prof. J.T. Spencer
Rohypnol (flunitrazepam)
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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.
Effects enhanced in combination w/alcohol
Quick acting- Sedation in 20-30 minutes
“Amnesia”
Odorless, colorless, tasteless
Low-cost drug, less than $5.00 per tablet.
Addictive
Chem 113, Prof. J.T. Spencer
Rohypnol (flunitrazepam)
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Street Names: Roofies, Rophies, Roche, Forget-me Pill,
Circles, Mexican Valium, Rib, Roach-2, Roopies, Rope,
Ropies, Ruffies, and Roaches
 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.
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Chem 113, Prof. J.T. Spencer
Rohypnol (flunitrazepam)
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–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
Ecstasy
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Synthetic
Hallucinogenic and amphetamine-like effects (originally
appetite suppressant)
Decreased inhibitions, increased self-awareness
Increased heart rate and blood pressure, muscle tension,
teeth grinding, nausea, inc. body temp., confusion, anxiety,
paranoia
Chronic abuse- seizures, muscle breakdown, stroke, kidney
failure, CV problems, brain damage
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 above
Chem 113, Prof. J.T. Spencer
Date Rape Drugs
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Instant Testing Market
DrinkSafe Date Rape Test Pack
Date Rape Coaster
Chem 113, Prof. J.T. Spencer
Date Rape Drugs
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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
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Chem 113, Prof. J.T. Spencer
Anabolic Steroids
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Anabolic Steroids
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Synthetic compounds chemically related to testosterone
Anabolic effects (increased muscle growth) w/o
androgenic effects (development of male sex
characteristics)
Not yet accomplished
Used by athletes to enhance performance- not shown in
studies
Controlled dangerous substance, regulation of sale and
availability to public by DEA
Side effects- liver malfunctions, liver cancer, female
masculinization, infertility, dec. sex drive, dec. bone
growth in teenagers, depression, mood and personality
changes (“Roid Rage”)
Chem 113, Prof. J.T. Spencer
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Anabolic Steroids
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Controlled Substances Act
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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
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Schedule I
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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, Methaqualone
Chem 113, Prof. J.T. Spencer
Schedule II
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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, hydrocodone
Chem 113, Prof. J.T. Spencer
Schedule III
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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, dronabinol
Chem 113, Prof. J.T. Spencer
Schedule IV
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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
Phenobarbital, Librium, Darvon, Xanax, Valium
(tranquilizers)
Chem 113, Prof. J.T. Spencer
Schedule V
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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
Collection and Preservation of Drug52
Evidence
 Properly
packaged and labeled
 Original container
 Background info
 Drug-screening tests
Chem 113, Prof. J.T. Spencer
Drug Identification
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Chromatography- used for separating and tentative
identification
Spectrometry- IR, MS, NMR, etc…
Chem 113, Prof. J.T. Spencer
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Drug Identification
 Screening
Tests- Color Tests, nonspecific,
preliminary
 Confirmation Tests- a single test that
specifically identifies a substance
Chem 113, Prof. J.T. Spencer
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Color Tests
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First technique
 Fast and simple
 Test strips change color when exposed to specific
drug
 Useful in field
 Not conclusive
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Chem 113, Prof. J.T. Spencer
Color Tests
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 Marquis-
purple- heroin, morphine
 Marquis- orange-brown- amphetamine
 Dillie-Koppanyl- violet-blue- barbiturates
 Duquenois-Levine- purple-marijuana
 Van Urk- blue-purple- LSD
 Scott- blue  pink- cocaine
Chem 113, Prof. J.T. Spencer
Microcrystalline Tests
 Crystals
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form (different colors and shapes)
when suspect substance is mixed w/reagent
 More specific and accurate
 Hundreds of tests
 Rapid
Chem 113, Prof. J.T. Spencer
Spectrophotometry
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Sample must be pure
Selective absorption of light by drugs
Electromagnetic Radiation directed at sample and
absorption is measured and graphed
UV-Ultraviolet, inconclusive
IR-Infrared, specific
Chem 113, Prof. J.T. Spencer
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Chromatography
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Complements color and crystal tests
 Separate drugs from diluents
 Tentative identification
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Chem 113, Prof. J.T. Spencer
Mass Spectrometry
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GCMS-Gas Chromatography/Mass Spectrometer
Substances separated by gas chromatography then
molecules broken apart when bombarded w/ high-energy
electrons
Each drug has unique fragment pattern
Chem 113, Prof. J.T. Spencer