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16. Nicotine, Caffeine,
Ethanol & ?!
-the Legal Drugs
chapter 23
Tobacco = Nicotine
+'Tar' & Carcinogens
Tobacco smoke contains
>4000 compounds;
~400 are poisons,
~40 are carcinogens –
(several proven for humans)
Nicotine*, although ‘toxic’, is the addictive material;
the 'tar', carcinogens and particulates do the 'killing'.
* LD50(mg/kg): 230 oral, 0.3 i.v.(inhale 2mg/cig)
“Tobacco products are the only materials legally
sold that, when used as intended by the producer,
will lead to premature death in >50% of the users"
N
N
Nicotine
so simple
so nasty
CH3
The Nicotine 'Habit'
Partly because of access to decades of tobaccocompany research the mechanism of nicotine action,
and addiction, is now proven. Nicotine acts on
receptors in the mid-brain to release excess
dopamine (stimulant) but receptors become
desensitized and tolerance develops. Experienced
smokers increase their intake (eg. inhale more
deeply, etc.), more to avoid withdrawal symptoms
(restlessness, can't concentrate, reduced heart rate,
depression) than to get a 'hit'.
Sir Walter's Deadly Gift
North American stats (below world averages!)
• 20-25% of population still smokes(the power of
'social pressures')
• 30%/yr try 'to quit', ~3% of these are successful
(50% continue after major surgery)
• ~500,000/yr die prematurely due to effects of
tobacco smoking
Tobacco Trivia
20% of smoker's hemoglobin is permanently bound
with CO
A lung-full of 'smoke' contains~ 1015 OH radicals
Kicking the habit
• Nicotine patches
Unless they are abused!
Nicotine as a treatment
• Duke Univ. study March 2008
• Nicotine patches boosted schizophrenics
short term memory and mental processing
abilities and improved attention spans
Ethanol(alcohol)
– a History
At least 6000 yrs ago; first
'synthetic' chemical
(biotechnology!), ~3700 BC
Egyptians made wine,
Sumerians made beer.
Distillation 'invented' ~1500AD, separate ethanol
(bp78o) and water(bp100o) to concentrate alcohol %.
In 1700's British customs agents poured 'whisky' on
gunpowder and ignited it; if it burned (>50% 'alcohol‘)
that was proof the whisky was 'good', ie.100%.
Thus the term proof = 2x the % ethanol
Ethanol - Chemistry
Fermentation ofglucose:
 CH3CH2OH + CO2
the microorganisms are
'inactivated' at ~15%
ethanol(beer, wine);
anything stronger must be
'fortified'(sherry) or distilled(spirits).
From anything starch/sugar,eg.
barley(beer), grains(whiskies), corn(bourbon),
grapes(wine), potatoes(vodka), rice(saki), rum
(sugar cane), raisins(arak/raki), artichokes(cinar)
beer(Germany), whisky(Scotland), bourbon(US),
wine (France), vodka(Russia), arak(Hungary),
saki(Japan); Greece?, Jamaica?, Newfoundland?
World’s oldest licensed Distillery
• Bushmills (Antrim Coast: Northern Ireland)
Ethanol Consumption
Per capita in 1999
(in liters/yr of 95%
ethanol)
Western Europe
Eastern Europe
Latin America
North America
Australasia
Rest of world
~9.01
~6.82
~4.03
~6.51
~7.61
~2.42
Luxemborg
13.3
Portugal
11.2
France/Ireland 10.8
……………………….
USA
6.5
6.2
1)dropping 2)rising 3)steady Canada
Ethanol - Breakdown
CH3CH2OH CH3CH=O
ethanol
acetaldehyde
 CH3COOH CO2+H2O
acetic acid
liver processes blood
supply(~6L) every 4 min
liver burns up ethanol (=> 7Cal/g) first
(apparent stimulant)
excess acetaldehyde 'ties up' serotonin in the
brain(depressant, etc.)
cirrhosis = fat deposits/lesions on the liver
Ethanol - that's the Limit!
Body (liver) can 'detoxify' ~30mL(1oz.)/hr
# drinks1
BAC2(mg/dL)
Effect
2
0.05
mild sedation
4
0.10
lack of coordination
6
0.15
obvious intoxication
10
0.30
unconscious
20
0.50
possible death
1)'1oz' for a 70 kg person 2)Blood Alcohol Conc'n,%
Breathalyser oxidizes ethanol to acetic acid using
dichromate(yellow) to chromate(green)
2008 : IR spectroscopy used
Ethanol - the Ups
LD50 = 13mL(~11g)/kg
• moderate use enhances:
social interactions,
enjoyment of food
• statistical correlation of longer (happier?) life
with ~1'drink' per day
• powerful phytochemical antioxidant (resveratrol)
in red wine(grape skins?)
• almost 60% of NA over 12yr consume alcohol
each month
Moderate Alcohol Consumption
• Dulls cravings for sweets
• Combined with exercise, produces more
heart-protective effects than exercise alone
• Red wine: increased heart protection due to
trans-resveratrol “French paradox”
• Bio-beer: Rice Univ. Students genetically
modify yeast to produce trans-resveratrol in
Dec. 2008!
Ethanol - the Downs
NA data
• ~150,000 (300/day) die of alcohol-related causes,
eg. 50% of highway fatalities
• ~11 million alcoholics(40X the heroin addicts)
• 40% of admissions to mental institutions are
alcohol related
• alcoholics: 10X higher suicide rate; 12yrs less life
• Fetal Alcohol Syndrome (1-2 /1000 births, ~700/yr
in Canada(more than Down's Syndrome &
Spina Bifida combined
Effects of Alcohol in cold temps
• Alcohol causes increased blood flow to
skin: hence warming sensation
• But reduced core temperature results: thus
increased danger of hypothermia
“Warm ups”
• Tailgaters actually cooling down!
Ethanol - 'Trivia'
on sex-".. drink provokes the desire, but takes away
the performance", Shakespeare, Macbeth, Act II
NA college students spend $7-10 billion/yr on
alcohol (more than on soda, coffee, milk, juice
and books); and get drunk more often than same
age persons who do not attend college
most Orientals consume much less alcohol than
Caucasians, partly due to 'flushing syndrome'
(headaches,dizziness)
Caffeine-the World's 'Innocuous'
Stimulant
LD50 = 130mg/kg(200mg for an adult 'hit')
(but what about children!?)
Increases Ca++ in brain cells, ? blocks adenosine
(nucleic acid, neurotransmitter) receptors;
both effects cause increased brain activity
More than 500-600 mg/day regularly can cause:
irregular pulse, ulcers, insomnia, diuretic,
decreases Ca uptake to bones by ~35%
Addictive? - increased tolerance, withdrawal
symptoms
Not so innocuous if…….
• You’re pregnant: 2 cups of coffee per day
doubles miscarriage risk
• Caffeine readily crosses the placental
barrier
• Early exposure most dangerous: fetus has
underdeveloped metabolic system
O
R
O
CH3
N
N
N
N
CH3
If ‘R’ is:
H = theobromine(tea, diuretic)
CH3 = caffeine(stimulant)
Caffeine Sources
Filter coffee(6oz cup)
Tea(6oz)
Chocolate milk
dark
Colas(1 can)
No-Doz(1 tablet)
Anacin tablet
cold 'remedies'
150 mg
30-90
15
45
40-50
100
30
25
Caffeine - Trivia
For children, 1 cola drink = 4 cups coffee for adult
in NA: 1 million kg/yr caffeine is added to food
(mainly 'soft' drinks),
guarana vine (Amazon) contains enough
caffeine to mimic cocaine as CNS stimulant
Can you guess………………
The country which consumes the
most coffee per capita is…..
Pick one
•
•
•
•
•
•
USA
Canada
Turkey
Colombia
Ireland
Finland
Energy Drink mania on campus
What is Taurine and why is it there?
• 2-aminoethanesulfonic acid, major
constituent of bile; 1st isolated from ox bile
(L. taurus)
Properties of Taurine
• Alleviates muscle fatigue (in mice) in strenuous
workouts
• Often used in bodybuilding in combination with
creatine and anabolic steroids
• Reduces blood pressure (offsets caffeine?)
• Related to cysteine: premature infants may need it
if they lack the enzyme needed to make cysteine
• Essential for Cats!!
Nicotine, Caffeine, Alcohol
• Inter-related re: consumption?
• Smokers tend to consume more tea/coffeee
and alcohol (Feb 2008 study in the Journal:
Nutrition) than non smokers
• Both caffeine and nicotine are appetite
suppressants
Marijuana
Cannabis sativa(CS)
=> hemp(tough fibers
for rope)
Marijuana: dried leaves/flowers/seeds of CS
(in '80s = ~1% THC, in '00 = ~7% THC)
Hashish: compressed resin/juice from CS
Long history of use in 'religious' rituals and some
medicinal use, especially in India
In NA as intoxicant
(increases pulse rate,
distorts senses,
impairs motor function),
2nd to ethanol
No longer a 'cottage industry'; in NA est. at ~$40
billion/yr, ie. 3rd behind GM (and Exxon!)*
* Moves to #2 in 2002 !
Canada = #3 supplier to US(after Mexico&Columbia)
Marijuana - Effects
LD50(THC, mg/kg): 1200 oral, 100 i.v., 42 inhaled
• High doses - moderate addiction, intense anxiety
• Moderate but long term use - damages lungs,
hampers immune system*, lowers 'mental'
functions* (* about same as alcohol/tobacco)
• Benefits - glaucoma treatment (reduces eye
pressure); heightens enjoyment of food; relieves
nausea; reduces perception of pain(used to
comfort cancer patients or those with advanced
HIV on chemotherapy or radiation); (?) treatment of
muscle spasms/epilepsy.
Marijuana – the
‘active’ ingredient
CH3
OH
H3C
H3C
O
(CH2)4CH3
Tetrahydrocannabinol(THC)
UN report 2007
• Canada tops industrialized world in p/c
marijuana consumption (4x average)
• % use in 15-64 age range:Papua New
Guinea & Micronesia 29 Ghana 21.5,
Zambia 17.7
• Canada 5th overall in world 16.8%
Canadian “policy”
• Liberal gov’t in early 2000’s tried to
decriminalize possession of small amounts
(<30grams) did not pass
• Oct 2007 P.M. Harper announces new
National Anti-Drug Strategy (not law)
• Proposal: 1 year jail for dealers
• 2 years for>500 plants
• 6 months for 1 plant if trafficking
Provinces enter the fray
• ON (May 2003) ruling that possession of < 30 grams was
not a criminal offence
• BC, NS, PEI agreed: Alberta and Sask anti.
• July 13th 2007; Ont. Prov. court rules criminal possession
laws for cannabis are unconstitutional
• Feds trying to enforce “unconstitutional law”
• Toronto police “ no change in how we deal with
possession …..for now” (2007)
Other countries
• Netherlands: tolerated but illegal: Cannabis
can be bought in small amounts in “coffee
shops” if 18
• Spain/Portugal: personal consumption and
home cultivation Ok. Buying/selling is an
offence
• NZ. Possession of any amount is illegal;
fines up to 500$
Death penalty if in …
• Saudi Arabia, Indonesia, Malaysia, UAE,
Thailand, Singapore, China
USA
• State jurisdiction: Colorado/Mass : up to 1
oz possession is decriminalized
• Alaska: 2 oz’s and cultivation of 25 plants
for personal use
• 12 states have approved it for medical us; 6
others decriminalization
‘Decriminalize'! . Will We?. or Won't We?
Yes! "After all it is no worse than tobacco or
alcohol", but...
• don't have many long-term(25+ yr.) studies,
• compared to tobacco, marijuana smoke has 5X the CO content
3X the 'tar'(more at end of joint)
For lung 'damage': 1 joint = ~5 cigarettes
For lung 'impairment': 1 joint = ~15 cigs
No! "It will only lead to use of hard drugs" => =>
Class poll on marijuana
decriminalization
• Yes
• No
• Needs more study
Other drug use
• Canada #3 in world for p/c cocaine use ;
Spain and England #1 &2
• For heroin, amphetamines and ecstasy,
Canada at or below world usage
• UN conclusion: “world drug situation has
stabilized and has been brought under
control”……….do you agree???
March 2008
• UN drug control board tells Canada to shut
safe injection sites
• “safe crackpipe” programs in Vancouver,
Toronto and (Ottawa)
• Governments should not allow trade in
“drug equipment”
• Other side: harm reduction-reduces spread
of AIDs through dirty needle etc.

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