Week 2 B

Question 1

What is Amphetamine?

Answer 1

Also called benzedrine:used to counteract fatigue and increase endurance

Question 2

Things to note about structure

Answer 2

It is a beta-phenethylamine
It has a chiral centre (next to N)
Thus…2 optical isomers (D and L)
Dexedrine: D –isomer: rotates plane of polarized light in the dextro-rotatory direction and is a strong CNS Stimulant
Used as an elixir (tonic)

Question 3

First use of benzedrine

Answer 3

“benzedrine inhaler” –used to clear nasal passages, since benzedrine shrinks the nasal mucosa

Question 4

Legitimate uses of amphetamines

Answer 4

To treat narcolepsy (epileptic seizure disorder-person keeps falling asleep!)
Also (paradoxically) they calm down hyperkinetic children: perhaps due to release of serotonin

Question 5

Effects of moderate amphetamine

Answer 5

1. CNS stimulation: mood elevation, better concentration 2. Delay the onset of fatigue
2. Increase blood pressure 4. Increase respiration rate 5. raise blood sugar levels 6. dilate bronchii 7. divert blood flow from internal organs to skeletal muscle 8. constrict nasal mucous membranes 9 depress appetite 10. Improve athletic performance!!

Question 6

Methamphetamine optical isomers

Answer 6

Methamphetamine has a chiral centre (next to N ), thus D and L isomers exist
VERY different activities
D isomer: Strong CNS stimulant and banned from medical use in most countries
L isomer only stimulates the peripheral nervous system and is available as an OTC nasal inhaler in some countries

Question 7

Bennies

Answer 7

Benzedrine: stimulants often used by Baseball players (pitchers) to get hopped up and put more speed on the fastball (they think!)

Question 8

What is in “Aleve”: cold and sinus remedy?

Answer 8

2 active ingredients are (a) pseudoephedrine (a decongestant) and naproxen sodium ( a non steroidal anti-inflammatory agent (NSAID)).
Naproxen was approved to treat arthritis and other inflammation in 1976

Question 9

Things to note about Naproxen

Answer 9

Chiral centre!
3 carbon acid sidechain like ibuprophen
2 benzene rings vs. one for ASA, IBP
Available in the enteric form (because can be corrosive to stomach)
Sold as naproxen sodium –ie the Na salt of the carboxylic acid

Question 10

Naproxen is pure D isomer

Answer 10

D isomer is a strong analgesic used to treat arthritis pain
L isomer causes liver damage with NO analgesic effect
So…desirable to separate D and L

Question 11

Crystal Meth

Answer 11

Crystalline form of methamphetamine (methedrine or speed), mixture of D and L isomers
Same as benzedrine except N-CH3.
Easily made from pseudoephedrine (in decongestant medications)
Can be snorted , smoked, injected or swallowed

Question 12

Ecstasy

Answer 12

Semi-synthetic, patented by Merck in 1914 and then abandoned for ~60 years
Used in late 70’s for psychotherapy
Popular at raves:mood elevator
Known as MDMA : methylenedioxymethamphetamine
Raises blood pressure, heart rate, body temp.

Question 13

“Bath Salts; new in 2011-2”

Answer 13

Synthetic mixture of 3 stimulants:
Produce euphoria/lack of sleep and often violent behaviour
Contain mephedrone, Methylone and MDPV as active components
All related to methamphetamine, but alcohol oxidized to ketone (“one” suffix)
Also beta-phenethyamine derivatives

Question 14

Caffeine on blood vessels

Answer 14

Interestingly, caffeine acts as a vasodilator of the coronary arteries and hence increased peripheral circulation
BUT….caffeine acts as a vasoconstrictor to blood vessels in the brain

Question 15

Caffeine is an alkaloid

Answer 15

a natural product with physiological activity which contains 1 or more N atoms in its chemical structure

Question 16

Properties of Taurine

Answer 16

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!!

Question 17

Medical uses of Caffeine

Answer 17

Useful as a CNS stimulant if needed: increases peripheral circulation
Can be useful in treating migraine headaches (with ergot alkaloids)
Caffeine acts as a vasoconstrictor in the brain: one theory of migraines suggest they are due to increased blood flow to the brain ( due to vasodilation)
Women 2-3 x more likely to have migraines

Question 18

The cigarette as an efficient drug delivery system

Answer 18

Inhalation of smoke in lungs causes a rapid distribution of nicotine to the brain (within 10 seconds of inhalation)
Nicotine causes release of dopamine from the brain and stimulates the adrenal glands to secrete adrenaline
Need to sustain dopamine levels results in desire for repeated use

Question 19

Pharmacological effects of Nicotine

Answer 19

CNS: Stimulation
Respiration: rate increased
Heart rate: increased
Vascular system: Increased blood pressure ; constriction of peripheral vessels
Adrenal system: release of epinephrine (adrenaline)
GI tract: increased peristalsis
Kidneys: reduced urine flow
Blood composition: Elevated levels of free fatty acids –possible hardening of the arteries
HDL (“good cholesterol”) levels: reduced

Question 20

Cigarettes

Answer 20

Cigarette smoking is the SINGLE MOST cause of death and disability in NA

Question 21

Skin Patches

Answer 21

Designed to wean a smoker off nicotine over a 7-10 week period
3 strengths available: 21, 14 &7 mg of nicotine per day
BUT…can lead to rashes, insomnia, seats, rapid heart rate

Question 22

Nicotine as a treatment

Answer 22

Nicotine patches boosted schizophrenics short term memory and mental processing abilities and improved attention spans