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Integrated Drug Structure, Action, and Therapeutics > Stimulants and Drugs of Abuse - Proteau > Flashcards

Stimulants and Drugs of Abuse - Proteau Flashcards

1
Q

What stimulants use 1A2?

A

Caffeine, theophylline, MDMA

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2
Q

What stimulants use MAO?

A

Mescaline

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3
Q

What stimulants use 2D6?

A

MDMA, atomoxetine

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4
Q

What stimulants use esterases?

A

Methylphenidate

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5
Q

What drug uses hydrolysis and oxidation? What induction and inhibition properties does it have?

A

Modafinil. It inhibits 2C19 moderately and induces 3A4 moderately.

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6
Q

Why does THC have so many different metabolites?

A

Because it can be oxidized in multiple areas.

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7
Q

How is nabilone different than THC?

A

It has fewer sites of oxidation because of the double-bonded oxygen (blocking allylic P450 oxidation) and the double methyl group (blocks benzylic oxidation)

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8
Q

What structural feature seems to contribute to the euphoric effects of the cannabinoids?

A

The closed ring contributes to the euphoric effects. Opening the ring in cannabidiol seems to be the reason there are no euphoric effects.

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9
Q

What is something that could affect the metabolism of caffeine?

A

It is metabolized by 1A2, which can be induced by cigarette smoke. SO smokers usually need to drink more caffeine to feel the effects than non-smokers. There are also genetic polymorphisms associated with 1A2, so caffeine can affect people differently.

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10
Q

What is caffeine metabolized to?

A

1A2 to paraxanthine (3 methyl is preferentially removed), then to 1-methyl uric acid (7 methyl removed).

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11
Q

How is theophylline structurally similar to caffeine?

A

Same except it has the 7-methyl removed.

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12
Q

What is theophylline used for?

A

A bronchodilator to treat asthma.

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13
Q

What is the metabolism of theophylline?

A

1A2 can help it undergoes metabolism to 1- or 3-methylxanthine or 1,3-dimethy uric acid.

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14
Q

What structural feature of amphetamine blocks MAO metabolism?

A

The alpha methyl.

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15
Q

Does the S or R enantiomer of amphetamine have greater CNS stimulant effects?

A

The S has greater stimulant effects.

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16
Q

What metabolism does amphetamine undergo?

A

P450 de-amination reaction to phenylacetone (inactive)

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17
Q

What is the lysine prodrug of dextroamphetamine? What enantiomer(s) is/are used?

A

Lisdexamphetamine (S enantiomer)

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18
Q

What is the prodrug of both amphetamine and theophylline? What is required to release the active component?

A

Fenethylline. P450 oxidative release is required (slow). It is schedule I in US.

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19
Q

How is amphetamine modified to get phentermine?

A

Add 2nd alpha-methyl, which further decreases the rate of metabolism. There are reduced stimulant properties compared to amphetamine (less habit-forming).

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20
Q

What drugs are used to manage obesity?

A

Phentermine, Diethylpropion

21
Q

What does N-methylation do to amphetamine?

A

It increases the CNS activity and increases the abuse potential. (This is methamphetamine). The lipophilicity is increased, which gives it more rapid CNS access.

22
Q

In methamphetamine, which isomer has greater stimulant properties?

A

The S isomer has greater stimulant properties. The R enantiomer is levmetamphetamine, which was formerly in Vick’s vapor inhaler. (This would make you test positive for meth).

23
Q

What does carbonyl substitution on the beta carbon do? Bulky diethyl group substitution?

A

Both reduce stimulant properties.

24
Q

Diethylpropion has what properties compared to amphetamine?

A

Decreased stimulant and decreased potential relative to other amphetamines. Used to manage weight-loss.

25
Q

What is the active ingredient in peyote cactus?

A

Mescaline

26
Q

What structural features does mescaline have?

A

Alkoxy aromatic ring substituents. Leads to psychotomimetic and hallucinogenic effects (5HT effects). Poor oral activity.

27
Q

What metabolism does mescaline go through?

A

Rapid MAO metabolism (A and B)

28
Q

What is MDMA an irreversible inhibitor of?

A

2D6

29
Q

How is MDMA metabolized?

A

MDMA uses 2D6 and 1A2 to remove catechol.

30
Q

What does COMT do?

A

Removes H and add CH3 to O-ring.

31
Q

What part does COMT play in the metabolism of MDMA?

A

It forms HMMA from the 2D6 and 1A2 product.

32
Q

What does oxidation do to the MDMA metabolite?

A

It forms an orthoquinone metabolite (two double-bonded oxygens). This possibly contributes to neurotoxic effects.

33
Q

What drug has a capped catechol that helps contribute to good oral activity and good CNS access?

A

MDMA

34
Q

What is methylphenidate formulated as?

A

R,R and S,S racemates. Dexmethylphenidate is active, and available as a separate product.

35
Q

What metabolism does methylphenidate undergo? What product does it form?

A

T1/2 = 2-3 hours, using esterase to form ritalinic acid (inactive)

36
Q

What antidepressant is also an irreversible inhibitor of CYP2D6 like MDMA?

A

Paroxetine

37
Q

What is atomoxetine

A

A selective NE reuptake inhibitor. A non-stimulant treating ADHD.

38
Q

What metabolism dose atomoxetine undergo?

A

2D6 major metabolism to 4-hydroxyatomoxetine (active) and then glucuronidation to an inactive product.

39
Q

What is the half-life of atomoxetine?

A

EM = 5 hours, PM = 20 hours

40
Q

What structural features is this lacking to be an antidepressant?

A

Lacking EWGs on rings that would make it an SSRI. Does not inhibit 2D6.

41
Q

What is the half-life of the active metabolite of atomoxetine?

A

6-8 hours

42
Q

What does modafinil treat?

A

Narcolepsy. It promotes wakefulness through an unclear mechanism.

43
Q

What is modafinil formulated as?

A

As a racemic mixture. Lone electron pair occupies fourth site. Both enantiomers are active, but R has the longer half-life of 15 hours (3-fold over S). R also has better pharmacodynamics than the mixture.

44
Q

What is the metabolism of modafinil?

A

1) Hydrolysis of primary amide
2) Oxidation to the sulfone
(both are inactive)

45
Q

What is the name of the separately marketed R enantiomer of modafinil?

A

Armodafanil (Nuvigil)

46
Q

What are the induction/inhibition properties of the modafinil enantiomers?

A
  • Induce 3A4 moderately

- Inhibit 2C19 moderately

47
Q

What drug has a slighter longer duration and is improved over THC?

A

Nabilone. It is improved because it varies less in its oxidative potential.

48
Q

What drug is in clinical trials for treating certain types of seizures?

A

Cannabidiol.

Integrated Drug Structure, Action, and Therapeutics (20 decks)

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