PY420 (Med. Chem. I)							Quiz # 4
November 19, 1996							Dr. Riley

Answers are given in RED!
Answer the following questions about the drug structures shown below.

1. Match the drug structures with their correct structural classification. 
	(    5  )   Indole alkyl amine		(    2  )   Dibenzazepine
	(    3  )   Butyrophenone		(    6  )   Alpha-Hydrazino acid
	(    4  )   Phenothiazine		(    1  )   Phenethyllamine
2. Match the drug structures with their correct pharmacological action. 
	(    6  )  DOPA decarboxylase inhibitor	(    1  )  5-HT releasing agent
	(    4  )  Dopamine receptor antagonist	(    2  )  Biogenic amine reuptake inhibitor
		   (D2 =  D1 blocking potency)	(    5  )  Dopamine receptor antagonist
	(    3  )  Biogenic amine neurotransmitter
		   (D2 > D1 blocking potency)
3. List the drug structures (by #) that are organic bases.

1 and 2 (2º-amines), 3 and 4 (3º-amines), 5 (1º-amine) and 6 (hydrazine)

4. Answer the following questions about drug #1.
a. Drug #1 is an anorectic (appetite suppressant) that affects the neurotransmitter:

Serotonin (5-HT) releasing agents

b. Drug #1 is a poor substrate for MAO. What specific structural feature of drug #1 is responsible for this.

The alpha-CH3 group reduces affinity of this drug for MAO.

c. The neurochemical actions of drug #1 ARE stereoselective.

5. Draw structures of analogues of drug #2 having the following properties::

a. Greater inhibitory potency at 5-HT uptake sites.

b. A carbon bioisostere having similar therapeutic utility.

6. Briefly describe a possible therapeutic advantage for a derivative of drug #3 which has R = OC(CH2)8CH3 instead of R = H.

7. Draw the structure of an analogue of drug #4 that has greater dopamine receptor blocking potency.

8. Draw the structure of a metabolite of drug #5 resulting from MAO activity.

9. Answer the following questions about drug #6:
a. Draw the ionic structure of drug #6 as it would exist at physiologic pH.

b. Drug #6 is an inhibitor of the enzyme aromatic aminoacid decarboxylase. Show the metabolic reaction catalyzed by this enzyme and comment on the therapeutic rationale for inhibiting this reaction.

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