Questions: Organic Medicinal Chemistry

1. What is the pharmacologic of the drug below:

A. vasodilator
B. vasoconstrictor
C. both A and B

2. Which of the following drugs is classified as a lipid lowering agent?

A. B. C. both A and B

3. These drugs reduces sugar absorption, except:

A. B. C.

4. An alpha receptor pharmacologic activity of adrenergic amines are produced if the substituent attached to N is:
A. ethyl B. isopropyl C. tertbutyl D. methyl

5. Which of the following statements concerning adrenergic agonist are TRUE?

I. catecholamines are deactivated by the methylation of the methyl hydroxyl group
II. the ethylamine chain is essential to their activity
III. N-substituent alter drug duration of action only
A. I and II B. III only C. II and III
6. It is also known as CATECHOL:
A. methyl hydroxyl phenol C. phenoxymethyl
B. methyl hydroxyl benzene D. none of the choices
7. Barbiturates containing a sulfur atom in its structure are usually:
A. short acting C. long acting
B. intermediate acting D. ultra short acting
8. Which of the following opioids contains a phenanthrene nucleus?
A. Morphine C. Methadone
B. Meperidine D. Fentanyl
9. Thimerosal is an anti-infective agent patented by Eli Lilly and Company under the trade name Merthiolate. Thiomersal is a
compound used as a preservative in vaccines since the 1930s to prevent bacterial and fungal contamination, but it was later
found to contribute to the development of autism and other brain development disorders in children. What is the metal ion
component of thimerosal that may cause these adverse effects?
A. Phosphorus B. Sulfur C. Sodium D. Mercury

10. It is a competitive inhibitor of para-aminobenzoic acid

A. Sulfanilamide B. Sulfadiazine C. Sulfathiazole D. all of the above

 
  

11.Which of the following drugs is poorly absorbed in the stomach due to acid-catalyzed degradation

A. B. C.

12. Ascorbic acid and tetracycline are:

A. enols C. ethers
B. esters D. amines
13. It structurally contains benzylsulfonyl ureas:
A. oral hypoglycemic C. anti-inflammatory
B. diuretics D. spasmolytic
14. The functional group of Codeine and Scopolamine is a/an:
A. amine C. ester
B. alcohol D. ether
15. It is chemically known as hydroxybenzoic acid:
A. acetic acid C. oxalic acid
B. salicylic acid D. citric acid
16. 1,3-dimethylxanthine is:
A. caffeine C. theophylline
B. theobromine D. aminophylline
17. Which of the following liquid anesthetics is the least volative?
A. diethyl ether C. chloroform
B. methoxyflurane D. halothane
18. All of the following anesthetics are gases at room temperature, EXCEPT:
A. nitrous oxide C. ethylene
B. halothane D. cyclopropane
19. Local anesthetic that is derivative of benzoic acid is:
A. Lidocaine C. Dibucaine
B. Procaine D. Bupivacaine
20. Xanthine derivatives are indicated in/for:
A. asthma C. antipyretic
B. analgesic D. epilepsy
21. Which of the following is a weak acid:
A. Phenobarbital C. Quinine
B. Codeine D. Reserpine
22. Paracetamol is a/an:
A. salicylate C. aniline derivative
B. pyrazolone D. azocaine detivative
23. Which of the following is not a phenothiazine derivatie?
A. Nortriptyline C. Thioridazine
B. Chlorpromazine D. Flupenazine
24. Which of the following anesthetic is most volatile?
A. methoxyflurane C. halothane
B. diethyl ether D. chloroform
25. Procaine is a/an:
A. amine C. alcohol
B. ester D. ketone

 
  

26. The onset and duration of barbiturate action is mainly a function of its:
A. lipid solubility C. plasma binding
B. renal excretion D. method of administration
27. In which of the following groups of drugs is the mechanism of action for diuresis
associated with a free –SO2NH2 group?
A. carbonic anhydrase inhibitor C. aldosterone antagonists
B. mercurial diuretics D. thiazide diuretics
28. It is the structural analog of Diphenoxylate
A. Dilantin C. Meperidine
B. Codeine D. Naloxone
29. The antihypertensive agent Diazoxide is most similar in chemical structure to which of the following diuretics
A. Spironolactone C. Acetazolamide
B. Furosemide D. Hydrochlorthiazide
30. The piperidine moiety of morphine is common with the following analgesics, except:
A. Methadone C. Oxycodone
B. Hydroxymorphone D. Heroin
31. Of the congeners, the one that is used primarily for its analgesic activity is:
A. Diphenoxylate C. Pentazocaine
B. Hydroxymorphone D. Apomorphine
32. The activity of the following drugs is dependent upon a p-phenyl-N-alkylpiperidine, except.
A. Meperidine C. Imipramine
B. Morphine D. Diphenoxylate
33. Dibenzazepine derivatives having a methyl or dimethyl aminopropyl group attached to thering nitrogen have:
A. local anesthetic activity C. opioid antagonistic property
B. antidepressant property D. general anesthetic property
34. Which of the following compounds, because of its chemical relationship to Fluphenazine would most likely cause similar
side effects?
A. Thioridazine C. Chlorpromazine
B. Prochlorpenazine D. Triflupromazine
For numbers 35-39, refer to the structure below:

35. Name this natural alkaloid:

A. Atropine C. Phenylpropanolamine
B. Morphine D. Spingosine
36. Which is true about substitution of 6-OH group?
A. its removal increases the activity
B. its acetylation increases its addictive property
C. its methylation decreases analgesic property
D. its methylation result to increase polarity
37. What is expected of the pharmacokinetic property of this drug?
A. it is easily hydrolyzed
B. it passes through the blood brain barrier more readily than N-dealkylated analogue
C. the unprotonated tertiary nitrogen accounts for its ease of excretion

 
  

D. its sulfate salt is stored in adipose tissue

38. Which is true about substitution of phenolic –OH group?
A. its removal increases analgesic property
B. methylation removes the analgesic property of the drug when administered intra-cerebrally
C. acetylation decreases the chance of the drug passing through the blood-brain barrier
D. increasing electron density by adding electron withdrawing substituent at C-1 position inactivates the drug.
39. Which part of the molecule is not required for analgesia?
A. Ring A C. nitrogen atom
B. ether bridge D. C7-C8 double bond

40. The following drugs are classified as a macrolide, except:

A. Kanamycin B. Azithromycin C. Erythromycin D. Klarithromycin

41. The optimal diuretic activity of benzthiazides on certain structural features. These includes:
I. saturation of the 3,4-double bond increases potency
II. methyl groups at position 2 decreases potency
III. replacement of the sulfonyl group in position 1 shortens the activity
A. I only C. I and II
B. III only D. II and III
42. Amide type local anesthetics are:
A. short acting C. long acting
B. intermediate acting D. none of the choices
43. Antibacterial potencies of primary alcohol increases with molecular weight up to ____ only:
A. C 3 C. C 6
B. C 4 D. C 8
44. 1,3-butadiene is classified as:
A. allenic C. propanone
B. conjugated D. A and C
45. The following are semi-synthetic penicillins, EXCEPT:
A. Methicillin C. Pen G
B. Ampicillin D. Cloxacillin
46. Which of the following Erythromycin is least susceptible to gastric acid degradation?
I. estolate II. base III. ethylsuccinate
A. I only C. I and II
B. III only D. II and III
47. Macrocyclic lactones containing 12 to 20 carbon atoms in the primary ring:
A. Penicillins C. Macrolides
B. Aminoglycosides D. Cephalosphorins
48. Which of the following agents has/have a beta-phenylethylamine structure with the phenyl moiety containing
ortho-dihydroxy substitution?
I. Epinephrine II. Ephedrine III. Dopamine
A. I only D. II and III
B. II only E. I, II and III
C. I and III
49.The number of carbon atoms separating the amino from phenyl ring that will produce maximal sympathomimetic
activity is:
A. 1 B. 2 C. 3 D. 4 E. 5

 
  

50. What is the common use of drugs possessing the structure given below?

A. Anticonvulsant D. Antipsychotic
B. Sedative-hypnotic E. Antidepressant
C. Intravenous anesthetics
51. Which of the following barbiturates is the most water-soluble?
A. Amobarbital D. Secobarbital
B. Methohexital E. Phenobarbital
C. Pentobarbital
52. Which of the following metabolites of methoxyflurane is primarily responsible for the nephrotoxicity associated with this
inhalation anesthetic?
A. Fluoride C. Dichloroacetic acid
B. Oxalic acid D. Bromide
53. Agents possessing the structure given below are most commonly used for what condition?

A. Seizure disorder D. Psychosis

B. Bacterial infection E. Bipolar disorder
C. Anticholinesterase

54. What is the most potent effect of trimethyl substitutions in positions 1, 3, and 7 of the xanthine molecule?
A. Diuresis C. CNS stimulation
B. Coronary vasodilation D. Skeletal muscle relaxation
55. Which of the following drug is also known as 1,3-dimethylxanthine?
A. Theophylline C. Pentoxifylline
B. Caffeine D. Doxofylline
56. Which of the following drugs has the following structure: CH3CH2CH2C(CH3CH2CH2)HCOOH
A. Carbamazepine C. Ethacrynic acid
B. Primadone D. Valproic acid
57. This drug is also known by the chemical name, (+)-N,alpha-dimethylphenylamine
A. Amphetamine C. Ephedrine
B. Methamphetamine D. Phentermine
58. The potent vasoconstrictor Angiotensin II is a polypeptide containing how many amino acids?
A. 5 C. 15
B. 8 D. 20
59. Which of the following agents is an example of an H2 antihistamine?
A. Ranitidine C. Omeprazole
B. Hydroxyzine D. Terfenadine
60. The proton pump inhibitors are chemically known as?
A. ethenediamines C. hydropropanes
B. propanimidamides D. benzimidazoles
61. Which functional moieties generally make up the hydrophilic center of local anesthetics?

 
  

A. thiols C. primary or secondary alcohols

B. secondary or tertiary amines D. carboxylate
62. Which portion of the general structure of the local anesthetics is important in the ability of the drug to penetrate
through the cell membrane of the axon?
A. Lipophilic center C. Amide group
B. Ester group D. Hydrophilic center
63. Which of the following choices correctly illustrates the general structure of local anesthetics?
A. lipophilic center – bridge – ester/amide – hydrophilic center
B. bridge – lipophilic center –hydrophilic center - ester/amide
C. lipophilic center –ester/amide - bridge – hydrophilic center
D. hydrophilic center– bridge – ester/amide – lipophilic center
64. Which portion of the general structure of the local anesthetics is responsible for binding to the sodium channels?
A. Lipophilic center C. Hydrophilic center
B. Ester group D. Bridge alkyl group

65. The structure below represents what therapeutic class?

A. Diazoxide C. Thiazide
B. Sulfonamide D. Sulfonylurea
66. Which hormone possesses the following structure?

A. Glucogen C. Thyroxine
B. Estrogen D. Insulin
67. What are the active forms of Simvastatin and Lovastatin than can inhibit the rate- limiting step in
cholesterol synthesis?
A. alpha-hydroxy acids C. enols
B. beta-hydroxy acids D. 2-ketones
68. What is the IUPAC name of Valproic acid?
A. 2-methylpropanoic acid C. 2-propylpentanoic acid
B. 2-ethylbutanoic acid D. 2-butylhexanoic acid
69. What is the common functional moiety present in the molecules of the clinically useful Carbonic Anhydrase Inhibitor?
A. benzene C. chlorobenzene
B. CH3 D. SNO2H2
70. Which of the following compounds is classified as a “thiazide-like diuretic” because its mechanism of action and
pharmacologic properties are similar to the thiazides although its chemical structure does not have the benzothiadiazine-1, 1-
dioxide nucleus?
A. Chlorthalidone C. Benzthiazide
B. Furosemide D. Hydrochlorthiazide
71. Which of the following compounds is a 5-sulfamoylanthranilic acid derivative?
A. Furosemide C. Sulfadiazine
B. Cocaine D. Indapamide
72. Which of the following gases is associated with the mechanism of action of drugs like Sildenifil and Nitroglycerin?
A. carbon dioxide C. nitric oxide

 
  

B. oxygen D. nitrous oxide

73. Which of the following Calcium channel blockers is a benzothiazepine?
A. Verapamil C. Diltiazem
B. Nifedipine D. Amlodipine
74. Which clinically useful analgesic possesses the structure given below?

A. Acetaminophen C. Aspirin
B. Diclofenac D. Ibuprofen
75. What is the clinical use of the dextro isomer of the opioid N-methylmorphinan?
A. analgesic C. anesthetics
B. sedative D. antitussive
76. Which of the following opioids contains a phenanthrene nucleus?
A. Morphine C. Methadone
B. Meperidine D. Fentanyl
77. The simplest ketone is:
A. methadone C. propanone
B. ethanone D. butanone

78. Which of the following neuromuscular blockers possesses a steroid nucleus?

A. Atracurium C. Tubocurarine
B. Pancuronium D. Doxacurium

79. Which of the following drugs will promote a broader volume of distribution?

A. B. C. D. none of the choices

80. A natural acetylcholinesterase inhibitor used as antidote for atropine overdose.

A. physostigmine C. pyridostigmine
B. neostigmine D. none of the choices
81. Which of the following group is present in a parasympathomimetic drug?
A. trimethylammonium group C. phenylethylamine
B. ethylester D. catecholamine
82. A drug is a substrate of COMT if it has:
N
A. B. CH2CH2NH2 C. OH D. R C O O CH2CH3
OH

N
83. The following drug has the imidazoline nucleus except:
A. Xylometazoline C. Naphazoline
B. Oxymetazoline D. phenylephrine
84. A synthetic acetylcholinesterase inhibitor with benzanaminium parent compound used as antidote for tubocurarine
poisoning.
A. physostigmine C. pyridostigmine
B. neostigmine D. none of the choices

 
  

Refer to the structure of Vitamin K for nos. 85-89:

R1
R2

R3

R4

85. What substituent must be attached to R2 for optimum antihemorrhagic activity?

A. Methyl C. dimethylamino
B. alkyl group containing 10 or more carbon atoms D. all
86. All of the following can be an R3 substituent except:
A. dimethylamino C. OH
B. phytyl D. OCH
87. The following will contribute to increase antihemorrhagic activity except:
A. R4 is a OH group C. Ring A is substituted
B. R3 is an alkyl group containing more than 10 Carbon atoms D. R2 is methyl
88. What is the functional group present in R1 and R4 of Vitamin K4.
A. Ketone C. Alcohol
B. Ester D. Carboxylic acid
89. What is the functional group present in R1 and R4 of Vitamin K1.
A. Ketone C. Alcohol
B. Ester D. Carboxylic acid
90. Side chain substituent at carbon 3 of vitamin K1 is called
A. phytyl C. carbonyl
B. prenyl D. carboxyl

91-94: Choices: A. Short Acting – Acetylcholinesterase inhibitor

B. Long Acting – Acetylcholinesterase inhibitor

B 91. B 93.

A 92. A 94.

95-98. Choices: A. Direct Acting Adrenergic Agonist

B. Direct Acting Cholinergic Agonist
C. Indirect Acting Adrenergic Agonist
D. Indirect Acting Cholinergic Agonist

 
  

D 95. C 97.

A 96. B 98.

99. Determine the appropriate drug for the treatment asthma?

A. B. C.
Salbutamol
100. Determine the appropriate drug for the treatment hypertension?

A. B. C.
Propranolol- Beta blocker