Benztropine

IUPAC nomenclature

(3-endo)-3-(Diphenylmethoxy)-8-methyl-8-azabicyclo[3.2.1]octane

Classification

Benztropine is an acetylcholine antagonist. It is a muscarinic antagonist.

Physiochemical Properties

Mechanism of Action

Benztropine inhibits uptake of dopamine and thus, helps in reducing the symptoms of Parkinson’s diseases.

Structure Activity Relationship

• Either R₁ or R₂ must be heterocyclic or carbocyclic.
• The R₃ group can be hydrogen, hydroxyl, hydroxymethyl or amide.
• Most potent derivatives has X as an ester.
• X can also be either oxygen or absent completely.
• The N substituent can be quaternary ammonium salt or tertiary amine or both with different alkyl groups.
• Maximum potency obtained when the distance between the ring substituted carbons is 2 carbon units.

Method of synthesis

i. Diphenylmethane undergoes bromination to form bromodiphenylmethane.

ii. It is followed by condensation with tropine and purification to get benztropin.

Therapeutic Uses

Benztropine is used for:

• Treatment of symptoms of Parkinson’s disease

Side Effects

Side effects of benztropine are:

• Dry mouth
• Dizziness
• Constipation
• Blurred vision
• Nervousness
• Nausea
• Flushing

MCQ

Q.1 Match the following with correct SAR of the drug benztropine-

 a) i-A, ii-D

b) i-A, ii-C

c) i-B, ii-C

d) i-C, ii-D

Q.2 Correct sequence for the True/False for correct IUPAC names of the drug can be?

• Benztropine: (3-endo)-3-(Diphenylmethoxy)-8-methyl-8-azabicyclo[3.2.1]octane
• Fesoterodine: [2-[(1R)-3-(Di(propan-2-yl)amino)-1-phenylpropyl]-4-(hydroxymethyl)phenyl] 2-methylpropanoate
• Flurazepam: 8-chloro-6-(2-fluorophenyl)-1-methyl-4H-imidazo[1,5-a][1,4]benzodiazepine
• Midazolam: 7-Chloro-1-[2-(diethylamino)ethyl]-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one

a) TFTF

b) TTFF

c) FFTT

d) TTFT

Q.3 Number of chiral carbons present in the structure of Benztropine?

a) 0

b) 1

c) 2

d) 3

Q.4 Benztropine helps in reducing the symptoms of Parkinson’s diseases by?

a) Stimulating the uptake of dopamine

b) Binding with GABA receptor complex

c) Inhibiting the uptake of dopamine

d) Both a) and b)

Q.5 Which amongst the following is a therapeutic use of drug benztropine?

a) Treatment of Insomnia

b) Treatment of Alzheimer’s disease

c) Treatment of Parkinson’s disease

d) Treatment of Asthma

Q.6 Which of the following drug and their classification are correct?

I. Benztropine: acetylcholine antagonist

II. Fesoterodine: Nitrogen mustard

III. Flurazepam: benzodiazepine sedative hypnotic

IV. Midazolam: Acetylcholine Nicotinic receptor antagonist

a) I, III

b) I, III, IV

c) II, IV

d) I, II, III, IV 

Q.7 When bromodiphenyl methane undergoes condensation with tropine, the drug formed is?

a) Midazolam

b) Fesoterodine

c) Benztropine

d) Methysergide 

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ANSWERS

1-a

2-b

3-d

4-c

5-c

6-a

7-c