Nitroglycerine

Or

Glyceryl trinitrate

IUPAC nomenclature

1,3-dinitrooxypropan-2-yl nitrate; [3-(nitrooxy)-2-[(nitrooxy)methyl]propyl] nitrate; 1,2,3-trinitroxypropane.

Classification

• Organic nitrate antianginal drug

Physiochemical Properties

Mechanism of Action

i. Conversion of nitroglycerine into nitric oxide (NO) by mitochondrial aldehyde dehydrogenase (mtALDH).

ii. NO activates enzyme guanylate cyclase.

iii. This activates the synthesis of cyclic guanosin 3’,5’-monophosphate (cGMP).

iv. Due to this, there is an activation of the cascade of protein kinase-dependent phosphorylation events in the smooth muscles.

v. Relaxation is caused in the smooth muscles due to dephosphorylation of the myosin light chain of smooth muscles, due to which, there is increased in blood flow in veins, arteries and cardiac tissues.

vi. Heart has to do lesser work and blood pressure and angina tension also reduces. There is increased blood flow in the myocardium.

Structure Activity Relationship

General structure activity of organic nitrate antianginal drugs be summarized as:

• The number of nitrate groups determines the potency of organic nitrate for guanylate cyclase activation.
• Increase in nitric group increases the potency.
• Increase in lipophillicity doesn’t have major effect over activation of drug.

Method of synthesis

Nitration of glycerol with nitric acid produces nitroglycerine. [2]

Medicinal Uses

Nitroglycerine is used for treatment of:

• Angina and chest pain due to cardiovascular disease.
• Peri-operative hypertension
• Inducing intra-operative hypotension
• Acute heart failure
• Pain caused by anal fissure
• Prevention of acute angina attacks

Side Effects

Side effects of Nitroglycerine are:

• Headache
• Nausea
• Dizziness
• Lightheadedness
• Flushing
• Allergic reactions

MCQs

Q.1 Match the following with correct SAR of the organic nitrate antianginal drugs-

 a) i-A, ii-C

b) i-A, ii-D

c) i-B, ii-C

d) i-B, ii-D

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

• Nitroglycerine: 1,3-dinitrooxypropan-2-yl nitrate; [3-(nitrooxy)-2-[(nitrooxy)methyl]propyl] nitrate; 1,2,3-trinitroxypropane.
• Diclofenac: [2-(2,6-Dichloroanilino)phenyl]acetic acid
• Levallorphan: (−)-17-allylmorphinan-3-ol
• Sodium salicylate: Sodium;2-hydroxybenzoate

a) FFTF

b) FFFF

c) TTFT

d) TTTT

Q.3 Molecular weight of drug nitroglycerine is?

a) 227.09 gm/mol

b) 652.36 gm/mol

c) 142.45 gm/mol

d) 741 gm/mol

Q.4 Conversion of nitroglycerine into NO is done by?

a) Nitrase enzyme

b) Mitochondrial aldehyde dehyrogenase enzyme

c) Mitochondrial deaminase enzyme

d) None of the above

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

a) Treatment of angina

b) Treatment of prostate cancer

c) As an antidiabetic drug

d) As an anesthetic

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

I. Nitroglycerine: Organic nitrate antianginal drug

II. Physostigmine: Cholinestrase inhibitor

III. Felbamate: Anticonvulsant

IV. Mechlorethamine: Antineoplastic drug

a) I ,II, III

b) II, IV

c) I, II, III, IV

d) I, III 

Q.7 Nitroglycerine can be prepared by nitration of?

a) Glyceraldehyde

b) Glycerol

c) Trinitroglyceraldehyde

d) Trinitroglycerol

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ANSWERS

1-b

2-d

3-a

4-b

5-a

6-c

7-b

REFERENCES