Methysergide

IUPAC nomenclature

(6aR,9R)-N-[(2S)-1-Hydroxybutan-2-yl]-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide.

Classification

Methysergide is an ergot alkaloid. It is a serotonin antagonist.

Physiochemical Properties

Mechanism of Action

• It directly stimulates the CNS which stimulates the smooth muscles leads to vasoconstriction
• It also produces some α-adrenergic blockings. [1]

Structure Activity Relationship

• d-isomers of lysergic acid is inactive. It must be in the l-form.
• Antimigraine effect of the drug is due to the 9-10 double bond.

Method of synthesis

Methyl group and butanolamide group is added to the lysergic acid to give methysergide. [2]

Therapeutic Uses

Methysergide is used for:

• Migraine headaches
• Cluster headaches
• Prevention of migrains

 Side Effects

Side effects of methysergide are:

• Retroperitoneal fibrosis
• Left-side cardiac valve dysfunction

MCQs

Q.1 “(6aR,9R)-N-[(2S)-1-Hydroxybutan-2-yl]-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide” is the IUPAC nomenclature of which drug?

a) Methysergide

b) Propanolol

c) Phenoxybenzamine

d) Tamsulosin

Q.2 Melting point of Methysergide is?

a) 124°C

b) 195°C

c) 221°C

d) 143°C

Q.3 Match the following with correct classifications of the drugs.

 a) i-B, ii-C, iii-A, iv-D

b) i-D, ii-A, iii-C, iv-B

c) i-C, ii-A, iii-D, iv-B

d) i-C, ii-A, iii-B, iv-D

Q.4 Correct steps for the mechanism of action of the drug methysergide?

I. Vasoconstriction

II. Stimulation of smooth muscles

III. Stimulation of CNS

a) III – II – I

b) I – III – II

c) II – I – III

d) II – III – I

Q.5   Correct sequence for True and False for the given statements related with the SAR of drug methysergide?

• d-isomers of lysergic acid is inactive. It must be in the l-form.
• Antimigraine effect of the drug is due to the 9-10 double bond.

a) TT

b) FT

c)TF

d)FF

Q.6 When methyl group and butanolamide groups are added to the lysergic acid, it produces?

a) Methamphetamine

b) Alfuzosin

c) Tetrahydrozoline

d) Oxymetazoline

 Q.7 The drug Methysergide is mainly used for?

a) Hypotension

b) Hypertension

c) Migraine headache

d) None of these

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ANSWERS

1-a

2-b

3-d

4-a

5-a

6-c

7-c

REFERENCES