Isocyclamine

An anticholinergic drug

Isocyclamine
INN
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Routes of administration
Pregnancy category
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Legal status
CAS Number	77-29-8
PubChem	7180
DrugBank
ChemSpider	6910
KEGG	D04695

Isocyclamine is a pharmaceutical drug that belongs to the class of anticholinergic agents. It is primarily used for its effects on the nervous system, particularly in the treatment of gastrointestinal disorders and spasms.

Chemical Structure and Properties

Chemical structure of isocyclamine

Isocyclamine is chemically known as 2-(1-cyclohexyl-1-phenyl-3-pyrrolidinyl)ethanol. It has a molecular formula of C₁₈H₂₇NO and a molecular weight of 273.42 g/mol. The structure consists of a pyrrolidine ring, a cyclohexane ring, and a phenyl group, which contribute to its anticholinergic properties.

Pharmacology

Isocyclamine acts as an anticholinergic agent by inhibiting the action of the neurotransmitter acetylcholine at muscarinic receptors. This inhibition leads to a decrease in involuntary muscle movements and secretions, making it useful in treating conditions like irritable bowel syndrome and other gastrointestinal disorders characterized by excessive motility and spasms.

Medical Uses

Isocyclamine is used in the management of various conditions that benefit from its anticholinergic effects. These include:

• Irritable bowel syndrome
• Peptic ulcer disease
• Spastic colon
• Gastritis

Side Effects

The use of isocyclamine can lead to several side effects, typical of anticholinergic drugs. These may include:

• Dry mouth
• Blurred vision
• Constipation
• Urinary retention
• Tachycardia

Mechanism of Action

Isocyclamine works by blocking the muscarinic acetylcholine receptors in the central nervous system and peripheral nervous system. This blockade reduces the effects of acetylcholine, leading to decreased muscle contractions and secretions in the gastrointestinal tract.

Synthesis

The synthesis of isocyclamine involves the reaction of cyclohexanone with phenylmagnesium bromide to form a tertiary alcohol, which is then reacted with pyrrolidine to yield the final product.

Related Pages

• Anticholinergic
• Muscarinic receptor
• Gastrointestinal tract
• Neurotransmitter