Semester-IV
Sub Name-medicinal chemistry-I (sub code-BP-402T)
Cholinergic Neurotransmitters
Objective
Biosynthesis and catabolism of acetylcholine.
Cholinergic receptors (Muscarinic and Nicotinic) and their distribution.
Metabolism of acetylcholine
Cholinergic receptors & their distribution
Parasympathomimetic Agents
A Parasympathomimetic drug, sometimes called a cholinomimetic drug or cholinergic
receptor stimulating agent is a substance that stimulates the parasympathetic nervous
system (PSNS). These chemicals are also called cholinergic drugs because acetylcholine (ACh)
is the neurotransmitter used by the PSNS. Chemicals in this family can act either directly by
stimulating the nicotinic or muscarinic receptors (thus mimicking acetylcholine), or indirectly by
inhibiting cholinesterase, promoting acetylcholine release, or other mechanisms.
Mechanism of Action
Acholinergic, Parasympathomimetic, synthetic analog of acetylcholine that stimulates
muscarinic, postganglionic parasympathetic receptors. Therapeutic Effect: Results in smooth
muscle contraction of the airways and increased tracheobronchial secretions.
1. Acetylcholine
trimethylammonium carbamate
2. Carbachol
(2-hydroxyethyl) trimethylammonium chloride carbamate.
3. Bethanechol
(2-hydroxypropyl) trimethylammonium chloride carbamate β-methylcholine chloride
carbamate
4. Methacholine
(2-hydroxypropyl) trimethylammonium chloride acetate
5. Pilocarpine
3-Ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)-methyl] furan-2 (3H)-one
6. Physostigmine
(3as,8ar)-1,3a,8-trimethyl-1H,2H,3H,3ah,8H,8ah-pyrrolo[2,3-b] indole-5-yl N-
methylcarbamate
7. Neostigmine
(m-hydroxyphenyl) trimethylammonium bromide dimethylcarbamate
8. Pyridostigmine
3-hydroxy-1-methylpyridinium bromide dimethylcarmate
9. Edrophonium chloride
Ethyl (m-hydroxyphenyl) trimethylammonium chloride
10. Tacrine hydrochloride
1,2,3,4-tetrahydro-9-aminoacridine hydrochloride
11. Ambenonium chloride
[oxalylbis (iminoethylene) ]bis [o-chlorobenzyl) diethyl ammonium] dichloride
12. Isofluorphate
Bis(propan-2-yl) fluorophosphates
13. Echothiophate iodide
(2-mercaptoethyl) trimethylammonium iodide
14. Parathione
O,O-diethyl-O-p-nitro phenyl phosphorothioate
15. Malathion
2-[(dimethoxyphosphinothioyl) thio] butanedioic acid diethyl ester
16. Pralidoxime chloride
2-formyl-1-methylpyridinium chloride oxime
Uses of Parasympathomimetic Agents
• Pilocarpine can be used to treat some disorders of the eye, such as glaucoma, which is
characterized by elevated intraocular pressure.
• Pilocarpine is an effective treatment for glaucoma because one effect is to contract the
ciliary muscle, which allows for fluid drainage of the eye.
Adverse effects of Parasympathomimetic Agents
• Cardiovascular symptoms: bradycardia, hypotension.
• Gastrointestinal symptoms: ↑ salivation, diarrhea, abdominal pain, uncontrolled urination.
• Increased sweating, salivation, and gastric secretion.
• Nausea.
• Ocular symptoms: miosis, lacrimation.
Cholinergic Blocking Agents:
Cholinergic Blocking Agents Drugs that block or inhibit the actions of acetylcholine (ACh) in
the parasympathetic nervous system (PSNS).
1. Atropine sulphate
(8-methyl-8-azabicylo [3.2.1] octan-3-yl) 3-hydroxy-2-phenylpropanoate
2. Hyoscyamine sulphate
[1R,5S)-8-methyl-8-azabicylo [3.2.1] octan-3-yl] (2S)-3-hydroxy-2-phenylpropanoate
sulfuric acid
3. Scopolamine hydrobromide
(1S, 3S, 5R, 6R,7S)-6,7-Epoxytropan-3-yl (2S)-3-hydroxy-2-phenylpropanoate
4. Homatropine hydrobromide
(8-methyl-8-azabicylo [3.2.1] octan-3yl) 2-hydroxy-2-phenylacetate hydrobromide
5. Ipratropium bromide
(8-methyl-8-propan-2-yl-8-azoniabicyclo [3.2.1] octan-3yl) 2-hydroxy-2-phenylpropanoate
bromide
6. Tropicamide
7. Cyclopentolate hydrochloride
2-dimethylaminoethyl 1-hydroxy-α-phenylcyclopentaneacetate hydrochloride
8. Clidinium bromide
3-hydroxy-1-methylquinuclidinium bromide
9. Dicyclomine hydrochloride
2-(diethyl amino) ethyl bicyclohexyl-1-carboxylate hydrochloride
10. Glycopyrrolate
3-hydroxy-1,1-dimethylpyrrolidinium bromide α-cyclopentylmandelate
11. Methantheline bromide
Diethyl(2-hydroxyethyl) methyl ammonium bromide xanthenes-9-carboxylate
12. Propantheline bromide
(2-hydroxy-ethyl) diisopropylmethylammonim bromide xanthenes-9-carboxylate
13. Benztropine mesylate
3α-(diphenylmethoxy)-1αH, 5α H-tropane methanesulfonate
14. Orphenadrine citrate
N,Ndimethyl-2-(o-methyl-α-phenylbenzyloxy) ethylamine citrate
15. Biperidine hydrochloride
1-bicyclo [2.2.1] hept-5-en-2yl]-1-phenyl-3-(piperidin-1-yl)propan-1-ol hydrochloride
16. Procyclidine hydrochloride
1-cyclohexyl-1phenyl-3-pyrrolidin-1-ol-ylpropan-1-ol hydrochloride
17. Tridihexethyl chloride
(3-cyclohexyl-3-hydroxy-3-phenylpropyl) trimethylammonium chloride
18. Isopropamide iodide
(3-carbamoyl-3,3-diphenylpropyl) diisopropylmethylammonim iodide
19. Ethopropazine hydrochloride
10-[2-(diethyl amino) propyl]phenothiazine monohydrochloride
Uses of Cholinergic Blocking Agents:
• Dizziness (including vertigo and motion sickness-related symptoms)
• Extrapyramidal symptoms, a potential side-effect of antipsychotic medications.
• Gastrointestinal disorders (e.g., peptic ulcers, diarrhea, pylorospasm, diverticulitis, ulcerative
colitis, nausea, and vomiting)
• Genitourinary disorders (e.g., cystitis, urethritis, and prostatitis)
• Insomnia, although usually only on a short-term basis
• Respiratory disorders (e.g., asthma, chronic bronchitis, and chronic obstructive pulmonary
disease [COPD]).
Adverse effects of Cholinergic Blocking Agents
• excess including seizures,
• muscle weakness, bradycardia, bronchoconstriction,
• Lacrimation, salivation, bronchorrhea, vomiting, and diarrhea.
Leaning outcomes
➢ Students know about the chemical synthesis of some drugs
