Tropicamide

Tropicamide

Cat Number
API1508754
CAS Number
1508-75-4

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CAS Number
1508-75-4
EINECS
216-140-2
Storage
2-8℃
Synonyms
(2R)-N-ethyl-3-hydroxy-2-phenyl-N-(pyridin-4-ylMethyl)propanaMide
Molecular Formula
C17H20N2O2
Molecular Weight
284.35
Smiles
CCN(CC1=CC=NC=C1)C(=O)C(CO)C2=CC=CC=C2
Appearance
White solid
Melting Point
98℃
Boiling Point
493℃
Relative Density
1.16
pKa
5.3
General Description
Tropicamide is a synthetic anticholinergic agent of the tropane class, derived from tropic acid and a substituted pyridine base. It is specifically used in ophthalmology and characterized by the shortest duration of action among clinically employed mydriatic and cycloplegic agents.
Mechanism of Action
Tropicamide competitively antagonizes muscarinic cholinergic receptors in the iris sphincter and ciliary muscles, preventing acetylcholine binding and resulting in mydriasis and cycloplegia. Its relatively low receptor binding affinity compared to atropine and cyclopentolate accounts for its shorter duration of action.
Application
Used in ophthalmology for diagnostic mydriasis and cycloplegia. Tropicamide is a short-acting anticholinergic agent with the fastest onset and shortest duration of action among clinically employed mydriatics, providing convenient pupil dilation for fundus examination and refraction assessment with minimal post-procedural recovery time.

Tropicamide is a muscarinic acetylcholine receptor antagonist with moderate binding selectivity for the M4 receptor subtype. In rodent models of parkinsonian tremor induced by the muscarinic agonist pilocarpine or the dopamine antagonist pimozide, tropicamide suppressed tremulous jaw movements in a dose-dependent manner. Analysis of dose-response curves revealed that tropicamide showed approximately the same potency as the nonselective muscarinic antagonist atropine for suppression of pilocarpine-induced jaw movements, but was more potent than atropine for suppression of pimozide-induced jaw movements. In contrast, atropine was more potent than tropicamide in impairing performance on visual stimulus detection and delayed nonmatch-to-position tasks. These findings demonstrate that tropicamide can exert antiparkinsonian effects distinct from its conventional ophthalmic use.

Fig. 1 Mean number of individual tremulous jaw movements after injection of pimozide or pimozide plus various doses of tropicamide or atropine. (Betz A J.; <i>et al</i>. 2007) Fig. 1 Mean number of individual tremulous jaw movements after injection of pimozide or pimozide plus various doses of tropicamide or atropine. (Betz A J.; et al. 2007)

References

  1. Betz A J, et al. The muscarinic receptor antagonist tropicamide suppresses tremulous jaw movements in a rodent model of parkinsonian tremor: possible role of M4 receptors. Psychopharmacology, 2007, 194(3): 347-359.

Tropicamide-loaded cubic liquid crystalline nanoparticles were prepared using ultrasound-assisted fragmentation of cubic liquid crystalline bulk phases with Pluronic F127 as dispersant. The morphology of the nanoparticles was nearly cubical as observed by transmission electron microscopy, and small angle X-ray scattering confirmed the coexistence of D and P phase cubic structures. The optimized cubic nanoparticles showed in vitro corneal permeation of tropicamide across isolated porcine cornea comparable to the commercial preparation Tropicacyl. In vivo mydriatic response study demonstrated a remarkably higher area under the mydriatic response curve for cubic nanoparticles compared to Tropicacyl.

Fig. 2  Transmission electron micrograph of tropicamide-loaded cubic nanoparticles. (Verma P, Ahuja M. 2016) Fig. 2 Transmission electron micrograph of tropicamide-loaded cubic nanoparticles. (Verma P, Ahuja M. 2016)

References

  1. Verma P, Ahuja M. Cubic liquid crystalline nanoparticles: optimization and evaluation for ocular delivery of tropicamide. Drug delivery, 2016, 23(8): 3043-3054.

Why is Tropicamide preferred for brief ophthalmic examinations?

Tropicamide has the shortest duration of mydriasis (4-6 hours vs. up to 2 weeks for atropine), due to its lower muscarinic receptor binding affinity and faster washout kinetics.

What storage conditions are required?

Should be stored at 2-8℃ in a tightly sealed container, protected from light and moisture.

What purity grade is available?

Supplied as a high-purity grade suitable for ophthalmic R&D and pharmaceutical manufacturing.

Can packaging be customized?

Packaging and order quantities are customizable to meet specific R&D and production needs.
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