1508-75-4 Usage
Description
Tropicamide, also known as N-ethyl-2-phenyl-N-(4-pyridylmethyl)hydracrylamide (Mydriacyl), is a potent anticholinergic drug used primarily for ophthalmic purposes. It is a M4 muscarinic acetylcholine receptor antagonist that effectively induces mydriasis (dilation of the pupil) and cycloplegia (paralysis of the ciliary muscle of the eye). Tropicamide is characterized by its rapid onset and relatively short duration of action, making it a preferred choice in certain diagnostic procedures and treatments.
Uses
Used in Ophthalmology:
Tropicamide is used as an anticholinergic and mydriatic drug for diagnostic procedures such as measurement of refractive errors and examination of the fundus of the eye. It is particularly useful in inducing mydriasis and cycloplegia, which are essential for a thorough examination of the eye's interior.
Used in Pre-Operative Mydriasis:
Tropicamide is used as a mydriatic drug for reaching pre-operative mydriasis, ensuring that the patient's pupils are sufficiently dilated before undergoing ophthalmic surgery.
Used in Testing Narrow-Angle Glaucoma:
Tropicamide is utilized as a diagnostic tool for testing narrow-angle glaucoma, a condition where the drainage angle between the iris and cornea is too narrow, potentially leading to increased intraocular pressure.
Used in Antidepressant and Nutrient Applications:
Tropicamide serves as an antidepressant and nutrient, with an LD50 (rat) value of 1634 mg/kg intraperitoneally.
Used in Treatment of Acute Iritis, Iridocyclitis, and Keratitis:
Tropicamide is used as a mydriatic drug in the examination and treatment of acute iritis, iridocyclitis, and keratitis, conditions that involve inflammation of the eye. Its shorter duration of action makes it less likely to cause a rise in intraocular pressure compared to more potent, longer-lasting drugs.
Chemical Properties:
Tropicamide is a crystalline solid with the chemical formula N-ethyl-2-phenyl-N-(4-pyridylmethyl)hydracrylamide.
Brand Names:
Some of the brand names for Tropicamide include Mydriacyl (Alcon) and Tropicacyl (Akorn).
It is important to note that Tropicamide is contraindicated in patients with glaucoma, either known or suspected, and should not be used in the presence of a shallow anterior chamber. Additionally, no allergic reactions or ocular damage has been observed with this drug, and it has modest selectivity for the M4 receptor due to the ability to clone various muscarinic receptor subtypes.
Ophthalmic drugs
Tropicamide is an anticholinergic agent. At room temperature, it is a white crystalline powder and is odorless. It is slightly soluble in water and easily soluble in ethanol, dilute hydrochloric acid, sulfuric acid and chloroform. It can block the excitement of iris sphincter and ciliary muscle induced by acetylcholine. Its 0.5% solution can cause mydriasis while its 1% solution can cause ciliary muscle paralysis and mydriasis. Clinically it is mainly used for the treatment of eye drops mydriasis and paralysis.
Tropicamide is the synthetic derivative of tropic acid. It has a relative low dissociation constant with good intraocular permeability and strong tissue diffusion capability which may be the underlying mechanism for its quick onset but short maintaining time. After the drop of the 0.5% or 1% solution of this product, the instillation dilation and paralysis adjustment can reach peak within 20-30 minutes. Then the effect gradually decreases with adjusting paralysis (residual) for 2 to 6 hours and mydriasis (residual) for about 7 hours. Tropicamide is similar drug as atropine which can cause a dramatic increase on the angle closure glaucoma intraocular pressure as well as possibly stimulate undiagnosed angle-closure glaucoma.
The potency of ciliary muscle paralysis adjustment of tropicamide eye drops is closely related with the doses used, its 0.25%, 0.5%, 0.75% and 1% four concentrations can all adjust paralysis. After instillation, the maximum degree of residual adjustment is 0.25%: diopter: 3.17; 1% diopter: 3.17. The residue adjustment degree can be maintained in cases of the refraction being 2.0 or less, 0.75% and 1% solutions can maintain for 40 minutes while 0.5% can only maintain about 15 minutes. After a drop of 1% solution, have the second drop after 5 to 25 minutes and by doing this, we can get more satisfactory ciliary muscle paralysis effect for about 20 to 30 minutes. After 2 to 6 hours, you can read books and newspapers with the adjustment function being able to recover to the level before drop within 6 hours.
The above information is edited by the lookchem of Dai Xiongfeng.
Originator
Mydriacyl,Alcon,US,1959
Manufacturing Process
A solution of 82 parts by weight of γ-chloromethyl-pyridine-hydrochloride in 60
parts of water is added dropwise, at 0° to 5°C, to 250 parts by weight of a
50% aqueous ethyl amine solution. The mixture is stirred for 1 hour at 60°C,
whereupon it is cooled down and separated in the cold with solid potassium
hydroxide. The oil formed is separated off, dried over potassium hydroxide
and distilled. The ethyl-(γ-picolyl)-amine formed boils over at 103° to 104°C
under a pressure of 13 mm Hg. Its dihydrochloride melts at 198° to 200°C.
To a mixture of 48.7 parts by weight of ethyl-(γ-picolyl)-amine and 36 parts
by weight of dry pyridine in 220 parts by weight of dry chloroform is slowly
added, while stirring and cooling with ice water, crude acetyltropic acid
chloride prepared from 60 parts by weight of tropic acid. To complete the
reaction, the mixture is stirred for one additional hour at 23°C. Thereupon the
chloroform solution is diluted with 200 parts by weight of ether and agitated
with 3 N hydrochloric acid. The weakly Congo acid solution is heated for 1
hour in a steam bath, the acetyl group of the reaction product being thereby
split off, and the mixture is filtered over charcoal.
Upon adding concentrated ammonia in excess, the condensation product
separates and is taken up in chloroform. The chloroform solution is dried and
distilled, the tropic acid N-ethyl-N-(γ-picolyl)-amide being thereby obtained in
the form of a thick oil, which crystallizes after prolonged time and which then
melts at 96° to 97°C.
Therapeutic Function
Anticholinergic (ophthalmic)
Biological Activity
M 4 selective muscarinic receptor antagonist.
Biochem/physiol Actions
M4 muscarinic acetylcholine receptor antagonist.
Synthesis
Tropicamide, N-(4-piridinylmethyl)-N-ethyl-β-hydroxy-α-phenylpropionamide (14.1.41), is synthesized by reacting O-acetyltropyl chloride with ethyl
(4-piridinylmethyl)amine and the subsequent acidic hydrolysis of the acetyl group in the
resulting amide (14.1.40) [31].
Veterinary Drugs and Treatments
Tropicamide, like atropine, causes mydriasis and cycloplegia, but
has more mydriatic than cycloplegic activity. Tropicamide has a
more rapid onset (maximum mydriasis in 15 – 30 minutes) of action
and a shorter duration of action (pupil returns to normal in
6 – 12 hours in most animals) than does atropine, thereby making
it more useful for funduscopic examinations. In dogs, intraocular
pressure is apparently not affected by tropicamide. Tropicamide is
also indicated following cataract removal to prevent synechiae formation
that is associated with post-cataract atropine administration.
As the half-life of tropicamide is shorter than that of atropine,
this allows iris contraction preventing synechial adhesions.
Check Digit Verification of cas no
The CAS Registry Mumber 1508-75-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,5,0 and 8 respectively; the second part has 2 digits, 7 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 1508-75:
(6*1)+(5*5)+(4*0)+(3*8)+(2*7)+(1*5)=74
74 % 10 = 4
So 1508-75-4 is a valid CAS Registry Number.
InChI:InChI=1/C17H20N2O2/c1-2-19(12-14-8-10-18-11-9-14)17(21)16(13-20)15-6-4-3-5-7-15/h3-11,16,20H,2,12-13H2,1H3/t16-/m1/s1
1508-75-4Relevant articles and documents
Cobalt-catalyzed direct α-hydroxymethylation of amides with methanol as a C1 source
Ma, Ben,Sun, Rongxia,Yang, Jingya
supporting information, p. 1382 - 1385 (2022/02/05)
Herein, we report a cobalt-catalyzed α-hydroxymethylation of amides with methanol under mild conditions. Using CoCl2·6H2O as an inexpensive and efficient catalyst, some important bioactive β-hydroxyamides were obtained in moderate to excellent yields. The
N-ethylpyridine methylamine mesylate crystal, preparation process thereof and application of N-ethylpyridine methylamine mesylate crystal in preparation of tropicamide
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Paragraph 0025, (2020/04/17)
The invention discloses an N-ethylpyridine methylamine mesylate crystal, a preparation process thereof and the application of the N-ethylpyridine methylamine mesylate crystal in the preparation of tropicamide. Mesylate of N-ethylpyridine methylamine mesylate crystal is prepared from N-ethylpyridine methylamine and methylsulfonic acid, when X-ray powder diffraction is used, and the crystal has diffraction peaks at about 9.49 degrees, 13.16 degrees, 16.18 degrees, 19.10 degrees, 20.54 degrees, 23.24 degrees, 26.96 degrees and 34.63 degrees. The preparation method comprises the following steps ofdissolving the N-ethylpyridine methylamine in an organic solvent, and stirring at room temperature or heating and stirring until a material is completely dissolved; slowly adding acid, and crystallizing; and carrying out heat preservation aging, filtering and drying to obtain the tropicamide key starting material N-ethylpyridine methylamine mesylate crystal. The method is simple to operate and obvious in purification effect, the salt form impurity content and the crystal form impurity content prepared by crystallization are low, the purity is high, and the industrial production is facilitated.
Process for preparing N- ethylpyridine methylamine hydrochloride crystal, and application thereof in preparation of itemamide (by machine translation)
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, (2020/05/02)
An application N - of,ethylpyridine methylamine hydrochloride crystal, prepared by dissolving N -ethylpyridine methylamine N - in an organic solvent, at room temperature or heating X - in an organic solvent is stirred until the material is completely dissolved, is stirred until the material is completely dissolved or stirred at about 9.73 °, 14.61 °, 17.98 °, 18.49 °, 20.36 °, 24.63 °, 27.21 ° with a diffraction peak, and is stirred. N - through a,ray powder diffractogram, for drying to obtain the supported product amide key starting material, ethyl-pyridine methylamine hydrochloride; is prepared by filtering, and drying. The crystal has the advantages of simple operation, purification effect, crystallization and high N -purity crystal, form impurity content in the, preparation of the itemamide hydrochloride, crystal . and is, simple and convenient, operation. (by machine translation)
