1508-75-4 Usage
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).
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 academic research and scientific papers
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
Preparation method of topivacamide
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Paragraph 0014; 0050-0054, (2021/04/03)
The invention relates to a preparation method of topivacamide. The method comprises the following steps: (1) adding 3-hydroxy-2-phenylpropionic acid and toluene into a beaker, stirring uniformly, carrying out nitrogen displacement, protecting, and carrying out heating reflux until the mixture is insoluble; respectively adding triethylamine and acetyl chloride in the reaction, heating and refluxinguntil the solution is clear, cooling to room temperature, dropwise adding thionyl chloride, continuously reacting, and concentrating under reduced pressure to obtain 2-chlorocarbonyl-2-phenyl ethyl ester; and (2) preparing another jacketed bottle, adding ethylpyridine-4-ylmethylamine, triethylamine and methylbenzene, replacing with nitrogen, protecting, cooling, and slowly dropwise adding 2-chlorocarbonyl--2phenyl ethyl ester into the methylbenzene solution; after the dripping is finished, continuously reacting; (3) after the reaction is completed, dropwise adding water, carrying out liquid separation extraction, washing with saline water, adding a 3N hydrochloric acid solution into a toluene layer for hydrolysis, cooling to room temperature, carrying out liquid separation, separating toobtain a water phase, and washing with water phase ethyl acetate; (4) cooling, dropwise adding a saturated sodium bicarbonate aqueous solution to adjust the pH value, extracting with ethyl acetate, and concentrating an organic phase to obtain a faint yellow oily matter; and (5) dissolving the oily substance crude product with ethyl acetate, slowly dropwise adding heptane, crystallizing, carrying out suction filtration, and washing to obtain the target product topivacamide.
Process for preparing N- ethylpyridine methylamine hydrochloride crystal, and application thereof in preparation of itemamide (by machine translation)
-
Paragraph 0026, (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)
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.
N- Ethylpyridine methylamine hydrochloride and crystal, preparation process and application thereof
-
, (2020/03/17)
The invention discloses N -ethyl-pyridine methylamine trifluoroacetate, and a crystal. preparation process and application N - thereof to prepare N -ethylpyridine methylamine hydrochloride crystals, by slowly adding X -ethyl-pyridine methylamine, in an organic solvent 15.12 °, 15.45 °, 17.68 °, 20.68 °, 22.62 °, 23.25 °, 24.75 °, 29.54 ° at room temperature or heating. to fully dissolve N -ethyl-pyridine methylamine . through heating for, hours to prepare the ethyl-pyridine methylamine trifluoroacetate crystals . The method is simple in operation and;% in crystal form impurity content, obtained by dry-adding trifluoroacetic acid; crystals, at about, at room temperature or, in a heating mode of heating the crystals at a temperature ranging from, N - degrees, to a. material completely-dissolving solution.
Synthetic method of tropicamide
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Paragraph 0062; 0067; 0072; 0077; 0082, (2018/03/24)
The invention relates to a production method of chemical medicines and particularly relates to a synthetic method of tropicamide. The synthetic method comprises the steps of carrying out hydrolysis and acylation on the raw material, namely diethyl phenylmalonate, condensing diethyl phenylmalonate with N-ethyl-4-methylpyridine amine, and generating reduction reaction with hydroboron, so as to obtain tropicamide. The synthetic method has the beneficial effects that the raw material cost is low, the properties of an intermediate product are stable, impurities are few, the operation steps such aspurification are reduced, and the process is simplified; reaction conditions are safe and mild, extremely toxic substances are not introduced, and the industrial amplified production is promoted; andby optimizing the raw material ratio, the total yield of the reaction is increased to be 65% and is greatly increased, and the production cost is lowered.
Thiazolidinone, oxazolidinone, and imidazolone derivatives for treating non-inflammatory gastrointestinal tract disorders
-
, (2008/06/13)
A method is provided for using Cav2.2 subunit calcium channel modulators, particularly thiazolidinone, oxazolidinone, and imidazolone derivatives, to treat non-inflammatory gastrointestinal tract disorders.
