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Tropicamide

HCID 5593
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
1508-75-4
Standard SMILES
CCN(Cc1ccncc1)C(=O)C(CO)c1ccccc1
InChIKey
BGDKAVGWHJFAGW-UHFFFAOYSA-N
Molecular formula
C17H20N2O2
Average molar mass
284.35 g/mol
Monoisotopic mass
284.15247789

Overview

Tropicamide is a member of acetamides.

Names & identifiers

Preferred name
Tropicamide
IUPAC
N-ethyl-3-hydroxy-2-phenyl-N-(pyridin-4-ylmethyl)propanamide
English name
Tropicamide
Molecular formula
C17H20N2O2
Molecular weight
284.35

Names & synonyms

tropicamide1508-75-4MydriacylBistropamideTropicacylN-ethyl-3-hydroxy-2-phenyl-N-(pyridin-4-ylmethyl)propanamideMydriafairVisumidriaticTropicamidumTropicamidaTropimilRo 1-7683
Show more names
Tropicamidropicamidemydrinmydrummydriatro1-7683Mydrapid
N-Ethyl-2-phenyl-N-(4-pyridylmethyl)hydracrylamideDTXSID8045220N-Ethyl-N-(4-pyridylmethyl)tropamideN-Ethyl-alpha-(hydroxymethyl)-N-(4-pyridinylmethyl)benzeneacetamideN0A3Z5XTC6NSC-757372Benzeneacetamide, N-ethyl-alpha-(hydroxymethyl)-N-(4-pyridinylmethyl)-RO-1-7683

Database identifiers

CAS
1508-75-4
PubChem CID
5593
DTXSID
DTXSID8045220
ChEMBL
CHEMBL1200604
ChEBI
CHEBI:9757
UNII
N0A3Z5XTC6
EC Number
216-140-2

Properties

Computed structural properties

XLogP
1.5
Topological polar surface area
53.4 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
6
Heavy atoms
21
Formal charge
0
Complexity
310

Experimental & physicochemical properties

LogP1.3
Solubility · 2 items

3.75e-01 g/L

>42.7 [ug/mL] (The mean of the results at pH 7.4)

Human Drugs · 5 items

Breast Feeding; Lactation; Mydriatics; Muscarinic Antagonists; Parasympatholytics

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Pharmaceuticals

Diagnostic agents > Ophthalmic medicines

Melting Point96.5 °C
Physical DescriptionSolid
Collision Cross Section · 2 items

170.4 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

169.5 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
98 °C · 98 °C
Boiling point
492.8 · 492.8±45.0 °C(Predicted)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Danger

H302 (98.4%): Harmful if swallowed [Warning Acute toxicity, oral]

P233, P260, P261, P264, P264+P265, P270, P271, P272, P280, P284, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 62 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (98.4%)

Toxicology

Adverse EffectsOcular adverse events include transient stinging, photophobia, superficial punctate keratitis, blurred vision, and a rise in intraocular pressure.
Toxicity Summary · 1 item

Although tropicamide is a short-acting drug, and the frequency of associated adverse events is rare, there are certain instances when reversal of mydriasis is necessary, including decreasing the risk of angle-closure glaucoma, improving blurry vision, and decreasing recovery time for patient comfort. Presumably, a cholinergic agent like pilocarpine should be able to undo the effects of an anticholinergic drug. However, several studies have reported conflicting pupillary responses. At times, only a partial reversal was observed.

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Safety data

Chemistry & industry

Pharmacology

ATC Code · 4 items

S01FA06

S - Sensory organs

QS - Sensory organs

S01FA06

Protein BindingThe extent of protein binding has not been established. Tropicamide binds to albumin.
Pharmacodynamics · 1 item

Tropicamide is an anticholinergic drug and that works by non‐selectively blocking muscarinic receptors to cause mydriasis and cycloplegia. It relaxes the pupillary sphincter to dilate the pupil. The onset of tropicamide‐induced mydriasis is about 10 to 15 minutes, with optimal effect occurring 25 to 30 minutes post-administration. Mydriasis caused by tropicamide wears off within four to eight hours, but it was seen up to 24 hours in some individuals. Tropicamide hinders accommodation by causing the contraction of the ciliary muscle. The cycloplegic effect occurs within 20 to minutes following administration, with a duration of action of four to 10 hours. Tropicamide can elevate intraocular pressure. The ophthalmic use of tropicamide is not typically associated with serious systemic adverse events. One randomized pilot study showed that oral tropicamide alleviated perceived symptoms of sialorrhea in patients with Parkinson's Disease: anticholinergics are believed to restore the dopaminergic to cholinergic activity imbalance in neurodegenerative diseases. Similarly in one case report, tropicamide administered via ophthalmic solution relieved clozapine-induced sialorrhea. Interestingly, in rodent models, tropicamide suppressed drug-induced tremulous jaw movements which are often used as a model of parkinsonian tremor: the significance of this finding requires further investigations.

Mechanism of Action · 1 item

Muscarinic acetylcholine receptors are involved in numerous ocular functions. The M<sub>3</sub> subtype is predominantly expressed by smooth muscle cells of the sphincter pupillae, which is a circular muscle of the iris, and ciliary muscles. In response to light or binding of acetylcholine, M<sub>3</sub> receptor signalling leads to contraction of the sphincter pupillae and pupil constriction. Contraction of the ciliary muscle via M<sub>3</sub> receptor signalling also leads to accommodation, adjusting the lens for near vision. The eye is also innervated by parasympathetic nerves: ciliary ganglion neurons project to the ciliary body and the sphincter pupillae muscle of the iris to control ocular accommodation and pupil constriction. Tropicamide is a non-selective muscarinic antagonist that binds to all subtypes of muscarinic receptors. By binding to muscarinic receptors, tropicamide relaxes the pupillary sphincter muscle and causes pupil dilation. By blocking the muscarinic receptors of the ciliary body, tropicamide also prevents accommodation. Like other muscarinic antagonists, tropicamide inhibits the parasympathetic drive, allowing the sympathetic nervous system responses to dominate. Tropicamide is thought to ameliorate sialorrhea by blocking M<sub>4</sub> receptors expressed on salivary glands and reducing hypersalivation.

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Nikkaji
J3.670F
Density
1.161 · 1.161±0.06 g/cm3(Predicted)
storage temp.
2 · 2-8°C
solubility
45 % · 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 4.3 mg/mL
form
solid
pka
5.3 · pKa 5.3 (Uncertain)
color
white
Water Solubility
0.2 g/L · 0.2g/L(25 ºC)
λmax
254 nm · 254nm(HCl aq.)(lit.)
Merck
14 · 14,9780
Major Application
pharmaceutical (small molecule)
InChI
InChI=1S/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
InChIKey
BGDKAVGWHJFAGW-UHFFFAOYSA-N
SMILES
C(CO)(C(=O)N(CC)CC1=CC=NC=C1)C1C=CC=CC=1
CAS DataBase Reference
1508 · 1508-75-4(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
0 A3Z5XTC6 · N0A3Z5XTC6
ATC code
1 FA06,S01FA56 · S01FA06,S01FA56
NIST Chemistry Reference
Tropicamide(1508-75-4)
UNSPSC Code
41116107 · 41116107
NACRES
77 · NA.77
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302+H312+H332-H315-H317-H319-H335
Precautionary statements
261 · P261-P280-P301+P312-P302+P352+P312-P304+P340+P312-P305+P351+P338
target organs
Respiratory system
Hazard Codes
Xn,Xi
Risk Statements
20 · 20/21/22-36/37/38-42/43-41-37/38-22
Safety Statements
22 · 22-26-36-36/37/39
WGK Germany
3 · 3
RTECS
1487860 · CY1487860
HS Code
29333990 · 29333990
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
4 DermalAcute · Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Skin Irrit. 2Skin Sens. 1STOT SE 3
wgk
3
rtecs
CY1487860
hs_code
29333990
risk_code
20/21/22-36/37/38-42/43-41-37/38-22
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xn,Xi
safety_code
22-26-36-36/37/39
Storage Class
11 - Combustible Solids
target organs
Respiratory system
Hazard statements
H302+H312+H332-H315-H317-H319-H335
Hazard Classifications
Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Skin Irrit. 2Skin Sens. 1STOT SE 3
Precautionary statements
P261-P280-P301+P312-P302+P352+P312-P304+P340+P312-P305+P351+P338
Biological Half-LifeTropicamide has a plasma half-life of 30 minutes.
Metabolism/MetabolitesNo information can be found.
FDA Pharmacological Classification · 6 items

N0A3Z5XTC6

TROPICAMIDE

Established Pharmacologic Class [EPC] - Anticholinergic

Mechanisms of Action [MoA] - Cholinergic Antagonists

Tropicamide is an Anticholinergic. The mechanism of action of tropicamide is as a Cholinergic Antagonist.

TROPICAMIDE

MeSH Pharmacological Classification · 2 items

Agents that dilate the pupil. They may be either sympathomimetics or parasympatholytics.

Drugs that bind to but do not activate MUSCARINIC RECEPTORS, thereby blocking the actions of endogenous ACETYLCHOLINE or exogenous agonists. Muscarinic antagonists have widespread effects including actions on the iris and ciliary muscle of the eye, the heart and blood vessels, secretions of the respiratory tract, GI system, and salivary glands, GI motility, urinary bladder tone, and the central nervous system.

Absorption, Distribution and Excretion · 4 items

Following ocular administration of 40 μL drops of 0.5% tropicamide in female subjects, tropicamide reached its mean peak concentration in plasma of 2.8 ± 1.7 ng/mL (mean ± SD) at five minutes.

No information can be found.

No information can be found.

No information can be found.

Cellular LocationsMembrane

Uses & manufacturing

UsesUse (kg; approx.) in Germany (2009): >10
Use ClassificationPharmaceuticals
Applications · 6 items

UsesIt can be used as an anti-cholinergic drugs or mydriatic drug. It is a kind of M4 muscarinic acetylcholine receptor antagonist.

UsesTropicamide, like cyclopentolate, is used in ophthalmoscopy for reaching pre-operational mydraises and for testing narrow-angle glaucoma.

Usesantidepressant, nutrient; LD50(rat) 1634 mg/kg ip

UsesOphthalmic anticholinergic. Mydriatic

UsesIndicated to induce mydriasis (dilation of the pupil) and cycloplegia (paralysis of the ciliary muscle of the eye) in diagnostic procedures, such as measurement of refractive errors and examination of the fundus of the eye.

General DescriptionTropicamide, N-ethyl-2-phenyl-N-(4-pyridylmethyl)hydracrylamide (Mydriacyl), is aneffective anticholinergic for ophthalmic use when mydriasisis produced by relaxation of the sphincter muscle ofthe iris, allowing adrenergic innervation of the radial muscleto dilate the pupil. Its maximum effect is achieved inabout 20 to 25 minutes and lasts for about 20 minutes,with complete recovery in about 6 hours. Its action ismore rapid in onset and wears off more rapidly thanthat of most other mydriatics. To achieve mydriasis, either0.5% or 1.0% concentration may be used, althoughcycloplegia is achieved only with the stronger solution.Its uses are much the same as those described above formydriatics in general, but opinions differ on whether thedrug is as effective as homatropine, for example, inachieving cycloplegia. For mydriatic use, however, in examinationof the fundus and treatment of acute iritis,iridocyclitis, and keratitis, it is quite adequate; and becauseof its shorter duration of action, it is less prone toinitiate a rise in intraocular pressure than the more potent,longer-lasting drugs. As with other mydriatics, however,pupil dilation can lead to increased intraocular pressure.In common with other mydriatics, it is contraindicated inpatients with glaucoma, either known or suspected, andshould not be used in the presence of a shallow anteriorchamber. Thus far, no allergic reactions or ocular damagehas been observed with this drug. The ability to clone thevarious muscarinic receptor subtypes has allowed the observationthat tropicamide has modest selectivity for theM4 receptor.

Upstream & downstream products

Upstream raw materials

EthylamineHydrochloric acidEthanamine, N-(4-pyridinylmethylene)-Acetyltropylic chloride2-Phenyl-malonic acid monoethyl ester4-(Ethylaminomethyl)pyridineTropic acidDiethyl phenylmalonate4-Pyridinecarboxaldehyde

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
温州共赢化学有限公司+86-0086-577-64498589 +86-15355981851 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
Baoji Guokang Healthchem co.,ltd+8615604608665 15604608665 · [email protected]
Jai Radhe Sales+(91)-(79)-26431096/65255722 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
Syntechem Co.,Ltd[email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
武汉凯威斯科技有限公司86-027-67849912 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
上海相辉医药科技有限公司13761987713 · [email protected]
上海泰坦科技股份有限公司4006009262 13023226327 · [email protected]
武汉丰泰威远科技有限公司+86-27-8746-5837 +86-18627785180 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
孝感深远化工有限公司15527621225; 15527621225 · [email protected]
云南西力生物技术股份有限公司0871-65217109 · [email protected]
法姆瑞斯医药科技(北京)有限公司18901358086 · [email protected]
玛雅试剂+86 (573) 82222445 (0)18006601000 452520369 · [email protected]
斯百全化学(上海)有限公司021-021-021-67601398-809-809-809 15221380277 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
上海思域化工科技有限公司86-21-34053660 · [email protected]
AdooQ BioScience, LLC+1 (866) 930-6790 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
泰州天鸿生化科技有限公司0523-86132544 15366717810 · [email protected]
Clearsynth Labs Limited+91-22-26355700 · [email protected]
湖北鑫源顺医药化工有限公司13971561712, 13995564702, 027-50664929 · [email protected]
安徽科迪达化工有限公司0554-2106669 · [email protected]
成都零六生物科技有限公司400-1166-196 13458535857 · [email protected]
上海御略医药科技有限公司021-60345187 13671753212 · [email protected]
南京百鑫德诺生物科技有限公司025-58849295 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
湖北巨胜科技有限公司027-59599241 18871490274 · [email protected]
重庆朗天制药有限公司023-68980308 · [email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
桦特昇生物科技(武汉)有限公司027-59207879 1972026995 18140587686 · [email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
上海昕凯医药科技有限公司21-619849051-1 18521059765 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
九鼎化学(上海)科技有限公司4009209199 · [email protected]
BOC Sciences16314854226; +8616314854226 · [email protected]
西安天广源生物科技有限公司+86-029-86333380 +86-18829239519 · [email protected]
Alfa Chemistry+1-5166625404 · [email protected]
sgtlifesciences pvt ltd+91-8790379245 · [email protected]
Qiuxian Baitai New Material Co., LTD+86-19932103556 · [email protected]

Additional notes

DefinitionChEBI: Tropicamide is a member of acetamides.