N-ethyl-3-hydroxy-2-phenyl-N-(pyridin-4-ylmethyl)propanamide

• ChemBase ID: 688
• Molecular Formular: C17H20N2O2
• Molecular Mass: 284.3529
• Monoisotopic Mass: 284.15247789
• SMILES: O=C(N(Cc1ccncc1)CC)C(c1ccccc1)CO
• Canonical SMILES: CCN(C(=O)C(c1ccccc1)CO)Cc1ccncc1
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: N-ethyl-3-hydroxy-2-phenyl-N-(pyridin-4-ylmethyl)propanamide
• IUPAC Traditional name: tropicamide; triaminic DM; N-ethyl-3-hydroxy-2-phenyl-N-(pyridin-4-ylmethyl)propanamide
• Brand Name: I-Picamide; Minims Tropicamide; Mydriacyl; Mydriafair; Mydriaticum; Ocu-Tropic; Opticyl; Paremyd; Spectro-Cyl; Tropicacyl
• Synonyms: N-ethyl-3-hydroxy-2-phenyl-N-(pyridin-4-ylmethyl)propanamide; Tropicamid; Tropicamide; Mydriacyl; N-Ethyl-α-(hydroxymethyl)-N-(4-pyridinylmethyl)benzeneacetamide; N-Ethyl-N-(γ-picolyl)tropamide; Tropic Acid-N-ethyl-N-(γ-picolyl)amide; Tropicamide; Visumidriatic; N-Ethyl-2-phenyl-N-4-[-pyridyl-methyl]hydracrylamide; N-Ethyl-2-phenyl-N-(4-pyridylmethyl)hydracrylamide; Ro 1-7683; Tropicamide

Database IDs

• CAS Number: 1508-75-4
• EC Number: 216-140-2
• MDL Number: MFCD00058580
• PubChem SID: 46505924; 160964151; 24277879
• PubChem CID: 5593

CALCULATED PROPERTIES

JChem

• Acid pKa: 15.183162
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.2676235
• LogD (pH = 7.4): 1.3756077
• Log P: 1.3772274
• Molar Refractivity: 82.5347 cm^3
• Polarizability: 31.894777 Å^3
• Polar Surface Area: 53.43 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.42
• LOG S: -2.88
• Solubility (Water): 3.75e-01 g/l

PROPERTIES

Physical Property

• Solubility: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble4.3 mg/mL; Chloroform; ethanol: soluble5.6 mg/mL; H2O: insoluble
• Apperance: Off-White Solid; white solid
• Melting Point: 96°C; 96-97°C
• Hydrophobicity(logP): 1.3

Safety Information

• Storage Condition: -20°C Freezer; 2-8°C
• RTECS: CY1487860
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-36/37/38-42/43; R:22
• Safety Statements: 22-26-36; S:36/37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H315-H317-H319-H332-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: AChR
• Gene Information: human ... CHRM4(1132)
• Mechanism of Action: Muscarine receptor antagonist; Parasympatholytic; Spasmolytic

Product Information

• Salt Data: Free Base
• Application(s): Mydriatic; Spasmolytic

DETAILS

MP Biomedicals - 02157144

(N-Ethyl-2-phenyl-N-4-[-pyridyl-methyl]hydracrylamide)

DrugBank - DB00809

• Drug Groups: approved
• Description: One of the muscarinic antagonists with pharmacologic action similar to atropine and used mainly as an ophthalmic parasympatholytic or mydriatic. [PubChem]
• Indication: Indicated 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.
• Pharmacology: Tropicamide belongs to the group of medicines called anti-muscarinics. Tropicamide blocks the receptors in the muscles of the eye (muscarinic receptors). These receptors are involved controlling the pupil size and the shape of the lens. By blocking these receptors, tropicamide produces dilatation of the pupil (mydriasis) and prevents the eye from accommodating for near vision (cycloplegia). Tropicamide is given as eye drops to dilate the pupil and relax the lens so that eye examinations can be carried out thoroughly.
• Toxicity: Overdose can casue dry mouth, blurred vision, photophobia, hallucinations and rapid/irregular pulse.
• Affected Organisms: Humans and other mammals
• Protein Binding: 45%
• External Links: Wikipedia; Drugs.com

Sigma Aldrich - T9778

Biochem/physiol Actions
M4 muscarinic acetylcholine receptor antagonist.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. T9778.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - T892650

Ophthalmic anticholinergic. Mydriatic.

REFERENCES

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