Description
Muscarinic receptors are G protein-coupled acetylcholine receptors that play diverse roles. Five subtypes (M1-5) have been identified, which preferentially couple to various effector systems based on their G protein interaction. Tropicamide is a muscarinic acetylcholine receptor (mAChR) antagonist (pKi = 7.2 in chicken heart) that displays 3-fold selectivity for M4. When applied as eye drops, it produces temporary mydriasis (pupil dilation; EC50 = 6 µg/ml) and cycloplegia (ciliary muscle paralysis; EC50 = 25 µg/ml). Tropicamide has been used to probe mAChR activity in a mouse model of fragile X syndrome.
Synonyms
Benzeneacetamide, N-ethyl-α-(hydroxymethyl)-N-(4-pyridinylmethyl)-; Hydracrylamide, N-ethyl-2-phenyl-N-(4-pyridylmethyl)-; N-Ethyl-α-(hydroxymethyl)-N-(4-pyridinylmethyl)benzeneacetamide; (±)-Tropicamide; Bistropamide; Epitromina; Minims; Mydramide; Mydrapid; Mydriacyl; Mydriat; Mydriaticum; Mydril; Mydrin; Mydrin M; Mydrin P; Mydrum; N-Ethyl-2-phenyl-N-(4-pyridylmethyl)hydracrylamide; N-Ethyl-N-(γ-picolyl)tropamide; Ro 1-7683; Tropic acid-N-ethyl-N-(γ-picolyl)amide; Visumidriatic
IUPAC Name
N-ethyl-3-hydroxy-2-phenyl-N-(pyridin-4-ylmethyl)propanamide
Molecular Formula
C17H20N2O2
Canonical SMILES
CCN(CC1=CC=NC=C1)C(=O)C(CO)C2=CC=CC=C2
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
Boiling Point
492.8±45.0°C at 760 mmHg
Solubility
Soluble in Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
Appearance
Off-white Solid
Application
Muscarinic Antagonists