A selective muscarinic M4 antagonist
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Tropicamide

Item No. 16606

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-ethyl-α-(hydroxymethyl)-N-(4-pyridinylmethyl)-benzeneacetamide
CAS Number
1508-75-4
Synonyms
  • Ro 1-7683
Molecular Formula
C17H20N2O2
Formula Weight
284.4
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlEthanol:PBS(pH 7.2) (1:1): 0.5 mg/ml
λmax
256 nm
SMILES
OCC(C(N(CC1=CC=NC=C1)CC)=O)C2=CC=CC=C2
InChi Code
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
InChi Key
BGDKAVGWHJFAGW-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 g

    $36

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    5 g

    $153

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    Product 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.1,2Tropicamide is a muscarinic acetylcholine receptor (mAChR) antagonist (pKi = 7.2 in chicken heart) that displays 3-fold selectivity for M4.1,3,4 When applied as eye drops, it produces temporary mydriasis (pupil dilation; EC50 = 6 µg/ml) and cycloplegia (ciliary muscle paralysis; EC50 = 25 µg/ml).5 Tropicamide has been used to probe mAChR activity in a mouse model of fragile X syndrome.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lazareno, S., Buckley, N.J., and Roberts, F.F. Characterization of muscarinic M4 binding sites in rabbit lung, chicken heart, and NG108-15 cell. Mol. Pharmacol. 38(6), 805-815 (1990).

    2. Liao, C.F., Themmen, A.P.N., Joho, R., et al. Molecular cloning and expression of a fifth muscarinic acetylcholine receptor. The Journal of Biological Chemisty 264(13), 7328-7337 (1989).

    3. Lazareno, S., and Birdsall, N.J.M. Pharmacological characterization of acetylcholine-stimulated [35S]-GTPγS binding mediated by human muscarinic m1-m4 receptors: Antagonist studies. Br. J. Pharmacol. 109(4), 1120-1127 (1993).

    4. Hernández, M., Símonsen, U., Prieto, D., et al. Different muscarinic receptor subtypes mediating the phasic activity and basal tone of pig isolated intravesical ureter. Br. J. Pharmacol. 110(4), 1413-1420 (1993).

    5. Smith, S.E. Dose-response relationships in tropicamide-induced mydriasis and cycloplegia. Br. J. Clin. Pharmacol. 1(1), 37-40 (1974).

    6. Veeraragavan, S., Bui, N., Perkins, J.R., et al. The modulation of fragile X behaviors by the muscarinic M4 antagonist, tropicamide. Behav. Neurosci. 125(5), 783-790 (2011).