N-Acetyldopamine

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N-Acetyldopamine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
  • InChI=1S/C10H13NO3/c1-7(12)11-5-4-8-2-3-9(13)10(14)6-8/h2-3,6,13-14H,4-5H2,1H3,(H,11,12)
    Key: OFSAJYZMIPNPHE-UHFFFAOYSA-N
  • CC(=O)NCCC1=CC(=C(C=C1)O)O
Properties
C10H13NO3
Molar mass 195.218 g·mol−1
Appearance colorless solid
Hazards
GHS labelling:[1]
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N-Acetyldopamine is the organic compound with the formula CH3C(O)NHCH2CH2C6H3(OH)2. It is the N-acetylated derivative of dopamine. This compound is a reactive intermediate in sclerotization, the process by which insect cuticles are formed by hardening molecular precursors. The catechol substituent is susceptible to redox and crosslinking.[2][3]

References

  1. ^ "N-Acetyldopamine". pubchem.ncbi.nlm.nih.gov. Retrieved 26 February 2022.
  2. ^ Andersen, Svend Olav (2010). "Insect cuticular sclerotization: A review". Insect Biochemistry and Molecular Biology. 40 (3): 166–178. doi:10.1016/j.ibmb.2009.10.007. PMID 19932179.
  3. ^ Kramer, Karl J.; Kanost, Michael R.; Hopkins, Theodore L.; Jiang, Haobo; Zhu, Yu Cheng; Xu, Rongda; Kerwin, J.L; Turecek, F. (2001). "Oxidative conjugation of catechols with proteins in insect skeletal systems". Tetrahedron. 57 (2): 385–392. doi:10.1016/S0040-4020(00)00949-2.
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