N-Acetyldopamine

N-Acetyldopamine
Identifiers
CAS Number	2494-12-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:125678;
ChEMBL	ChEMBL137743;
ChemSpider	90825;
PubChem CID	100526;
CompTox Dashboard (EPA)	DTXSID70179656 ;
	InChI 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;
	SMILES CC(=O)NCCC1=CC(=C(C=C1)O)O;
Properties
Chemical formula	C10H13NO3
Molar mass	195.218 g·mol−1
Appearance	Colorless solid
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	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). Infobox references

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

^ "N-Acetyldopamine". pubchem.ncbi.nlm.nih.gov. Retrieved 26 February 2022.
^ 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.
^ 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.

[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.

[2]

[3]

[1]

Identifiers

CAS Number	2494-12-4^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:125678
ChEMBL	ChEMBL137743
ChemSpider	90825
PubChem CID	100526
CompTox Dashboard (EPA)	DTXSID70179656
InChI 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
SMILES CC(=O)NCCC1=CC(=C(C=C1)O)O
Properties
Chemical formula	C₁₀H₁₃NO₃
Molar mass	195.218 g·mol⁻¹
Appearance	Colorless solid
Hazards
GHS labelling:^[1]
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	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). Infobox references