| Identification | Back Directory | [Name]
PALDA | [CAS]
136181-87-8 | [Synonyms]
PALDA
N-PALMITOYL DOPAMINE
N-[2-(3,4-DIHYDROXYPHENYL)ETHYL]HEXADECANAMIDE
Hexadecanamide, N-[2-(3,4-dihydroxyphenyl)ethyl]- | [Molecular Formula]
C24H41NO3 | [MDL Number]
MFCD08457915 | [MOL File]
136181-87-8.mol | [Molecular Weight]
391.59 |
| Hazard Information | Back Directory | [Description]
Several different fatty acyl dopamine analogs, such as N-arachidonoyl dopamine (NADA), N-oleoyl dopamine (ODA) and N-palmitoyl dopamine (PALDA), have been isolated and characterized from bovine brain. Structurally, PALDA is the amide of palmitic acid and dopamine and is therefore a “hybrid” analog which incorporates components of both the anandamide-like and dopamine neurotransmitter pathways. Unlike NADA and ODA, PALDA is nearly inactive as a vanilloid receptor 1 (VR1) ligand and fails to elicit hyperalgesic or nocifensive responses in vivo. However, PALDA exhibits an “entourage” effect at concentrations of 0.1-10 μM by potentiating the VR1-mediated effects of NADA and anandamide. | [Uses]
PALDA is an endogenous fatty acid dopamide. | [Definition]
ChEBI:N-palmitoyl dopamine is a fatty amide resulting from the formal condensation of the carboxy group of hexadecanoic acid with the amino group of dopamine. It is present as an endogenous compound in the mammalian brain. It is a monocarboxylic acid amide, a fatty amide, a member of catechols and a N-(fatty acyl)-dopamine. It is functionally related to a hexadecanoic acid and a dopamine. | [Biological Activity]
Endogenous fatty acid dopamide that displays 'entourage' effects on endovanilloids NADA and anandamide. Inactive at TRPV1 and CB 1 receptors (at concentrations up to 5 μ M) and does not inhibit AMT or FAAH (IC 50 > 25 μ M). However, potentiates TRPV1-mediated effects of NADA; lowers EC 50 from ~ 90 to ~ 30 nM. | [storage]
Store at -20°C | [References]
[1] SUSAN M. HUANG. Identification of a New Class of Molecules, the Arachidonyl Amino Acids, and Characterization of One Member That Inhibits Pain*[J]. The Journal of Biological Chemistry, 2001, 19 1: 42639-42644. DOI: 10.1074/jbc.m107351200
[2] CONSTANCE J CHU. N-oleoyldopamine, a novel endogenous capsaicin-like lipid that produces hyperalgesia.[J]. The Journal of Biological Chemistry, 2003, 278 16: 13633-13639. DOI: 10.1074/jbc.m211231200
[3] LUCIANO DE PETROCELLIS. Actions of two naturally occurring saturated N-acyldopamines on transient receptor potential vanilloid 1 (TRPV1) channels[J]. British Journal of Pharmacology, 2009, 143 2: 251-256. DOI: 10.1038/sj.bjp.0705924 |
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