136181-87-8

Usage

Uses

1. Used in Pharmaceutical Applications:
PALDA is used as a modulator for vanilloid receptor 1 (VR1) due to its ability to potentiate the VR1-mediated effects of NADA and anandamide. This makes it a potential candidate for the development of novel therapeutic strategies targeting the VR1 receptor.
2. Used in Research and Development:
PALDA is used as a research compound for studying the interactions between fatty acyl dopamine analogs and the vanilloid receptor 1 (VR1). Its unique "entourage" effect can provide valuable insights into the development of new drugs and therapies that target the VR1 receptor and related pathways.
3. Used in Neurotransmission Studies:
PALDA is used as a research tool to investigate the role of dopamine neurotransmitter pathways and their interaction with anandamide-like systems. This can contribute to a better understanding of the complex mechanisms underlying neurotransmission and the development of new treatments for neurological disorders.

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.

InChI:InChI=1/C24H41NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-24(28)25-19-18-21-16-17-22(26)23(27)20-21/h16-17,20,26-27H,2-15,18-19H2,1H3,(H,25,28)

Upstream product

• 146788-12-7 C₂₁H₄₀O₄ 
• 62-31-7 dopamine hydrochloride 
• 57-10-3 1-hexadecylcarboxylic acid 
• 708261-28-3 N-(3,4-dimethoxy-β-phenylethyl)hexadecanamide 
• 51-61-6 dopamine 
• 623-65-4 palmitic anhydride 
• 645-31-8 3-hydroxytyramine hydrobromide 

Relevant academic research and scientific papers

Newly synthesized dopamine ester derivatives and assessment of their antioxidant, antimicrobial and hemolytic activities

Preparation of dopamine derivatives was carried out as a response to the increasing demand for new lipophilized antioxidants in food, cosmetic and pharmaceutical industries. A large series of dopamine esters (DA-C3 to DA-C18:1) with

MEDICAL COMPOUNDS

There is provided a medical compound comprising a synthetic flavone derivative, according to the formula (I) with allotment in position C-3 of a group as shown below: Formula (I) wherein at least two of R2-R6 a re H, and the remainin

Efficient N-acyldopamine synthesis

N-Acyldopamines are endogenous analogs of capsaicin that exhibit cannabinoid-like activities and were identified from brain extracts. Among them, N-arachidonoyldopamine (AADA) and N-oleoyldopamine (ODA) were characterized as transient receptor potential vanilloid type V1 channel (TRPV1) ligands. Recently, it was shown that N-acyldopamines may possess diverse physiological roles in addition to their ligand activities. To study the multiple functions and action mechanisms of endogenous N-acyldopamines, a simple and efficient method of N-acyldopamine synthesis was investigated. The eighteen potentially endogenous N-acyl-dopamines and two deuterated ones, N-palmitoyl dopamine-d5 and N-stearoyl dopamine-d5, were efficiently synthesized without protective groups in CH2Cl2 under optimized conditions using propylphosphoric acid cyclic anhydride (PPACA) as a condensation agent.

Structure and thermotropic phase behavior of a homologous series of bioactive N-acyldopamines

N-Acyldopamines (NADAs), which are present in mammalian nervous tissues, exhibit interesting biological and pharmacological properties. In the present study, a homologous series of NADAs with varying acyl chains (n = 12-20) have been synthesized and characterized. Differential scanning calorimetric studies show that in the dry state the transition temperatures, enthalpies, and entropies of NADAs exhibit odd-even alternation with the values corresponding to the even chain length series being slightly higher. Both even and odd chain length NADAs display a linear dependence of the transition enthalpies and entropies on the chain length. However, odd-even alternation was not observed in the calorimetric properties upon hydration, although the transition enthalpies and entropies exhibit linear dependence. Linear least-squares analyses yielded incremental values contributed by each methylene group to the transition enthalpy and entropy and the corresponding end contributions. N-Lauroyldopamine (NLDA) crystallized in the monoclinic space group C2/c with eight symmetry-related molecules in the unit cell. Single-crystal X-ray diffraction studies show that NLDA molecules are organized in the bilayer form, with a head-to-head (and tail-to-tail) arrangement of the molecules. Water-mediated hydrogen bonds between the hydroxyl groups of the dopamine moieties of opposing layers and N-H···O hydrogen bonds between the amide groups of adjacent molecules in the same layer stabilize the crystal packing. These results provide a thermodynamic and structural basis for investigating the interaction of NADAs with other membrane lipids, which are expected to provide clues to understand how they function in vivo, e.g., as signaling molecules in the modulation of pain.

Synthesis, DNA binding and antitumor evaluation of styelsamine and cystodytin analogues

A series of N-14 sidechain substituted analogues of styelsamine (pyrido[4,3,2-mn]acridine) and cystodytin (pyrido[4,3,2-mn]acridin-4-one) alkaloids have been prepared and evaluated for their DNA binding affinity and antiproliferative activity towards a pa

Evaluation of endogenous fatty acid amides and their synthetic analogues as potential anti-inflammatory leads

A series of endogenous fatty acid amides and their analogues (1-78) were prepared, and their inhibitory effects on pro-inflammatory mediators (NO, IL-1β, IL-6, and TNF-α) in LPS-activated RAW264.7 cells were evaluated. Their inhibitory activity on the pro-inflammatory chemokine MDC in IFN-γ-activated HaCaT cells was also examined. The results showed that the activity is strongly dependent on the nature of the fatty acid part of the molecules. As expected, the amides derived from enone fatty acids showed significant activity and were more active than those derived from other types of fatty acids. A variation of the amine headgroup also altered bioactivity profile remarkably, possibly by modulating cell permeability. Regarding the amine part of the molecules, N-acyl dopamines exhibited the most potent activity (IC50 ～2 μM). This is the first report of the inhibitory activity of endogenous fatty acid amides and their analogues on the production of nitric oxide, cytokines (IL-1β, IL-6, and TNF-α) and the chemokine MDC. This study suggests that the enone fatty acid-derived amides (such as N-acyl ethanolamines and N-acyl amino acids) and N-acyl dopamines may be potential anti-inflammatory leads.

N-docosahexaenoyl, 3 hydroxytyramine: A dopaminergic compound that penetrates the blood-brain barrier and suppresses appetite

Fatty acids with varying chain lengths (2-22 carbon atoms long) and degrees of unsaturation (0-6 double bonds) were used to synthesize dopaminergic compounds for a study of the carrier mediated transport of dopamine (DA) to the brain. The most active carrier was the all cis C22:6 fatty acid [docosahexaenoic acid,( DHA)]which increased DA uptake through the blood-brain barrier by greater than 7.5 fold. The DHA-DA compound, NMI 8739, depressed the general locomotor activity of mice in a dose dependent manner. It also suppressed the appetite of Balb c mice and Charles River rats by 50% and 95% respectively at a dose of 10 mg/kg. Daily administration of NMI-8739 for a three week period did not induce tolerance. These results demonstrate DHA's potential for the carrier mediated transport of small molecules to the brain.