| Stereochemistry | ACHIRAL |
| Molecular Formula | C26H43NO3 |
| Molecular Weight | 417.6245 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCC\C=C/CCCCCCCC(=O)NCCC1=CC(O)=C(O)C=C1
InChI
InChIKey=QQBPLXNESPTPNU-KTKRTIGZSA-N
InChI=1S/C26H43NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-26(30)27-21-20-23-18-19-24(28)25(29)22-23/h9-10,18-19,22,28-29H,2-8,11-17,20-21H2,1H3,(H,27,30)/b10-9-
| Molecular Formula | C26H43NO3 |
| Molecular Weight | 417.6245 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Optical Activity | NONE |
N-oleoyldopamine is an endogenous lipid compound found in the mammalian brain. It has been found to be a capsaicin receptor (TRPV1) agonist. Activation of the capsaicin receptor induces glutamate release and paraventricular nucleus postsynaptic firing. N-oleoyldopamine has been reported to induce the influx of calcium in TRPV1-transfected HEK293 human embryonic kidney cells.
CNS Activity
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 3.2 µM [EC50] | |||
| 36.0 nM [EC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
PubMed
Sample Use Guides
Effects of the endogenous lipid N-oleoyldopamine (OLDA) were analyzed on the rat transient receptor potential cation channel subfamily V member 1 (TRPV1)-expressing HT1080 human fibrosarcoma cell line (HT5-1). The EC50 of capsaicin and OLDA on the 45Ca2+ accumulation of rat TRPV1-expressing HT5-1 cells was 36 nM and 1.8 microM, respectively. The efficacy of OLDA was 60% as compared to the maximum response of capsaicin. OLDA (330 nM to 3.3 microM) caused a transient increase in fluorescence of fura-2 loaded cultured small trigeminal neurons of the rat and rat TRPV1-transfected HT5-1 cells.
