Details
| 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 |
|
| 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.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| N-oleoyldopamine enhances glucose homeostasis through the activation of GPR119. | 2010-01 |
|
| N-oleoyl-dopamine decreases muscle rigidity induced by reserpine in rats. | 2009-03-25 |
|
| AMG 9810 [(E)-3-(4-t-butylphenyl)-N-(2,3-dihydrobenzo[b][1,4] dioxin-6-yl)acrylamide], a novel vanilloid receptor 1 (TRPV1) antagonist with antihyperalgesic properties. | 2005-04 |
|
| N-oleoyldopamine, a novel endogenous capsaicin-like lipid that produces hyperalgesia. | 2003-04-18 |
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.
| Substance Class |
Chemical
Created
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on
Edited
Mon Mar 31 23:01:34 GMT 2025
by
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on
Mon Mar 31 23:01:34 GMT 2025
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| Record UNII |
T87P7X9XSZ
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| Record Status |
Validated (UNII)
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