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Details

Stereochemistry ACHIRAL
Molecular Formula C26H43NO3
Molecular Weight 417.6255
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of N-OLEOYLDOPAMINE

SMILES

CCCCCCCC/C(/[H])=C(/[H])\CCCCCCCC(=NCCc1ccc(c(c1)O)O)O

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-

HIDE SMILES / InChI

Molecular Formula C26H43NO3
Molecular Weight 417.6255
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.

CNS Activity

Curator's Comment:: Human data unavailable, known CNS active in mice.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
3.2 µM [EC50]
36.0 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
N-oleoyldopamine, a novel endogenous capsaicin-like lipid that produces hyperalgesia.
2003 Apr 18
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 Apr
N-oleoyldopamine enhances glucose homeostasis through the activation of GPR119.
2010 Jan
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
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
by admin
on Sat Jun 26 04:47:39 UTC 2021
Edited
by admin
on Sat Jun 26 04:47:39 UTC 2021
Record UNII
T87P7X9XSZ
Record Status Validated (UNII)
Record Version
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Name Type Language
N-OLEOYLDOPAMINE
Systematic Name English
(9Z)- N-(2-(3,4-DIHYDROXYPHENYL)ETHYL)-9-OCTADECENAMIDE
Systematic Name English
Code System Code Type Description
EPA CompTox
105955-11-1
Created by admin on Sat Jun 26 04:47:39 UTC 2021 , Edited by admin on Sat Jun 26 04:47:39 UTC 2021
PRIMARY
PUBCHEM
5282106
Created by admin on Sat Jun 26 04:47:39 UTC 2021 , Edited by admin on Sat Jun 26 04:47:39 UTC 2021
PRIMARY
CAS
105955-11-1
Created by admin on Sat Jun 26 04:47:39 UTC 2021 , Edited by admin on Sat Jun 26 04:47:39 UTC 2021
PRIMARY
FDA UNII
T87P7X9XSZ
Created by admin on Sat Jun 26 04:47:39 UTC 2021 , Edited by admin on Sat Jun 26 04:47:39 UTC 2021
PRIMARY
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7.5 nM IC50 vs arachidonate 5-lipoxygenase