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Details

Stereochemistry ACHIRAL
Molecular Formula C19H39NO2
Molecular Weight 313.5185
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of N-(2-HYDROXYETHYL)HEPTADECANAMIDE

SMILES

CCCCCCCCCCCCCCCCC(=O)NCCO

InChI

InChIKey=GCCFMSAXQJECNH-UHFFFAOYSA-N
InChI=1S/C19H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-19(22)20-17-18-21/h21H,2-18H2,1H3,(H,20,22)

HIDE SMILES / InChI

Molecular Formula C19H39NO2
Molecular Weight 313.5185
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

N-(2-HYDROXYETHYL)HEPTADECANAMIDE (or heptadecanoyl ethanolamide) is a synthetic analog of palmitoyl ethanolamide (PEA). This analog is unlikely to be present in any natural tissue, and so can be used as an internal standard for quantitative analysis. It was shown, that heptadecanoyl ethanolamide potentiates the Ca2+ influx response to arachidonyl ethanolamide several fold in cells expressing human recombinant VR1.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
'Entourage' effects of N-acyl ethanolamines at human vanilloid receptors. Comparison of effects upon anandamide-induced vanilloid receptor activation and upon anandamide metabolism.
2002 Jun

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
It was studied the effects of a series of N-acyl ethanolamines upon the Ca2+-influx in hVR1-HEK293 cells in the absence and presence of 1 μM anandamide (AEA). With the exception of N-acyl ethanolamine palmitoylethanolamide (PEA), none of the N-acyl ethanolamines produced a Ca2+-response per se in the hVR1-HEK293 cells. The response to AEA was greatly potentiated by the C12:0, Heptadecanoylethanolamide (C17:0), C18:0 and C18:1 compounds, so that in the case of the C12:0 compound (lauroylethanolamine), the response to 1 μM AEA became maximal.
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:35:19 GMT 2023
Edited
by admin
on Sat Dec 16 09:35:19 GMT 2023
Record UNII
Q750804J30
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
N-(2-HYDROXYETHYL)HEPTADECANAMIDE
Systematic Name English
HEPTADECANOYL ETHANOLAMIDE
Common Name English
HEPTADECANAMIDE, N-(2-HYDROXYETHYL)-
Systematic Name English
N-(HEPTADECANOYL)-ETHANOLAMINE
Systematic Name English
MARGAROYL-ETHANOLAMINE
Systematic Name English
Code System Code Type Description
CAS
53832-59-0
Created by admin on Sat Dec 16 09:35:19 GMT 2023 , Edited by admin on Sat Dec 16 09:35:19 GMT 2023
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PUBCHEM
14455158
Created by admin on Sat Dec 16 09:35:19 GMT 2023 , Edited by admin on Sat Dec 16 09:35:19 GMT 2023
PRIMARY
EPA CompTox
DTXSID10560544
Created by admin on Sat Dec 16 09:35:19 GMT 2023 , Edited by admin on Sat Dec 16 09:35:19 GMT 2023
PRIMARY
FDA UNII
Q750804J30
Created by admin on Sat Dec 16 09:35:19 GMT 2023 , Edited by admin on Sat Dec 16 09:35:19 GMT 2023
PRIMARY