PALMIDROL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H37NO2
Molecular Weight	299.4919
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCCCCCCCCCCCC(=O)NCCO

InChI

InChIKey=HXYVTAGFYLMHSO-UHFFFAOYSA-N

InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)19-16-17-20/h20H,2-17H2,1H3,(H,19,21)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16884908 | https://www.ncbi.nlm.nih.gov/pubmed/28265364 | https://www.ncbi.nlm.nih.gov/pubmed/17876302

Palmidrol (palmitoylethanolamide, PEA) is a natural fatty acid amide found in a variety of foods, which was initially identified in egg yolk. It is an endogenous compound, locally synthesized in animal and human tissues and body fluids, to protect against perturbing inflammation. In addition to its anti-inflammatory activity, palmidrol (palmitoylethanolamide, PEA) also produces analgesia, neuroprotection, and possesses anti-epileptic properties. It also reduces gastrointestinal motility and cancer cell proliferation, as well as protecting the vascular endothelium in the ischemic heart. The physiological stimuli that regulate palmidrol (palmitoylethanolamide, PEA) levels in mammalian tissues are largely unknown, however, multiple studies indicate that this lipid accumulates during cellular stress, particularly following tissue injury. Palmidrol (palmitoylethanolamide, PEA) is a potent and selective agonist of orphan receptor GPR55.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Peroxisome proliferator-activated receptor alpha 62 Target ID: CHEMBL239 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15465922	Activator 1430		3.1 µM [EC50]
G-protein coupled receptor 55 6 Target ID: CHEMBL1075322 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17876302	Agonist 2678		4.0 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Chronic pain 9 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27220803	Palliative		Approved 8429	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Receptor-independent effects of natural cannabinoids in rat peritoneal mast cells in vitro.	2001 Apr 23	11336796
Effects of the cannabimimetic fatty acid derivatives 2-arachidonoylglycerol, anandamide, palmitoylethanolamide and methanandamide upon IgE-dependent antigen-induced beta-hexosaminidase, serotonin and TNF alpha release from rat RBL-2H3 basophilic leukaemic cells.	2001 Jul	11485041
Progesterone up-regulates anandamide hydrolase in human lymphocytes: role of cytokines and implications for fertility.	2001 Jun 15	11390466
Anticonvulsant activity of N-palmitoylethanolamide, a putative endocannabinoid, in mice.	2001 Mar	11442148
Antinociceptive activity of the endogenous fatty acid amide, palmitylethanolamide.	2001 May 11	11426841
Purification and characterization of an acid amidase selective for N-palmitoylethanolamine, a putative endogenous anti-inflammatory substance.	2001 Sep 21	11463796
Effect on cancer cell proliferation of palmitoylethanolamide, a fatty acid amide interacting with both the cannabinoid and vanilloid signalling systems.	2002 Aug	12570018
Release of fatty acid amides in a patient with hemispheric stroke: a microdialysis study.	2002 Aug	12154273
Low fatty acid amide hydrolase and high anandamide levels are associated with failure to achieve an ongoing pregnancy after IVF and embryo transfer.	2002 Feb	11818522
Antiinflammatory action of endocannabinoid palmitoylethanolamide and the synthetic cannabinoid nabilone in a model of acute inflammation in the rat.	2002 Jan	11786493
Therapeutic effect of the endogenous fatty acid amide, palmitoylethanolamide, in rat acute inflammation: inhibition of nitric oxide and cyclo-oxygenase systems.	2002 Oct	12359622
N-acylethanolamines are metabolized by lipoxygenase and amidohydrolase in competing pathways during cottonseed imbibition.	2002 Sep	12226518
Esters, retroesters, and a retroamide of palmitic acid: pool for the first selective inhibitors of N-palmitoylethanolamine-selective acid amidase.	2003 Oct 9	14521402
An endogenous cannabinoid tone attenuates cholera toxin-induced fluid accumulation in mice.	2003 Sep	12949722
Inhibitory effect of anandamide on resiniferatoxin-induced sensory neuropeptide release in vivo and neuropathic hyperalgesia in the rat.	2003 Sep 19	12941436
Selective antiepileptic effects of N-palmitoylethanolamide, a putative endocannabinoid.	2004 Oct	15461672
The search for the palmitoylethanolamide receptor.	2005 Aug 19	15963531
Effects of saturated long-chain N-acylethanolamines on voltage-dependent Ca2+ fluxes in rabbit T-tubule membranes.	2005 Feb 15	15639235
Emollients with endocannabinoids in the treatment of uremic pruritus: discussion of the therapeutic options.	2005 Jun	15967006
Involvement of the cannabimimetic compound, N-palmitoyl-ethanolamine, in inflammatory and neuropathic conditions: review of the available pre-clinical data, and first human studies.	2005 Jun	15910891
A second N-acylethanolamine hydrolase in mammalian tissues.	2005 Jun	15910884
Accumulation of anandamide: evidence for cellular diversity.	2005 Jun	15910883
Molecular characterization of N-acylethanolamine-hydrolyzing acid amidase, a novel member of the choloylglycine hydrolase family with structural and functional similarity to acid ceramidase.	2005 Mar 25	15655246
Endogenous cannabinoid receptor agonists inhibit neurogenic inflammations in guinea pig airways.	2005 Sep	16103691
Cannabinoid receptors and endocannabinoids: evidence for new players.	2006 Apr 28	16796380
Oxyhomologues of anandamide and related endolipids: chemoselective synthesis and biological activity.	2006 Apr 6	16570929
High-throughput screening for the discovery of inhibitors of fatty acid amide hydrolase using a microsome-based fluorescent assay.	2006 Aug	16760367
Structure-based design of a FAAH variant that discriminates between the N-acyl ethanolamine and taurine families of signaling lipids.	2006 Aug 1	16866346
A FAAH-regulated class of N-acyl taurines that activates TRP ion channels.	2006 Aug 1	16866345
MimyX cream.	2006 Jan-Feb	16522980
Modulation of P-glycoprotein activity by cannabinoid molecules in HK-2 renal cells.	2006 Jul	16715117
Molecular packing and intermolecular interactions in two structural polymorphs of N-palmitoylethanolamine, a type 2 cannabinoid receptor agonist.	2006 Jul	16609146
Deorphanization of a G protein-coupled receptor for oleoylethanolamide and its use in the discovery of small-molecule hypophagic agents.	2006 Mar	16517404
[Topical cannabinoid agonists. An effective new possibility for treating chronic pruritus].	2006 Sep	16874533
The psychedelic haze of inflammation.	2007 Jan	16554178
Palmitoylethanolamide, endocannabinoids and related cannabimimetic compounds in protection against tissue inflammation and pain: potential use in companion animals.	2007 Jan	16324856

Patents

Sample Use Guides

In Vivo Use Guide

Ultra-micronized palmitoylethanolamide 600 mg twice daily.

Route of Administration: Oral

In Vitro Use Guide

Palmitoylethanolamide (PEA) potently enhances the anti-proliferative effects of arachidonoylethanolamide (AEA) on human breast cancer cells (HBCCs), in part by inhibiting the expression of fatty acid amide hydrolase (FAAH), the major enzyme catalyzing AEA degradation. PEA (1-10 microM) enhanced in a dose-related manner the inhibitory effect of AEA on both basal and nerve growth factor (NGF)-induced HBCC proliferation, without inducing any cytostatic effect by itself. PEA (5 microM) decreased the IC50 values for AEA inhibitory effects by 3-6-fold. The effect of PEA was due in part to inhibition of AEA degradation, since treatment of MCF-7 breast cancer cells with 5 microM PEA caused an approximately 30-40% down-regulation of FAAH expression and activity.

Name

Type

Language

PALMIDROL

Official Name

English

N-(2-HYDROXYETHYL)PALMITAMIDE

Systematic Name

English

PALMITAMIDE MEA [INCI]

Common Name

English

SCI-110 component palmitoylethanolamide

Code

English

PALMITIC MONOETHANOLAMIDE

Common Name

English

PALMITOYLETHANOLAMIDE [NFLIS-DRUG]

Common Name

English

HEXADECANAMIDE, N-(2-HYDROXYETHYL)-

Systematic Name

English

PALMITOYLETHANOLAMIDE

Common Name

English

N-(2-HYDROXYETHYL)-PALMITIDE

Common Name

English

N(2-HYDROXYETHYL)PALMITIDE

Common Name

English

PALMITAMIDE MEA

Official Name

English

N-PALMITOYL ETHANOLAMIDE

Systematic Name

English

PALMIDROL [MART.]

Common Name

English

PEA (Chemical)

Common Name

English

N(2-HYDROXYETHYL) PALMITIDE

Common Name

English

N-PALMITOYLETHANOLAMINE

Systematic Name

English

PALMDROL PRODES

Brand Name

English

N-(2-HYDROXYETHYL)HEXADECANAMIDE

Systematic Name

English

PALMITIC ACID MONOETHANOLAMIDE

Common Name

English

palmidrol [INN]

Common Name

English

LEVAGEN

Brand Name

English

NSC-23320

Code

English

PALMITOYL ETHANOLAMIDE

Common Name

English

FSD-201

Code

English

PALMIDROL [MI]

Common Name

English

2-PALMITAMIDOETHANOL

Systematic Name

English

IMPULSIN

Brand Name

English

N-HEXADECANOYLETHANOLAMINE

Systematic Name

English

Palmidrol [WHO-DD]

Common Name

English

LORAMINE P 256

Brand Name

English

AM 3112

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C2198