Oleamide (BioDeep_00000002283)

 

Secondary id: BioDeep_00000408474

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


(9Z)-octadec-9-enamide

化学式: C18H35NO (281.2719)
中文名称: 油酸酰胺
谱图信息: 最多检出来源 Homo sapiens(blood) 18.78%

Reviewed

Last reviewed on 2024-07-02.

Cite this Page

Oleamide. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/oleamide (retrieved 2024-12-22) (BioDeep RN: BioDeep_00000002283). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CCCCCCCC/C=C\CCCCCCCC(=O)N
InChI: InChI=1S/C18H35NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H2,19,20)/b10-9-

描述信息

Oleamide is an amide of the fatty acid oleic acid. It is an endogenous substance: it occurs naturally in the body of animals. It accumulates in the cerebrospinal fluid during sleep deprivation and induces sleep in animals. It is being studied as a potential medical treatment for mood and sleep disorders, and cannabinoid-regulated depression. The mechanism of action of oleamides sleep inducing effects is an area of current research. It is likely that oleamide interacts with multiple neurotransmitter systems. Oleamide is structurally related to the endogenous cannabinoid anandamide, and has the ability to bind to the CB1 receptor as a full agonist.

Oleamide. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=301-02-0 (retrieved 2024-07-02) (CAS RN: 301-02-0). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Oleamide is an endogenous fatty acid amide which can be synthesized de novo in the mammalian nervous system, and has been detected in human plasma.

同义名列表

41 个代谢物同义名

(cis)-9-Octadecenoic acid amide; (Z)-Octadec-9-enoic acid amide; (Z)-Octadec-9-enoate amide; trans-9,10-Octadecenoamide; (cis)-9-Octadecenoic acid; cis-9,10-Octadecenoamide; Oleylamide, (e)-isomer; (9Z)-Octadec-9-enamide; (cis)-9-Octadecenoate; (9Z)-9-Octadecenamide; (Z)-9-Octadecenamide; 14C-Labeled oleamide; (9Z)-Octadecenamide; 9,10-Octadecenamide; 9Z-octadecenamide; Octadecene amide; 9-Octadecenamide; Oleic acid amide; Aliphatic amide; Petrac slip-eze; Polydis TR 121; Elaidoylamide; Diamide O 200; Crodamide or; Unislip 1759; Oleate amide; Diamit O 200; Oleyl amide; Crodamide O; Armoslip CP; Tocris-0878; Kemamide O; Oleylamide; Adogen 73; Oleamide; Slip-eze; Armid O; Amide O; ELD; Oleamide; Oleamide



数据库引用编号

15 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

40 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(40)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

7 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表
Cytoplasm 11 AXIN2, BCL2, CNR1, CNR2, GJA1, MAPK14, MAPK8, NOS2, PIK3R6, PTGS2, TLR4
Peripheral membrane protein 2 PIK3R6, PTGS2
Endosome membrane 1 TLR4
Endoplasmic reticulum membrane 5 BCL2, FAAH, GJA1, GJB1, PTGS2
Nucleus 6 AXIN2, BCL2, GJA1, MAPK14, MAPK8, NOS2
cytosol 7 AXIN2, BCL2, GJA1, MAPK14, MAPK8, NOS2, PIK3R6
dendrite 3 CNR2, HTR2A, HTR7
centrosome 1 AXIN2
nucleoplasm 4 GJA1, MAPK14, MAPK8, NOS2
Cell membrane 10 CNR1, GJA1, GJB1, GJB2, GPRC5A, HTR2A, HTR7, PIK3R6, TLR4, TRPV1
Cell projection, axon 2 CNR1, HTR2A
Multi-pass membrane protein 10 CATSPER3, CNR1, FAAH, GJA1, GJB1, GJB2, GPRC5A, HTR2A, HTR7, TRPV1
Synapse 2 HTR7, MAPK8
cell junction 1 GJA1
cell surface 1 TLR4
dendritic shaft 1 HTR2A
glutamatergic synapse 4 CNR1, FAAH, HTR2A, MAPK14
Golgi apparatus 1 GJA1
Golgi membrane 2 GJA1, INS
growth cone 1 CNR1
neuronal cell body 2 HTR2A, TRPV1
postsynapse 1 FAAH
presynaptic membrane 2 CNR1, HTR2A
Cytoplasm, cytosol 1 NOS2
Presynapse 3 CNR1, FAAH, HTR2A
acrosomal vesicle 1 CATSPER3
plasma membrane 13 AXIN2, CATSPER3, CNR1, CNR2, GJA1, GJB2, GPRC5A, HTR2A, HTR7, NOS2, PIK3R6, TLR4, TRPV1
Membrane 5 BCL2, FAAH, PIK3R6, TLR4, TRPV1
apical plasma membrane 1 GJA1
axon 3 CNR1, HTR2A, MAPK8
caveola 2 HTR2A, PTGS2
extracellular exosome 1 GPRC5A
endoplasmic reticulum 6 BCL2, CATSPER3, CNR2, FAAH, GJA1, PTGS2
extracellular space 1 INS
perinuclear region of cytoplasm 3 GJB2, NOS2, TLR4
gap junction 2 GJA1, GJB2
intercalated disc 1 GJA1
mitochondrion 3 BCL2, GJA1, MAPK14
protein-containing complex 2 BCL2, PTGS2
intracellular membrane-bounded organelle 2 GJA1, GPRC5A
Microsome membrane 2 FAAH, PTGS2
Single-pass type I membrane protein 1 TLR4
Secreted 1 INS
extracellular region 2 INS, MAPK14
Mitochondrion outer membrane 2 BCL2, CNR1
Single-pass membrane protein 2 BCL2, FAAH
mitochondrial outer membrane 2 BCL2, CNR1
motile cilium 1 CATSPER3
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 2 TLR4, TRPV1
actin cytoskeleton 1 CNR1
perikaryon 1 CNR2
beta-catenin destruction complex 1 AXIN2
cytoplasmic vesicle 1 HTR2A
nucleolus 1 GPRC5A
Cytoplasm, P-body 1 NOS2
P-body 1 NOS2
Early endosome 1 TLR4
vesicle 1 GPRC5A
postsynaptic membrane 3 CNR2, HTR2A, TRPV1
Cytoplasm, perinuclear region 1 NOS2
Membrane raft 2 CNR1, GJA1
pore complex 1 BCL2
Cytoplasm, cytoskeleton 1 FAAH
focal adhesion 1 GJA1
GABA-ergic synapse 2 CNR1, TRPV1
Peroxisome 1 NOS2
peroxisomal matrix 1 NOS2
Cell junction, gap junction 3 GJA1, GJB1, GJB2
connexin complex 3 GJA1, GJB1, GJB2
contractile muscle fiber 1 GJA1
fascia adherens 1 GJA1
intermediate filament 1 GJA1
lateral plasma membrane 3 GJA1, GJB1, GJB2
nuclear speck 1 MAPK14
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Postsynaptic cell membrane 1 TRPV1
Cell projection, ruffle 1 TLR4
ruffle 1 TLR4
receptor complex 2 GPRC5A, TLR4
Cell projection, neuron projection 1 TRPV1
neuron projection 1 PTGS2
phagocytic cup 1 TLR4
cytoskeleton 1 FAAH
spindle pole 1 MAPK14
organelle membrane 1 FAAH
Endomembrane system 1 FAAH
endosome lumen 1 INS
Membrane, caveola 1 HTR2A
Cell projection, cilium, flagellum membrane 1 CATSPER3
Cytoplasmic vesicle membrane 1 GPRC5A
cell body fiber 1 HTR2A
Cell projection, dendrite 2 CNR2, HTR2A
Golgi-associated vesicle membrane 1 GJA1
cell body 1 GJB2
myelin sheath 1 BCL2
trans-Golgi network membrane 1 HTR7
lipopolysaccharide receptor complex 1 TLR4
ficolin-1-rich granule lumen 1 MAPK14
secretory granule lumen 2 INS, MAPK14
Golgi lumen 1 INS
endoplasmic reticulum lumen 2 INS, PTGS2
phosphatidylinositol 3-kinase complex 1 PIK3R6
phosphatidylinositol 3-kinase complex, class IA 1 PIK3R6
transport vesicle 1 INS
tight junction 1 GJA1
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
neurofilament 1 HTR2A
endoplasmic reticulum-Golgi intermediate compartment 1 GJB2
extrinsic component of cytoplasmic side of plasma membrane 1 CNR2
basal dendrite 1 MAPK8
Cell projection, dendritic spine membrane 1 TRPV1
dendritic spine membrane 1 TRPV1
cell-cell contact zone 1 GJA1
astrocyte projection 1 GJB2
cortical cytoskeleton 1 NOS2
BAD-BCL-2 complex 1 BCL2
G protein-coupled serotonin receptor complex 1 HTR2A
phosphatidylinositol 3-kinase complex, class IB 1 PIK3R6
CatSper complex 1 CATSPER3


文献列表

  • Carolina Y Reyes-Soto, Mariana Villaseca-Flores, Enid A Ovalle-Noguez, Jade Nava-Osorio, Sonia Galván-Arzate, Edgar Rangel-López, Marisol Maya-López, Socorro Retana-Márquez, Isaac Túnez, Alexey A Tinkov, Tao Ke, Michael Aschner, Abel Santamaría. Oleamide Reduces Mitochondrial Dysfunction and Toxicity in Rat Cortical Slices Through the Combined Action of Cannabinoid Receptors Activation and Induction of Antioxidant Activity. Neurotoxicity research. 2022 Dec; 40(6):2167-2178. doi: 10.1007/s12640-022-00575-7. [PMID: 36069981]
  • Prapakorn Wisitpongpun, Pachuen Potup, Kanchana Usuwanthim. Oleamide-Mediated Polarization of M1 Macrophages and IL-1β Production by Regulating NLRP3-Inflammasome Activation in Primary Human Monocyte-Derived Macrophages. Frontiers in immunology. 2022; 13(?):856296. doi: 10.3389/fimmu.2022.856296. [PMID: 35514993]
  • Andrzej L Dawidowicz, Michal P Dybowski, Michal Rombel, Rafal Typek. Improving the sensitivity of estimating CBD and other xenobiotics in plasma samples: Oleamide-induced transient matrix effect. Journal of pharmaceutical and biomedical analysis. 2021 Sep; 204(?):114265. doi: 10.1016/j.jpba.2021.114265. [PMID: 34298472]
  • Yasuyuki Kobayashi, Natsumi Watanabe, Tomoya Kitakaze, Keiichiro Sugimoto, Takeshi Izawa, Kenji Kai, Naoki Harada, Ryoichi Yamaji. Oleamide rescues tibialis anterior muscle atrophy of mice housed in small cages. The British journal of nutrition. 2021 08; 126(4):481-491. doi: 10.1017/s0007114520004304. [PMID: 33143796]
  • Hui Li, Yan Wang, Shizhao Ma, Chaoqun Zhang, Hua Liu, Dianxing Sun. Clinical significance of small molecule metabolites in the blood of patients with different types of liver injury. Scientific reports. 2021 06; 11(1):11642. doi: 10.1038/s41598-021-91164-9. [PMID: 34079030]
  • Ahmed Wahab Obeng, Yaw Duah Boakye, Theresa Appiah Agana, Georgina Isabella Djameh, Daniel Boamah, Francis Adu. Anti-trypanosomal and anthelminthic properties of ethanol and aqueous extracts of Tetrapleura tetraptera Taub. Veterinary parasitology. 2021 Jun; 294(?):109449. doi: 10.1016/j.vetpar.2021.109449. [PMID: 33991727]
  • Avik Roy, Madhuchhanda Kundu, Sudipta Chakrabarti, Dhruv R Patel, Kalipada Pahan. Oleamide, a Sleep-Inducing Supplement, Upregulates Doublecortin in Hippocampal Progenitor Cells via PPARα. Journal of Alzheimer's disease : JAD. 2021; 84(4):1747-1762. doi: 10.3233/jad-215124. [PMID: 34744082]
  • Unchaleeporn Ameamsri, Arunrat Chaveerach, Runglawan Sudmoon, Tawatchai Tanee, Steve Peigneur, Jan Tytgat. Oleamide in Ipomoea and Dillenia Species and Inflammatory Activity Investigated through Ion Channel Inhibition. Current pharmaceutical biotechnology. 2021; 22(2):254-261. doi: 10.2174/1389201021666200607185250. [PMID: 32515307]
  • Abdirahman Elmi, Rosella Spina, Arnaud Risler, Stéphanie Philippot, Ali Mérito, Raphaël E Duval, Fatouma Mohamed Abdoul-Latif, Dominique Laurain-Mattar. Evaluation of Antioxidant and Antibacterial Activities, Cytotoxicity of Acacia seyal Del Bark Extracts and Isolated Compounds. Molecules (Basel, Switzerland). 2020 May; 25(10):. doi: 10.3390/molecules25102392. [PMID: 32455580]
  • Marisol Maya-López, Leonardo C Rubio-López, Ivana V Rodríguez-Alvarez, Julián Orduño-Piceno, Yuliza Flores-Valdivia, Aline Colonnello, Edgar Rangel-López, Isaac Túnez, Oscar Prospéro-García, Abel Santamaría. A Cannabinoid Receptor-Mediated Mechanism Participates in the Neuroprotective Effects of Oleamide Against Excitotoxic Damage in Rat Brain Synaptosomes and Cortical Slices. Neurotoxicity research. 2020 Jan; 37(1):126-135. doi: 10.1007/s12640-019-00083-1. [PMID: 31286434]
  • Tian Li, Zhi F Zhou, Ping Zhang, Kun Qian, Tian C Zhang. Enhancing nitrobenzene biodegradation in aquatic systems: Feasibility of using plain soil as an inoculant and effects of adding ascorbic acid and peptone. Chemosphere. 2020 Jan; 239(?):124806. doi: 10.1016/j.chemosphere.2019.124806. [PMID: 31726521]
  • I Lacatusu, N Badea, D Udeanu, L Coc, A Pop, C Cioates Negut, C Tanase, R Stan, A Meghea. Improved anti-obesity effect of herbal active and endogenous lipids co-loaded lipid nanocarriers: Preparation, in vitro and in vivo evaluation. Materials science & engineering. C, Materials for biological applications. 2019 Jun; 99(?):12-24. doi: 10.1016/j.msec.2019.01.071. [PMID: 30889655]
  • Jie Zhang, Sudeepa Bhattacharyya, Robert C Hickner, Alan R Light, Christopher J Lambert, Bruce K Gale, Oliver Fiehn, Sean H Adams. Skeletal muscle interstitial fluid metabolomics at rest and associated with an exercise bout: application in rats and humans. American journal of physiology. Endocrinology and metabolism. 2019 01; 316(1):E43-E53. doi: 10.1152/ajpendo.00156.2018. [PMID: 30398905]
  • Kuljeet S Gugnani, Nguyen Vu, Alejandro N Rondón-Ortiz, Mark Böhlke, Timothy J Maher, Alejandro J Pino-Figueroa. Neuroprotective activity of macamides on manganese-induced mitochondrial disruption in U-87 MG glioblastoma cells. Toxicology and applied pharmacology. 2018 02; 340(?):67-76. doi: 10.1016/j.taap.2017.12.014. [PMID: 29288688]
  • Oluwakemi Josephine Awakan, Sylvia Omonirume Malomo, Abdullahi Adeyinka Adejare, Adedoyin Igunnu, Olubunmi Atolani, Abiodun Humphrey Adebayo, Bamidele Victor Owoyele. Anti-inflammatory and bronchodilatory constituents of leaf extracts of Anacardium occidentale L. in animal models. Journal of integrative medicine. 2018 01; 16(1):62-70. doi: 10.1016/j.joim.2017.12.009. [PMID: 29397096]
  • Hui Li, Su-Fang Fan, Yan Wang, Shi-Gang Shen, Dian-Xing Sun. Rapid Detection of Small Molecule Metabolites in Serum of Hepatocellular Carcinoma Patients Using Ultrafast Liquid Chromatography-Ion Trap-Time of Flight Tandem Mass Spectrometry. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry. 2017; 33(5):573-578. doi: 10.2116/analsci.33.573. [PMID: 28496060]
  • Li Sun, Yufang Lu, Herbert J Kronzucker, Weiming Shi. Quantification and enzyme targets of fatty acid amides from duckweed root exudates involved in the stimulation of denitrification. Journal of plant physiology. 2016 Jul; 198(?):81-8. doi: 10.1016/j.jplph.2016.04.010. [PMID: 27152459]
  • Woong-Suk Yang, Sung Ryul Lee, Yong Joon Jeong, Dae Won Park, Young Mi Cho, Hae Mi Joo, Inhye Kim, Young-Bae Seu, Eun-Hwa Sohn, Se Chan Kang. Antiallergic Activity of Ethanol Extracts of Arctium lappa L. Undried Roots and Its Active Compound, Oleamide, in Regulating FcεRI-Mediated and MAPK Signaling in RBL-2H3 Cells. Journal of agricultural and food chemistry. 2016 May; 64(18):3564-73. doi: 10.1021/acs.jafc.6b00425. [PMID: 27087645]
  • J A Kaplan, P Barthélémy, M W Grinstaff. Self-assembled nanofiber hydrogels for mechanoresponsive therapeutic anti-TNFα antibody delivery. Chemical communications (Cambridge, England). 2016 Apr; 52(34):5860-3. doi: 10.1039/c6cc02221a. [PMID: 27049283]
  • Almerinda Di Venere, Enrico Dainese, Filomena Fezza, Beatrice Clotilde Angelucci, Nicola Rosato, Benjamin F Cravatt, Alessandro Finazzi-Agrò, Giampiero Mei, Mauro Maccarrone. Rat and human fatty acid amide hydrolases: overt similarities and hidden differences. Biochimica et biophysica acta. 2012 Nov; 1821(11):1425-33. doi: 10.1016/j.bbalip.2012.07.021. [PMID: 22877990]
  • Ziqing Hei, Ailan Zhang, Jing Wei, Xiaoliang Gan, Yanling Wang, Gangjian Luo, Xiaoyun Li. Lipopolysaccharide effects on the proliferation of NRK52E cells via alternations in gap-junction function. The journal of trauma and acute care surgery. 2012 Jul; 73(1):67-72. doi: 10.1097/ta.0b013e318256a0fe. [PMID: 22743374]
  • Hu Song, Jun-sheng Peng, Dong-sheng Yao, Da-ling Liu, Zu-li Yang, Yan-ping Du, Jun Xiang. Metabolic disorders of fatty acids and fatty acid amides associated with human gastric cancer morbidity. Chinese medical journal. 2012 Mar; 125(5):757-63. doi: . [PMID: 22490569]
  • Emma K Farrell, Yuden Chen, Muna Barazanji, Kristen A Jeffries, Felipe Cameroamortegui, David J Merkler. Primary fatty acid amide metabolism: conversion of fatty acids and an ethanolamine in N18TG2 and SCP cells. Journal of lipid research. 2012 Feb; 53(2):247-56. doi: 10.1194/jlr.m018606. [PMID: 22095832]
  • Michal Ciborowski, Joanna Teul, Jose Luis Martin-Ventura, Jesús Egido, Coral Barbas. Metabolomics with LC-QTOF-MS permits the prediction of disease stage in aortic abdominal aneurysm based on plasma metabolic fingerprint. PloS one. 2012; 7(2):e31982. doi: 10.1371/journal.pone.0031982. [PMID: 22384120]
  • Angela I Calderón, Johayra Simithy-Williams, Mahabir P Gupta. Antimalarial natural products drug discovery in Panama. Pharmaceutical biology. 2012 Jan; 50(1):61-71. doi: 10.3109/13880209.2011.602417. [PMID: 22196582]
  • Gayong Shim, Su-Eun Han, Yong-Hee Yu, Sangbin Lee, Han Young Lee, Kwangmeyung Kim, Ick Chan Kwon, Tae Gwan Park, Young Bong Kim, Yong Seok Choi, Chan-Wha Kim, Yu-Kyoung Oh. Trilysinoyl oleylamide-based cationic liposomes for systemic co-delivery of siRNA and an anticancer drug. Journal of controlled release : official journal of the Controlled Release Society. 2011 Oct; 155(1):60-6. doi: 10.1016/j.jconrel.2010.10.017. [PMID: 20971142]
  • Enrico Adriano, Luisa Perasso, Isabella Panfoli, Silvia Ravera, Carlo Gandolfo, Gianluigi Mancardi, Alessandro Morelli, Maurizio Balestrino. A novel hypothesis about mechanisms affecting conduction velocity of central myelinated fibers. Neurochemical research. 2011 Oct; 36(10):1732-9. doi: 10.1007/s11064-011-0488-0. [PMID: 21553257]
  • Ranjith Munigunti, Nicholas Nelson, Vanisree Mulabagal, Mahabir P Gupta, Reto Brun, Angela I Calderón. Identification of oleamide in Guatteria recurvisepala by LC/MS-based Plasmodium falciparum thioredoxin reductase ligand binding method. Planta medica. 2011 Oct; 77(15):1749-53. doi: 10.1055/s-0030-1271080. [PMID: 21567357]
  • Bénédicte Desforges, Philippe Savarin, Ouissame Bounedjah, Stéphanie Delga, Loïc Hamon, Patrick A Curmi, David Pastré. Gap junctions favor normal rat kidney epithelial cell adaptation to chronic hypertonicity. American journal of physiology. Cell physiology. 2011 Sep; 301(3):C705-16. doi: 10.1152/ajpcell.00128.2011. [PMID: 21677260]
  • Caixia Chen, Xin Jin, Xianglan Meng, Chengwei Zheng, Yanhui Shen, Yiqing Wang. Inhibition of TNFα-induced adhesion molecule expression by (Z)-(S)-9-octadecenamide, N-(2-hydroxyethyl,1-methyl). European journal of pharmacology. 2011 Jun; 660(2-3):305-9. doi: 10.1016/j.ejphar.2011.04.009. [PMID: 21510930]
  • Jiang-shan Lian, Wei Liu, Shao-rui Hao, Yong-zheng Guo, Hai-jun Huang, De-ying Chen, Qing Xie, Xiao-ping Pan, Wei Xu, Wen-xia Yuan, Lan-juan Li, Jian-rong Huang. A serum metabonomic study on the difference between alcohol- and HBV-induced liver cirrhosis by ultraperformance liquid chromatography coupled to mass spectrometry plus quadrupole time-of-flight mass spectrometry. Chinese medical journal. 2011 May; 124(9):1367-73. doi: . [PMID: 21740750]
  • Bing Liu, Qin Wang, Dong-dong Yuan, Xiao-ting Hong, Liang Tao. Berberine potentizes apoptosis induced by X-rays irradiation probably through modulation of gap junctions. Chinese medical journal. 2011 Apr; 124(8):1221-8. doi: . [PMID: 21543001]
  • Almudena Sánchez-Villegas, Lisa Verberne, Jokin De Irala, Miguel Ruíz-Canela, Estefanía Toledo, Lluis Serra-Majem, Miguel Angel Martínez-González. Dietary fat intake and the risk of depression: the SUN Project. PloS one. 2011 Jan; 6(1):e16268. doi: 10.1371/journal.pone.0016268. [PMID: 21298116]
  • Matthew S Thimgan, Yasuko Suzuki, Laurent Seugnet, Laura Gottschalk, Paul J Shaw. The perilipin homologue, lipid storage droplet 2, regulates sleep homeostasis and prevents learning impairments following sleep loss. PLoS biology. 2010 Aug; 8(8):. doi: 10.1371/journal.pbio.1000466. [PMID: 20824166]
  • Ming-Ching Cheng, Yaw-Bee Ker, Tung-Hsi Yu, Li-Yun Lin, Robert Y Peng, Chiung-Huei Peng. Chemical synthesis of 9(Z)-octadecenamide and its hypolipidemic effect: a bioactive agent found in the essential oil of mountain celery seeds. Journal of agricultural and food chemistry. 2010 Feb; 58(3):1502-8. doi: 10.1021/jf903573g. [PMID: 20078072]
  • Yunping Qiu, Guoxiang Cai, Mingming Su, Tianlu Chen, Xiaojiao Zheng, Ye Xu, Yan Ni, Aihua Zhao, Lisa X Xu, Sanjun Cai, Wei Jia. Serum metabolite profiling of human colorectal cancer using GC-TOFMS and UPLC-QTOFMS. Journal of proteome research. 2009 Oct; 8(10):4844-50. doi: 10.1021/pr9004162. [PMID: 19678709]
  • Darren Locke, Andrew L Harris. Connexin channels and phospholipids: association and modulation. BMC biology. 2009 Aug; 7(?):52. doi: 10.1186/1741-7007-7-52. [PMID: 19686581]
  • Bo-Guang Wang, Yan Zhou, Zhi-Cheng Feng, Hui-Xuan Liu. [Research on source profile of aerosol organic compounds in leather plant]. Huan jing ke xue= Huanjing kexue. 2009 Apr; 30(4):993-6. doi: ". [PMID: 19544995]
  • Dagmar Koethe, Daniela Schreiber, Andrea Giuffrida, Christian Mauss, Johannes Faulhaber, Bernd Heydenreich, Martin Hellmich, Rudolf Graf, Joachim Klosterkötter, Daniele Piomelli, F Markus Leweke. Sleep deprivation increases oleoylethanolamide in human cerebrospinal fluid. Journal of neural transmission (Vienna, Austria : 1996). 2009 Mar; 116(3):301-5. doi: 10.1007/s00702-008-0169-6. [PMID: 19137236]
  • Renjie Zhang, Helmuth Möhwald, Dirk G Kurth. One-step formation of straight nanostripes from a mammal lipid-oleamide directly on highly oriented pyrolytic graphite. Langmuir : the ACS journal of surfaces and colloids. 2009 Feb; 25(4):2290-3. doi: 10.1021/la8035506. [PMID: 19125608]
  • Gregory P Mueller, William J Driscoll. Biosynthesis of oleamide. Vitamins and hormones. 2009; 81(?):55-78. doi: 10.1016/s0083-6729(09)81003-0. [PMID: 19647108]
  • Igor A Butovich. On the lipid composition of human meibum and tears: comparative analysis of nonpolar lipids. Investigative ophthalmology & visual science. 2008 Sep; 49(9):3779-89. doi: 10.1167/iovs.08-1889. [PMID: 18487374]
  • Gino Serra, Walter Fratta. A possible role for the endocannabinoid system in the neurobiology of depression. Clinical practice and epidemiology in mental health : CP & EMH. 2007 Nov; 3(?):25. doi: 10.1186/1745-0179-3-25. [PMID: 18021439]
  • Igor A Butovich, Eduardo Uchiyama, James P McCulley. Lipids of human meibum: mass-spectrometric analysis and structural elucidation. Journal of lipid research. 2007 Oct; 48(10):2220-35. doi: 10.1194/jlr.m700237-jlr200. [PMID: 17626978]
  • Xiu Yan Wei, Jing Yu Yang, Ying Xu Dong, Chun Fu Wu. Anxiolytic-like effects of oleamide in group-housed and socially isolated mice. Progress in neuro-psychopharmacology & biological psychiatry. 2007 Aug; 31(6):1189-95. doi: 10.1016/j.pnpbp.2007.04.008. [PMID: 17521793]
  • William J Driscoll, Shalini Chaturvedi, Gregory P Mueller. Oleamide synthesizing activity from rat kidney: identification as cytochrome c. The Journal of biological chemistry. 2007 Aug; 282(31):22353-63. doi: 10.1074/jbc.m610070200. [PMID: 17496328]
  • Gregory P Mueller, William J Driscoll. In vitro synthesis of oleoylglycine by cytochrome c points to a novel pathway for the production of lipid signaling molecules. The Journal of biological chemistry. 2007 Aug; 282(31):22364-9. doi: 10.1074/jbc.m701801200. [PMID: 17537719]
  • Geoffray Labar, Catherine Michaux. Fatty acid amide hydrolase: from characterization to therapeutics. Chemistry & biodiversity. 2007 Aug; 4(8):1882-902. doi: 10.1002/cbdv.200790157. [PMID: 17712824]
  • Yusuke Ohba, Yukiko Kanao, Nobuyoshi Morita, Eri Fujii, Mai Hohrai, Mayuko Takatsuji, Hideki Hirose, Daisaku Miura, Akihiro Watari, Masuo Yutsudo, Hanjun Zhao, Norikazu Yabuta, Akihiko Ito, Yasuyuki Kita, Hiroshi Nojima. Oleamide derivatives suppress the spontaneous metastasis by inhibiting connexin 26. International journal of cancer. 2007 Jul; 121(1):47-54. doi: 10.1002/ijc.22608. [PMID: 17290388]
  • Daisaku Miura, Yoshishige Kida, Hiroshi Nojima. Camellia oil and its distillate fractions effectively inhibit the spontaneous metastasis of mouse melanoma BL6 cells. FEBS letters. 2007 May; 581(13):2541-8. doi: 10.1016/j.febslet.2007.04.080. [PMID: 17499720]
  • Farida Goubaeva, Maya Mikami, Sarah Giardina, Bo Ding, Junichi Abe, Jay Yang. Cardiac mitochondrial connexin 43 regulates apoptosis. Biochemical and biophysical research communications. 2007 Jan; 352(1):97-103. doi: 10.1016/j.bbrc.2006.10.177. [PMID: 17107662]
  • G Irmisch, D Schläfke, W Gierow, S Herpertz, J Richter. Fatty acids and sleep in depressed inpatients. Prostaglandins, leukotrienes, and essential fatty acids. 2007 Jan; 76(1):1-7. doi: 10.1016/j.plefa.2006.09.001. [PMID: 17123808]
  • Kelly K Nichols, Bryan M Ham, Jason J Nichols, Corrie Ziegler, Kari B Green-Church. Identification of fatty acids and fatty acid amides in human meibomian gland secretions. Investigative ophthalmology & visual science. 2007 Jan; 48(1):34-9. doi: 10.1167/iovs.06-0753. [PMID: 17197513]
  • Ivan Tubert-Brohman, Orlando Acevedo, William L Jorgensen. Elucidation of hydrolysis mechanisms for fatty acid amide hydrolase and its Lys142Ala variant via QM/MM simulations. Journal of the American Chemical Society. 2006 Dec; 128(51):16904-13. doi: 10.1021/ja065863s. [PMID: 17177441]
  • Shalini Chaturvedi, William J Driscoll, Brenda M Elliot, Martha M Faraday, Neil E Grunberg, Gregory P Mueller. In vivo evidence that N-oleoylglycine acts independently of its conversion to oleamide. Prostaglandins & other lipid mediators. 2006 Dec; 81(3-4):136-49. doi: 10.1016/j.prostaglandins.2006.09.001. [PMID: 17085322]
  • H Paul Ehrlich, Bonnie Sun, Gregory C Saggers, Fatuma Kromath. Gap junction communications influence upon fibroblast synthesis of Type I collagen and fibronectin. Journal of cellular biochemistry. 2006 Jul; 98(4):735-43. doi: 10.1002/jcb.20852. [PMID: 16475185]
  • Cristiano Ruch Werneck Guimarães, Dale L Boger, William L Jorgensen. Elucidation of fatty acid amide hydrolase inhibition by potent alpha-ketoheterocycle derivatives from Monte Carlo simulations. Journal of the American Chemical Society. 2005 Dec; 127(49):17377-84. doi: 10.1021/ja055438j. [PMID: 16332087]
  • J Michael Walker, Jocelyn F Krey, Jay S Chen, Eivind Vefring, Jan A Jahnsen, Heather Bradshaw, Susan M Huang. Targeted lipidomics: fatty acid amides and pain modulation. Prostaglandins & other lipid mediators. 2005 Sep; 77(1-4):35-45. doi: 10.1016/j.prostaglandins.2004.09.017. [PMID: 16099389]
  • Michaela Egertová, Gregory J Michael, Benjamin F Cravatt, Maurice R Elphick. Fatty acid amide hydrolase in brain ventricular epithelium: mutually exclusive patterns of expression in mouse and rat. Journal of chemical neuroanatomy. 2004 Nov; 28(3):171-81. doi: 10.1016/j.jchemneu.2004.07.001. [PMID: 15482903]
  • Aron H Lichtman, Donmienne Leung, Christopher C Shelton, Alan Saghatelian, Christophe Hardouin, Dale L Boger, Benjamin F Cravatt. Reversible inhibitors of fatty acid amide hydrolase that promote analgesia: evidence for an unprecedented combination of potency and selectivity. The Journal of pharmacology and experimental therapeutics. 2004 Nov; 311(2):441-8. doi: 10.1124/jpet.104.069401. [PMID: 15229230]
  • David J Merkler, Geoffrey H Chew, Andrew J Gee, Kathleen A Merkler, Jean-Paul O Sorondo, Mitchell E Johnson. Oleic acid derived metabolites in mouse neuroblastoma N18TG2 cells. Biochemistry. 2004 Oct; 43(39):12667-74. doi: 10.1021/bi049529p. [PMID: 15449956]
  • Akihiko Ito, Nobuyoshi Morita, Daisaku Miura, Yu-Ichiro Koma, Tatsuki R Kataoka, Hiroshi Yamasaki, Yukihiko Kitamura, Yasuyuki Kita, Hiroshi Nojima. A derivative of oleamide potently inhibits the spontaneous metastasis of mouse melanoma BL6 cells. Carcinogenesis. 2004 Oct; 25(10):2015-22. doi: 10.1093/carcin/bgh208. [PMID: 15205356]
  • Dolores Martínez-González, Herlinda Bonilla-Jaime, Adriana Morales-Otal, Steven J Henriksen, Javier Velázquez-Moctezuma, Oscar Prospéro-García. Oleamide and anandamide effects on food intake and sexual behavior of rats. Neuroscience letters. 2004 Jun; 364(1):1-6. doi: 10.1016/j.neulet.2004.03.080. [PMID: 15193744]
  • F Rodríguez de Fonseca. [The endocannabinoid system and food intake control]. Revista de medicina de la Universidad de Navarra. 2004 Apr; 48(2):18-23. doi: . [PMID: 15382609]
  • Antonios Dougalis, George Lees, C Robin Ganellin. The sleep lipid oleamide may represent an endogenous anticonvulsant: an in vitro comparative study in the 4-aminopyridine rat brain-slice model. Neuropharmacology. 2004 Mar; 46(4):541-54. doi: 10.1016/j.neuropharm.2003.10.011. [PMID: 14975678]
  • Jiayuan Zhao, Peng Nan, Yang Zhong, Jiayuan Zhao, Peng Nan, Yang Zhong. Chemical composition of the essential oils of Clausena lansium from Hainan Island, China. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2004 Mar; 59(3-4):153-6. doi: 10.1515/znc-2004-3-401. [PMID: 15241914]
  • George Lees, Antonios Dougalis. Differential effects of the sleep-inducing lipid oleamide and cannabinoids on the induction of long-term potentiation in the CA1 neurons of the rat hippocampus in vitro. Brain research. 2004 Jan; 997(1):1-14. doi: 10.1016/j.brainres.2003.10.019. [PMID: 14715144]
  • Jinghua Huang, Huashou Li, Jun Yang, Yufen Chen, Yinghu Liu, Ning Li, Chengrong Nie. [Chemical components of Vetiveria zizanioides volatiles]. Ying yong sheng tai xue bao = The journal of applied ecology. 2004 Jan; 15(1):170-2. doi: . [PMID: 15139214]
  • Antonios Dougalis, George Lees, C Robin Ganellin. The sleep inducing brain lipid cis-oleamide (cOA) does not modulate serotonergic transmission in the CA1 pyramidal neurons of the hippocampus in vitro. Neuropharmacology. 2004 Jan; 46(1):63-73. doi: 10.1016/s0028-3908(03)00297-1. [PMID: 14654098]
  • Chun-Fu Wu, Chun-Li Li, Hong-Rui Song, Hua-Feng Zhang, Jing-Yu Yang, Yu-Ling Wang. Selective effect of oleamide, an endogenous sleep-inducing lipid amide, on pentylenetetrazole-induced seizures in mice. The Journal of pharmacy and pharmacology. 2003 Aug; 55(8):1159-62. doi: 10.1211/0022357021431. [PMID: 12956907]
  • Sandy J Wilson, Timothy W Lovenberg, Ann J Barbier. A high-throughput-compatible assay for determining the activity of fatty acid amide hydrolase. Analytical biochemistry. 2003 Jul; 318(2):270-5. doi: 10.1016/s0003-2697(03)00217-3. [PMID: 12814631]
  • Ho-Jin Heo, Young-June Park, Young-Min Suh, Soo-Jung Choi, Mi-Jeong Kim, Hong-Yon Cho, Yun-Jeong Chang, Bumshik Hong, Hye-Kyung Kim, Eunki Kim, Chang-Ju Kim, Byung-Gee Kim, Dong-Hoon Shin. Effects of oleamide on choline acetyltransferase and cognitive activities. Bioscience, biotechnology, and biochemistry. 2003 Jun; 67(6):1284-91. doi: 10.1271/bbb.67.1284. [PMID: 12843655]
  • P B Hedlund, P E Danielson, E A Thomas, K Slanina, M J Carson, J G Sutcliffe. No hypothermic response to serotonin in 5-HT7 receptor knockout mice. Proceedings of the National Academy of Sciences of the United States of America. 2003 Feb; 100(3):1375-80. doi: 10.1073/pnas.0337340100. [PMID: 12529502]
  • Anders Hamberger, Gunnar Stenhagen. Erucamide as a modulator of water balance: new function of a fatty acid amide. Neurochemical research. 2003 Feb; 28(2):177-85. doi: 10.1023/a:1022364830421. [PMID: 12608692]
  • Benjamin F Cravatt, Aron H Lichtman. The enzymatic inactivation of the fatty acid amide class of signaling lipids. Chemistry and physics of lipids. 2002 Dec; 121(1-2):135-48. doi: 10.1016/s0009-3084(02)00147-0. [PMID: 12505696]
  • Vadim Cherezov, Jeffrey Clogston, Yohann Misquitta, Wissam Abdel-Gawad, Martin Caffrey. Membrane protein crystallization in meso: lipid type-tailoring of the cubic phase. Biophysical journal. 2002 Dec; 83(6):3393-407. doi: 10.1016/s0006-3495(02)75339-3. [PMID: 12496106]
  • Natsuo Ueda. Endocannabinoid hydrolases. Prostaglandins & other lipid mediators. 2002 Aug; 68-69(?):521-34. doi: 10.1016/s0090-6980(02)00053-9. [PMID: 12432941]
  • Leanne Coyne, George Lees, Russell A Nicholson, Jian Zheng, Katherine D Neufield. The sleep hormone oleamide modulates inhibitory ionotropic receptors in mammalian CNS in vitro. British journal of pharmacology. 2002 Apr; 135(8):1977-87. doi: 10.1038/sj.bjp.0704651. [PMID: 11959801]
  • Vladimir A Krutovskikh, Colette Piccoli, Hiroshi Yamasaki, Horashi Yamasaki. Gap junction intercellular communication propagates cell death in cancerous cells. Oncogene. 2002 Mar; 21(13):1989-99. doi: 10.1038/sj.onc.1205187. [PMID: 11960371]
  • T C Jenkins, C S Adams. The biohydrogenation of linoleamide in vitro and its effects on linoleic acid concentration in duodenal contents of sheep. Journal of animal science. 2002 Feb; 80(2):533-40. doi: 10.2527/2002.802533x. [PMID: 11881938]
  • Tiziana Bisogno, Luciano De Petrocellis, Vincenzo Di Marzo. Fatty acid amide hydrolase, an enzyme with many bioactive substrates. Possible therapeutic implications. Current pharmaceutical design. 2002; 8(7):533-47. doi: 10.2174/1381612023395655. [PMID: 11945157]
  • G L Alberts, C L Chio, W B Im. Allosteric modulation of the human 5-HT(7A) receptor by lipidic amphipathic compounds. Molecular pharmacology. 2001 Dec; 60(6):1349-55. doi: 10.1124/mol.60.6.1349. [PMID: 11723242]
  • Y K Lo, K Y Tang, W N Chang, C H Lu, J S Cheng, K C Lee, K J Chou, C P Liu, W C Chen, W Su, Y P Law, C R Jan. Effect of oleamide on Ca(2+) signaling in human bladder cancer cells. Biochemical pharmacology. 2001 Nov; 62(10):1363-9. doi: 10.1016/s0006-2952(01)00772-9. [PMID: 11709196]
  • E Murillo-Rodríguez, M Giordano, R Cabeza, S J Henriksen, M Méndez Díaz, L Navarro, O Prospéro-García. Oleamide modulates memory in rats. Neuroscience letters. 2001 Nov; 313(1-2):61-4. doi: 10.1016/s0304-3940(01)02256-x. [PMID: 11684340]
  • W B Mendelson, A S Basile. The hypnotic actions of the fatty acid amide, oleamide. Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology. 2001 Nov; 25(5 Suppl):S36-9. doi: 10.1016/s0893-133x(01)00341-4. [PMID: 11682271]
  • S Huitrón-Reséndiz, L Gombart, B F Cravatt, S J Henriksen. Effect of oleamide on sleep and its relationship to blood pressure, body temperature, and locomotor activity in rats. Experimental neurology. 2001 Nov; 172(1):235-43. doi: 10.1006/exnr.2001.7792. [PMID: 11681856]
  • I Fedorova, A Hashimoto, R A Fecik, M P Hedrick, L O Hanus, D L Boger, K C Rice, A S Basile. Behavioral evidence for the interaction of oleamide with multiple neurotransmitter systems. The Journal of pharmacology and experimental therapeutics. 2001 Oct; 299(1):332-42. doi: . [PMID: 11561096]
  • M P Patricelli, B F Cravatt. Characterization and manipulation of the acyl chain selectivity of fatty acid amide hydrolase. Biochemistry. 2001 May; 40(20):6107-15. doi: 10.1021/bi002578r. [PMID: 11352748]
  • T C Jenkins, E J Thies, E E Mosley. Direct methylation procedure for converting fatty amides to fatty acid methyl esters in feed and digesta samples. Journal of agricultural and food chemistry. 2001 May; 49(5):2142-5. doi: 10.1021/jf001356x. [PMID: 11368568]
  • P C Schiller, G D'Ippolito, R Brambilla, B A Roos, G A Howard. Inhibition of gap-junctional communication induces the trans-differentiation of osteoblasts to an adipocytic phenotype in vitro. The Journal of biological chemistry. 2001 Apr; 276(17):14133-8. doi: 10.1074/jbc.m011055200. [PMID: 11278824]
  • J K Huang, C R Jan. Linoleamide, a brain lipid that induces sleep, increases cytosolic Ca2+ levels in MDCK renal tubular cells. Life sciences. 2001 Jan; 68(9):997-1004. doi: 10.1016/s0024-3205(00)01002-x. [PMID: 11212875]
  • R A Nicholson, J Zheng, C R Ganellin , B Verdon, G Lees. Anesthetic-like interaction of the sleep-inducing lipid oleamide with voltage-gated sodium channels in mammalian brain. Anesthesiology. 2001 Jan; 94(1):120-8. doi: 10.1097/00000542-200101000-00022. [PMID: 11135731]
  • D L Boger, H Sato, A E Lerner, M P Hedrick, R A Fecik, H Miyauchi, G D Wilkie, B J Austin, M P Patricelli, B F Cravatt. Exceptionally potent inhibitors of fatty acid amide hydrolase: the enzyme responsible for degradation of endogenous oleamide and anandamide. Proceedings of the National Academy of Sciences of the United States of America. 2000 May; 97(10):5044-9. doi: 10.1073/pnas.97.10.5044. [PMID: 10805767]
  • M Egertová, B F Cravatt, M R Elphick. Fatty acid amide hydrolase expression in rat choroid plexus: possible role in regulation of the sleep-inducing action of oleamide. Neuroscience letters. 2000 Mar; 282(1-2):13-6. doi: 10.1016/s0304-3940(00)00841-7. [PMID: 10713385]
  • A P Quist, S K Rhee, H Lin, R Lal. Physiological role of gap-junctional hemichannels. Extracellular calcium-dependent isosmotic volume regulation. The Journal of cell biology. 2000 Mar; 148(5):1063-74. doi: 10.1083/jcb.148.5.1063. [PMID: 10704454]
  • D D DeLuca, T C Jenkins. Feeding oleamide to lactating Jersey cows. 2. Effects on nutrient digestibility, plasma fatty acids, and hormones. Journal of dairy science. 2000 Mar; 83(3):569-76. doi: 10.3168/jds.s0022-0302(00)74916-2. [PMID: 10750115]
  • D M Lambert, V Di Marzo. The palmitoylethanolamide and oleamide enigmas : are these two fatty acid amides cannabimimetic?. Current medicinal chemistry. 1999 Aug; 6(8):757-73. doi: . [PMID: 10469890]
  • E A Thomas, B F Cravatt, J G Sutcliffe. The endogenous lipid oleamide activates serotonin 5-HT7 neurons in mouse thalamus and hypothalamus. Journal of neurochemistry. 1999 Jun; 72(6):2370-8. doi: 10.1046/j.1471-4159.1999.0722370.x. [PMID: 10349846]
  • L O Hanus, H M Fales, T F Spande, A S Basile. A gas chromatographic-mass spectral assay for the quantitative determination of oleamide in biological fluids. Analytical biochemistry. 1999 May; 270(1):159-66. doi: 10.1006/abio.1999.4083. [PMID: 10328778]