Anandamide - wikipedia Anandamide Anandamide Names IUPAC name ( 5Z, 8Z, 11Z, 14Z ) - N - ( 2 - hydroxyethyl ) icosa - 5, 8, 11, 14 - tetraenamide Other names N - arachidonoylethanolamine arachidonoylethanolamide Identifiers CAS Number 94421 - 68 - 8 3D model ( JSmol ) Interactive image Interactive image ChEBI CHEBI : 2700 ChemSpider 4445241 IUPHAR / BPS 2364 MeSH Anandamide PubChem CID 5281969 UNII UR5G69TJKH InChI InChI = 1S / C22H37NO2 / c1 - 2 - 3 - 4 - 5 - 6 - 7 - 8 - 9 - 10 - 11 - 12 - 13 - 14 - 15 - 16 - 17 - 18 - 19 - 22 ( 25 ) 23 - 20 - 21 - 24 / h6 - 7, 9 - 10, 12 - 13, 15 - 16, 24H, 2 - 5, 8, 11, 14, 17 - 21H2, 1H3, ( H, 23, 25 ) / b7 - 6 -, 10 - 9 -, 13 - 12 -, 16 - 15 - Key : LGEQQWMQCRIYKG - DOFZRALJSA - N InChI = 1 / C22H37NO2 / c1 - 2 - 3 - 4 - 5 - 6 - 7 - 8 - 9 - 10 - 11 - 12 - 13 - 14 - 15 - 16 - 17 - 18 - 19 - 22 ( 25 ) 23 - 20 - 21 - 24 / h6 - 7, 9 - 10, 12 - 13, 15 - 16, 24H, 2 - 5, 8, 11, 14, 17 - 21H2, 1H3, ( H, 23, 25 ) / b7 - 6 -, 10 - 9 -, 13 - 12 -, 16 - 15 - Key : LGEQQWMQCRIYKG - DOFZRALJBA SMILES O = C ( NCCO ) CCC C = C / C C = C / C C = C / C C = C / CCCCC CCCCC / C = C C / C = C C / C = C C / C = C CCCC ( = O ) NCCO Properties Chemical formula C H NO Molar mass 347.53 g / mol Except where otherwise noted, data are given for materials in their standard state ( at 25 ° C ( 77 ° F ), 100 kPa ). N verify ( what is ? ) Infobox references Anandamide, also known as N - arachidonoylethanolamine or AEA, is a fatty acid neurotransmitter derived from the non-oxidative metabolism of eicosatetraenoic acid ( arachidonic acid ) an essential ω - 6 polyunsaturated fatty acid. The name is taken from the Sanskrit & Pāli word ananda, which means `` joy, bliss, delight '', and amide. It is synthesized from N - arachidonoyl phosphatidylethanolamine by multiple pathways. It is degraded primarily by the fatty acid amide hydrolase ( FAAH ) enzyme, which converts anandamide into ethanolamine and arachidonic acid. As such, inhibitors of FAAH lead to elevated anandamide levels and are being pursued for therapeutic use. Contents 1 Physiological functions 2 Synthesis and degradation 3 Medical benefits 4 See also 5 References 6 External links Physiological functions See also : Neurobiological effects of physical exercise § Anandamide Anandamide was first described in 1992 by W.A. Devane and Lumír Hanuš. Anandamide 's effects can occur in either the central or peripheral nervous system. These distinct effects are mediated primarily by CB cannabinoid receptors in the central nervous system, and CB cannabinoid receptors in the periphery. The latter are mainly involved in functions of the immune system. Cannabinoid receptors were originally discovered as being sensitive to Δ - tetrahydrocannabinol ( Δ - THC, commonly called THC ), which is the primary psychoactive cannabinoid found in cannabis. The discovery of anandamide came from research into CB and CB, as it was inevitable that a naturally occurring ( endogenous ) chemical would be found to affect these receptors. Anandamide has been shown to impair working memory in rats. Studies are under way to explore what role anandamide plays in human behavior, such as eating and sleep patterns, and pain relief. Anandamide is also important for implantation of the early stage embryo in its blastocyst form into the uterus. Therefore, cannabinoids such as Δ - THC might influence processes during the earliest stages of human pregnancy. Peak plasma anandamide occurs at ovulation and positively correlates with peak estradiol and gonadotrophin levels, suggesting that these may be involved in the regulation of AEA ( anandamide ) levels. Subsequently, anandamide has been proposed as a biomarker of infertility, but so far lacks any predictive values in order to be used clinically. Anandamide plays a role in the regulation of feeding behavior, and the neural generation of motivation and pleasure. In addition, anandamide injected directly into the forebrain reward - related brain structure nucleus accumbens enhances the pleasurable responses of rats to a rewarding sucrose taste, and enhances food intake as well. Moreover, the acute beneficial effects of exercise ( termed as runner 's high ) seem to be mediated by anandamide in mice. Anandamide is the precursor of a class of physiologically active substances, the prostamides. Anandamide inhibits human breast cancer cell proliferation. Anandamide is found in chocolate together with two substances that might mimic the effects of anandamide, N - oleoylethanolamine and N - linoleoylethanolamine. Additionally, anandamide and other endocannabinoids are found in the model organism Drosophila melanogaster ( fruit fly ). Synthesis and degradation In humans, anandamide is biosynthesized from N - arachidonoyl phosphatidylethanolamine ( NAPE ). In turn NAPE arises by transfer of arachidonic acid from lecithin to the free amine of cephalin through an N - acyltransferase enzyme. Anandamide synthesis from NAPE occurs via multiple pathways and includes enzymes such as phospholipase A2, phospholipase C and NAPE - PLD. The crystal structure of NAPE - PLD in complex with phosphatidylethanolamine and deoxycholate shows how the cannabinoid anandamide is generated from membrane N - acylphosphatidylethanolamines ( NAPEs ), and reveals that bile acids - which are mainly involved in the adsorption of lipids in the small intestine - modulate its biogenesis. Endogenous anandamide is present at very low levels and has a very short half - life due to the action of the enzyme fatty acid amide hydrolase ( FAAH ), which breaks it down into free arachidonic acid and ethanolamine. Studies of piglets show that dietary levels of arachidonic acid and other essential fatty acids affect the levels of anandamide and other endocannabinoids in the brain. High fat diet feeding in mice increases levels of anandamide in the liver and increases lipogenesis. This suggests that anandamide may play a role in the development of obesity, at least in rodents. Paracetamol ( or acetaminophen in the U.S.A. ) is metabolically combined with arachidonic acid by FAAH to form AM404. This metabolite of paracetamol is a potent agonist at the TRPV1 vanilloid receptor, a weak agonist at both CB and CB receptors, and an inhibitor of anandamide reuptake. As a result, anandamide levels in the body and brain are elevated. In this fashion, paracetamol acts as a pro-drug for a cannabimimetic metabolite. This action may be partially or fully responsible for the analgesic effects of paracetamol. Endocannabinoid transporters for anandamide and 2 - arachidonoylglycerol include the heat shock proteins ( Hsp70s ) and fatty acid binding proteins ( FABPs ). Medical benefits It has been suggested that AM1172 could potentially be developed into a drug that would increase the brain 's anandamide levels to help treat anxiety and depression. Black pepper contains an alkaloid, Guineensine, which appears to be a relatively potent Anandamide reuptake inhibitor, thus increasing its physiological effects. Low dose intake has an anxiolytic effect. High dose intake in mice shows evident hippocampus death. It is not possible to train tolerable maximum high dosage for mice. Expired patents from 2004 exist that describe anandamide as a vitalising additive for alcoholic and non-alcoholic beverages, including combining it with another additive, Oleoylethanolamide, recited as an invention from Nestle, to increase the `` stimulus '' effect. The amount of anandamide in cacao is 0.5 μg per gram. According to associate statistics world cacao production in 2013 had a value of around five million metric tons annually with a rising tendency, but since the patent expired anyone is allowed to synthetically produce it and add it to food. 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Jump up ^ http://google.com/patents/DE202004013386U1?cl=da Jump up ^ Nehlig, A ( 2013 ). `` The neuroprotective effects of cocoa flavanol and its influence on cognitive performance ''. British Journal of Clinical Pharmacology. 75 ( 3 ) : 716 -- 727. PMC 3575938. PMID 22775434. doi : 10.1111 / j. 1365 - 2125.2012. 04378. x. Jump up ^ http://www.worldcocoafoundation.org/wp-content/uploads/Cocoa-Market-Update-as-of-4-1-2014.pdf External links Could anandamide be the missing link to `` runner 's high '' ? Accessed 2015 - 10 - 31 https://web.archive.org/web/20131215032041/http://www.harford.de/arne/articles/NeuroReport.pdf Cannabinoids Phytocannabinoids Alkylamides Caryophyllene CBC CBCV CBD CBDV CBG CBGM CBGV CBL CBDL CBN CBV Epigallocatechin gallate Gallocatechol Perrottetinene Serinolamide A THC THC - C4 THCA THCV Yangonin Active metabolites : 8, 11 - DiOH - THC 11 - COOH - THC 11 - OH - THC Endocannabinoids Arachidonoyl ethanolamide ( AEA ; anandamide ) 2 - Arachidonoylglycerol ( 2 - AG ) 2 - Arachidonyl glyceryl ether ( 2 - AGE ; noladin ether ) 2 - Oleoylglycerol ( 2 - OG ) N - Arachidonoyl dopamine ( NADA ) N - Arachidonylglycine ( NAGly ) 2 - Arachidonoyl lysophosphatidylinositol ( 2 - ALPI ) N - Arachidonoyl serotonin ( AA - 5 - HT ) Docosatetraenoylethanolamide ( DEA ) Lysophosphatidylinositol ( LPI ) Oleamide Oleoylethanolamide ( OEA ) Palmitoylethanolamide ( PEA ) RVD - Hpα Stearoylethanolamide ( SEA ) O - Arachidonoyl ethanolamine ( O - AEA ; virodhamine ) Synthetic cannabinoids Classical cannabinoids ( dibenzopyrans ) A-40174 A-41988 A-42574 Ajulemic acid AM - 087 AM - 411 AM - 855 AM - 905 AM - 906 AM - 919 AM - 926 AM - 938 AM - 2389 AM - 4030 AMG - 1 AMG - 3 AMG - 36 AMG - 41 Dexanabinol ( HU - 211 ) DMHP Dronabinol HHC HU - 210 HU - 243 JWH - 051 JWH - 133 JWH - 139 JWH - 161 JWH - 229 JWH - 359 KM - 233 L - 759,633 L - 759,656 Levonantradol ( CP 50, 5561 ) Menabitan Nabazenil Nabidrox ( Canbisol ) Nabilone Nabitan Naboctate O - 224 O - 581 O - 774 O - 806 O - 823 O - 1057 O - 1125 O - 1191 O - 1238 O - 2048 O - 2113 O - 2365 O - 2372 O - 2373 O - 2383 O - 2426 O - 2484 O - 2545 O - 2694 O - 2715 O - 2716 O - 3223 O - 3226 Parahexyl Pirnabine THC - O - acetate THC - O - phosphate Non-classical cannabinoids Cannabicyclohexanol CBD - DMH CP 47,497 ( C6 ) - CP 47,497 ( C9 ) - CP 47,497 CP 55,244 CP 55,940 HU - 308 HU - 320 HU - 331 HU - 336 HU - 345 HU - 446 HU - 465 HU - 910 HUF - 101 Nonabine O - 1376 O - 1422 O - 1601 O - 1656 O - 1657 O - 1660 O - 1663 O - 1871 SPA - 229 Tinabinol Benzoylindoles 1 - Butyl - 3 - ( 2 - methoxybenzoyl ) indole 1 - Butyl - 3 - ( 4 - methoxybenzoyl ) indole 1 - Pentyl - 3 - ( 2 - methoxybenzoyl ) indole AM - 630 AM - 679 AM - 694 AM - 1241 AM - 2233 GW - 405,833 ( L - 768,242 ) Pravadoline RCS - 4 WIN 54,461 Naphthoylindoles AM - 1220 AM - 1221 AM - 1235 AM - 2201 AM - 2232 CHM - 081 EAM - 2201 FUB - JWH - 018 JWH - 007 JWH - 015 JWH - 018 JWH - 019 JWH - 073 JWH - 081 JWH - 098 JWH - 116 JWH - 122 JWH - 149 JWH - 164 JWH - 182 JWH - 193 JWH - 198 JWH - 200 JWH - 210 JWH - 398 JWH - 424 MAM - 1220 MAM - 2201 NE - CHMIMO Naphthoylindazoles THJ - 018 THJ - 2201 Pyrrolobenzoxazines WIN 55,212 - 2 Naphthylmethylindoles JWH - 175 JWH - 176 JWH - 184 JWH - 185 JWH - 192 JWH - 194 JWH - 195 JWH - 196 JWH - 197 JWH - 199 Phenylacetylindoles Cannabipiperidiethanone JWH - 167 JWH - 203 JWH - 249 JWH - 250 JWH - 251 JWH - 302 RCS - 8 Indole - 3 - carboxamides 5F - ADBICA 5F - NNE1 5F - PCN 5F - SDB - 006 AB - FUBICA AB - PICA ADBICA ADB - FUBICA APICA CUMYL - BICA CUMYL - PICA CUMYL - 5F - PICA FDU - NNE1 MDMB - CHMICA MMB - 2201 MN - 25 ( UR - 12 ) NNE1 PX - 1 Org 28312 Org 28611 SDB - 006 STS - 135 Indole - 3 - carboxylates 5F - PB - 22 FDU - PB - 22 FUB - PB - 22 QUCHIC ( BB - 22 ) QUPIC ( PB - 22 ) NM - 2201 Tetramethylcyclo - propanoylindoles 5Br - UR - 144 5Cl - UR - 144 A-796,260 A-834,735 FUB - 144 UR - 144 XLR - 11 XLR - 12 Indazole - 3 - carboxamides 5Cl - APINACA 5F - ADB 5F - ADB - PINACA 5F - AMB 5F - APINACA 5F - CUMYL - PINACA 5F - EMB - PINACA AB - CHMINACA AB - FUBINACA AB - FUBINACA 2 - fluorobenzyl isomer AB - PINACA ADB - CHMINACA ADB - FUBINACA ADB - PINACA ADAMANTYL - THPINACA ADSB - FUB - 187 AMB - CHMINACA AMB - FUBINACA APINACA ( AKB48 ) APP - FUBINACA CUMYL - 4CN - BINACA CUMYL - PINACA CUMYL - THPINACA EMB - FUBINACA FUB - APINACA MDMB - FUBINACA MDMB - CHMINACA MN - 18 PX - 2 PX - 3 Tetramethylcyclo - propanoylindazoles FAB - 144 Naphthoylpyrroles JWH - 030 JWH - 147 JWH - 307 JWH - 369 JWH - 370 Eicosanoids AM - 883 AM - 1346 ACEA ACPA Methanandamide ( AM - 356 ) O - 585 O - 689 O - 1812 O - 1860 O - 1861 Pyrazolecarboxamides 5F - AB - FUPPYCA AB - CHFUPYCA AB - CHMFUPPYCA Others 4 - HTMPIPO 5F - PY - PICA 5F - PY - PINACA 5F - 3 - pyridinoylindole A-836,339 A-955,840 Abnormal cannabidiol AB - 001 BzODZ - EPyr AM - 1248 AM - 1714 AZ - 11713908 BAY 38 - 7271 BAY 59 - 3074 BIM - 018 CB - 13 CB - 86 CBS - 0550 CUMYL - 4CN - B7AICA CUMYL - 5F - P7AICA CUMYL - PEGACLONE FUBIMINA GSK - 554,418 A GW - 842,166 X JTE 7 - 31 LASSBio - 881 LBP - 1 Leelamine MDA - 7 MDA - 19 MEPIRAPIM NESS - 040C5 NMP - 7 O - 889 O - 1269 O - 1270 O - 1399 O - 1602 O - 2220 PF - 03550096 PSB - SB - 1202 PTI - 1 PTI - 2 QMPSB S - 444,823 SER - 601 Tedalinab URB - 447 VSN - 16 WIN 56,098 Allosteric CBR ligands Org 27569 Org 27759 Org 29647 RTI - 371 Pregnenolone Endocannabinoid enhancers ( inactivation inhibitors ) 4 - Nonylphenylboronic acid AM - 404 Arachidonoyl serotonin Arvanil BIA 10 - 2474 Biochanin A CAY - 10401 CAY - 10429 Genistein Guineesine IDFP JNJ 1661010 JNJ - 42165279 JZL184 JZL195 Kaempferol LY - 2183240 MK - 4409 O - 1624 O - 2093 Oleoylethanolamide ( OEA ) Olvanil Palmitoylethanolamide ( PEA ) PF - 04457845 PF - 622 PF - 750 PF - 3845 PHOP URB - 447 URB - 597 URB - 602 URB - 754 VDM - 11 Anticannabinoids ( antagonists / inverse agonists / antibodies ) AM - 251 AM - 281 AM - 630 AM - 1387 AM - 4113 AM - 6527 AM - 6545 BML - 190 Brizantin ( Бризантин ) CAY - 10508 CB - 25 CB - 52 CB - 86 Dietressa ( Диетресса ) Drinabant ( AVE1625 ) Hemopressin Ibipinabant ( SLV319 ) JTE - 907 LH - 21 LY - 320,135 MDA - 77 MJ - 15 MK - 9470 NESS - 0327 NIDA - 41020 O - 606 O - 1184 O - 1248 O - 1918 O - 2050 O - 2654 Otenabant ( CP - 945,598 ) PF - 514273 PipISB PSB - SB - 487 Rimonabant ( SR141716 ) Rosonabant ( E-6776 ) SR - 144,528 Surinabant ( SR147778 ) Taranabant ( MK - 0364 ) TM - 38837 VCHSR See also : Cannabinoid receptor modulators ( cannabinoids by pharmacology ) List of : AM cannabinoids JWH cannabinoids Designer drugs § Synthetic cannabimimetics Neurotransmitters Amino acid - derived Major excitatory / inhibitory systems : Glutamate system : Agmatine Aspartic acid ( aspartate ) Cycloserine Glutamic acid ( glutamate ) Glutathione Glycine GSNO GSSG Kynurenic acid NAA NAAG Proline Serine ; GABA system : GABA GABOB GHB ; Glycine system : α - Alanine β - Alanine Glycine Hypotaurine Proline Sarcosine Serine Taurine ; GHB system : GHB T - HCA ( GHC ) Biogenic amines : Monoamines : 6 - OHM Dopamine Epinephrine ( adrenaline ) NAS ( normelatonin ) Norepinephrine ( noradrenaline ) Serotonin ( 5 - HT ) ; Trace amines : 3 - Iodothyronamine N - Methylphenethylamine N - Methyltryptamine m - Octopamine p - Octopamine Phenylethanolamine Phenethylamine Synephrine Tryptamine m - Tyramine p - Tyramine ; Others : Histamine Neuropeptides : See here instead. Lipid - derived Endocannabinoids : 2 - AG 2 - AGE ( noladin ether ) 2 - ALPI 2 - OG AA - 5 - HT Anandamide ( AEA ) DEA LPI NADA NAGly OEA Oleamide PEA RVD - Hpα SEA Virodhamine ( O - AEA ) Neurosteroids : See here instead. Nucleobase - derived Nucleosides : Adenosine system : Adenosine ADP AMP ATP Vitamin - derived Cholinergic system : Acetylcholine Miscellaneous Gasotransmitters : Carbon monoxide ( CO ) Hydrogen sulfide ( H S ) Nitric oxide ( NO ) ; Candidates : Acetaldehyde Ammonia ( NH ) Carbonyl sulfide ( COS ) Nitrous oxide ( N O ) Sulfur dioxide ( SO ) Cannabinoid receptor modulators Receptor ( ligands ) CB Agonists ( abridged ; see here for more ) : 2 - AG 2 - AGE ( noladin ether ) 11 - Hydroxy - THC α - Amyrin β - Amyrin AB - CHMINACA AM - 1172 AM - 1220 AM - 1221 AM - 1235 AM - 2201 AM - 2232 Anandamide Arvanil AZ - 11713908 Cannabinol CB - 13 CP 47,497 CP 55,940 Dimethylheptylpyran DEA ECG EGCG Epicatechin Gallocatechol ( gallocatechin ) Honokiol HU - 210 JWH - 007 JWH - 015 JWH - 018 JWH - 073 Kavain L - 759,633 Levonantradol Menabitan Nabilone Nabitan NADA O - 1812 Oleamide Pravadoline Serinolamide A THC ( dronabinol ) UR - 144 WIN 55,212 - 2 Yangonin Antagonists : AM - 251 AM - 6545 Cannabidiol Cannabigerol Drinabant Falcarinol ( carotatoxin ) Hemopressin Ibipinabant LY - 320,135 MK - 9470 NESS - 0327 O - 2050 Otenabant PF - 514273 PipISB Rimonabant Rosonabant Surinabant Taranabant THCV TM - 38837 VCHSR Virodhamine Antibodies : Brizantin ( Бризантин ) Dietressa ( Диетресса ) Unknown / unsorted : MAFP CB Agonists : 2 - AG 2 - AGE ( noladin ether ) 3, 3 ' - Diindolylmethane 4 - O - Methylhonokiol α - Amyrin β - Amyrin A-796,260 A-834,735 A-836,339 AM - 1172 AM - 1221 AM - 1235 AM - 1241 AM - 2232 Anandamide AZ - 11713908 Cannabinol Caryophyllene CB - 13 CBS - 0550 CP - 55,940 GW - 405,833 ( L - 768,242 ) GW - 842,166 X HU - 308 JTE 7 - 31 JWH - 007 JWH - 015 JWH - 018 JWH - 73 JWH - 133 L - 759,633 L - 759,656 Magnolol MDA - 19 Nabitan NADA PF - 03550096 S - 444,823 SER - 601 Serinolamide A UR - 144 Tedalinab THC ( dronabinol ) THCV Tetrahydromagnolol Virodhamine Antagonists : 4 - O - Methylhonokiol AM - 630 BML - 190 Cannabidiol Honokiol JTE - 907 SR - 144,528 WIN 54,461 WIN 56,098 NAGly ( GPR18 ) Agonists : Abnormal cannabidiol ACPA AM251 Anandamide Cannabidiol NADGly THC ( dronabinol ) O - 1602 Antagonists : CID - 85469571 O - 1918 GPR55 Agonists : 2 - AGE ( noladin ether ) 2 - ALPI Abnormal cannabidiol AM - 251 CID1011163 CID1252842 CID1792579 CP 55,940 GSK - 494581A Lysophosphatidylinositol ML - 184 ML - 185 ML - 186 O - 1602 Oleoylethanolamide Palmitoylethanolamide THC ( dronabinol ) Antagonists : Cannabidiol CID - 16020046 ML - 191 ML - 192 ML - 193 O - 1918 PSB - SB - 487 PSB - SB - 1202 PSB - SB - 1203 Tetrahydromagnolol GPR119 Agonists : 2 - Oleoylglycerol Anandamide APD668 AR - 231,453 AS - 1269574 MBX - 2982 N - Oleoyldopamine Oleoylethanolamide Olvanil PSN - 375,963 PSN - 632,408 Transporter ( modulators ) eCBTs Inhibitors : 5 ' - DMH - CBD AM - 404 AM - 1172 Arachidonoyl serotonin Arvanil Cannabidiol Guineensine LY - 2183240 O - 2093 OMDM - 2 Paracetamol ( acetaminophen ) SB - FI - 26 UCM - 707 URB - 597 VDM - 11 WOBE490 WOBE491 WOBE492 Enzyme ( modulators ) FAAH Inhibitors : 4 - Nonylphenylboronic acid AACOCF AM - 404 Arachidonoyl serotonin BIA 10 - 2474 Biochanin A Genistein IDFP JNJ - 1661010 JNJ - 42165279 JZL - 195 Kaempferol LY - 2183240 MAFP Palmitoylisopropylamide Paracetamol ( acetaminophen ) PF - 3845 PF - 04457845 PF - 750 SA - 47 SA - 57 TAK 21d TC - F 2 UCM710 URB - 597 Activators : PDP - EA MAGL Inhibitors : ABX - 1431 IDFP JJKK 048 JW 642 JZL - 184 JZL - 195 JZP - 361 KML 29 MAFP MJN110 NAM Pristimerin URB - 602 ABHD6 Inhibitors : JZP - 169 JZP - 430 KT182 KT185 KT195 KT203 LEI - 106 ML294 ML295 ML296 UCM710 WWL - 70 ABHD12 Inhibitors : Betulinic acid Maslinic acid MAFP Oleanolic acid Orlistat ( tetrahydrolipstatin ) Ursolic acid Others Precursors : Phosphatidylethanolamine NAPE Diacylglycerol Others : 2 - PG ( directly potentiates activity of 2 - AG at CB receptor ) ARN - 272 ( FAAH - like anandamide transporter inhibitor ) See also Receptor / signaling modulators Cannabinoids ( cannabinoids by structure ) Glycine receptor modulators Receptor ( ligands ) GlyR Agonists : β - Alanine β - ABA ( BABA ) β - AIBA Caesium D - Alanine D - Serine GABA Glycine Hypotaurine Ivermectin L - Alanine L - Proline L - Serine L - Threonine MDL - 27531 Milacemide Picolinic acid Propofol Quisqualamine Sarcosine Taurine Positive modulators : Alcohols ( e.g., brometone, chlorobutanol ( chloretone ), ethanol ( alcohol ), tert - butanol ( 2M2P ), tribromoethanol, trichloroethanol, trifluoroethanol ) Alkylbenzene sulfonate Anandamide Barbiturates ( e.g., pentobarbital, sodium thiopental ) Chlormethiazole D12 - 116 Dihydropyridines ( e.g., nicardipine ) Etomidate Ginseng constituents ( e.g., ginsenosides ( e.g., ginsenoside - Rf ) ) Glutamic acid ( glutamate ) Ivermectin Ketamine Neuroactive steroids ( e.g., alfaxolone, pregnenolone ( eltanolone ), pregnenolone acetate, minaxolone, ORG - 20599 ) Nitrous oxide Penicillin G Propofol Tamoxifen Tetrahydrocannabinol Triclofos Tropeines ( e.g., atropine, bemesetron, cocaine, LY - 278584, tropisetron, zatosetron ) Volatiles / gases ( e.g., chloral hydrate, chloroform, desflurane, diethyl ether ( ether ), enflurane, halothane, isoflurane, methoxyflurane, sevoflurane, toluene, trichloroethane ( methyl chloroform ), trichloroethylene ) Xenon Zinc Antagonists : 2 - Aminostrychnine 2 - Nitrostrychnine 4 - Phenyl - 4 - formyl - N - methylpiperidine αEMBTL Bicuculline Brucine Cacotheline Caffeine Colchicine Colubrine Cyanotriphenylborate Dendrobine Diaboline Endocannabinoids ( e.g., 2 - AG, anandamide ( AEA ) ) Gaboxadol ( THIP ) Gelsemine iso - THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N - Methylbicuculline N - Methylstrychnine N, N - Dimethylmuscimol Nipecotic acid Pitrazepin Pseudostrychnine Quinolines ( e.g., 4 - hydroxyquinoline, 4 - hydroxyquinoline - 3 - carboxylic acid, 5, 7 - CIQA, 7 - CIQ, 7 - TFQ, 7 - TFQA ) RU - 5135 Sinomenine Strychnine Thiocolchicoside Tutin Negative modulators : Amiloride Benzodiazepines ( e.g., bromazepam, clonazepam, diazepam, flunitrazepam, flurazepam ) Corymine Cyanotriphenylborate Daidzein Dihydropyridines ( e.g., nicardipine, nifedipine, nitrendipine ) Furosemide Genistein Ginkgo constituents ( e.g., bilobalide, ginkgolides ( e.g., ginkgolide A, ginkgolide B, ginkgolide C, ginkgolide J, ginkgolide M ) ) Imipramine NBQX Neuroactive steroids ( e.g., 3α - androsterone sulfate, 3β - androsterone sulfate, deoxycorticosterone, DHEA sulfate, pregnenolone sulfate, progesterone ) Opioids ( e.g., codeine, dextromethorphan, dextrorphan, levomethadone, levorphanol, morphine, oripavine, pethidine, thebaine ) Picrotoxin ( i.e., picrotin and picrotoxinin ) PMBA Riluzole Tropeines ( e.g., bemesetron, LY - 278584, tropisetron, zatosetron ) Verapamil Zinc NMDAR See here instead. Transporter ( blockers ) GlyT1 ACPPB ALX - 1393 ALX - 5407 ( NFPS ) AMG - 747 ASP2535 Bitopertin ( RG1678 / RO4917838 ) CP - 802079 Ethanol ( alcohol ) Glycyldodecylamide GSK1018921 LY - 2365109 Opiranserin ORG - 24598 ORG - 25935 ( SCH - 900435 ) PF - 02545920 PF - 03463275 PF - 04958242 Sarcosine SSR - 103,800 SSR - 504,734 GlyT2 Amoxapine Ethanol ( alcohol ) NAGly ORG - 25543 See also Receptor / signaling modulators GABA receptor modulators GABA receptor positive modulators Ionotropic glutamate receptor modulators TRP channel modulators TRPA Activators 4 - Hydroxynonenal 4 - Oxo - 2 - nonenal 4, 5 - EET 12S - HpETE 15 - Deoxy - Δ - prostaglandin J2 α - Sanshool ( ginger, Sichuan and melegueta peppers ) Acrolein Allicin ( garlic ) Allyl isothiocyanate ( mustard, radish, horseradish, wasabi ) AM404 Bradykinin Cannabichromene ( cannabis ) Cannabidiol ( cannabis ) Cannabigerol ( cannabis ) Cinnamaldehyde ( cinnamon ) CR gas ( dibenzoxazepine ; DBO ) CS gas ( 2 - chlorobenzal malononitrile ) Curcumin ( turmeric ) Dehydroligustilide ( celery ) Diallyl disulfide Dicentrine ( Lindera spp. ) Farnesyl thiosalicylic acid Formalin Gingerols ( ginger ) Hepoxilin A3 Hepoxilin B3 Hydrogen peroxide Icilin Isothiocyanate Ligustilide ( celery, Angelica acutiloba ) Linalool ( Sichuan pepper, thyme ) Methylglyoxal Methyl salicylate ( wintergreen ) N - Methylmaleimide Nicotine ( tobacco ) Oleocanthal ( olive oil ) Paclitaxel ( Pacific yew ) Paracetamol ( acetaminophen ) PF - 4840154 Phenacyl chloride Polygodial ( Dorrigo pepper ) Shogaols ( ginger, Sichuan and melegueta peppers ) Tear gases Tetrahydrocannabinol ( cannabis ) Thiopropanal S - oxide ( onion ) Umbellulone ( Umbellularia californica ) WIN 55,212 - 2 Blockers Dehydroligustilide ( celery ) Nicotine ( tobacco ) Ruthenium red TRPC Activators Adhyperforin ( St John 's wort ) Diacyl glycerol GSK1702934A Hyperforin ( St John 's wort ) Substance P Blockers DCDPC DHEA - S Flufenamic acid GSK417651A GSK2293017A Meclofenamic acid N - ( p - amylcinnamoyl ) anthranilic acid Niflumic acid Pregnenolone sulfate Progesterone Pyr3 Tolfenamic acid TRPM Activators ADP - ribose BCTC Calcium ( intracellular ) Cold Coolact P Cooling Agent 10 CPS - 369 Eucalyptol ( eucalyptus ) Frescolat MGA Frescolat ML Geraniol Hydroxycitronellal Icilin Linalool Menthol ( mint ) PMD 38 Pregnenolone sulfate Rutamarin ( Ruta graveolens ) Steviol glycosides ( e.g., stevioside ) ( Stevia rebaudiana ) Sweet tastants ( e.g., glucose, fructose, sucrose ; indirectly ) Thio - BCTC WS - 3 WS - 12 WS - 23 Blockers Capsazepine Clotrimazole DCDPC Flufenamic acid Meclofenamic acid Mefenamic acid N - ( p - amylcinnamoyl ) anthranilic acid Nicotine ( tobacco ) Niflumic acid Ruthenium red Rutamarin ( Ruta graveolens ) Tolfenamic acid TPPO TRPML Activators MK6 - 83 PI ( 3, 5 ) P SF - 22 TRPP Activators Triptolide ( Tripterygium wilfordii ) Blockers Ruthenium red TRPV Activators 2 - APB 5 ', 6 ' - EET 9 - HODE 9 - oxoODE 12S - HETE 12S - HpETE 13 - HODE 13 - oxoODE 20 - HETE α - Sanshool ( ginger, Sichuan and melegueta peppers ) Allicin ( garlic ) AM404 Anandamide Bisandrographolide ( Andrographis paniculata ) Camphor ( camphor laurel, rosemary, camphorweed, African blue basil, camphor basil ) Cannabidiol ( cannabis ) Cannabidivarin ( cannabis ) Capsaicin ( chili pepper ) Carvacrol ( oregano, thyme, pepperwort, wild bergamot, others ) DHEA Diacyl glycerol Dihydrocapsaicin ( chili pepper ) Estradiol Eugenol ( basil, clove ) Evodiamine ( Euodia ruticarpa ) Gingerols ( ginger ) GSK1016790A Heat Hepoxilin A3 Hepoxilin B3 Homocapsaicin ( chili pepper ) Homodihydrocapsaicin ( chili pepper ) Incensole ( incense ) Lysophosphatidic acid Low pH ( acidic conditions ) Menthol ( mint ) N - Arachidonoyl dopamine N - Oleoyldopamine N - Oleoylethanolamide Nonivamide ( PAVA ) ( PAVA spray ) Nordihydrocapsaicin ( chili pepper ) Paclitaxel ( Pacific yew ) Paracetamol ( acetaminophen ) Phorbol esters ( e.g., 4α - PDD ) Piperine ( black pepper, long pepper ) Polygodial ( Dorrigo pepper ) Probenecid Protons Rutamarin ( Ruta graveolens ) Resiniferatoxin ( RTX ) ( Euphorbia resinifera / pooissonii ) Shogaols ( ginger, Sichuan and melegueta peppers ) Tetrahydrocannabivarin ( cannabis ) Thymol ( thyme, oregano ) Tinyatoxin ( Euphorbia resinifera / pooissonii ) Tramadol Vanillin ( vanilla ) Zucapsaicin Blockers α - Spinasterol ( Vernonia tweediana ) AMG - 517 Asivatrep BCTC Cannabigerol ( cannabis ) Cannabigerolic acid ( cannabis ) Cannabigerovarin ( cannabis ) Cannabinol ( cannabis ) Capsazepine DCDPC DHEA DHEA - S Flufenamic acid GRC - 6211 HC - 067047 Lanthanum Meclofenamic acid N - ( p - amylcinnamoyl ) anthranilic acid NGD - 8243 Niflumic acid Pregnenolone sulfate RN - 1734 RN - 9893 Ruthenium red SB - 705498 Tolfenamic acid See also : Receptor / signaling modulators Ion channel modulators Retrieved from `` https://en.wikipedia.org/w/index.php?title=Anandamide&oldid=796323605 '' Categories : Endocannabinoids Neurotransmitters Fatty acid amides Biomolecules Alcohols CB1 receptor agonists CB2 receptor agonists Glycine receptor agonists Glycine receptor antagonists Euphoriants Hidden categories : CS1 maint : Uses authors parameter Chemical articles with multiple compound IDs Multiple chemicals in an infobox that need indexing Articles without KEGG source Articles with changed CASNo identifier Articles containing unverified chemical infoboxes All articles with unsourced statements Articles with unsourced statements from April 2017 Articles with unsourced statements from May 2017 Wikipedia articles needing clarification from February 2017 Talk Contents About Wikipedia Čeština Deutsch Español فارسی Français Italiano עברית Magyar Nederlands 日本 語 Norsk Polski Русский Српски / srpski Srpskohrvatski / српскохрватски Suomi Svenska தமிழ் Українська اردو 中文 Edit links This page was last edited on 20 August 2017, at 01 : 31. 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Question: interferes with anandamide function as it connects to the same receptors in the brain
Answer: Δ9-tetrahydrocannabinol (Δ9-THC, commonly called THC)