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Polyunsaturated Alkamides

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Definition: Amides composed of unsaturated aliphatic FATTY ACIDS linked with AMINES by an amide bond. They are most prominent in ASTERACEAE; PIPERACEAE; and RUTACEAE; and also found in ARISTOLOCHIACEAE; BRASSICACEAE; CONVOLVULACEAE; EUPHORBIACEAE; MENISPERMACEAE; POACEAE; and SOLANACEAE. They are recognized by their pungent taste and for causing numbing and salivation.     
Examples Capsaicin 		Other names Isobutylamides, Polyunsaturated; Alkylamides, Polyunsaturated; Alkamides, Polyunsaturated; Polyunsaturated Isobutylamides; Polyunsaturated Alkylamides
 
SubstanceCAS Registry & nameCategoriesSourceDrugs*
N-isobutyldodeca-2E,4E,8Z,10Z-tetraenamide  0   *Polyunsaturated Alkamides. Phytother Res. 2010 Aug;24(8):1195-201
2-methyl-2'-F-anandamide  0   *Polyunsaturated Alkamides. Endocr Relat Cancer 2010 Jun;17(2):495-503
15-hydroxyanandamide  0   *Arachidonic Acids *Polyunsaturated Alkamides. Biochimie 2010 Apr;92(4):378-87
(2E,4E,8Z,10E)-N-(2-methylpropyl)dodeca-2,4,8,10-tetraenamide  0   *Polyunsaturated Alkamides. Chem Biodivers. 2008 Feb;5(2):346-51
AM-1346  0   *Arachidonic Acids *Polyunsaturated Alkamides. Psychopharmacology (Berl) 2006 Oct;188(3):315-23
daryamide B  0   *Polyenes *Polyunsaturated Alkamides. J Nat Prod 2006 Dec;69(12):1756-9
daryamide C  0   *Polyenes *Polyunsaturated Alkamides. J Nat Prod 2006 Dec;69(12):1756-9
daryamide A  0   *Polyenes *Polyunsaturated Alkamides. J Nat Prod 2006 Dec;69(12):1756-9
3-methoxy-7-acetylaegeline  0   *Benzene Derivatives Polyunsaturated Alkamides. J Nat Prod 2005 Aug;68(8):1297-9
3-methoxyaegeline  0   *Benzene Derivatives *Polyunsaturated Alkamides. J Nat Prod 2005 Aug;68(8):1297-9
dodeca-2Z,4E,10Z-trien-8-ynoic acid isobutylamide  0   *Fatty Acids, Unsaturated *Polyunsaturated Alkamides. J Nat Prod 2005 May;68(5):772-6
N-(pyridin-3-ylmethyl)-3-(5-chloro-1-(4-chlorobenzyl)-indol-3-yl)propanamide  0   *Indoles *Pyridines Propane/*analogs & derivatives Polyunsaturated Alkamides. Bioorg Med Chem Lett. 2004 Nov 1;14(21):5441-4
N-isobutyl-2E-decenamide  0   *Polyunsaturated Alkamides. J Agric Food Chem. 2004 Jul 28;52(15):4700-4
N-methoxy-2,2,3,3-tetramethylcyclopropane carboxamide  0   *Cyclopropanes Polyunsaturated Alkamides. J Med Chem 2004 Aug 12;47(17):4316-26
N-(8-methoxy-10,11-dihydro-5H-dibenzo(a,d)cycloheptene-10-ylmethyl)butyramide  0   *Dibenzocycloheptenes Polyunsaturated Alkamides Receptors, Melatonin/antagonists & inhibitors. J Med Chem 2004 Aug 12;47(17):4202-12
N-(8-methoxy-10,11-dihydro-5H-dibenzo(a,d)cycloheptene-10-ylmethyl)propionamide  0   *Dibenzocycloheptenes Polyunsaturated Alkamides Receptors, Melatonin/antagonists & inhibitors. J Med Chem 2004 Aug 12;47(17):4202-12
isodihydropiperlonguminine  0   *Phenylpropionates *Polyunsaturated Alkamides. Nat Prod Res. 2004 Jun;18(3):247-51
syncarpamide  0   Norepinephrine/*analogs & derivatives Polyunsaturated Alkamides. J Nat Prod 2004 Jan;67(1);88-90
N-isobutyl-2E,4E,12E-tetradecatrien-8,10-diynamide  0   *Fatty Acids, Unsaturated *Polyunsaturated Alkamides. J Nat Prod 2003 Sep;66(9):1229-31
N-isobutyl-2E,4E,12Z-tetradecatrien-8,10-diynamide  0   *Fatty Acids, Unsaturated *Polyunsaturated Alkamides. J Nat Prod 2003 Sep;66(9):1229-31
N-(3-(1-methyl-4-piperidinyl)-1H-pyrrolo(3,2-b)pyridin-5-yl)propanamide  0   *Piperidines *Bicyclo Compounds, Heterocyclic Polyunsaturated Alkamides. J Med Chem 2003 Jul 3;46(14):3060-71
N-(3-(1-methyl-4-piperidinyl)-1H-pyrrolo(3,2-b)pyridin-5-yl)acetamide  0   *Piperidines *Bicyclo Compounds, Heterocyclic Polyunsaturated Alkamides. J Med Chem 2003 Jul 3;46(14):3060-71
3-(1-methyl-4-phenylacetyl-1H-2-pyrrolyl)-N-hydroxypropenamide  0   *Hydroxamic Acids *Pyrroles Polyunsaturated Alkamides Histone Deacetylases/antagonists & inhibitors. J Med Chem 2003 Feb 13;46(4):512-24
2,4,8,10-dodecatetraenoic acid isobutylamide  0   *Fatty Acids, Unsaturated *Polyunsaturated Alkamides. Planta Med 2001 Dec;67(9):863-4
N-benzylhexadecanamide  0   *Polyunsaturated Alkamides. Phytochemistry 2002 Jan;59(1):105-10
N-benzyl-5-oxo-6,8-octadecadienamide  0   *Polyunsaturated Alkamides. Phytochemistry 2002 Jan;59(1):105-10
N-(3-furylmethyl)eicosa-5,8,11,14-tetraenamide  0   *Arachidonic Acids *Furans *Polyunsaturated Alkamides. J Med Chem 2001 Dec 20;44(26):4505-8
N-(pyridin-4-yl)-(1-(4-fluorobenzyl)indol-3-yl)acetamide  0   *Indoleacetic Acids *Pyridines Polyunsaturated Alkamides. J Med Chem 1999 Feb 25;42(4):638-48
11-hydroperoxy-5,8,12,14-eicosatetraenoylethanolamide  0   *Ethanolamines *Fatty Acids, Unsaturated *Polyunsaturated Alkamides. Biochem Biophys Res Commun 1998 Jul 9;248(1):33-8
linoleoyl ethanolamide  68171-52-8   *Linoleic Acids *Polyunsaturated Alkamides. Adv Exp Med Biol 1997;407:341-6
mead ethanolamide  0   *Polyunsaturated Alkamides 8,11,14-Eicosatrienoic Acid/*analogs & derivatives. Mol Pharmacol 1995 Aug;48(2):288-92
7,10,13,16-docosatetraenylethanolamide  150314-35-5   *Ethanolamines *Fatty Acids, Unsaturated *Polyunsaturated Alkamides. J Med Chem 1993 Oct 1;36(20):3032-4
homo-gamma-linolenylethanolamide  150314-34-4   *Ethanolamines *Fatty Acids, Unsaturated *Polyunsaturated Alkamides. J Med Chem 1993 Oct 1;36(20):3032-4
anandamide  94421-68-8 5,8,11,14-Eicosatetraenamide, N-(2-hydroxyethyl)-, (all-Z)  *Arachidonic Acids *Polyunsaturated Alkamides Cannabinoids Receptor, Cannabinoid, CB2.
Pharma Action Calcium Channel Blockers ; Endocannabinoids 		Science 1992 Dec 18;258(5090):1882-4
hazaleamide  81427-15-8 2,4,8,11-Tetradecatetraenamide, N-(2-methylpropyl)-, (E,E,Z,Z)  *Fatty Acids, Unsaturated *Polyunsaturated Alkamides Plant Extracts. Chem Pharm Bull (Tokyo) 1992 Sep;40(9):2325-30
Ro 24-0238  120555-31-9   *Pyridines *Polyunsaturated Alkamides. Agents Actions 1991 Sep;31(1-2):181-4
phthoxazolin  130288-22-1 4,6,8-Decatrienamide, 3-hydroxy-2,2,4-trimethyl-10-(5-oxazolyl)-, (Z,Z,E)-(+)  *Fatty Alcohols *Oxazoles *Polyunsaturated Alkamides. J Antibiot (Tokyo) 1990;43(8):1034
N-isobutyl-2,4-eicosadienamide  54794-71-7   *Fatty Acids, Unsaturated *Polyunsaturated Alkamides. Yao Hsueh Hsueh Pao 1989;24(10):789
BTG 502  99083-11-1   *Naphthalenes *Polyunsaturated Alkamides. Mol Pharmacol 1989;36(2):280
glidobactin F  119259-72-2 2,4-Decadienamide, N-(2-hydroxy-1-(((10-hydroxy-5-methyl-2,7-dioxo-1,6-diazacyclododec-3-en-8-yl)amino)carbonyl)propyl)-, (5S-(3E,5R*,8R*(1R*(2E,4E),2S*),10R*))  *Peptides *Polyunsaturated Alkamides. J Antibiot (Tokyo) 1988;41(12):1906
manumycin  52665-74-4 2,4-Decadienamide, N-(5-hydroxy-5-(7-((2-hydroxy-5-oxo-1-cyclopenten-1-yl)amino)-7-oxo-1,3,5-heptatrienyl)-2-oxo-7-oxabicyclo(4.1.0)hept-3-en-3-yl)-2,4,6-trimethyl  *Polyenes *Polyunsaturated Alkamides.
Pharma Action Anti-Bacterial Agents ; Enzyme Inhibitors 		J Antibiot (Tokyo) 1987;40(11):1530
(2-aminoethyl)-10,12-tricosadiynamide  113377-11-0   *Fatty Acids, Unsaturated *Polyunsaturated Alkamides. Science 1988;239(4835):50
ICI 164384  98007-99-9 Estra-1,3,5(10)-triene-7-undecanamide, N-butyl-3,17-dihydroxy-N-methyl-, (7alpha,17beta)  Estradiol/*analogs & derivatives Polyunsaturated Alkamides.
Pharma Action Estrogen Antagonists 		J Endocrinol 1987;112(3):R7
curromycin B  97412-77-6 4,6,8-Decatrienamide, 3-hydroxy-N-(6-hydroxy-9-(8-hydroxy-1,5,7-trimethyl-3,6-dioxo-2-oxa-5-azaspiro(3.4)oct-8-yl)-9-methoxy-7-methyl-2,4-nonadienyl)-2,2,4-trimethyl-10-(2-methyl-5-oxazolyl)  Oxazoles *Polyunsaturated Alkamides. J Antibiot (Tokyo) 1985;38(7):964
curromycin A  97412-76-5 4,6,8-Decatrienamide, 3-hydroxy-N-(6-hydroxy-9-(8-hydroxy-1-(methoxymethyl)-5,7-dimethyl-3,6-dioxo-2-oxa-5-azaspiro(3.4)oct-8-yl)-9-methoxy-7-methyl-2,4-nonadienyl)-2,2,4-trimethyl-10-(2-methyl-5-oxazolyl)  *Polyunsaturated Alkamides Oxazoles. J Antibiot (Tokyo) 1985;38(5):669
U 56407  87695-80-5 2,4,6-Decatrienamide, N-(5-hydroxy-5-(7-((2-hydroxy-5-oxo-1-cyclopenten-1-yl)amino)-7-oxo-1,3,5-heptatrienyl)-2-oxo-7-oxabicyclo(4.1.0)hept-3-en-3-yl)-9-methyl  *Polyunsaturated Alkamides Polyenes. J Antibiot (Tokyo) 1983;36(8):950
3,4-dichlorophenyl propenylisobutylamide  82351-05-1 2-Propenamide, 3-(3,4-dichlorophenyl)-N-(1-methylpropyl)  *Propionates *Polyunsaturated Alkamides. Yao Hseuh Hseuh Pao 1982;17(10):736
3,4,13-trihydroxy-tetradeca-5,7,9,11-tetraynoic acid-gamma-lactone  83475-38-1 2(3H)-Furanone, dihydro-4-hydroxy-5-(9-hydroxy-1,3,5,7-decatetraynyl)  *Polyacetylenes *Polyunsaturated Alkamides. Arch Microbiol 1982;132(2):194
10-hydroxy-undeca-2,4,6,8-tetraynamide  83475-37-0 2,4,6,8-Undecatetraynamide, 10-hydroxy  *Polyacetylenes Polyunsaturated Alkamides. Arch Microbiol 1982;132(2):194
fagaramide  60045-88-7   *Cinnamates *Dioxoles *Polyunsaturated Alkamides. Planta Med 1982;44(1):54
piperine  7780-20-3   *Alkaloids *Piperidines *Benzodioxoles *Polyunsaturated Alkamides Cytochrome P-450 Enzyme System/antagonists & inhibitors Piper nigrum TRPV Cation Channels.
pellitorine  18836-52-7   *Fatty Acids, Unsaturated *Polyunsaturated Alkamides.
N-(2-methylbenzyl)linoleamide  14417-88-0   *Linoleic Acids *Polyunsaturated Alkamides. Fukuoka Igaku Zasshi 65(7):465;1974; Xenobiotica 6(6):329;1976

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Sources: NLM Medical Subject Headings, NIH UMLS, Drugs@FDA, FDA AERS original data copyright United States Government. No endorsement implied. Last modified 6/6/2012
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