Chemical compound
Pharmaceutical compound
Elemicin is aphenylpropene , a naturalorganic compound , and is a constituent of several plant species'essential oils .[ 1] [ 2]
Elemicin is a constituent of theoleoresin and the essential oil ofCanarium luzonicum [ 1] nutmeg andmace , with it composing 2.4% and 10.5% of those oils respectively.[ 2] myristicin , differing only by myristicin's methyl group that joins the two oxygen atoms that make up its dioxymethy moiety, with both constituents being found in nutmeg and mace.
Elemicin was first isolated from elemi oil usingvacuum distillation . Specifically, the substance was collected between 162-165 °C at a reduced pressure of 10torr .[ 3] [ 4]
Elemicin has beensynthesized fromsyringol andallyl bromide usingWilliamson ether synthesis andClaisen rearrangement .[ 5] [ 6] electrophilic aromatic substitution entering thepara Cope rearrangement .[ 7] aromatic ether being blocked by ethers in bothortho -positions. When blocked the allyl group migrates to thepara -position, in this case with yields above 85%.[ 8]
Elemicin has been used to synthesize the proto-alkaloid mescaline .[ 9]
Raw nutmeg causesanticholinergic -like effects, which are attributed to elemicin andmyristicin .[ 10] [ 11] [ 12]
Elemicin's psychoactivity is still a point of research, however some research suggests it may act like an agonist of the5-HT2A receptors , similar to many psychedelics.[ 13] deliriant -like effects than psychedelic ones.[ 14]
^a b Villanueva MA, Torres RC, Baser KH, Özek T, Kürkçüoglu M (1993). "The Composition of Manila Elemi Oil".Flavour and Fragrance Journal .8 :35– 37.doi :10.1002/ffj.2730080107 . ^a b Leela N (2008).Chemistry of Spices ISBN 9781845934057 ^ "Constituents of Essential Oils. Elemicin, a High-boiling Constituent of Elemi Oil, and the Displacement of Alkyloxygroups in the Benzene Nucleus by Hydrogen" Journal of the Chemical Society, Abstracts .94 (A493):557– 558. 1908.doi :10.1039/CA9089400493 .^ Semmler F (1908)."Zur Kenntnis der Bestandteile der ätherischen Öle. (Über das Elemicin, einen hochsiedenden Bestandteil des Elemiöls, und über Ersetzung von Alkyloxy-gruppen am Benzolkern durch Wasserstoff.)" .Berichte der Deutschen Chemischen Gesellschaft .41 (2):1768– 1775.doi :10.1002/cber.19080410240 . ^ Mauthner F (1918)."Die Synthese des Elemicins und Isoelemicins" .Justus Liebigs Annalen der Chemie .414 (2):250– 255.doi :10.1002/jlac.19184140213 . ^ "Synthesis of Elemicin and of isoElemicin".Journal of the Chemical Society, Abstracts .114 : i428. 1918.doi :10.1039/CA9181400421 . ^ Thomas L (2005).Named Organic Reactions, 2nd Edition ISBN 978-0470010402 ^ Adams R (1944). "The Claisen Rearrangement".Organic Reactions . Vol. II. New York: John Wiley & Sons, Inc. pp. 2–44 [44].doi :10.1002/0471264180.or002.01 .ISBN 978-0471264187 {{cite book }}:ISBN / Date incompatibility (help ) ^ Hahn G, Wassmuth H (1934). "Über β-[Oxyphenyl]-äthylamine und ihre Umwandlungen, I. Mitteil.: Synthese des Mezcalins".Berichte der Deutschen Chemischen Gesellschaft (A and B Series) .67 (4):696– 708.doi :10.1002/cber.19340670430 . ^ McKenna A, Nordt SP, Ryan J (August 2004). "Acute nutmeg poisoning".European Journal of Emergency Medicine .11 (4):240– 241.doi :10.1097/01.mej.0000127649.69328.a5 .PMID 15249817 .S2CID 21133983 . ^ Shulgin AT, Sargent T, Naranjo C (December 1967)."The chemistry and psychopharmacology of nutmeg and of several related phenylisopropylamines" .Psychopharmacology Bulletin .4 (3): 13.PMID 5615546 . Archived fromthe original (pdf) on 2014-04-20. Retrieved2015-09-02 . ^ "elemicin" ,The Free Dictionary , retrieved2022-10-28 ^ Evaluation of 5-HT2A Receptor Agonistic Property of Elemicin ^ Kelly BD, Gavin BE, Clarke M, Lane A, Larkin C (March 2003). "Nutmeg and psychosis".Schizophrenia Research .60 (1):95– 96.doi :10.1016/s0920-9964(02)00204-9 .PMID 12505144 .S2CID 7540364 .
mAChRs Tooltip Muscarinic acetylcholine receptors
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Precursors (andprodrugs )
nAChRs Tooltip Nicotinic acetylcholine receptors
Agonists PAMs Tooltip positive allosteric modulators )5-HIAA 6-Chloronicotine A-84,543 A-366,833 A-582,941 A-867,744 ABT-202 ABT-418 ABT-560 ABT-894 Acetylcholine Altinicline Anabasine Anatabine Anatoxin-a AR-R17779 Bephenium hydroxynaphthoate Butinoline Butyrylcholine Carbachol Choline Choline m-bromophenyl ether Cotinine Cytisine Decamethonium Desformylflustrabromine Dianicline Dimethylphenylpiperazinium Epibatidine Epiboxidine Ethanol (alcohol) Ethoxysebacylcholine EVP-4473 EVP-6124 Galantamine GTS-21 Ispronicline Ivermectin JNJ-39393406 Levamisole Lobeline MEM-63,908 (RG-3487) Morantel Nicotine (tobacco )NS-1738 PHA-543,613 PHA-709,829 PNU-120,596 PNU-282,987 Pozanicline Pyrantel Rivanicline RJR-2429 Sazetidine A SB-206553 Sebacylcholine SIB-1508Y SIB-1553A SSR-180,711 Suberyldicholine Suxamethonium (succinylcholine) Suxethonium (succinyldicholine) TC-1698 TC-1734 TC-1827 TC-2216 TC-5214 TC-5619 TC-6683 Tebanicline Tribendimidine Tropisetron UB-165 Varenicline WAY-317,538 XY-4083 Antagonists NAMs Tooltip negative allosteric modulators )
Precursors (andprodrugs )
