Elemicin: Difference between revisions
Appearance
Content deleted Content added
Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChEMBL KEGG. |
m new link |
||
(106 intermediate revisions by 53 users not shown) | |||
Line 1: | Line 1: | ||
{{Short description|Chemical compound}} |
|||
{{Drugbox |
{{Drugbox |
||
| Watchedfields = changed |
|||
| verifiedrevid = 399900314 |
|||
| verifiedrevid = 410138806 |
|||
| IUPAC_name = 1,2,3-trimethoxy-5-allylbenzene |
|||
| IUPAC_name = 1,2,3-Trimethoxy-5-(prop-2-en-1-yl)benzene |
|||
| image = Elemicin.png |
|||
| image = ElemicinSVG.svg |
|||
| KEGG = C10451 |
|||
| alt = Skeletal formula of elemicin |
|||
| InChI = 1/C12H16O3/c1-5-6-9-7-10(13-2)12(15-4)11(8-9)14-3/h5,7-8H,1,6H2,2-4H3 |
|||
| image2 = Elemicin-3D-balls.png |
|||
| InChIKey = BPLQKQKXWHCZSS-UHFFFAOYAD |
|||
| alt2 = Ball-and-stick model of the elemicin molecule |
|||
| smiles1 = O(c1cc(cc(OC)c1OC)C\C=C)C |
|||
| ChEMBL = 458690 |
|||
<!--Clinical data-->| tradename = |
|||
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|||
| pregnancy_category = |
|||
| StdInChI = 1S/C12H16O3/c1-5-6-9-7-10(13-2)12(15-4)11(8-9)14-3/h5,7-8H,1,6H2,2-4H3 |
|||
| legal_status = Uncontrolled |
|||
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|||
| dependency_liability = None |
|||
| StdInChIKey = BPLQKQKXWHCZSS-UHFFFAOYSA-N |
|||
| addiction_liability = Low / None |
|||
| CAS_number = 487-11-6 |
|||
| ATC_prefix = |
|||
| ATC_suffix = |
|||
| PubChem = 10248 |
|||
| DrugBank = |
|||
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|||
| ChemSpiderID = 9830 |
|||
| chemical_formula = C<sub>12</sub>H<sub>16</sub>O<sub>3</sub> |
|||
| molecular_weight = 208.25 g/mol |
|||
| smiles = C=CCC1=CC(OC)=C(OC)C(OC)=C1 |
|||
| bioavailability = |
|||
| protein_bound = |
|||
| metabolism = |
|||
| elimination_half-life = |
|||
| excretion = |
|||
| pregnancy_category= |
|||
| legal_status = Uncontrolled |
|||
| routes_of_administration = Oral |
| routes_of_administration = Oral |
||
<!--Pharmacokinetic data-->| bioavailability = |
|||
| protein_bound = |
|||
| metabolism = |
|||
| elimination_half-life = |
|||
| excretion = <!--Identifiers--> |
|||
| CAS_number_Ref = {{cascite|correct|??}} |
|||
| CAS_number = 487-11-6 |
|||
| UNII_Ref = {{fdacite|correct|FDA}} |
|||
| UNII = HSZ191AKAN |
|||
| ATC_prefix = |
|||
| ATC_suffix = |
|||
| PubChem = 10248 |
|||
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
|||
| DrugBank = |
|||
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|||
| ChemSpiderID = 9830 |
|||
| KEGG_Ref = {{keggcite|correct|kegg}} |
|||
| KEGG = C10451 |
|||
| ChEMBL_Ref = {{ebicite|correct|EBI}} |
|||
| ChEMBL = 458690 |
|||
<!--Chemical data-->| C = 12 |
|||
| H = 16 |
|||
| O = 3 |
|||
| smiles = C=CCC1=CC(OC)=C(OC)C(OC)=C1 |
|||
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|||
| StdInChI = 1S/C12H16O3/c1-5-6-9-7-10(13-2)12(15-4)11(8-9)14-3/h5,7-8H,1,6H2,2-4H3 |
|||
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|||
| StdInChIKey = BPLQKQKXWHCZSS-UHFFFAOYSA-N |
|||
}} |
}} |
||
'''Elemicin''' is a [[phenylpropene]], a natural [[organic compound]], and is a constituent of several plant species' [[essential oils]].<ref name='Baser' /><ref name=ChemOfSpices /> |
|||
'''Elemicin''' is a [[phenylpropene]], a natural [[organic compound]], and is a constituent of the [[essential oil]] of [[nutmeg]]. It is partially responsible for the psychoactive effects of nutmeg.<ref name='Shulgin'>{{Cite journal | first1 = Alexander T. | last1 = Shulgin | author1-link = Alexander Shulgin | last2 = Sargent | first2 = Thornton W. | last3 = Naranjo | first3 = Claudio | title = Chemistry and psychopharmacology of nutmeg and of several related phenylisopropylamines | journal = United States, Public Health Service Publication | year = 1967 | issue = 1645 | pages = 202–214}}</ref> Elemicin is also a minor constituent of the oleoresin and essential oil of Manila elemi (''[[Canarium luzonicum]]''). One study found it to comprise 2.4% of the fresh essential oil.<ref name='Baser'>{{cite journal | first1 = Kemal Hüsnü Can .| last1 = Baser | last2 = Özek | first2 = Temel | last3 = Kürkçüoglu | first3 = Mine | last4 = Villanueva | first4 = Merle A. | first5 = Rosalinda C. | title = The Composition of Manila Elemi Oil | journal = Flavour and Fragrance Journal | year = 1993 | volume = 8 | pages = 35–37 | url=http://itdi.dost.gov.ph/R&D/cmd/elemioil.pdf |format=PDF | doi = 10.1002/ffj.2730080107|last5 = Torres}}</ref> Raw nutmeg has caused [[anticholinergic]]-like effects in a patient, attributed to elemicin, as well as [[myristicin]]. <ref name="pmid15249817">{{cite journal | author = McKenna A, Nordt SP, Ryan J | title = Acute nutmeg poisoning | journal = European Journal of Emergency Medicine : Official Journal of the European Society for Emergency Medicine | volume = 11 | issue = 4 | pages = 240–1 | year = 2004 | month = August | pmid = 15249817 | doi = | url = http://meta.wkhealth.com/pt/pt-core/template-journal/lwwgateway/media/landingpage.htm?issn=0969-9546&volume=11&issue=4&spage=240}}</ref> |
|||
==Natural occurrence== |
|||
Elemicin is a constituent of the [[oleoresin]] and the essential oil of ''[[Canarium luzonicum]]'' (also referred to as elemi). Elemicin is named after this tree. One study found it to compose 2.4% of the fresh essential oil.<ref name='Baser'> |
|||
{{cite journal | vauthors = Villanueva MA, Torres RC, Baser KH, Özek T, Kürkçüoglu M | title = The Composition of Manila Elemi Oil | journal = Flavour and Fragrance Journal | year = 1993 | volume = 8 | pages = 35–37 | doi = 10.1002/ffj.2730080107 }}</ref> Elemicin is also present in the oils of the spices [[nutmeg]] and [[mace (spice)|mace]], with it composing 2.4% and 10.5% of those oils respectively.<ref name=ChemOfSpices>{{cite book| vauthors = Leela N |title=Chemistry of Spices|year=2008|publisher=Biddles Ltd. |location=Calicut, Kerala, India |isbn=9781845934057|pages=165–188 [170] |url=https://books.google.com/books?id=5WY08iuJyawC&q=Chemistry+of+Spices}}</ref> Structurally, elemicin is similar to [[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. |
|||
==Isolation== |
|||
Elemicin was first isolated from elemi oil using [[vacuum distillation]]. Specifically, the substance was collected between 162-165 °C at a reduced pressure of 10 [[torr]].<ref>{{cite journal |title=Constituents of Essential Oils. Elemicin, a High-boiling Constituent of Elemi Oil, and the Displacement of Alkyloxygroups in the Benzene Nucleus by Hydrogen|journal=Journal of the Chemical Society, Abstracts|year=1908|volume=94|issue=A493|pages=557–558|url=https://books.google.com/books?id=JGJFAQAAIAAJ&q=Constituents+of+Essential+Oils.+Elemicin%2C+a+High-boiling+Constituent+of+Elemi+Oil%2C+and+the+Displacement+of+Alkyloxygroups+in+the+Benzene+Nucleus+by+Hydrogen&pg=PA557|doi=10.1039/CA9089400493}}</ref><ref>{{cite journal| vauthors = Semmler F |title=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.)|journal=Berichte der Deutschen Chemischen Gesellschaft|date=1908|volume=41|issue=2|pages=1768–1775 |doi=10.1002/cber.19080410240 |url=https://zenodo.org/record/1426299}}</ref> |
|||
==Preparation== |
|||
Elemicin has been [[Organic synthesis|synthesized]] from [[syringol]] and [[allyl bromide]] using [[Williamson ether synthesis]] and [[Claisen rearrangement]].<ref>{{cite journal| vauthors = Mauthner F |title=Die Synthese des Elemicins und Isoelemicins|journal=Justus Liebigs Annalen der Chemie|year=1918|volume=414|issue=2|pages=250–255|doi=10.1002/jlac.19184140213|url=https://zenodo.org/record/1427645}}</ref><ref>{{cite journal |title=Synthesis of Elemicin and of isoElemicin|journal=Journal of the Chemical Society, Abstracts|year=1918|volume=114|pages=i428|doi=10.1039/CA9181400421}}</ref> The [[electrophilic aromatic substitution]] entering the [[Arene substitution pattern|''para'']]-position was made possible by secondary [[Cope rearrangement]].<ref>{{cite book| vauthors = Thomas L |title=Named Organic Reactions, 2nd Edition|year=2005|publisher=John Wiley & Sons, Ltd.|location=Wolfsburg, Germany|isbn=978-0470010402|pages=58–60 [59]|url=https://books.google.com/books?id=-BEdbO-08WMC&q=Named+Organic+Reactions,+2nd+Edition+2005}}</ref> This is due to syringol's allyl [[aromatic]] [[ether]] being blocked by ethers in both ''ortho''-positions. When blocked the allyl group migrates to the ''para''-position, in this case with yields above 85%.<ref>{{cite book| vauthors = Adams R |title=Organic Reactions| volume = II |year=1944|publisher=John Wiley & Sons, Inc.|location=New York|pages=2–44 [44]|doi=10.1002/0471264180.or002.01 |chapter=The Claisen Rearrangement |isbn=978-0471264187 }}</ref> |
|||
==Uses== |
|||
Elemicin has been used to synthesize the proto-[[alkaloid]] [[mescaline]].<ref>{{cite journal| vauthors = Hahn G, Wassmuth H |title=Über β-[Oxyphenyl]-äthylamine und ihre Umwandlungen, I. Mitteil.: Synthese des Mezcalins |journal=Berichte der Deutschen Chemischen Gesellschaft (A and B Series) |year=1934 |volume=67 |issue=4 |pages=696–708 |doi= 10.1002/cber.19340670430}}</ref> |
|||
==Pharmacology== |
|||
Raw nutmeg causes [[anticholinergic]]-like effects, which are attributed to elemicin and [[myristicin]].<ref name="pmid15249817"> |
|||
{{cite journal | vauthors = McKenna A, Nordt SP, Ryan J | title = Acute nutmeg poisoning | journal = European Journal of Emergency Medicine | volume = 11 | issue = 4 | pages = 240–241 | date = August 2004 | pmid = 15249817 | doi = 10.1097/01.mej.0000127649.69328.a5 | s2cid = 21133983 }}</ref><ref>{{cite journal | vauthors = Shulgin AT, Sargent T, Naranjo C | title = The chemistry and psychopharmacology of nutmeg and of several related phenylisopropylamines | journal = Psychopharmacology Bulletin | volume = 4 | issue = 3 | pages = 13 | date = December 1967 | pmid = 5615546 | url = http://bitnest.ca/external.php?id=%250E%253D9%250F%2524G%252F%2518B%255B%255B4%2522.FXQ%255CO%2500TK | access-date = 2015-09-02 | url-status = dead | format = pdf | archive-url = https://web.archive.org/web/20140420142511/http://bitnest.ca/external.php?id=%250E%253D9%250F%2524G%252F%2518B%255B%255B4%2522.FXQ%255CO%2500TK | archive-date = 2014-04-20 }}</ref> Elemicin inhibits Stearoyl-CoA Desaturase 1 (SCD1) by metabolic activation. Elemicin is one of the main components in aromatic food and has antimicrobial, antioxidant, and antiviral activities. Elemicin possesses genotoxicity and carcinogenicity.<ref>{{Cite web |title=Elemicin |url=https://www.chemsrc.com/en/cas/487-11-6_954455.html |access-date=2022-10-28 |website=www.chemsrc.com |language=en}}</ref><ref>{{Cite web |title=Elemicin {{!}} Stearoyl-CoA Desaturase (SCD) Inhibitor {{!}} Targetmol |url=https://www.targetmol.com/compound/elemicin |website=targetmol.com}}</ref> Excess consumption of raw nutmeg results in delirium and disorientation.<ref>{{Citation |title=elemicin |url=https://medical-dictionary.thefreedictionary.com/elemicin |work=The Free Dictionary |access-date=2022-10-28}}</ref> |
|||
Elemicin's psychoactivity is still a point of research, however some research suggests it may act like an agonist of the [[5-HT2A receptor|5-HT2A receptors]], similar to many psychedelics.<ref>[http://herbpedia.wdfiles.com/local--files/attachments/Elemicin_2014_Journal.pdf Evaluation of 5-HT2A Receptor Agonistic Property of Elemicin]</ref> However, this is controversial as the psychoactive effects of elemicin and plants it is found in, such as nutmeg, seem to cause more [[deliriant]]-like effects than psychedelic ones.<ref>{{cite journal | vauthors = Kelly BD, Gavin BE, Clarke M, Lane A, Larkin C | title = Nutmeg and psychosis | journal = Schizophrenia Research | volume = 60 | issue = 1 | pages = 95–96 | date = March 2003 | pmid = 12505144 | doi = 10.1016/s0920-9964(02)00204-9 | s2cid = 7540364 }}</ref> |
|||
== See also == |
|||
* [[Nutmeg oil]] |
|||
* [[Myristicin]] |
|||
* [[Phenylpropanoid]] |
|||
== References == |
== References == |
||
{{Reflist |
{{Reflist}} |
||
{{Hallucinogens}} |
|||
{{Cholinergics}} |
{{Cholinergics}} |
||
{{Phenylpropene}} |
{{Phenylpropene}} |
||
[[Category:Phenylpropenes]] |
[[Category:Phenylpropenes]] |
||
[[Category:O-methylated phenylpropanoids]] |
|||
[[Category:Phenol ethers]] |
[[Category:Phenol ethers]] |
||
[[Category: |
[[Category:Allyl compounds]] |
||
[[Category:O-methylated natural phenols]] |
|||
{{hallucinogen-stub}} |
|||
[[de:Elemicin]] |
|||
[[it:Elemicina]] |
|||
[[ru:Элемицин]] |