Hordenine: Difference between revisions
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'''Hordenine''' (''N'',''N''-dimethyl-4-hydroxyphenylethylamine) is a [[phenethylamine]] [[alkaloid]] with antibacterial and [[antibiotic]] properties. It works as a [[stimulant]] in [[mammal]]s, increasing heart rate and blood pressure whilst stimulating the release of [[norepinephrine]].<ref>{{cite journal|title=Pharmacological effects of hordenine|journal=Dtsch Tierarztl Wochenschr. |date=June1995|first=|last=|coauthors=Institut fur Pharmakologie, Toxikologie und Pharmazie, Tierarztlichen Hochschule Hannover |volume=102|issue=6|pages=228–32|id=|format=|accessdate=2011-12-14 |pmid=8582256}}</ref> The effects of hordenine are typically short-lasting, with research carried out on horses suggesting that the animals were no longer |
'''Hordenine''' (''N'',''N''-dimethyl-4-hydroxyphenylethylamine) is a [[phenethylamine]] [[alkaloid]] with antibacterial and [[antibiotic]] properties. It works as a [[stimulant]] in [[mammal]]s, increasing heart rate and blood pressure whilst stimulating the release of [[norepinephrine]].<ref>{{cite journal|title=Pharmacological effects of hordenine|journal=Dtsch Tierarztl Wochenschr. |date=June1995|first=|last=|coauthors=Institut fur Pharmakologie, Toxikologie und Pharmazie, Tierarztlichen Hochschule Hannover |volume=102|issue=6|pages=228–32|id=|format=|accessdate=2011-12-14 |pmid=8582256}}</ref> The effects of hordenine are typically short-lasting, with research carried out on horses suggesting that the animals were no longer affected after 30 minutes.<ref>{{cite journal|title=Hordenine: pharmacology, pharmacokinetics and behavioural effects in the horse|journal=Equine Veterinary Journal |date=November1990|first=|last=|coauthors=Frank M, Weckman TJ, Wood T, Woods WE, Tai CL, Chang SL, Ewing A, Blake JW, Tobin T. |volume=22|issue=6|pages=437–41|id=|format=|accessdate=2011-12-14 |pmid=2269269}}</ref> It is produced in nature by several varieties of plants in the family ''[[Cactaceae]]'' and by some in ''[[Acacia]]''.<ref>[http://www.csdl.tamu.edu/FLORA/Wilson/481/medbot/Medical.htm www.csdl.tamu.edu]</ref> |
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==Occurrence in nature== |
==Occurrence in nature== |
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Revision as of 21:49, 16 March 2012
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| Names | |
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| IUPAC name
4-(2-Dimethylaminoethyl)phenol
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| Other names
N,N-Dimethyltyramine; Peyocactin; Anhaline
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.007.920 |
| KEGG | |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C10H15NO | |
| Molar mass | 165.236 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Hordenine (N,N-dimethyl-4-hydroxyphenylethylamine) is a phenethylamine alkaloid with antibacterial and antibiotic properties. It works as a stimulant in mammals, increasing heart rate and blood pressure whilst stimulating the release of norepinephrine.[1] The effects of hordenine are typically short-lasting, with research carried out on horses suggesting that the animals were no longer affected after 30 minutes.[2] It is produced in nature by several varieties of plants in the family Cactaceae and by some in Acacia.[3]
Occurrence in nature
Sprouting barley (Hordeum vulgare) seeds contain hordenine as the main alkaloid in their roots.[4] The alkaloid is also present in reed canarygrass (Phalaris arundinacea), a tall perennial grass, and in Ungernia trisphaera, a small flowering species.[5]
Peyote (Lophophora williamsii), San Pedro cactus (Echinopsis pachanoi), and Peruvian Torch cactus (Echinopsis peruviana) all produce high levels of this compound[citation needed], reportedly along with many other members of the Echinopsis genus[6]. These cacti also produce high levels of mescaline and other phenylethylamine compounds. Cacti in the genus Ariocarpus, Aztekium, Opuntia, Pereskia, and Coryphantha also produce these alkaloids, though not in high concentrations.[7] Obregonia contains Hordenine, with a reported yield of 0.002%.[8]
Antibacterial properties
Hordenine exhibits an inhibitory action against at least 18 strains of penicillin resistant Staphylococcus bacteria or MRSA.[9]
References
- ^ "Pharmacological effects of hordenine". Dtsch Tierarztl Wochenschr. 102 (6): 228–32. June1995. PMID 8582256.
{{cite journal}}:|access-date=requires|url=(help); Check date values in:|date=(help); Unknown parameter|coauthors=ignored (|author=suggested) (help) - ^ "Hordenine: pharmacology, pharmacokinetics and behavioural effects in the horse". Equine Veterinary Journal. 22 (6): 437–41. November1990. PMID 2269269.
{{cite journal}}:|access-date=requires|url=(help); Check date values in:|date=(help); Unknown parameter|coauthors=ignored (|author=suggested) (help) - ^ www.csdl.tamu.edu
- ^ "The distribution and formation tyramine methylpherase during germination of barly" (PDF). Journal of Biological Chemistry. February1963. Retrieved 2008-02-01.
{{cite journal}}: Check date values in:|date=(help); Cite has empty unknown parameter:|coauthors=(help) - ^ The Alkaloids: A Review of Chemical Literature: volume 4 (Specialist Periodical Reports). The Chemical Society. 1974. p. 130. ISBN 0-851862-87-X.
{{cite book}}:|access-date=requires|url=(help); Unknown parameter|coauthors=ignored (|author=suggested) (help) - ^ www.erowid.org
- ^ Peyote and Other Psychoactive Cacti. Berkley, CA, USA: Ronin Publishing. 1997. ISBN 0-914171-95-X. Retrieved 2011-12-14.
{{cite book}}: Unknown parameter|coauthors=ignored (|author=suggested) (help) - ^ "Cactus alkaloids. XI. Isolation of tyramine, N-methyltyramine, and hordenine from Obregonia denegrii". Economic Botany. 25 (4): 382–384. December1971. doi:10.1007/BF02985205.
{{cite journal}}:|access-date=requires|url=(help); Check date values in:|date=(help); Unknown parameter|coauthors=ignored (|author=suggested) (help) - ^ www.phytomedical.com[dead link]