Hordenine

Hordenine
IUPAC name

4-(2-Dimethylaminoethyl)phenol
Other names

N,N-Dimethyltyramine; Peyocactin; Anhaline
Identifiers
CAS number 3595-05-9 Y
PubChem 68313
ChemSpider 61609 Y
KEGG C06199 Y
ChEBI CHEBI:5764 Y
ChEMBL CHEMBL505789 Y
Jmol-3D images Image 1
Properties
Molecular formula C10H15NO
Molar mass 165.23 g mol−1
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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 effected 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 Hordeum vulgare (barley) seeds contain hordenine as the main alkaloid in their roots.[4]

Peyote (Lophophora williamsii), San Pedro cactus (Echinopsis pachanoi), and Peruvian Torch cactus (Echinopsis peruviana) all produce high levels of this compound. 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.[5] Obregonia contains Hordenine, with a reported yield of 0.002%.[6]

Antibacterial properties

Hordenine exhibits an inhibitory action against at least 18 strains of penicillin resistant Staphylococcus bacteria.[7]

References

  1. ^ "Pharmacological effects of hordenine". Dtsch Tierarztl Wochenschr. 102 (6): 228-32. June1995. http://www.ncbi.nlm.nih.gov/pubmed/8582256. Retrieved 2011-12-14. 
  2. ^ "Hordenine: pharmacology, pharmacokinetics and behavioural effects in the horse". Equine Veterinary Journal 22 (6): 437-41. November1990. http://www.ncbi.nlm.nih.gov/pubmed/2269269. Retrieved 2011-12-14. 
  3. ^ www.csdl.tamu.edu
  4. ^ "The distribution and formation tyramine methylpherase during germination of barly". Journal of Biological Chemistry. February1963. http://www.jbc.org/cgi/reprint/238/2/676.pdf. Retrieved 2008-02-01. 
  5. ^ Peyote and Other Psychoactive Cacti. Berkley, CA, USA: Ronin Publishing. 1997. ISBN 0-914171-95-X. http://books.google.co.uk/books?hl=en&lr=&id=pFeOluzNEGsC. Retrieved 2011-12-14. 
  6. ^ "Cactus alkaloids. XI. Isolation of tyramine, N-methyltyramine, and hordenine from Obregonia denegrii". Economic Botany 25 (4): 382-384. December1971. http://dx.doi.org/10.1007/BF02985205. Retrieved 2011-12-14. 
  7. ^ www.phytomedical.com
Phenethylamines
Psychedelics: 2C-B • 2C-B-FLY • 2C-C • 2C-D • 2C-E • 2C-F • 2C-G • 2C-I • 2C-N • 2C-P • 2C-SE • 2C-T • 2C-T-2 • 2C-T-4 • 2C-T-7 • 2C-T-8 • 2C-T-9 • 2C-T-13 • 2C-T-15 • 2C-T-17 • 2C-T-21 • 2C-TFM • 2C-YN • Allylescaline • DESOXY • Escaline • Isoproscaline • Jimscaline • Macromerine • MEPEA • Mescaline • Metaescaline • Methallylescaline • Proscaline • Psi-2C-T-4 • TCB-2
Stimulants: 2-OH-PEA • β-Me-PEA • Hordenine • N-Me-PEA • Phenethylamine (PEA)
Entactogens: Lophophine • MDPEA • MDMPEA
Others: BOH • DMPEA
Amphetamines
Phenylisopropylamines
Psychedelics: 3C-BZ • 3C-E • 3C-P • Aleph • Beatrice • Bromo-DragonFLY • D-Deprenyl • DMA • DMCPA • DMMDA • DOB • DOC • DOEF • DOET • DOI • DOM • DON • DOPR • DOTFM • Ganesha • MMDA • MMDA-2 • Psi-DOM • TMA • TeMA
Stimulants: 4-MA • 4-MMA • 4-MTA • 5-IT • Alfetamine • Amfecloral • Amfepentorex • Amphetamine (Dextroamphetamine, Levoamphetamine) • Amphetaminil • Benfluorex • Benzphetamine • Cathine • Clobenzorex • Dimethylamphetamine • Ephedrine (EPH) • Ethylamphetamine • Fencamfamine • Fencamine • Fenethylline • Fenfluramine (Dexfenfluramine) • Fenproporex • Fludorex • Furfenorex • Isopropylamphetamine • Lefetamine • Mefenorex • Methamphetamine (Dextromethamphetamine, Levomethamphetamine) • Methoxyphenamine • MMA • Norfenfluramine • Oxilofrine • Ortetamine • PBA • PCA • Phenpromethamine • PFA • PFMA • PIA • PMA • PMEA • PMMA • Phenylpropanolamine (PPA) • Prenylamine • Propylamphetamine • Pseudoephedrine (PSE) • Sibutramine • Tiflorex (Flutiorex) • Tranylcypromine • Xylopropamine • Zylofuramine
Entactogens: 5-APDB • 6-APB • 6-APDB • EDA • IAP • MDA • MDEA • MDHMA (FLEA) • MDMA ("Ecstasy") • MDOH • MMDMA • NAP • TAP
Others: Amiflamine • DFMDA • D-Deprenyl • L-Deprenyl (Selegiline)
Phentermines
Stimulants: Chlorphentermine • Cloforex • Clortermine • Etolorex • Mephentermine • Pentorex (Phenpentermine) • Phentermine
Entactogens: MDPH • MDMPH
Cathinones
Stimulants: Amfepramone • Brephedrone • Buphedrone • Bupropion (Amfebutamone) • Cathinone (Propion) • Dimethylcathinone (Dimethylpropion, Metamfepramone) • Ethcathinone (Ethylpropion) • Flephedrone • Methcathinone (Methylpropion) • Mephedrone • Methedrone
Entactogens: Ethylone • Methylone
Phenylisobutylamines
Entactogens: 4-CAB • 4-MAB • Ariadne (α-Et-DOM) • BDB (J) • Butylone (bk-MBDB) • EBDB (Ethyl-J) • Eutylone (bk-EBDB) • MBDB (Methyl-J)
Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines
Stimulants: α-PBP • α-PPP • α-PVP • MDPBP • MDPPP • MDPV • MOPPP • MPBP • MPHP • MPPP • Naphyrone • PEP • Prolintane • Pyrovalerone
Catecholamines
(and relatives..)
6-FNE • 6-OHDA • α-Me-DA • α-Me-TRA • Adrenochrome • Ciladopa • D-DOPA (Dextrodopa) • Dopamine • Epinephrine (Adrenaline) • Epinine • Fenclonine • Ibopamine • L-DOPA (Levodopa) • L-DOPS (Droxidopa) • L-Phenylalanine • L-Tyrosine • meta-Octopamine • meta-Tyramine • Metanephrine • Metirosine • Methyldopa • Nordefrin (Levonordefrin) • Norepinephrine (Noradrenaline) • Normetanephrine • para-Octopamine • para-Tyramine
Miscellaneous