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Hordenine

IUPAC name	4-(2-dimethylaminoethyl)phenol
Other names	N,N-Dimethyltyramine Peyocactin
Identifiers
CAS number	3595-05-9
PubChem	68313
SMILES	`CN(C)CCC1=CC=C(C=C1)O`
Properties
Molecular formula	C₁₀H₁₅NO
Molar mass	165.23 g mol⁻¹
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 phenylethylamine alkaloid with antibacterial and antibiotic properties. It stimulates the release of norepinephrine in mammals. It is produced in nature by several varieties of plants in the family Cactaceae and by some in Acacia.^[1]

[edit] Occurrence in nature

Sprouting Hordeum vulgare (barley) seeds contain hordenine as the main alkaloid in their roots.^[2]

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, Opuntia, Pereskia, and Coryphantha also produce these alkaloids, though not in high concentrations.

Aztekium also contains it.

". . .it has been shown that hordenine, N, N-Dimethyl-hydroxyphenylethylamine, exhibits an inhibitory action against at least 18 strains of penicillin resistant Staphylococcus bacteria."^[3]

[edit] External links

Hordenine Info

[edit] References

^ www.csdl.tamu.edu
^ "THE DISTRIBUTION AND FORMATION OF TYRAMINE METHYLPHERASE DURING GERMINATION OF BARLEY". THE JOURNAL OF BIOLOGICAL. CHEMISTRY. February1963. http://www.jbc.org/cgi/reprint/238/2/676.pdf. Retrieved 2008-02-01.
^ www.phytomedical.com

v • d • e Phenethylamines

Phenethylamines	Psychedelics: 2C-B • 2C-B-FLY • 2C-C • 2C-D • 2C-E • 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 • DMPEA • Escaline • Isoproscaline • Jimscaline • Macromerine • MEPEA • Mescaline • Metaescaline • Methallylescaline • Proscaline • Psi-2C-T-4 • TCB-2 Stimulants: 2-OH-PEA • α-Et-PEA • β-Me-PEA • Hordenine • N-Me-PEA • Phenethylamine (PEA) Entactogens: Lophophine • MDPEA • MDMPEA

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Phentermines	Stimulants: Chlorphentermine • Clortermine • Mephentermine • Phenpentermine • Phentermine Entactogens: MDPH • MDMPH

Cathinones	Stimulants: Brephedrone • Buphedrone • Bupropion (Amfebutamone) • Cathinone (Propion) • Diethylcathinone (Diethylpropion, Amfepramone) • Dimethylcathinone (Dimethylpropion, Metamfepramone) • Ethcathinone (Ethylpropion) • Flephedrone • Methcathinone (Methylpropion) • Mephedrone • Methedrone Entactogens: Ethylone • Methylone

Butanamines	Entactogens: BDB (J) • BOH (Hydroxy-J) • Butylone (bk-MBDB) • EBDB (Ethyl-J) • MBDB (Methyl-J; "Eden")

Catecholamines (and relatives..)	6-OHDA • α-Me-DA • α-Me-TRA • Adrenochrome • D-DOPA (Dextrodopa) • Dopamine • Epinephrine (Adrenaline) • Epinine • Fenclonine • Ibopamine • L-DOPA (Levodopa) • L-DOPS (Droxidopa) • L-Phenylalanine • L-Tyrosine • Metanephrine • Metirosine • Methyldopa • Nordefrin (Levonordefrin) • Norepinephrine (Noradrenaline) • Normetanephrine • Octopamine • Tyramine

Miscellaneous	Amidephrine • Arbutamine • Cafedrine • Denopamine • Dobutamine • Dopexamine • Etafedrine • Etilefrine • Gepefrine • Isoprenaline (Isoproterenol) • Isoetarine • Metaraminol • Methoxamine • Methoxyphenamine • Norfenefrine • Orciprenaline • Phenylephrine (Neosynephrine) • Phenoxybenzamine • Prenalterol • Propranolol • Salbutamol (Albuterol; Levosalbutamol) • Synephrine (Oxedrine) • Theodrenaline • Xamoterol

Retrieved from "http://en.wikipedia.org/wiki/Hordenine"

Categories: Natural phenethylamine alkaloids | Phenols