Hordenine

Hordenine: Hordenine

IUPAC name

4-(2-Dimethylaminoethyl)phenol

Other names

N,N-Dimethyltyramine; Peyocactin

Identifiers

CAS number 3595-05-9

PubChem 68313

ChemSpider 61609^Y

KEGG C06199^Y

ChEBI CHEBI:5764^Y

ChEMBL CHEMBL505789^Y

Jmol-3D images Image 1

SMILES

Oc1ccc(cc1)CCN(C)C

InChI

InChI=1S/C10H15NO/c1-11(2)8-7-9-3-5-10(12)6-4-9/h3-6,12H,7-8H2,1-2H3^Y
Key: KUBCEEMXQZUPDQ-UHFFFAOYSA-N^Y
InChI=1/C10H15NO/c1-11(2)8-7-9-3-5-10(12)6-4-9/h3-6,12H,7-8H2,1-2H3
Key: KUBCEEMXQZUPDQ-UHFFFAOYAA

Properties

Molecular formula C₁₀H₁₅NO

Molar mass 165.23 g mol⁻¹

Y (verify) (what is: Y/N?)
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 stimulates the release of norepinephrine in mammals, working as a stimulant. It is produced in nature by several varieties of plants in the family Cactaceae and by some in Acacia.^[1]

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.^{[citation needed]} 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.

Hordenine exhibits an inhibitory action against at least 18 strains of penicillin resistant Staphylococcus bacteria.^[3]

References

^ www.csdl.tamu.edu

^ "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.

^ www.phytomedical.com^{[dead link]}

v · d · ePhenethylamines

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

Categories:
Natural phenethylamine alkaloids
Phenols

Hordenine

IUPAC name 4-(2-Dimethylaminoethyl)phenol
Other names N,N-Dimethyltyramine; Peyocactin
Identifiers
CAS number	3595-05-9
PubChem	68313
ChemSpider	61609^Y
KEGG	C06199^Y
ChEBI	CHEBI:5764^Y
ChEMBL	CHEMBL505789^Y
Jmol-3D images	Image 1
SMILES Oc1ccc(cc1)CCN(C)C
InChI InChI=1S/C10H15NO/c1-11(2)8-7-9-3-5-10(12)6-4-9/h3-6,12H,7-8H2,1-2H3^Y Key: KUBCEEMXQZUPDQ-UHFFFAOYSA-N^Y InChI=1/C10H15NO/c1-11(2)8-7-9-3-5-10(12)6-4-9/h3-6,12H,7-8H2,1-2H3 Key: KUBCEEMXQZUPDQ-UHFFFAOYAA
Properties
Molecular formula	C₁₀H₁₅NO
Molar mass	165.23 g mol⁻¹
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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Look at other dictionaries:

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HORDÉNINE — Alcaloïde, dont la formule brute est C10H15ON, extrait des touraillons d’orge (germes d’orge séparés du malt des brasseries). Il s’agit de l’orge Hordenum vulgare , de la famille des graminées. Léger remarqua que les infusions de touraillons… … Encyclopédie Universelle
hordenine — A biogenic amine first isolated from barley; increases blood pressure. [L. hordeum, barley, + in] … Medical dictionary
hordenine — hor·de·nine … English syllables
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Hordenine

Occurrence in nature

References

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Hordenine

Occurrence in nature

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