Hordenine

Hordenine
Names
	IUPAC name 4-(2-Dimethylaminoethyl)phenol
	Other names N,N-Dimethyltyramine; Peyocactin; Anhaline
Identifiers
CAS Number	3595-05-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:5764 ;
ChEMBL	ChEMBL505789 ;
ChemSpider	61609 ;
ECHA InfoCard	100.007.920
KEGG	C06199 ;
PubChem CID	68313;
CompTox Dashboard (EPA)	DTXSID2046096 ;
	InChI InChI=1S/C10H15NO/c1-11(2)8-7-9-3-5-10(12)6-4-9/h3-6,12H,7-8H2,1-2H3 Key: KUBCEEMXQZUPDQ-UHFFFAOYSA-N ; 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;
	SMILES Oc1ccc(cc1)CCN(C)C;
Properties
Chemical formula	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). verify (what is ?) 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 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]}

[1] "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)

[2] "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)

[3] www.csdl.tamu.edu

[4] "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)

[5] 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)

[erowid-6] www.erowid.org

[7] 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)

[8] "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)

[phytomedical-9] www.phytomedical.com^{[dead link]}

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v t e Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine Phenpromethamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-AL 3C-BZ 3C-E 3C-MAL 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 ZDCM-04 Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L-Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DiFMDA Selegiline (also D-Deprenyl)
Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine
Cathinones	Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone
Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D-DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L-DOPA (Levodopa) L-DOPS (Droxidopa) L-Phenylalanine L-Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101 Venlafaxine