3-Methoxytyramine

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3-Methoxytyramine

IUPAC name 4-(2-aminoethyl)-2-methoxyphenol
Identifiers
CAS number	554-52-9
PubChem	1669
ChemSpider	61670^Y
MeSH	3-methoxytyramine
Jmol-3D images	Image 1 Image 2
SMILES CC1=C(C=CC(=C1O)O)CCN Oc1c(c(ccc1O)CCN)C
InChI InChI=1S/C9H13NO2/c1-6-7(4-5-10)2-3-8(11)9(6)12/h2-3,11-12H,4-5,10H2,1H3^Y Key: NSEVRAZZUOXAHQ-UHFFFAOYSA-N^Y InChI=1/C9H13NO2/c1-6-7(4-5-10)2-3-8(11)9(6)12/h2-3,11-12H,4-5,10H2,1H3 Key: NSEVRAZZUOXAHQ-UHFFFAOYAQ
Properties
Molecular formula	C₉H₁₃NO₂
Molar mass	167.21 g/mol
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

3-Methoxytyramine (3-MT), also known as 3-methoxy-4-hydroxyphenethylamine, is a metabolite of the neurotransmitter dopamine formed by the introduction of a methyl group to dopamine by the enzyme catechol-O-methyl transferase (COMT). 3-MT can be further metabolized by the enzyme monoamine oxidase (MAO) to form homovanillic acid (HVA), which is then typically excreted in the urine.

Originally thought to be inactive, 3-MT has recently been shown to act as an agonist of the TAAR1.^[1]

3-Methoxytyramine is also naturally found in the prickly pear (genus Opuntia).^[2]

References

^ Sotnikova TD, Beaulieu JM, Espinoza S, et al. (2010). "The dopamine metabolite 3-methoxytyramine is a neuromodulator". Plos One 5 (10): e13452. doi:10.1371/journal.pone.0013452. . PMID 20976142. http://dx.plos.org/10.1371/journal.pone.0013452.
^ Neuwinger, Hans Dieter (1996). "Cactaceae". African ethnobotany: poisons and drugs: chemistry, pharmacology, toxicology. CRC Press. pp. 271. ISBN 978-3-8261-0077-2. http://books.google.com/books?id=_j8ueEmakD0C&pg=PA271&lpg=PA271. Retrieved on June 12, 2009 through Google Book Search.

Neurotransmitter metabolic intermediates

catecholamines

Anabolism (tyrosine→epinephrine)	Tyrosine → Levodopa → Dopamine → Norepinephrine → Epinephrine

Catabolism/ metabolites	dopamine: DOPAL · DOPAC · MOPET · Hydroxytyrosol · 3-Methoxytyramine · Homovanillic acid norepinephrine: 3,4-Dihydroxymandelic acid · Normetanephrine · Vanillylmandelic acid · 3-Methoxy-4-hydroxyphenylglycol · Dihydroxyphenylethylene glycol epinephrine: Metanephrine

tryptophan→serotonin

anabolism: 5-Hydroxytryptophan
catabolism: 5-Hydroxyindoleacetic acid

serotonin→melatonin

Normelatonin

M: MET

mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m

k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon

m(A16/C10),i(k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)

TAAR Ligands

TAAR1

Agonists	Selective: O-Phenyl-3-iodotyramine • RO5166017; Non-selective: 3-Iodothyronamine • 3-Methoxytyramine • 5-MeO-DMT • Amphetamine • Apomorphine • Bromocriptine • Bufotenin • DMT • DOI • Dopamine • LSD • m-Octopamine • m-Tyramine • MDMA • Methamphetamine • N-Methylphenethylamine • N-Methyltryptamine • N-Methyltyramine • Nomifensine • Norepinephrine • p-Octopamine • p-Tyramine • Phenethylamine • Serotonin • Synephrine • Tryptamine; Unknown: RG7351 * Note that many other phenethylamines, tryptamines, ergolines, and thyronamines are either known to or are likely to act as non-selective TAAR1 agonists as well.

Antagonists	Selective: EPPTB (RO5212773)

v t e Phenethylamines

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 ß-Me-PEA Hordenine N-Me-PEA Phenethylamine 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 Ethylamphetamine Fencamfamine Fencamine Fenethylline Fenfluramine (Dexfenfluramine) Fenproporex Fludorex Furfenorex Gepefrine Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Norfenfluramine Oxilofrine Ortetamine PBA PCA Phenpromethamine PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 5-APDB 6-APB 6-APDB EDA IAP MDA MDEA MDHMA MDMA MDOH MMDMA NAP TAP Others: Amiflamine DFMDA Selegiline (also D-Deprenyl)

Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH

Cathinones	Stimulants: Amfepramone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Flephedrone Methcathinone Mephedrone Methedrone Entactogens: Ethylone Methylone

Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine

Phenylalkylpyrrolidines	Stimulants: a-PBP a-PPP a-PVP MDPBP MDPPP MDPV MOPPP 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 Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine

Miscellaneous	Amidephrine Arbutamine Cafedrine Denopamine Dobutamine Dopexamine Etafedrine Famprofazone Hexapradol Methoxamine Phenoxybenzamine Prenalterol Pronethalol Propranolol Salbutamol (Levosalbutamol) Theodrenaline UWA-101 Xamoterol

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