3-Methoxytyramine

From Wikipedia, the free encyclopedia

3-Methoxytyramine

IUPAC name 4-(2-aminoethyl)-2-methoxyphenol
Other names 3-O-methyldopamine
Identifiers
CAS number	554-52-9^N
PubChem	1669
ChemSpider	1606^N
MeSH	3-methoxytyramine
Jmol-3D images
SMILES COc1cc(ccc1O)CCN
InChI InChI=1S/C9H13NO2/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,6,11H,4-5,10H2,1H3^N Key: DIVQKHQLANKJQO-UHFFFAOYSA-N^N InChI=1/C9H13NO2/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,6,11H,4-5,10H2,1H3 Key: DIVQKHQLANKJQO-UHFFFAOYAB
Properties
Molecular formula	C₉H₁₃NO₂
Molar mass	167.21 g/mol
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 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 physiologically inactive, 3-MT has recently been shown to act as an agonist of the TAAR1.^[1]

Occurrence

3-Methoxytyramine occurs naturally in the prickly pear cactus (genus Opuntia),^[2] and is in general widespread throughout the Cactaceae.^[3] It has also been found in crown gall tumors on Nicotiana sp.^[4]

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. PMC 2956650. PMID 20976142.
↑ Neuwinger, Hans Dieter (1996). "Cactaceae". African ethnobotany: poisons and drugs: chemistry, pharmacology, toxicology. CRC Press. p. 271. ISBN 978-3-8261-0077-2. Retrieved on June 12, 2009 through Google Book Search.
↑ T. A. Smith (1977). "Phenethylamine and related compounds in plants." Phytochem. 16 9-18.
↑ S. D. Mitchell, J. L. Firmin and D. O. Gray (1984). "Enhanced 3-methoxytyramine levels in crown gall tumours and other undifferentiated plant tissues." Biochem J. 221 891-5.

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)

Trace amine-associated receptor (TAAR) ligands

TAAR1

Agonists

Selective:	O-Phenyl-3-iodotyramine RO5166017

Non-selective:	3-Iodothyronamine 3-Methoxytyramine 5-MeO-DMT Amphetamine Bromocriptine DMT DOI Dopamine LSD m-Octopamine m-Tyramine MDMA Methamphetamine N-Methylphenethylamine N-Methyltryptamine N-Methyltyramine Norepinephrine p-Octopamine p-Tyramine Phenethylamine Serotonin Synephrine Tryptamine; Unknown: RG7351

Antagonists

Selective: EPPTB (RO5212773)

*Note that other phenethylamines, tryptamines, ergolines, and thyronamines are either known to or are likely to act as non-selective TAAR1 agonists as well.

v t e Phenethylamines

Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-FLY βk-2C-B 2C-C 2C-D 2C-E 2C-EF 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: Phenylethanolamine Hordenine Phenethylamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA

Amphetamines	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: 3-FMA 4-MA 4-MMA 4-MTA 5-IT Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamine Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Fludorex Furfenorex Gepefrine Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Norfenfluramine L-Norpseudoephedrine Oxilofrine Ortetamine PBA PCA Phenpromethamine PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 5-APB 5-APDB 5-MAPB 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 N,N-Dimethyldopamine 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 Pronethalol Salbutamol (Levosalbutamol) Theodrenaline UWA-101

This article is issued from Wikipedia. The text is available under the Creative Commons Attribution/Share Alike; additional terms may apply for the media files.

3-Methoxytyramine

Occurrence

See also

References