Trace amine

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Trace amines are an endogenous group of amines structurally and metabolically related to classical monoamine neurotransmitters, such as dopamine, norepinephrine, and serotonin. Compared to the classical monoamines, they are present in trace concentrations. They are distributed heterogeneously throughout the mammalian brain and peripheral nervous tissues and exhibit high rates of metabolism. Although they can be synthesized within parent monoamine neurotransmitter systems, there is evidence that suggests that some of them may comprise their own independent neurotransmitter systems.^[1]

Trace amines may play very significant roles in the coordination of biogenic monoamine-based synaptic physiology. At high concentrations, they have well-characterized presynaptic ‘‘amphetamine-like’’ effects on monoamine release, reuptake and biosynthesis; at lower concentrations, they possess postsynaptic modulatory effects that potentiate the activity of other neurotransmitters, particularly dopamine and serotonin.^[1] A family of G protein coupled receptors known as TAARs (trace amine associated receptors) has been characterized to be responsive to trace amines^[2] and structurally related psychoactive drugs, such as amphetamine, MDMA, LSD, and DMT.^[3] Like dopamine, noradrenaline, and serotonin, the trace amines have been implicated in a vast array of human disorders of affect and cognition, such as depression^[4] and schizophrenia.^[5]

A thorough review of trace amines and trace amine receptors that discusses the historical evolution of this research particularly well is that of Grandy.^[6]

List of trace amines

Metabolic pathway of phenylalanine

Graphic of trace amine and catecholamine metabolism

L-Phenylalanine

L-Tyrosine

L-Dopa

N-Methylphenethylamine

COMT

Phenethylaminergic trace amines and the catecholamines are derivatives of phenylalanine.

Phenethylamines (related to catecholamines, such as dopamine and norepinephrine):
- β-Phenethylamine^[7] (PEA)
- 3-Methoxytyramine
- N-Methylphenethylamine^[7] (endogenous amphetamine isomer)
- m-Tyramine^[7]
- p-Tyramine^[7]
- N-Methyltyramine^[7]
- m-Octopamine^[7]
- p-Octopamine^[7]
Thyronamines, such as 3-iodothyronamine (T₁AM), compounds derived from thyroid hormones
Tryptamines (indoleamines, related to serotonin):
- Tryptamine
- N,N-Dimethyltryptamine (DMT), an endogenous psychedelic compound

References

↑ 1.0 1.1 Burchett SA, Hicks TP. The mysterious trace amines: protean neuromodulators of synaptic transmission in mammalian brain. Prog Neurobiol. 2006 Aug;79(5-6):223-46.
↑ Lindemann L, Ebeling M, Kratochwil NA, Bunzow JR, Grandy DK, Hoener MC. Trace amine-associated receptors form structurally and functionally distinct subfamilies of novel G protein-coupled receptors. Genomics. 2005 Mar;85(3):372-85.
↑ Bunzow JR, Sonders MS, Arttamangkul S, Harrison LM, Zhang G, Quigley DI, Darland T, Suchland KL, Pasumamula S, Kennedy JL, Olson SB, Magenis RE, Amara SG, Grandy DK. Amphetamine, 3,4-methylenedioxymethamphetamine, lysergic acid diethylamide, and metabolites of the catecholamine neurotransmitters are agonists of a rat trace amine receptor. Mol Pharmacol. 2001 Dec;60(6):1181-8.
↑ Davis, B.A., Boulton, A.A., 1994. The trace amines and their acidic metabolites in depression—an overview. Prog. Neuropsychopharmacol. Biol. Psychiatry 18, 17–45.
↑ O’Reilly, R.L., Davis, B.A., 1994. Phenylethylamine and schizophrenia. Prog Neuropsychopharmacol. Biol. Psychiatry 18, 63–75.
↑ D. K. Grandy (2007). "Trace amine-associated receptor 1—Family archetype or iconoclast?" Pharmacology & Therapeutics 116 (3) 355-390.
↑ 7.0 7.1 7.2 7.3 7.4 7.5 7.6 Broadley, KJ (March 2010). "The vascular effects of trace amines and amphetamines". Pharmacology & therapeutics 125 (3): 363–75. doi:10.1016/j.pharmthera.2009.11.005. PMID 19948186.

Endocannabinoids

Others

See also Template:Neuropeptides

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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

Tryptamines

Thyroid hormone metabolic intermediates

Tyrosine / iodotyrosine

Thyronine / iodothyronine

3'-Monoiodothyronine
3,3'-Diiodothyronine
3,3',5-Triiodothyronine (T₃)
3,3',5'-Triiodothyronine (Reverse T₃)
3,5,3',5'-Tetraiodothyronine (Thyroxine, T₄)

Thyronamine / iodothyronamine

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)

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