Thyronamine

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Thyronamine


IUPAC name 4-[4-(2-Aminoethyl)phenoxy]phenol
Identifiers
CAS number	500-78-7^Y
PubChem	3083601
ChemSpider	2340781^Y
MeSH	thyronamine
ChEMBL	CHEMBL201896^Y
Jmol-3D images	Image 1
SMILES O(c1ccc(cc1)CCN)c2ccc(O)cc2
InChI InChI=1S/C14H15NO2/c15-10-9-11-1-5-13(6-2-11)17-14-7-3-12(16)4-8-14/h1-8,16H,9-10,15H2^Y Key: OVUVNKDANCKDCK-UHFFFAOYSA-N^Y InChI=1/C14H15NO2/c15-10-9-11-1-5-13(6-2-11)17-14-7-3-12(16)4-8-14/h1-8,16H,9-10,15H2 Key: OVUVNKDANCKDCK-UHFFFAOYAP
Properties
Molecular formula	C₁₄H₁₅NO₂
Molar mass	229.27 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 (77 °F), 100 kPa)
Infobox references

Thyronamine refers both to a molecule, and to derivatives of that molecule: a family of decarboxylated and deiodinated metabolites of the thyroid hormones thyroxine (T4) and 3,5,3'-triiodothyronine (T3).

Types

The group includes:

Thyronamine (T0AM)
3-Iodothyronamine (T1AM), which is the most notable one as it is a trace amine found in the nervous system. It is a possible candidate for the natural ligand of the trace amine-associated receptor TAAR1 (TAR1), a G protein-coupled receptor located in the cell membrane^[1]
3,5-Diiodothyronamine (T2AM)
3,5,3'-Triiodothyronamine (T3AM)

References

↑ Piehl S, Hoefig CS, Scanlan TS, Köhrle J (2011). "Thyronamines - Past, Present, and Future". Endocrine Reviews 32 (1): 64–80. doi:10.1210/er.2009-0040. PMID 20880963.

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)

M: END

anat/phys/devp/horm

noco (d)/cong/tumr, sysi/epon

proc, drug (A10/H1/H2/H3/H5)

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

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Thyronamine

Types

See also

References