3-Iodothyronamine

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3-Iodothyronamine

IUPAC name 4-[4-(2-Amino-ethyl)-2-iodo-phenoxy]-phenol
Other names T₁AM
Identifiers
CAS number	712349-95-6
ChemSpider	8126125^Y
Jmol-3D images	Image 1 Image 2
SMILES OC1=CC=C(OC2=C(I)C=C(CCN)C=C2)C=C1 Ic2cc(ccc2Oc1ccc(O)cc1)CCN
InChI InChI=1S/C14H14INO2/c15-13-9-10(7-8-16)1-6-14(13)18-12-4-2-11(17)3-5-12/h1-6,9,17H,7-8,16H2^Y Key: XIINYOJWNGOUPF-UHFFFAOYSA-N^Y InChI=1/C14H14INO2/c15-13-9-10(7-8-16)1-6-14(13)18-12-4-2-11(17)3-5-12/h1-6,9,17H,7-8,16H2 Key: XIINYOJWNGOUPF-UHFFFAOYAJ
Properties
Molecular formula	C₁₄H₁₄INO₂
Molar mass	355.17 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-Iodothyronamine (T₁AM) is an endogenous thyronamine. T₁AM is a high-affinity ligand for the trace amine-associated receptor TAAR1 (TAR1, TA1), a recently discovered G protein-coupled receptor.^[1]^[2] T₁AM is the most potent TAAR1 agonist yet discovered.^[3] Activation of TAAR1 by T₁AM results in the production of large amounts of cAMP. This effect is coupled with decreased body temperature and cardiac output.^[4] Wu et al have pointed out that this relationship is not typical of the endocrine system, indicating that TAAR1 activity may not be coupled to G-proteins in some tissues, or that T₁AM may interact with other receptor subtypes.^[3]

T₁AM may be part of a signaling pathway to modulate cardiac function, as the compound can induce negative inotropic effects and decrease cardiac output.^[5]

External links

MeSH 3-iodothyronamine

References

^ Scanlan T, Suchland K, Hart M, Chiellini G, Huang Y, Kruzich P, Frascarelli S, Crossley D, Bunzow J, Ronca-Testoni S, Lin E, Hatton D, Zucchi R, Grandy D (2004). "3-Iodothyronamine is an endogenous and rapid-acting derivative of thyroid hormone". Nat. Med. 10 (6): 638–42. doi:10.1038/nm1051. PMID 15146179.
^ Hart M, Suchland K, Miyakawa M, Bunzow J, Grandy D, Scanlan T (2006). "Trace amine-associated receptor agonists: synthesis and evaluation of thyronamines and related analogues". J. Med. Chem. 49 (3): 1101–12. doi:10.1021/jm0505718. PMID 16451074.
^ ^a ^b Wu, S. Y.; Green, W. L.; Huang, W. S.; Hays, M. T.; Chopra, I. J. (2005). "Alternate Pathways of Thyroid Hormone Metabolism". Thyroid 15 (8): 943–958. doi:10.1089/thy.2005.15.943. PMID 16131336. edit
^ "New compound may act to keep thyroid activity in check". http://www.eurekalert.org/pub_releases/2004-05/ohs-ncm051404.php. Retrieved 2008-05-30.
^ Chiellini G, Frascarelli S, Ghelardoni S, Carnicelli V, Tobias SC, Debarber A, Brogioni S, Ronca-Testoni S, Cerbai E, Grandy DK, Scanlan TS, Zucchi R. (2007). "Cardiac effects of 3-iodothyronamine: a new aminergic system modulating cardiac function". The FASEB journal : official publication of the Federation of American Societies for Experimental Biology 21 (7): 1597–608. doi:10.1096/fj.06-7474com. PMID 17284482.

Thyroid hormone metabolic intermediates

Tyrosine / iodotyrosine

Monoiodotyrosine · Diiodotyrosine

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

3-Iodothyronamine · 3,3',5-Triiodothyronamine

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)

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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3-Iodothyronamine