Thyronamine: Difference between revisions

Thyronamine
Names
	Preferred IUPAC name 4-[4-(2-Aminoethyl)phenoxy]phenol
Identifiers
CAS Number	500-78-7 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL201896 ;
ChemSpider	2340781 ;
MeSH	thyronamine
PubChem CID	3083601;
CompTox Dashboard (EPA)	DTXSID60198174 ;
	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 Key: OVUVNKDANCKDCK-UHFFFAOYSA-N ; 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;
	SMILES O(c1ccc(cc1)CCN)c2ccc(O)cc2;
Properties
Chemical formula	C14H15NO2
Molar mass	229.279 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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Latest revision as of 18:26, 21 October 2024

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), an intracellular G protein-coupled receptor^[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.

[1] 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.

[1]

@@ Line 1: / Line 1: @@
 {{Chembox
+| Verifiedfields = changed
-| verifiedrevid = 418302300
+| Watchedfields = changed
+| verifiedrevid = 470609845
 | ImageFile = Thyronamine.svg
 | ImageSize = 200px
 | ImageFile2 = Thyronamine3d.png
 | ImageSize2 = 200px
-| IUPACName = 4-[4-(2-Aminoethyl)phenoxy]phenol
+| PIN = 4-[4-(2-Aminoethyl)phenoxy]phenol
 | OtherNames =
-| Section1 = {{Chembox Identifiers
+|Section1={{Chembox Identifiers
-|   ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
+| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
 | ChemSpiderID = 2340781
 | 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
@@ Line 18: / Line 20: @@
 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
 | StdInChIKey = OVUVNKDANCKDCK-UHFFFAOYSA-N
-| CASNo_Ref = {{cascite|correct|??}}
+| CASNo_Ref = {{cascite|changed|??}}
 | CASNo = 500-78-7
-|   PubChem = 3083601
+| PubChem = 3083601
-|   SMILES = O(c1ccc(cc1)CCN)c2ccc(O)cc2
+| SMILES = O(c1ccc(cc1)CCN)c2ccc(O)cc2
-|   MeSHName = thyronamine
+| MeSHName = thyronamine
   }}
-| Section2 = {{Chembox Properties
+|Section2={{Chembox Properties
-|   C=14|H=15|N=1|O=2
+| C=14 | H=15 | N=1 | O=2
-|   Appearance =
+| Appearance =
-|   Density =
+| Density =
-|   MeltingPt =
+| MeltingPt =
-|   BoilingPt =
+| BoilingPt =
   }}
-| Section3 = {{Chembox Hazards
+|Section3={{Chembox Hazards
-|   Solubility =
+| MainHazards =
-|   MainHazards =
+| FlashPt =
-|   FlashPt =
+| AutoignitionPt =
-|   Autoignition =
   }}
 }}
@@ Line 45: / Line 46: @@
 * 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]]<ref>{{cite journal | author = Piehl S, Hoefig CS, Scanlan TS, Köhrle J | year = 2011 | title = Thyronamines - Past, Present, and Future | journal = Endocrine Reviews | volume = 32 | pages = 64–80 | doi = 10.1210/er.2009-0040 | pmid = 20880963 | issue = 1}}</ref>
+* [[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), an intracellular [[G protein-coupled receptor]]<ref>{{cite journal | vauthors = Piehl S, Hoefig CS, Scanlan TS, Köhrle J | year = 2011 | title = Thyronamines - Past, Present, and Future | journal = Endocrine Reviews | volume = 32 | pages = 64–80 | doi = 10.1210/er.2009-0040 | pmid = 20880963 | issue = 1| doi-access = free }}</ref>
 * 3,5-Diiodothyronamine (T2AM)
 * [[3,5,3'-Triiodothyronamine]] (T3AM)
@@ Line 55: / Line 56: @@
 ==References==
 {{Reflist}}
 {{Thyroid hormone intermediates}}
@@ Line 63: / Line 63: @@
 [[Category:Biogenic amines]]
 [[Category:Phenethylamines]]
-[[Category:Phenols]]
+[[Category:4-Hydroxyphenyl compounds]]
+[[Category:Thyroid]]
+[[Category:TAAR1 agonists]]
-[[de:Thyronamine]]
-[[fa:تیرونامین]]
-[[fr:Thyronamine]]
-[[ja:チロナミン]]
-[[sr:Tironamin]]
-[[zh:类甲腺质]]

v t e Thyroid hormone metabolic intermediates
Tyrosine / iodotyrosine	3-Iodotyrosine Diiodotyrosine
Thyronine / iodothyronine	3'-Monoiodothyronine 3,3'-Diiodothyronine 3,5-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
Iodothyroacetate / iodothyroacetic acid	Triiodothyroacetate (TRIAC)

v t e Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine Phenpromethamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-AL 3C-BZ 3C-E 3C-MAL 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 ZDCM-04 Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L-Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DiFMDA Selegiline (also D-Deprenyl)
Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine
Cathinones	Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone
Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP 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	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101 Venlafaxine

Latest revision as of 18:26, 21 October 2024

Types

See also

References