Amthamine

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Amthamine

IUPAC name 5-(2-aminoethyl)-4-methyl-1,3-thiazol-2-amine
Other names 5-(2-aminoethyl)-4-methyl-2-thiazolamine 2-amino-5-(2-aminoethyl)-4-methylthiazole
Identifiers
CAS number	142437-67-0
PubChem	126688
ChemSpider	112538^Y
ChEMBL	CHEMBL293762^Y
Jmol-3D images	Image 1 Image 2
SMILES CC1=C(SC(=N1)N)CCN n1c(c(sc1N)CCN)C
InChI InChI=1S/C6H11N3S/c1-4-5(2-3-7)10-6(8)9-4/h2-3,7H2,1H3,(H2,8,9)^Y Key: LHVRFUVVRXGZPV-UHFFFAOYSA-N^Y InChI=1/C6H11N3S/c1-4-5(2-3-7)10-6(8)9-4/h2-3,7H2,1H3,(H2,8,9) Key: LHVRFUVVRXGZPV-UHFFFAOYAV
Properties
Molecular formula	C₆H₁₁N₃S
Molar mass	157.236 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

Amthamine is a histamine agonist selective for the H₂ subtype.^[1] It has been used in vitro and in vivo to study gastric secretion,^[2] as well as other functions of the H₂ receptor.^[3]^[4]^[5]

References

^ Eriks JC, van der Goot H, Sterk GJ, Timmerman H. Histamine H2-receptor agonists. Synthesis, in vitro pharmacology, and qualitative structure-activity relationships of substituted 4- and 5-(2-aminoethyl)thiazoles. Journal of Medicinal Chemistry. 1992 Aug 21;35(17):3239-46. PMID 1507209
^ Coruzzi G, Timmerman H, Adami M, Bertaccini G (July 1993). "The new potent and selective histamine H2 receptor agonist amthamine as a tool to study gastric secretion". Naunyn Schmiedebergs Arch Pharmacol 348 (1): 77–81. doi:10.1007/BF00168540. PMID 8377843.
^ Ezeamuzie CI, Philips E. Histamine H(2) receptors mediate the inhibitory effect of histamine on human eosinophil degranulation. British Journal of Pharmacology. 2000 Oct;131(3):482-8. PMID 11015298
^ Fernandez N, Monczor F, Baldi A, Davio C, Shayo C. Histamine H2 receptor trafficking: role of arrestin, dynamin, and clathrin in histamine H2 receptor internalization. Molecular Pharmacology. 2008 Oct;74(4):1109-18. PMID 18617631
^ Threlfell S, Exley R, Cragg SJ, Greenfield SA. Constitutive histamine H2 receptor activity regulates serotonin release in the substantia nigra. Journal of Neurochemistry. 2008 Nov;107(3):745-55. PMID 18761715

Histaminergics

Receptor
ligands

H₁	Agonists: 2-Pyridylethylamine • Betahistine • Histamine • HTMT • UR-AK49 Antagonists: 1st generation: 4-Methyldiphenhydramine • Alimemazine • Antazoline • Azatadine • Bamipine • Benzatropine (Benztropine) • Bepotastine • Bromazine • Brompheniramine • Buclizine • Captodiame • Carbinoxamine • Chlorcyclizine • Chloropyramine • Chlorothen • Chlorphenamine • Chlorphenoxamine • Cinnarizine • Clemastine • Clobenzepam • Clocinizine • Cyclizine • Cyproheptadine • Dacemazine • Deptropine • Dexbrompheniramine • Dexchlorpheniramine • Dimenhydrinate • Dimetindene • Diphenhydramine • Diphenylpyraline • Doxylamine • Embramine • Etybenzatropine (Ethylbenztropine) • Etymemazine • Histapyrrodine • Homochlorcyclizine • Hydroxyethylpromethazine • Hydroxyzine • Isopromethazine • Isothipendyl • Meclozine • Mepyramine (Pyrilamine) • Mequitazine • Methafurylene • Methapyrilene • Methdilazine • Moxastine • Niaprazine • Orphenadrine • Oxatomide • Oxomemazine • Phenindamine • Pheniramine • Phenyltoloxamine • Pimethixene • Piperoxan • Promethazine • Propiomazine • Pyrrobutamine • Talastine • Thenalidine • Thenyldiamine • Thiazinamium • Thonzylamine • Tolpropamine • Tripelennamine • Triprolidine; 2nd generation: Acrivastine • Astemizole • Azelastine • Cetirizine • Clemizole • Clobenztropine • Ebastine • Emedastine • Epinastine • Ketotifen • Latrepirdine • Levocabastine • Loratadine • Mebhydrolin • Mizolastine • Olopatadine • Rupatadine • Setastine • Terfenadine; "3rd generation": Desloratadine • Fexofenadine • Levocetirizine; Miscellaneous: Tricyclic antidepressants (Amitriptyline, Doxepin, Trimipramine, etc) • Tetracyclic antidepressants (Mianserin, Mirtazapine, etc) • Serotonin antagonist and reuptake inhibitors (Trazodone, Nefazodone) • Typical antipsychotics (Chlorpromazine, Thioridazine, etc) • Atypical antipsychotics (Clozapine, Olanzapine, Quetiapine, etc)

H₂	Agonists: Amthamine • Betazole • Dimaprit • Histamine • HTMT • Impromidine • UR-AK49 Antagonists: Burimamide • Cimetidine • Ebrotidine • Famotidine • Lafutidine • Lavoltidine/Loxtidine • Lupitidine • Metiamide • Niperotidine • Nizatidine • Oxmetidine • Ranitidine • Roxatidine

H₃	Agonists: α-Methylhistamine • Cipralisant • Histamine • Imetit • Immepip • Immethridine • Methimepip • Proxyfan Antagonists: A-349,821 • A-423,579 • ABT-239 • Betahistine • Burimamide • Ciproxifan • Clobenpropit • Conessine • GSK-189,254 • Impentamine • Iodophenpropit • JNJ-5,207,852 • MK-0249 • NNC-38-1,049 • PF-03654746 • Pitolisant • SCH-79,687 • Thioperamide • VUF-5,681

H₄	Agonists: 4-Methylhistamine • Histamine • VUF-8,430 Antagonists: JNJ-7,777,120 • Thioperamide • VUF-6,002

Reuptake
inhibitors

Vesicular

VMAT inhibitors

Ibogaine • Reserpine • Tetrabenazine

Enzyme
inhibitors

Anabolism

HDC inhibitors

Catechin • Meciadanol • Naringenin • Tritoqualine

Catabolism

HNMT inhibitors	Amodiaquine • Diphenhydramine • Harmaline • Quinacrine • Tacrine

DAO inhibitors	Aminoguanidine

Others

Precursors	L-Histidine

Cofactors	Vitamin B6 (pyridoxine, pyridoxamine, pyridoxal → Pyridoxal phosphate)

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