From Wikipedia, the free encyclopedia
Amthamine
Names
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
ChEMBL
ChemSpider
UNII
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
CC1=C(SC(=N1)N)CCN
n1c(c(sc1N)CCN)C
Properties
C6 H11 N3 S
Molar mass
157.236 g/mol
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
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, J. C; Van Der Goot, H; Sterk, G. J; Timmerman, H (1992). "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 . 35 (17): 3239–46.
doi :
10.1021/jm00095a021 .
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-Schmiedeberg's Arch Pharmacol . 348 (1): 77–81.
doi :
10.1007/BF00168540 .
PMID
8377843 .
S2CID
20132912 .
^ Ezeamuzie, C. I; Philips, E (2000).
"Histamine H(2) receptors mediate the inhibitory effect of histamine on human eosinophil degranulation" . British Journal of Pharmacology . 131 (3): 482–8.
doi :
10.1038/sj.bjp.0703556 .
PMC
1572337 .
PMID
11015298 .
^ Fernandez, N; Monczor, F; Baldi, A; Davio, C; Shayo, C (2008). "Histamine H2 receptor trafficking: Role of arrestin, dynamin, and clathrin in histamine H2 receptor internalization". Molecular Pharmacology . 74 (4): 1109–18.
doi :
10.1124/mol.108.045336 .
hdl :
11336/25894 .
PMID
18617631 .
S2CID
21485434 .
^ Threlfell, S; Exley, R; Cragg, S. J; Greenfield, S. A (2008).
"Constitutive histamine H2 receptor activity regulates serotonin release in the substantia nigra" . Journal of Neurochemistry . 107 (3): 745–55.
doi :
10.1111/j.1471-4159.2008.05646.x .
PMID
18761715 .
H1
Agonists Antagonists
Others:
Atypical antipsychotics (e.g.,
aripiprazole ,
asenapine ,
brexpiprazole ,
brilaroxazine ,
clozapine ,
iloperidone ,
olanzapine ,
paliperidone ,
quetiapine ,
risperidone ,
ziprasidone ,
zotepine )
Phenylpiperazine
antidepressants (e.g.,
hydroxynefazodone ,
nefazodone ,
trazodone ,
triazoledione )
Tetracyclic antidepressants (e.g.,
amoxapine ,
loxapine ,
maprotiline ,
mianserin ,
mirtazapine ,
oxaprotiline )
Tricyclic antidepressants (e.g.,
amitriptyline ,
butriptyline ,
clomipramine ,
desipramine ,
dosulepin (dothiepin) ,
doxepin ,
imipramine ,
iprindole ,
lofepramine ,
nortriptyline ,
protriptyline ,
trimipramine )
Typical antipsychotics (e.g.,
chlorpromazine ,
flupenthixol ,
fluphenazine ,
loxapine ,
perphenazine ,
prochlorperazine ,
thioridazine ,
thiothixene )
H2
H3
H4