1-Methylmedmain

vanc 6 1-Methylmedmain.svg skin-invert-image 225px Serotonin receptor modulator; Serotonin antagonist or partial agonist None 28027-41-0 244184 213520 298780 1,2-Dimethyl-3-ethyl-5-dimethylaminoindole 3-ethyl-N,N,1,2-tetramethylindol-5-amine 14 20 2 CCC1=C(N(C2=C1C=C(C=C2)N(C)C)C)C 1S/C14H20N2/c1-6-12-10(2)16(5)14-8-7-11(15(3)4)9-13(12)14/h7-9H,6H2,1-5H3 MVBMCSOTTKNKHD-UHFFFAOYSA-N 1-Methylmedmain, also known as 1,2-dimethyl-3-ethyl-5-dimethylaminoindole, is a serotonin receptor modulator and indole derivative related to the neurotransmitter serotonin. Shaw E, Woolley DW May 1954 Pharmacological properties of some antimetabolites of serotonin having unusually high activity on isolated tissues The Journal of Pharmacology and Experimental Therapeutics 111 1 43–53 10.1016/S0022-3565(25)11181-6 13163844 Woolley DW, Shaw E July 1954 Some neurophysiological aspects of serotonin British Medical Journal 2 4880 122–126 10.1136/bmj.2.4880.122 2079253 13172487 Fludzinski P, Wittenauer LA, Schenck KW, Cohen ML November 1986 2,3-Dialkyl(dimethylamino)indoles: interaction with 5HT1, 5HT2, and rat stomach fundal serotonin receptors Journal of Medicinal Chemistry 29 11 2415–2418 10.1021/jm00161a048 3783602 It is the 1-methyl derivative of medmain. The drug has low-potency serotonin antagonist or partial agonist activity, with low affinity for serotonin 5-HT1 and 5-HT2 receptors (IC50 half-maximal inhibitory concentration = >1,000nM) but greater activity against the serotonin receptors in the rat stomach fundus strip (KB = 48nM) (thought to represent the serotonin 5-HT2B receptor). Audia JE, Evrard DA, Murdoch GR, Droste JJ, Nissen JS, Schenck KW, Fludzinski P, Lucaites VL, Nelson DL, Cohen ML July 1996 Potent, selective tetrahydro-beta-carboline antagonists of the serotonin 2B (5HT2B) contractile receptor in the rat stomach fundus Journal of Medicinal Chemistry 39 14 2773–2780 10.1021/jm960062t 8709108 However, SAR data has been published for the 2-methyl-3-ethyl-5- (dimethylamino)indole (“medmain”) series of 5HT2B (“fundal”) receptor antagonists, from which the indolylureas were derived.20 It has similar potency as medmain, but lacks medmain's convulsant activity. 1-Methylmedmain was described and studied by E. Shaw and Dilworth Woolley in the 1950s. Other analogues of medmain have also been explored, but none had improved activity at the rat fundus strip serotonin 5-HT2B receptor compared to medmain and 1-methylmedmain. References Category:5-HT2B antagonists Category:Dimethylamino compounds Category:Ethyl compounds Category:Indoles Category:Methyl compounds Category:Serotonin receptor modulators