Chemistry:Medmain

From HandWiki

Medmain, also known as 2-methyl-3-ethyl-5-dimethylaminoindole, is a serotonin receptor modulator, convulsant, and indole derivative related to the neurotransmitter serotonin.[1][2][3][4] It has low-potency serotonin antagonist or partial agonist activity, with low affinity for serotonin 5-HT1 and 5-HT2 receptors (IC50 = >1,000 nM) but greater activity against the serotonin receptors in the rat stomach fundus strip (KB = 50 nM) (thought to represent the serotonin 5-HT2B receptor).[4][5][2] Owing to its convulsant activity, medmain was tested in animals but not in humans.[3] The drug was described and studied by E. Shaw and Dilworth Woolley in the 1950s.[4][2][3] A derivative, 1-methylmedmain, is also known, and has similar potency as a serotonin antagonist but lacks the convulsant activity of medmain.[3][4][6] Other analogues of medmain have been explored as well, but none had improved activity at the rat fundus strip serotonin 5-HT2B receptor compared to medmain and 1-methylmedmain.[4][5]

References

  1. ↑ Psychotropic Drugs and Related Compounds. National Institute of Mental Health. 1972. https://books.google.com/books?id=7Kxz_xcLr9sC&pg=PA130. Retrieved 8 April 2026. 
  2. ↑ 2.0 2.1 2.2 "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. May 1954. doi:10.1016/S0022-3565(25)11181-6. PMID 13163844. 
  3. ↑ 3.0 3.1 3.2 3.3 "Some neurophysiological aspects of serotonin". British Medical Journal 2 (4880): 122–126. July 1954. doi:10.1136/bmj.2.4880.122. PMID 13172487. 
  4. ↑ 4.0 4.1 4.2 4.3 4.4 "2,3-Dialkyl(dimethylamino)indoles: interaction with 5HT1, 5HT2, and rat stomach fundal serotonin receptors". Journal of Medicinal Chemistry 29 (11): 2415–2418. November 1986. doi:10.1021/jm00161a048. PMID 3783602. 
  5. ↑ 5.0 5.1 "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. July 1996. doi:10.1021/jm960062t. PMID 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". 
  6. ↑ "3-ethyl-N,N,1,2-tetramethylindol-5-amine". https://pubchem.ncbi.nlm.nih.gov/compound/244184. 



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