Jimscaline

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Jimscaline
Jimscaline.png
Systematic (IUPAC) name
(R)-(2,3-dihydro-4,5,6-trimethoxy-1H-inden-1-yl)aminomethane
Clinical data
Legal status Uncontrolled
Routes Oral
Identifiers
CAS number 890309-57-6 N
ATC code None
PubChem CID 11673493
ChemSpider 9848222 N
Chemical data
Formula C13H19NO3 
Mol. mass 237.294 g/mol
 N (what is this?)  (verify)

Jimscaline (C-(4,5,6-trimethoxyindan-1-yl)methanamine) is a conformationally-restricted derivative of the cactus-derived hallucinogen mescaline, which was discovered in 2006 by a team at Purdue University led by David E. Nichols. It acts as a potent agonist for the 5-HT2A and 5-HT2C receptors with the more active (R)-enantiomer having a Ki of 69 nM at the human 5-HT2A receptor, and around three times the potency of mescaline in drug-substitution experiments in animals.[1] This discovery that the side chain of the phenethylamine hallucinogens could be constrained to give chiral ligands with increased activity then led to the later development of the super-potent benzocyclobutene derivative TCB-2.[2][3]

See also[edit]

References[edit]

  1. ^ McLean TH, Chambers JJ, Parrish JC, Braden MR, Marona-Lewicka D, Kurrasch-Orbaugh D, Nichols DE (13 July 2006), "C-(4,5,6-trimethoxyindan-1-yl)methanamine: a mescaline analogue designed using a homology model of the 5-HT2A receptor.", Journal of Medicinal Chemistry 49 (14): 4269–74, doi:10.1021/jm060272y, PMID 16821786 
  2. ^ McLean TH, Parrish JC, Braden MR, Marona-Lewicka D, Gallardo-Godoy A, Nichols DE (21 September 2006), "1-Aminomethylbenzocycloalkanes: conformationally restricted hallucinogenic phenethylamine analogues as functionally selective 5-HT2A receptor agonists.", Journal of Medicinal Chemistry 49 (19): 5794–803, doi:10.1021/jm060656o, PMID 16970404 
  3. ^ Michael Robert Braden PhD. Towards a biophysical understanding of hallucinogen action. Purdue University 2007.