Jimscaline Explained

Jimscaline (C-(4,5,6-trimethoxyindan-1-yl)methanamine) is a conformationally-restricted derivative of the cactus-derived hallucinogen mescaline, which was reported in 2006 by a team at Purdue University led by David E. Nichols. It acts as a potent agonist for the 5-HT_2A and 5-HT_2C receptors with the more active (R)-enantiomer having a K_i of 69 nM at the human 5-HT_2A 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

• AMMI
• 2CB-Ind
• Mescaline

Notes and References

1. McLean TH, Chambers JJ, Parrish JC, Braden MR, Marona-Lewicka D, Kurrasch-Orbaugh D, Nichols DE . 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 . July 2006 . 16821786 . 10.1021/jm060272y . 10.1.1.690.1860 .
2. McLean TH, Parrish JC, Braden MR, Marona-Lewicka D, Gallardo-Godoy A, Nichols DE . 1-Aminomethylbenzocycloalkanes: conformationally restricted hallucinogenic phenethylamine analogues as functionally selective 5-HT2A receptor agonists . Journal of Medicinal Chemistry . 49 . 19 . 5794–803 . September 2006 . 16970404 . 10.1021/jm060656o . 10.1.1.688.9849 .
3. Michael Robert . Braden . vanc . Ph.D. . Towards a biophysical understanding of hallucinogen action. . Purdue University . 2007 . .