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Jimscaline

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Jimscaline
Systematic (IUPAC) name
(R)-(2,3-dihydro-4,5,6-trimethoxy-1H-inden-1-yl)aminomethane
Clinical data
Pregnancy cat.  ?
Legal status Uncontrolled
Routes Oral
Identifiers
CAS number ? YesY
ATC code None
PubChem CID 11673493
Chemical data
Formula C13H19NO3 
Mol. mass 237.294 g/mol
SMILES eMolecules & PubChem
 YesY(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 69nM 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]

[edit] See also

[edit] 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. 2006 Jul 13;49(14):4269-74. PMID 16821786
  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. 2006 Sep 21;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.
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