Jimscaline

Jimscaline
Clinical data
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	In general: uncontrolled;
Identifiers
	IUPAC name (R)-(2,3-dihydro-4,5,6-trimethoxy-1H-inden-1-yl)aminomethane;
CAS Number	890309-57-6 ;
PubChem CID	11673493;
ChemSpider	9848222 ;
UNII	EN7Y5Y6S8F;
CompTox Dashboard (EPA)	DTXSID30470414 ;
Chemical and physical data
Formula	C13H19NO3
Molar mass	237.299 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC1=C(C(=C2CC[C@H](C2=C1)CN)OC)OC;
	InChI InChI=1S/C13H19NO3/c1-15-11-6-10-8(7-14)4-5-9(10)12(16-2)13(11)17-3/h6,8H,4-5,7,14H2,1-3H3/t8-/m0/s1 ; Key:AFTIZGHFDCOQFS-QMMMGPOBSA-N ;
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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]

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See also