Jimscaline

Jimscaline
Clinical data
Other names	C-(4,5,6-Trimethoxyindan-1-yl)methanamine
Drug class	Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code	None;
Legal status
Legal status	In general: uncontrolled;
Identifiers
	IUPAC name (4,5,6-trimethoxy-2,3-dihydro-1H-inden-1-yl)methanamine;
CAS Number	890309-51-0 ;
PubChem CID	44413589;
ChemSpider	21376014 ;
UNII	EN7Y5Y6S8F;
ChEMBL	ChEMBL211309;
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(=C2CCC(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 ; Key:AFTIZGHFDCOQFS-UHFFFAOYSA-N ;
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Jimscaline, also known as C-(4,5,6-trimethoxyindan-1-yl)methanamine, is a conformationally-restricted derivative of the cactus-derived psychedelic drug 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 serotonin 5-HT_2A and 5-HT_2C receptors with the more active (R)-enantiomer having an affinity (K_i) of 69 nM at the human serotonin 5-HT_2A receptor, and around three times the potency of mescaline in drug discrimination tests in animals. This discovery that the side chain of the psychedelic phenethylamines could be constrained to give chiral ligands with increased activity then led to the later development of the highly-potent benzocyclobutene derivative TCB-2. Jimscaline is not a controlled substance in Canada as of 2025.