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.^[1] 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.^[2]^[3] Jimscaline is not a controlled substance in Canada as of 2025.^[4]