Article · Wikipedia archive · Last revised Jul 26, 2026

Jimscaline

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-HT2A and 5-HT2C receptors with the more active (R)-enantiomer having an affinity (Ki) of 69 nM at the human serotonin 5-HT2A 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.

Last revised
Jul 26, 2026
Read time
≈ 1 min
Length
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Citations
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Source
Wikipedia ↗
Jimscaline
Clinical data
Other namesC-(4,5,6-Trimethoxyindan-1-yl)methanamine
Drug classSerotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • (4,5,6-trimethoxy-2,3-dihydro-1H-inden-1-yl)methanamine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H19NO3
Molar mass237.299 g·mol−1
3D model (JSmol)
  • COC1=C(C(=C2CCC(C2=C1)CN)OC)OC
  • 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 X markN
  • Key:AFTIZGHFDCOQFS-UHFFFAOYSA-N X markN
 X markNcheckY (what is this?)  (verify)

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-HT2A and 5-HT2C receptors with the more active (R)-enantiomer having an affinity (Ki) of 69 nM at the human serotonin 5-HT2A 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-2.23 Jimscaline is not a controlled substance in Canada as of 2025.4

(R)-Jimscaline. source ↗
See also

See also

References

References

  1. McLean TH, Chambers JJ, Parrish JC, Braden MR, Marona-Lewicka D, Kurrasch-Orbaugh D, Nichols DE (July 2006). "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. CiteSeerX 10.1.1.690.1860. doi:10.1021/jm060272y. PMID 16821786.
  2. McLean TH, Parrish JC, Braden MR, Marona-Lewicka D, Gallardo-Godoy A, Nichols DE (September 2006). "1-Aminomethylbenzocycloalkanes: conformationally restricted hallucinogenic phenethylamine analogues as functionally selective 5-HT2A receptor agonists". Journal of Medicinal Chemistry. 49 (19): 5794–803. CiteSeerX 10.1.1.688.9849. doi:10.1021/jm060656o. PMID 16970404.
  3. Braden MR (2007). Towards a biophysical understanding of hallucinogen action (Ph.D. thesis). Purdue University. ProQuest 304838368.
  4. "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
External links