Jimscaline

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 N
  • Key:AFTIZGHFDCOQFS-UHFFFAOYSA-N N
 NY (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.[2][3] Jimscaline is not a controlled substance in Canada as of 2025.[4]

See also

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.
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