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Psychedelic phenethylamines
Jimscaline
Другие языки:

Jimscaline

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Jimscaline
Jimscaline.png
Clinical data
Routes of
administration		 Oral
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • (R)-(2,3-dihydro-4,5,6-trimethoxy-1H-inden-1-yl)aminomethane
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
Formula C13H19NO3
Molar mass 237.299 g·mol−1
3D model (JSmol)
  • COC1=C(C(=C2CC[C@H](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/t8-/m0/s1 ☒N
  • Key:AFTIZGHFDCOQFS-QMMMGPOBSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Jimscaline (C-(4,5,6-trimethoxyindan-1-yl)methanamine) is a conformationally-restricted derivative of the cactus-derived hallucinogen mescaline, which was discovered in 2006 by a team at Purdue University led by David E. Nichols. It acts as a potent agonist for the 5-HT2A and 5-HT2C receptors with the more active (R)-enantiomer having a Ki of 69 nM at the human 5-HT2A receptor, and around three times the potency of mescaline in drug-substitution experiments in animals. 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.

See also


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