jimscaline

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 424698111

| IUPAC_name = (R)-(2,3-dihydro-4,5,6-trimethoxy-1H-inden-1-yl)aminomethane

| image = Jimscaline.svg

| tradename =

| pregnancy_category =

| legal_status = Uncontrolled

| routes_of_administration = Oral

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 890309-57-6

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = EN7Y5Y6S8F

| ATC_prefix = none

| ATC_suffix =

| PubChem = 11673493

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 9848222

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = AFTIZGHFDCOQFS-QMMMGPOBSA-N

| C=13 | H=19 | N=1 | O=3

| smiles = COC1=C(C(=C2CC[C@H](C2=C1)CN)OC)OC

}}

Jimscaline (C-(4,5,6-trimethoxyindan-1-yl)methanamine) is a conformationally-restricted derivative of the cactus-derived hallucinogen 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 5-HT_2A and 5-HT_2C receptors with the more active (R)-enantiomer having a K_i of 69 nM at the human 5-HT_2A receptor, and around three times the potency of mescaline in drug-substitution experiments in animals.{{cite journal | vauthors = McLean TH, Chambers JJ, Parrish JC, Braden MR, Marona-Lewicka D, Kurrasch-Orbaugh D, Nichols DE | title = C-(4,5,6-trimethoxyindan-1-yl)methanamine: a mescaline analogue designed using a homology model of the 5-HT2A receptor | journal = Journal of Medicinal Chemistry | volume = 49 | issue = 14 | pages = 4269–74 | date = July 2006 | pmid = 16821786 | doi = 10.1021/jm060272y | citeseerx = 10.1.1.690.1860 }} 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.{{cite journal | vauthors = McLean TH, Parrish JC, Braden MR, Marona-Lewicka D, Gallardo-Godoy A, Nichols DE | title = 1-Aminomethylbenzocycloalkanes: conformationally restricted hallucinogenic phenethylamine analogues as functionally selective 5-HT2A receptor agonists | journal = Journal of Medicinal Chemistry | volume = 49 | issue = 19 | pages = 5794–803 | date = September 2006 | pmid = 16970404 | doi = 10.1021/jm060656o | citeseerx = 10.1.1.688.9849 }}{{cite thesis | first = Michael Robert | last = Braden | name-list-style = vanc | degree = Ph.D. | title = Towards a biophysical understanding of hallucinogen action. | publisher = Purdue University | date = 2007 | id = {{ProQuest|304838368}} }}