Jimscaline

Jimscaline
Clinical data
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	In general: uncontrolled;
Identifiers
	IUPAC name (R)-(2,3-dihydro-4,5,6-trimethoxy-1H-inden-1-yl)aminomethane;
CAS Number	890309-57-6 ;
PubChem CID	11673493;
ChemSpider	9848222 ;
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(=C2CC[C@H](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/t8-/m0/s1 ; Key:AFTIZGHFDCOQFS-QMMMGPOBSA-N ;
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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.^[1] 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.^[2]^[3]

References

^ 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.
^ 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.
^ Braden MR (2007). Towards a biophysical understanding of hallucinogen action (Ph.D. thesis). Purdue University. ProQuest 304838368.

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Clinical data

Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: uncontrolled
Identifiers
IUPAC name (R)-(2,3-dihydro-4,5,6-trimethoxy-1H-inden-1-yl)aminomethane
CAS Number	890309-57-6^N
PubChem CID	11673493
ChemSpider	9848222^N
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(=C2CC[C@H](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/t8-/m0/s1^N Key:AFTIZGHFDCOQFS-QMMMGPOBSA-N^N
^NY (what is this?) (verify)