| 词条 | Jimscaline |
| 释义 |
| Verifiedfields = changed | verifiedrevid = 424698111 | IUPAC_name = (R)-(2,3-dihydro-4,5,6-trimethoxy-1H-inden-1-yl)aminomethane | image = Jimscaline.png | tradename = | pregnancy_category = | legal_status = Uncontrolled | routes_of_administration = Oral | bioavailability = | metabolism = | elimination_half-life = | excretion = | CAS_number_Ref = {{cascite|changed|??}} | CAS_number = 890309-57-6 | 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 | molecular_weight = 237.294 g/mol | 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 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.[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] See also
References1. ^{{citation |authors=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 |date=13 July 2006 |volume=49 |issue=14 |pages=4269–74 |doi=10.1021/jm060272y |pmid=16821786|citeseerx=10.1.1.690.1860 }} {{hallucinogen-stub}}{{Hallucinogens}}{{Serotonergics}}{{Phenethylamines}}2. ^{{citation |authors=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 |date=21 September 2006 |volume=49 |issue=19 |pages=5794–803 |doi=10.1021/jm060656o |pmid=16970404|citeseerx=10.1.1.688.9849 }} 3. ^Michael Robert Braden PhD. Towards a biophysical understanding of hallucinogen action. Purdue University 2007. 5 : Psychedelic phenethylamines|Indanes|Phenol ethers|Serotonin receptor agonists|Phenethylamines |
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