| 词条 | TCB-2 |
| 释义 |
| verifiedrevid = 448096412 | IUPAC_name = [(7R)-3-Bromo-2,5-dimethoxy-bicyclo[4.2.0]octa-1,3,5-trien-7-yl]methanamine | image = TCB-2.png | tradename = | pregnancy_category = | legal_status = | routes_of_administration = Oral | bioavailability = | metabolism = | elimination_half-life = | excretion = | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 912440-88-1 | CAS_supplemental = 912342-36-0 (hydrobromide) | ATC_prefix = none | ATC_suffix = | PubChem = 16086382 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = | ChemSpiderID = 17245036 | ChEMBL = 379637 | C=11 | H=14 | Br=1 | N=1 | O=2 | smiles = COc1c(Br)cc(OC)c2c1CC2CN | StdInChI = 1S/C11H14BrNO2/c1-14-9-4-8(12)11(15-2)7-3-6(5-13)10(7)9/h4,6H,3,5,13H2,1-2H3/t6-/m0/s1 | StdInChIKey = MPBCKKVERDTCEL-LURJTMIESA-N }}TCB-2 is a hallucinogen discovered in 2006 by Thomas McLean working in the lab of David Nichols at Purdue University where it was named 2C-BCB.[1] It is a conformationally-restricted derivative of the phenethylamine 2C-B, also a hallucinogen, and acts as a potent agonist for the 5-HT2A and 5-HT2C receptors with a Ki of 0.26 nM at the human 5-HT2A receptor. In drug-substitution experiments in rats, TCB-2 was found to be of similar potency to both LSD and Br-DFLY, ranking it among the most potent phenethylamine hallucinogens yet discovered.[1] This high potency and selectivity has made TCB-2 useful for distinguishing 5-HT2A mediated responses from those produced by other similar receptors.[2] TCB-2 has similar but not identical effects in animals to related phenethylamine hallucinogens such as DOI, and has been used for studying how the function of the 5-HT2A receptor differs from that of other serotonin receptors in a number of animal models, such as studies of cocaine addiction and neuropathic pain.[3][4][5][6] See also
References1. ^1 {{cite journal | pmid = 16970404| year = 2006| author1 = McLean| first1 = T. H.| 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| last2 = Parrish| first2 = J. C.| last3 = Braden| first3 = M. R.| last4 = Marona-Lewicka| first4 = D| last5 = Gallardo-Godoy| first5 = A| last6 = Nichols| first6 = D. E.| doi = 10.1021/jm060656o| citeseerx = 10.1.1.688.9849}} {{Hallucinogens}}{{Serotonergics}}{{Phenethylamines}}2. ^{{cite journal | pmid = 18762202| pmc = 2635340| year = 2009| author1 = Chang| first1 = C. W.| title = Towards a quantitative representation of the cell signaling mechanisms of hallucinogens: Measurement and mathematical modeling of 5-HT1A and 5-HT2A receptor-mediated ERK1/2 activation| journal = Neuropharmacology| volume = 56 Suppl 1| pages = 213–25| last2 = Poteet| first2 = E| last3 = Schetz| first3 = J. A.| last4 = Gümüş| first4 = Z. H.| last5 = Weinstein| first5 = H| doi = 10.1016/j.neuropharm.2008.07.049}} 3. ^{{Cite journal | last1 = Fox | first1 = M. A. | last2 = French | first2 = H. T. | last3 = Laporte | first3 = J. L. | last4 = Blackler | first4 = A. R. | last5 = Murphy | first5 = D. L. | title = The serotonin 5-HT2A receptor agonist TCB-2: A behavioral and neurophysiological analysis | doi = 10.1007/s00213-009-1694-1 | journal = Psychopharmacology | volume = 212 | issue = 1 | pages = 13–23 | year = 2009 | pmid = 19823806 | pmc = }} 4. ^{{Cite journal | last1 = Aira | first1 = Z. | last2 = Buesa | first2 = I. | last3 = Salgueiro | first3 = M. | last4 = Bilbao | first4 = J. | last5 = Aguilera | first5 = L. | last6 = Zimmermann | first6 = M. | last7 = Azkue | first7 = J. J. | doi = 10.1016/j.neuroscience.2010.04.032 | title = Subtype-specific changes in 5-HT receptor-mediated modulation of C fibre-evoked spinal field potentials are triggered by peripheral nerve injury | journal = Neuroscience | volume = 168 | issue = 3 | pages = 831–841 | year = 2010 | pmid = 20412834 | pmc = }} 5. ^{{Cite journal | last1 = Katsidoni | first1 = V. | last2 = Apazoglou | first2 = K. | last3 = Panagis | first3 = G. | doi = 10.1007/s00213-010-1887-7 | title = Role of serotonin 5-HT2A and 5-HT2C receptors on brain stimulation reward and the reward-facilitating effect of cocaine | journal = Psychopharmacology | volume = 213 | issue = 2–3 | pages = 337–354 | year = 2010 | pmid = 20577718 | pmc = }} 6. ^{{Cite journal | last1 = Zhang | first1 = G. | last2 = Ásgeirsdóttir | first2 = H. N. | last3 = Cohen | first3 = S. J. | last4 = Munchow | first4 = A. H. | last5 = Barrera | first5 = M. P. | last6 = Stackman | first6 = R. W. | title = Stimulation of serotonin 2A receptors facilitates consolidation and extinction of fear memory in C57BL/6J mice | doi = 10.1016/j.neuropharm.2012.06.007 | journal = Neuropharmacology | year = 2012 | pmid = 22722027 | pmc = 3477617| volume=64 | pages=403–13}} 6 : Psychedelic phenethylamines|Bromoarenes|Phenol ethers|Benzocyclobutenes|5-HT2A agonists|5-HT2C agonists |
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