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Mendeley readers
Attention Score in Context
| Title |
1-Aminomethylbenzocycloalkanes: Conformationally Restricted Hallucinogenic Phenethylamine Analogues as Functionally Selective 5-HT2A Receptor Agonists
|
|---|---|
| Published in |
Journal of Medicinal Chemistry, August 2006
|
| DOI | 10.1021/jm060656o |
| Pubmed ID | |
| Authors |
Thomas H. McLean, Jason C. Parrish, Michael R. Braden, Danuta Marona-Lewicka, Alejandra Gallardo-Godoy, David E. Nichols |
| Abstract |
A series of conformationally restricted analogues of the hallucinogenic phenethylamine 1 (2,5-dimethoxy-4-bromophenethylamine, 2C-B) was synthesized to test several hypotheses concerning the bioactive conformation of phenethylamine ligands upon binding to the 5-HT(2A) receptor. These benzocycloalkane analogues were assayed for their receptor binding affinity and ability to activate downstream signaling pathways, and one exceptional compound was selected for testing in an in vivo drug discrimination model of hallucinogenesis. All compounds were examined in silico by virtual docking into a homology model of the 5-HT(2A) receptor. On the basis of these docking experiments, it was predicted that the R enantiomer of benzocyclobutene analogue 2 would be the most potent. Subsequent chemical resolution and X-ray crystallography confirmed this prediction, as (R)-2 proved to be equipotent to LSD in rats trained to discriminate LSD from saline. Thus, we propose that the conformation of 2 mimics the active binding conformation of the more flexible phenethylamine type hallucinogens. In addition, (R)-2 is one of the most potent and selective compounds yet discovered in the in vivo drug discrimination assay. Further, 2 was found to be a functionally selective agonist at the 5-HT(2A) receptor, having 65-fold greater potency in stimulating phosphoinositide turnover than in producing arachidonic acid release. If hallucinogenic effects are correlated with arachidonic acid production, such functionally selective 5-HT(2A) receptor agonists may lack the intoxicating properties of hallucinogens such as LSD. |
Mendeley readers
The data shown below were compiled from readership statistics for 114 Mendeley readers of this research output. Click here to see the associated Mendeley record.
Geographical breakdown
| Country | Count | As % |
|---|---|---|
| United States | 4 | 4% |
| Chile | 1 | <1% |
| Malta | 1 | <1% |
| Brazil | 1 | <1% |
| China | 1 | <1% |
| Denmark | 1 | <1% |
| Unknown | 105 | 92% |
Demographic breakdown
| Readers by professional status | Count | As % |
|---|---|---|
| Student > Ph. D. Student | 30 | 26% |
| Researcher | 18 | 16% |
| Student > Bachelor | 15 | 13% |
| Student > Master | 10 | 9% |
| Other | 9 | 8% |
| Other | 13 | 11% |
| Unknown | 19 | 17% |
| Readers by discipline | Count | As % |
|---|---|---|
| Chemistry | 31 | 27% |
| Agricultural and Biological Sciences | 19 | 17% |
| Neuroscience | 12 | 11% |
| Pharmacology, Toxicology and Pharmaceutical Science | 7 | 6% |
| Medicine and Dentistry | 7 | 6% |
| Other | 13 | 11% |
| Unknown | 25 | 22% |
Attention Score in Context
This research output has an Altmetric Attention Score of 3. This is our high-level measure of the quality and quantity of online attention that it has received. This Attention Score, as well as the ranking and number of research outputs shown below, was calculated when the research output was last mentioned on 24 August 2019.
All research outputs
#7,453,479
of 22,786,691 outputs
Outputs from Journal of Medicinal Chemistry
#12,752
of 22,061 outputs
Outputs of similar age
#22,966
of 66,547 outputs
Outputs of similar age from Journal of Medicinal Chemistry
#78
of 122 outputs
Altmetric has tracked 22,786,691 research outputs across all sources so far. This one is in the 44th percentile – i.e., 44% of other outputs scored the same or lower than it.
So far Altmetric has tracked 22,061 research outputs from this source. They typically receive a little more attention than average, with a mean Attention Score of 6.7. This one is in the 11th percentile – i.e., 11% of its peers scored the same or lower than it.
Older research outputs will score higher simply because they've had more time to accumulate mentions. To account for age we can compare this Altmetric Attention Score to the 66,547 tracked outputs that were published within six weeks on either side of this one in any source. This one is in the 15th percentile – i.e., 15% of its contemporaries scored the same or lower than it.
We're also able to compare this research output to 122 others from the same source and published within six weeks on either side of this one. This one is in the 2nd percentile – i.e., 2% of its contemporaries scored the same or lower than it.