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Diarylethylamines: Difference between revisions
>Peterdenkin59 |
>White m Reverted edits by Peterdenkin59 (talk) to last revision by Zoid |
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|+NMDAR binding affinities for five target 1,2-diphenylethylamines and reference compounds<ref>http://journals.plos.org/plosone/article/figure?id=10.1371/journal.pone.0157021.t001</ref> | |+ NMDAR binding affinities for five target 1,2-diphenylethylamines and reference compounds<ref>http://journals.plos.org/plosone/article/figure?id=10.1371/journal.pone.0157021.t001</ref> | ||
|- | |- | ||
!Compound | !Compound | ||
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|- | |- | ||
|[[PCP]]<ref>http://gradworks.umi.com/36/90/3690548.html</ref> | |[[PCP]]<ref>http://gradworks.umi.com/36/90/3690548.html</ref> | ||
|91 ± 1.3 | | 91 ± 1.3 | ||
|57.9 ± 0.8 | | 57.9 ± 0.8 | ||
|- | |- | ||
|[[Ketamine]] | |[[Ketamine]] | ||
|508.5 ± 30.1 | | 508.5 ± 30.1 | ||
|323.9 ± 19.2 | | 323.9 ± 19.2 | ||
|- | |- | ||
|[[Memantine]] | |[[Memantine]] | ||
|594.2 ± 41.3 | | 594.2 ± 41.3 | ||
|378.4 ± 26.3 | | 378.4 ± 26.3 | ||
|- | |- | ||
|(+)-[[MK-801]] | |(+)-[[MK-801]] | ||
|4.1 ± 1.6 | | 4.1 ± 1.6 | ||
|2.5 ± 1.0 | | 2.5 ± 1.0 | ||
|- | |- | ||
|[[Diphenidine]]* | |[[Diphenidine]]* | ||
|28.6 ± 3.5 | | 28.6 ± 3.5 | ||
|18.2 ± 2.2 | | 18.2 ± 2.2 | ||
|- | |- | ||
|2-MXP ([[Methoxphenidine]]) | |2-MXP ([[Methoxphenidine]]) | ||
|56.5 ± 5.8 | | 56.5 ± 5.8 | ||
|36.0 ± 3.7 | | 36.0 ± 3.7 | ||
|- | |- | ||
|3-MXP | |3-MXP | ||
|30.3 ± 2.6 | | 30.3 ± 2.6 | ||
|19.3 ± 1.7 | | 19.3 ± 1.7 | ||
|- | |- | ||
|4-MXP | |4-MXP | ||
|723.8 ± 69.9 | | 723.8 ± 69.9 | ||
|461.0 ± 44.5 | | 461.0 ± 44.5 | ||
|- | |- | ||
|2-Cl-Diphenidine* | |2-Cl-Diphenidine* | ||
|14.6 ± 2.1 | | 14.6 ± 2.1 | ||
|9.3 ± 1.3 | | 9.3 ± 1.3 | ||
|- | |- | ||
| colspan="3" style="text-align:center;" |<small>NMDAR binding affinites determined using [3H]-(+)-MK-801 in rat forebrain.<ref>http://journals.plos.org/plosone/article?id=10.1371/journal.pone.0157021</ref></small> | |colspan="3" style="text-align:center;" |<small>NMDAR binding affinites determined using [3H]-(+)-MK-801 in rat forebrain.<ref>http://journals.plos.org/plosone/article?id=10.1371/journal.pone.0157021</ref></small> | ||
<small>*Diphenidine is sometimes referred to as DPH in scientific studies despite this name already being in common use and widely accepted as meaning [[diphenhydramine]], an unrelated substance.</small> | <small>*Diphenidine is sometimes referred to as DPH in scientific studies despite this name already being in common use and widely accepted as meaning [[diphenhydramine]], an unrelated substance.</small> | ||
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|+Inhibition potencies of 1,2-diarylethylamines as monoamine transporter reuptake inhibitors.<ref>http://journals.plos.org/plosone/article/figure?id=10.1371/journal.pone.0157021.t001</ref> | |+ Inhibition potencies of 1,2-diarylethylamines as monoamine transporter reuptake inhibitors.<ref>http://journals.plos.org/plosone/article/figure?id=10.1371/journal.pone.0157021.t001</ref> | ||
|- | |- | ||
| colspan="4" style="text-align:center;" |IC<sub>50</sub> ± SEM (μM) | |colspan="4" style="text-align:center;" |IC<sub>50</sub> ± SEM (μM) | ||
|- | |- | ||
!Compound | !Compound | ||
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|DPH ([[Diphenidine]]) | |DPH ([[Diphenidine]]) | ||
|1.99 (0.91) | | 1.99 (0.91) | ||
|9.25 (0.97) | | 9.25 (0.97) | ||
|>10 μM | | >10 μM | ||
|- | |- | ||
|2-MXP ([[Methoxphenidine]]) | | 2-MXP ([[Methoxphenidine]]) | ||
|30.0 (0.81) | | 30.0 (0.81) | ||
|35.2 (2.04) | | 35.2 (2.04) | ||
|>10 μM | | >10 μM | ||
|- | |- | ||
|[[3-MXP]] | |[[3-MXP]] | ||
|0.587 (0.92) | | 0.587 (0.92) | ||
|2.71 (0.95) | | 2.71 (0.95) | ||
|>10 μM | | >10 μM | ||
|- | |- | ||
|[[4-MXP]] | |[[4-MXP]] | ||
|2.23 (0.96) | | 2.23 (0.96) | ||
|22.5 (1.75) | | 22.5 (1.75) | ||
|19.0 (1.12) | | 19.0 (1.12) | ||
|- | |- | ||
|[[2-Cl-DPH]] | |[[2-Cl-DPH]] | ||
|10.5 (0.65) | | 10.5 (0.65) | ||
|27.1 (1.02) | | 27.1 (1.02) | ||
|>10 μM | | >10 μM | ||
|- | |- | ||
| colspan="4" style="text-align:left;" |IC<sub>50</sub> values shown in μM. Hill slopes shown in parenthesis. ND-IC<sub>50</sub> values were not determined because compounds showed less than 50% inhibition of uptake at 10 μM during a preliminary screening. | |colspan="4" style="text-align:left;" |IC<sub>50</sub> values shown in μM. Hill slopes shown in parenthesis. ND-IC<sub>50</sub> values were not determined because compounds showed less than 50% inhibition of uptake at 10 μM during a preliminary screening. | ||
<small>Inhibition potencies of 1,2-diarylethylamines as monoamine transporter reuptake inhibitors.<ref>http://journals.plos.org/plosone/article?id=10.1371/journal.pone.0157021</ref></small> | <small>Inhibition potencies of 1,2-diarylethylamines as monoamine transporter reuptake inhibitors.<ref>http://journals.plos.org/plosone/article?id=10.1371/journal.pone.0157021</ref></small> | ||
|} | |} | ||
==List of substituted diarylethylamines== | == List of substituted diarylethylamines == | ||
{| class="wikitable" | {| class="wikitable" | ||
|- | |- | ||
! scope="col" |'''Compound''' | ! scope="col" | '''Compound''' | ||
! scope="col" style="width: 50px;" |'''R<sub>N1</sub>''' | ! scope="col" style="width: 50px;" | '''R<sub>N1</sub>''' | ||
! scope="col" style="width: 50px;" |'''R<sub>N2</sub>''' | ! scope="col" style="width: 50px;" | '''R<sub>N2</sub>''' | ||
! scope="col" style="width: 50px;" |'''R<sub>2</sub>''' | ! scope="col" style="width: 50px;" | '''R<sub>2</sub>''' | ||
! scope="col" |'''Structure''' | ! scope="col" | '''Structure''' | ||
|- | |- | ||
|[[Ephenidine]]||CH<sub>2</sub>CH<sub>3</sub>||H||H||[[File:Ephenidine.svg|170px]] | | [[Ephenidine]] || CH<sub>2</sub>CH<sub>3</sub> || H || H || [[File:Ephenidine.svg|170px]] | ||
|- | |- | ||
|[[Diphenidine]]||CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>-||CH<sub>2</sub>CH<sub>2</sub>-||H||[[File:Diphenidine.svg|170px]] | | [[Diphenidine]] || CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>- || CH<sub>2</sub>CH<sub>2</sub>- || H || [[File:Diphenidine.svg|170px]] | ||
|- | |- | ||
|[[Methoxphenidine]]||CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>-||CH<sub>2</sub>CH<sub>2</sub>-||OCH<sub>3</sub>||[[File:Methoxphenidine.svg|170px]] | | [[Methoxphenidine]] || CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>- || CH<sub>2</sub>CH<sub>2</sub>- || OCH<sub>3</sub> || [[File:Methoxphenidine.svg|170px]] | ||
|- | |- | ||
|} | |} | ||
==See also== | ==See also== | ||
* [[Responsible use]] | |||
*[[Responsible use]] | * [[Dissociative]] | ||
*[[Dissociative]] | * [[Arylcyclohexylamine]] | ||
*[[Arylcyclohexylamine]] | |||
==Literature== | ==Literature== | ||
* Wallach, J., Kang, H., Colestock, T., Morris, H., Bortolotto, Z. A., Collingridge, G. L., ... & Adejare, A. (2016). Pharmacological investigations of the dissociative ‘legal highs’ diphenidine, methoxphenidine and analogues. PLoS One, 11(6), e0157021. https://doi.org/10.1371/journal.pone.0157021 | |||
*Wallach, J., Kang, H., Colestock, T., Morris, H., Bortolotto, Z. A., Collingridge, G. L., ... & Adejare, A. (2016). Pharmacological investigations of the dissociative ‘legal highs’ diphenidine, methoxphenidine and analogues. PLoS One, 11(6), e0157021. https://doi.org/10.1371/journal.pone.0157021 | * Morris, H., & Wallach, J. (2014). From PCP to MXE: A comprehensive review of the non-medical use of dissociative drugs. Drug Testing and Analysis, 6(7–8), 614–632. https://doi.org/10.1002/dta.1620 | ||
*Morris, H., & Wallach, J. (2014). From PCP to MXE: A comprehensive review of the non-medical use of dissociative drugs. Drug Testing and Analysis, 6(7–8), 614–632. https://doi.org/10.1002/dta.1620 | * Wallach, J., & Brandt, S. D. (2018). 1, 2-Diarylethylamine-and Ketamine-Based New Psychoactive Substances. In New Psychoactive Substances (pp. 305-352). Springer, Cham. http://dx.doi.org/10.1007/164_2018_148 | ||
*Wallach, J., & Brandt, S. D. (2018). 1, 2-Diarylethylamine-and Ketamine-Based New | |||
==References== | ==References== | ||