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'''Diarylethylamines''' are a chemical class of [[psychoactive substances]] that produce [[dissociative]] effects when [[administered]]. [[Subjective effects]] are similar to those of [[arylcyclohexylamine]] dissociatives like [[PCP]] or [[ketamine]], although they differ in their chemical structure. | '''Diarylethylamines''' are a chemical class of [[psychoactive substances]] that produce [[dissociative]] effects when [[administered]]. [[Subjective effects]] are similar to those of [[arylcyclohexylamine]] dissociatives like [[PCP]] or [[ketamine]], although they differ in their chemical structure. | ||
Diarylethylamines are examples of contemporary designer drugs specifically chosen to mimic and/or replace the functional and structural features of commonly used illicit substances. They have been marketed on the online research chemicals market as a replacement for MXE and other dissociatives. | Diarylethylamines are examples of contemporary designer drugs specifically chosen to mimic and/or replace the functional and structural features of commonly used illicit substances. They have been marketed on the online research chemicals market as a replacement for [[MXE]] and other dissociatives. | ||
Very little is known about the human pharmacology, metabolism, and toxicity of these compounds. Many reports suggest that they may pose different and more pronounced risks than traditional dissociatives. | Very little is known about the human pharmacology, metabolism, and toxicity of these compounds. Many reports suggest that they may pose different and more pronounced risks than traditional dissociatives. | ||
| Line 10: | Line 10: | ||
{| class="wikitable mw-collapsible" width="50%" | {| class="wikitable mw-collapsible" width="50%" | ||
|- | |- | ||
|+ NMDAR binding affinities for five target 1,2-diphenylethylamines and reference compounds<ref> | |+NMDAR binding affinities for five target 1,2-diphenylethylamines and reference compounds<ref name="Pharma2016">{{cite journal | journal=PLOS ONE | title=Pharmacological Investigations of the Dissociative ‘Legal Highs’ Diphenidine, Methoxphenidine and Analogues | volume=11 | issue=6 | pages=e0157021 | date=17 June 2016 | url=https://journals.plos.org/plosone/article?id=10.1371/journal.pone.0157021 | issn=1932-6203 | doi=10.1371/journal.pone.0157021}}</ref> | ||
|- | |- | ||
!Compound | !Compound | ||
| Line 16: | Line 16: | ||
!K<sub>i</sub> ± SEM (nM) | !K<sub>i</sub> ± SEM (nM) | ||
|- | |- | ||
|[[PCP]]<ref> | |[[PCP]]<ref>{{cite journal | vauthors=((Wallach, J.)) | journal=UNIVERSITY OF THE SCIENCES IN PHILADELPHIA | title=Structure activity relationship (SAR) studies of arylcycloalkylamines as N-methyl-D-aspartate receptor antagonists | pages=626 | date= 2014 | url=https://www.semanticscholar.org/paper/Structure-activity-relationship-(SAR)-studies-of-as-Wallach/cc0f16999e363db74bd501f5a041083f6b0f6b5a}}</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]]* | ||
| 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- | |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 | | colspan="3" style="text-align:center;" |<small>NMDAR binding affinites determined using [3H]-(+)-MK-801 in rat forebrain.<ref name="Pharma2016" /></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> | |||
|} | |} | ||
== List of substituted diarylethylamines == | {| class="wikitable mw-collapsible" width="70%" | ||
|- | |||
|+Inhibition potencies of 1,2-diarylethylamines as monoamine transporter reuptake inhibitors.<ref name="Pharma2016" /> | |||
|- | |||
| colspan="4" style="text-align:center;" |IC<sub>50</sub> ± SEM (μM) | |||
|- | |||
!Compound | |||
!DAT | |||
!NET | |||
!SERT | |||
|- | |||
|DPH ([[Diphenidine]]) | |||
|1.99 (0.91) | |||
|9.25 (0.97) | |||
|>10 μM | |||
|- | |||
|2-MXP ([[Methoxphenidine]]) | |||
|30.0 (0.81) | |||
|35.2 (2.04) | |||
|>10 μM | |||
|- | |||
|[[3-MXP]] | |||
|0.587 (0.92) | |||
|2.71 (0.95) | |||
|>10 μM | |||
|- | |||
|[[4-MXP]] | |||
|2.23 (0.96) | |||
|22.5 (1.75) | |||
|19.0 (1.12) | |||
|- | |||
|[[2-Cl-DPH]] | |||
|10.5 (0.65) | |||
|27.1 (1.02) | |||
|>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. | |||
<small>Inhibition potencies of 1,2-diarylethylamines as monoamine transporter reuptake inhibitors.<ref name="Pharma2016" /></small> | |||
|} | |||
==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]] | |||
* [[Dissociative]] | *[[Responsible use]] | ||
* [[Arylcyclohexylamine]] | *[[Dissociative]] | ||
*[[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 | |||
* 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., 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., & 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 | *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 | |||
==References== | ==References== | ||
<references /> | <references /> | ||
[[Category:Chemical class]] | |||
[[Category:Diarylethylamine|*]] | |||
Latest revision as of 00:14, 29 August 2024
 |
This article is a stub. As such, it may contain incomplete or wrong information. You can help by expanding it. |
Diarylethylamines are a chemical class of psychoactive substances that produce dissociative effects when administered. Subjective effects are similar to those of arylcyclohexylamine dissociatives like PCP or ketamine, although they differ in their chemical structure.
Diarylethylamines are examples of contemporary designer drugs specifically chosen to mimic and/or replace the functional and structural features of commonly used illicit substances. They have been marketed on the online research chemicals market as a replacement for MXE and other dissociatives.
Very little is known about the human pharmacology, metabolism, and toxicity of these compounds. Many reports suggest that they may pose different and more pronounced risks than traditional dissociatives.
Pharmacology
| Compound | IC50 ± SEM (nM) | Ki ± SEM (nM) |
|---|---|---|
| PCP[2] | 91 ± 1.3 | 57.9 ± 0.8 |
| Ketamine | 508.5 ± 30.1 | 323.9 ± 19.2 |
| Memantine | 594.2 ± 41.3 | 378.4 ± 26.3 |
| (+)-MK-801 | 4.1 ± 1.6 | 2.5 ± 1.0 |
| Diphenidine* | 28.6 ± 3.5 | 18.2 ± 2.2 |
| 2-MXP (Methoxphenidine) | 56.5 ± 5.8 | 36.0 ± 3.7 |
| 3-MXP | 30.3 ± 2.6 | 19.3 ± 1.7 |
| 4-MXP | 723.8 ± 69.9 | 461.0 ± 44.5 |
| 2-Cl-Diphenidine* | 14.6 ± 2.1 | 9.3 ± 1.3 |
| NMDAR binding affinites determined using [3H]-(+)-MK-801 in rat forebrain.[1]
*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. | ||
| IC50 ± SEM (μM) | |||
| Compound | DAT | NET | SERT |
|---|---|---|---|
| DPH (Diphenidine) | 1.99 (0.91) | 9.25 (0.97) | >10 μM |
| 2-MXP (Methoxphenidine) | 30.0 (0.81) | 35.2 (2.04) | >10 μM |
| 3-MXP | 0.587 (0.92) | 2.71 (0.95) | >10 μM |
| 4-MXP | 2.23 (0.96) | 22.5 (1.75) | 19.0 (1.12) |
| 2-Cl-DPH | 10.5 (0.65) | 27.1 (1.02) | >10 μM |
| IC50 values shown in μM. Hill slopes shown in parenthesis. ND-IC50 values were not determined because compounds showed less than 50% inhibition of uptake at 10 μM during a preliminary screening.
Inhibition potencies of 1,2-diarylethylamines as monoamine transporter reuptake inhibitors.[1] | |||
List of substituted diarylethylamines
| Compound | RN1 | RN2 | R2 | Structure |
|---|---|---|---|---|
| Ephenidine | CH2CH3 | H | H | 
|
| Diphenidine | CH2CH2CH2- | CH2CH2- | H | 
|
| Methoxphenidine | CH2CH2CH2- | CH2CH2- | OCH3 | 
|
See also
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
- 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
References
- ↑ 1.0 1.1 1.2 1.3 "Pharmacological Investigations of the Dissociative 'Legal Highs' Diphenidine, Methoxphenidine and Analogues". PLOS ONE. 11 (6): e0157021. 17 June 2016. doi:10.1371/journal.pone.0157021. ISSN 1932-6203.
- ↑ Wallach, J. (2014). "Structure activity relationship (SAR) studies of arylcycloalkylamines as N-methyl-D-aspartate receptor antagonists". UNIVERSITY OF THE SCIENCES IN PHILADELPHIA: 626.