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Substituted phenidates: Difference between revisions

>BronzeManul
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>Larnaca
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[[File:sphenidate.png|thumb|right|300px||General formula of a phenidate molecule.]]
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'''Substituted phenidates''', also known as '''phenidates''', are a class of chemicals that include compounds with psychoactive effects.
[[File:Substituted_phenidate.svg|thumb|right|301px||Generic structure of a phenidate molecule.]]
'''Substituted phenidates''' (also known as '''phenidates''') refer to a class of compounds that predominantly produce traditional [[stimulant]] effects when [[administered]]. A substituted phenidate may be defined as an ester of ritalinic acid and its analogs.


==Chemistry==
==Chemistry==
Substituted phenidates are a chemical class based upon the molecule [[Methylphenidate]]. Methylphenidate is made up of a [[Substituted Phenethylamines|phenethylamine]] molecule with a carbon chain substitution at the R<sub>α</sub> position that links to the R<sub>N</sub> position forming a piperidine ring, and a substitution at the R<sub>β</sub> position of methyl acetate.
Substituted phenidates are a chemical class based upon the molecule [[methylphenidate]]. The molecular structure of methylphenidate is comprised of a [[Substituted Phenethylamines|phenethylamine]] core with a carbon chain substitution at the R<sub>α</sub> position that links to the R<sub>N</sub> position, forming a piperidine ring. It also includes a substitution at the R<sub>β</sub> position of methyl acetate.
 
==Pharmacology==
{{pharmacology}}
Substituted phenidates primarily act as [[reuptake inhibitors]] of the [[monoamine]] [[neurotransmitters]] [[dopamine]], [[norepinephrine]], and to a much lesser degree, [[serotonin]]. One study found that all substituted phenidates inhibited the norepinephrine and dopamine reuptake transporters 4 to >1,000-fold more potently than the serotonin transporter.<ref>{{cite journal | vauthors=((Luethi, D.)), ((Kaeser, P. J.)), ((Brandt, S. D.)), ((Krähenbühl, S.)), ((Hoener, M. C.)), ((Liechti, M. E.)) | journal=Neuropharmacology | title=Pharmacological profile of methylphenidate-based designer drugs | volume=134 | pages=133–140 | date= May 2018 | url=https://linkinghub.elsevier.com/retrieve/pii/S0028390817303878 | issn=00283908 | doi=10.1016/j.neuropharm.2017.08.020}}</ref>


== List of substituted phenidates ==
== List of substituted phenidates ==
{| class="wikitable sortable"
{| class="wikitable"
|-
|-
! scope="col" | '''Compound'''
! scope="col" | '''Compound'''
! scope="col" style="width: 50px;" | '''R<sub>2</sub>'''
! scope="col" style="width: 50px;" | '''R<sub>3</sub>'''
! scope="col" style="width: 50px;" | '''R<sub>3</sub>'''
! scope="col" style="width: 50px;" | '''R<sub>4</sub>'''
! scope="col" style="width: 50px;" | '''R<sub>4</sub>'''
! scope="col" style="width: 50px;" | '''R<sub>5</sub>'''
! scope="col" style="width: 50px;" | '''R<sub>6</sub>'''
! scope="col" style="width: 50px;" | '''R<sub>O</sub>'''
! scope="col" style="width: 50px;" | '''R<sub>O</sub>'''
! scope="col" | '''Structure'''
! scope="col" | '''Structure'''
|-
|-
| [[Methylphenidate]] || H || H || H || H || H || Methyl || [[File:Methyllphenidate.png|170px]]
| [[Methylphenidate]] || H || H || CH<sub>3</sub> || [[File:Methylphenidate.svg|170px]]
|-
|-
| [[Ethylphenidate]] || H || H || H || H || H || Ethyl || [[File:Ethyllphenidate.png|170px]]
| [[Ethylphenidate]] || H || H || CH<sub>2</sub>CH<sub>3</sub> || [[File:Ethylphenidate.svg|170px]]
|-
|-
| [[Isopropylphenidate]] || H || H || H || H || H || Isopropyl || [[File:Isopropylphenidate.png|170px]]
| [[Isopropylphenidate]] || H || H || CH(CH<sub>3</sub>)<sub>2</sub> || [[File:Isopropylphenidate.svg|170px]]
|-
|-
| [[Propylphenidate]] || H || H || H || H || H || Propyl || [[File:Propylphenidate.png|170px]]
| Propylphenidate || H || H || CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> || [[File:Propylphenidate.svg|170px]]
|-
|-
| [[3,4-CTMP]] || H || Cl || Cl || H || H || Methyl || [[File:34-ctmp.png|170px]]
| 4-Methylmethylphenidate || H || CH<sub>3</sub> || CH<sub>3</sub> || [[File:4-Methylmethylphenidate.svg|171px]]
|-
|-
| [[4F-MPH]] || H || H || F || H || H || Methyl || [[File:4-Fluoromethylphenidate.png|170px]]
| [[3,4-CTMP]] || Cl || Cl || CH<sub>3</sub> || [[File:3,4-CTMP.svg|171px]]
|-
|-
| [[4F-EPH]] || H || H || F || H || H || Ethyl || [[File:4F-EPH.png|170px]]
| [[4F-MPH]] || H || F || CH<sub>3</sub> || [[File:4F-MPH.svg|171px]]
|-
|-
| [[Methylnaphthidate]] || H || Benzene || Benzene || H || H || Methyl || [[File:Methylnaphthidate.png|170px]]
| [[4F-EPH]] || H || F || CH<sub>2</sub>CH<sub>3</sub> || [[File:4F-EPH.svg|171px]]
|-
|-
| [[Ethylnaphthidate]] || H || Benzene || Benzene || H || H || Ethyl || [[File:Ethylnaphthidate.png|170px]]
| [[Methylnaphthidate]] (''HDMP-28'') || CH=CH- || CH=CH- || CH<sub>3</sub> || [[File:Methylnaphthidate.svg|170px]]
|-
| Ethylnaphthidate (''HDEP-28'') || CH=CH- || CH=CH- || CH<sub>2</sub>CH<sub>3</sub> || [[File:Ethylnaphthidate.svg|170px]]
|-
|-
|}
|}
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==See also==
==See also==
*[[Responsible use]]
*[[Responsible use]]
*[[Psychedelics]]
*[[Phenethylamines]]
*[[Phenethylamines]]
*[[Substituted amphetamine]]
*[[Substituted amphetamine]]
*[[Entactogens]]
*[[Entactogens]]
*[[Stimulants]]
*[[Stimulants]]
==External links==
* [https://en.wikipedia.org/wiki/List_of_methylphenidate_analogues List of methylphenidate analogues (Wikipedia)]
==Literature==
* Luethi, D., Kaeser, P. J., Brandt, S. D., Krähenbühl, S., Hoener, M. C., & Liechti, M. E. (2017). Pharmacological profile of methylphenidate-based designer drugs. Neuropharmacology. https://doi.org/10.1016/j.neuropharm.2017.08.020
==References==
<references />
[[Category:Chemical class]]
[[Category:Phenidate|*]]
Retrieved from "http://psy.st/wiki/Substituted_phenidates"