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Substituted phenidates: Difference between revisions
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>LayerCZ m I added "methylphenidate hydrochloride extended-release" or basically just concerta as it lasts much longer than normal methylphenidate |
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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> | 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" | {| class="wikitable" | ||
|- | |- | ||
! scope="col" |'''Compound''' | ! scope="col" | '''Compound''' | ||
! 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>O</sub>''' | ! scope="col" style="width: 50px;" | '''R<sub>O</sub>''' | ||
! scope="col" |'''Structure''' | ! scope="col" | '''Structure''' | ||
|- | |- | ||
|[[Methylphenidate]]||H||H||CH<sub>3</sub>||[[File:Methylphenidate.svg|170px]] | | [[Methylphenidate]] || H || H || CH<sub>3</sub> || [[File:Methylphenidate.svg|170px]] | ||
|- | |- | ||
|[[Ethylphenidate]]||H||H||CH<sub>2</sub>CH<sub>3</sub>||[[File:Ethylphenidate.svg|170px]] | | [[Ethylphenidate]] || H || H || CH<sub>2</sub>CH<sub>3</sub> || [[File:Ethylphenidate.svg|170px]] | ||
|- | |- | ||
| | | [[Isopropylphenidate]] || H || H || CH(CH<sub>3</sub>)<sub>2</sub> || [[File:Isopropylphenidate.svg|170px]] | ||
|H | |||
|H | |||
|CH<sub>3</sub> | |||
|[[File: | |||
|- | |- | ||
| | | Propylphenidate || H || H || CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> || [[File:Propylphenidate.svg|170px]] | ||
|- | |- | ||
| | | 4-Methylmethylphenidate || H || CH<sub>3</sub> || CH<sub>3</sub> || [[File:4-Methylmethylphenidate.svg|171px]] | ||
|- | |- | ||
|4- | | [[3,4-CTMP]] || Cl || Cl || CH<sub>3</sub> || [[File:3,4-CTMP.svg|171px]] | ||
|- | |- | ||
|[[ | | [[4F-MPH]] || H || F || CH<sub>3</sub> || [[File:4F-MPH.svg|171px]] | ||
|- | |- | ||
|[[4F- | | [[4F-EPH]] || H || F || CH<sub>2</sub>CH<sub>3</sub> || [[File:4F-EPH.svg|171px]] | ||
|- | |- | ||
|[[ | | [[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]] | |||
|Ethylnaphthidate (''HDEP-28'')||CH=CH-||CH=CH-||CH<sub>2</sub>CH<sub>3</sub>||[[File:Ethylnaphthidate.svg|170px]] | |||
|- | |- | ||
|} | |} | ||
==See also== | ==See also== | ||
*[[Responsible use]] | *[[Responsible use]] | ||
*[[Phenethylamines]] | *[[Phenethylamines]] | ||
| Line 56: | Line 49: | ||
==External links== | ==External links== | ||
* [https://en.wikipedia.org/wiki/List_of_methylphenidate_analogues List of methylphenidate analogues (Wikipedia)] | |||
*[https://en.wikipedia.org/wiki/List_of_methylphenidate_analogues List of methylphenidate analogues (Wikipedia)] | |||
==Literature== | ==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 | |||
*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== | ||
Latest revision as of 01:10, 10 April 2025
 |
This article is a stub. As such, it may contain incomplete or wrong information. You can help by expanding it. |
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
Substituted phenidates are a chemical class based upon the molecule methylphenidate. The molecular structure of methylphenidate is comprised of a phenethylamine core with a carbon chain substitution at the Rα position that links to the RN position, forming a piperidine ring. It also includes a substitution at the Rβ position of methyl acetate.
Pharmacology
 |
This pharmacology section is incomplete. You can help by adding to it. |
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.[1]
List of substituted phenidates
| Compound | R3 | R4 | RO | Structure |
|---|---|---|---|---|
| Methylphenidate | H | H | CH3 | 
|
| Ethylphenidate | H | H | CH2CH3 | 
|
| Isopropylphenidate | H | H | CH(CH3)2 | 
|
| Propylphenidate | H | H | CH2CH2CH3 | 
|
| 4-Methylmethylphenidate | H | CH3 | CH3 | 
|
| 3,4-CTMP | Cl | Cl | CH3 | 
|
| 4F-MPH | H | F | CH3 | 
|
| 4F-EPH | H | F | CH2CH3 | 
|
| Methylnaphthidate (HDMP-28) | CH=CH- | CH=CH- | CH3 | 
|
| Ethylnaphthidate (HDEP-28) | CH=CH- | CH=CH- | CH2CH3 | 
|
See also
External links
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
- ↑ Luethi, D., Kaeser, P. J., Brandt, S. D., Krähenbühl, S., Hoener, M. C., Liechti, M. E. (May 2018). "Pharmacological profile of methylphenidate-based designer drugs". Neuropharmacology. 134: 133–140. doi:10.1016/j.neuropharm.2017.08.020. ISSN 0028-3908.