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Substituted phenidates: Difference between revisions
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'''Substituted phenidates''' (also known as '''phenidates''') | [[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== | ||
| Line 7: | Line 8: | ||
==Pharmacology== | ==Pharmacology== | ||
{{pharmacology}} | {{pharmacology}} | ||
Substituted phenidates primarily act as [[reuptake inhibitors]] of the [[monoamine]] [[neurotransmitters]] [[dopamine]] | 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 == | ||
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! scope="col" | '''Structure''' | ! scope="col" | '''Structure''' | ||
|- | |- | ||
| [[Methylphenidate]] || H || H || CH<sub>3</sub> || [[File: | | [[Methylphenidate]] || H || H || CH<sub>3</sub> || [[File:Methylphenidate.svg|170px]] | ||
|- | |- | ||
| [[Ethylphenidate]] || H || H || CH<sub>2</sub>CH<sub>3</sub> || [[File: | | [[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. | | [[Isopropylphenidate]] || H || H || CH(CH<sub>3</sub>)<sub>2</sub> || [[File:Isopropylphenidate.svg|170px]] | ||
|- | |- | ||
| Propylphenidate || H || H || CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> || [[File:Propylphenidate. | | 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 || H || CH<sub>3</sub> || CH<sub>3</sub> || [[File:4-Methylmethylphenidate.svg|171px]] | ||
|- | |- | ||
| [[3,4-CTMP]] || Cl || Cl || CH<sub>3</sub> || [[File: | | [[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]] || H || F || CH<sub>3</sub> || [[File:4F-MPH.svg|171px]] | ||
|- | |- | ||
| [[4F-EPH]] || H || F || CH<sub>2</sub>CH<sub>3</sub> || [[File:4F-EPH. | | [[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]] (''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. | | 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]] | ||
*[[Phenethylamines]] | *[[Phenethylamines]] | ||
*[[Substituted amphetamine]] | *[[Substituted amphetamine]] | ||
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*[[Stimulants]] | *[[Stimulants]] | ||
[[Category:Phenidate]] | ==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|*]] | |||
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.