Substituted phenidates

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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

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

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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.[1]

List of substituted phenidates

Compound R3 R4 RO Structure
Methylphenidate H H CH3 Methylphenidate.svg
Ethylphenidate H H CH2CH3 Ethylphenidate.svg
Isopropylphenidate H H CH(CH3)2 Isopropylphenidate.svg
Propylphenidate H H CH2CH2CH3 Propylphenidate.svg
4-Methylmethylphenidate H CH3 CH3 4-Methylmethylphenidate.svg
3,4-CTMP Cl Cl CH3 3,4-CTMP.svg
4F-MPH H F CH3 4F-MPH.svg
4F-EPH H F CH2CH3 4F-EPH.svg
Methylnaphthidate (HDMP-28) CH=CH- CH=CH- CH3 Methylnaphthidate.svg
Ethylnaphthidate (HDEP-28) CH=CH- CH=CH- CH2CH3 Ethylnaphthidate.svg

See also

External links

Literature

References

  1. 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.