Substituted phenidate

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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

Literature

References

  1. 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