Substituted phenidates

Generic structure of a phenidate molecule.

Substituted phenidates (also known as phenidates) are a class of chemicals that include compounds that predominantly produce traditional stimulant effects when administered. They may be defined as esters 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 R_α position that links to the R_N position, forming a piperidine ring. It also includes a substitution at the R_β 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.

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

• Responsible use
• Phenethylamines
• Substituted amphetamine
• Entactogens
• Stimulants

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