This is a list of methylphenidate (MPH or MPD) analogues, or Phenidates. The most well known compound from this family, methylphenidate, is widely prescribed around the world for the treatment of attention deficit hyperactivity disorder (ADHD) and certain other indications. Several other derivatives including rimiterol, phacetoperane and pipradrol also have more limited medical application. A rather larger number of these compounds have been sold in recent years as designer drugs, either as quasi-legal substitutes for illicit stimulants such as methamphetamine or cocaine, or as purported "study drugs" or nootropics.[1][2][3]
More structurally diverse compounds such as desoxypipradrol (and thus pipradrol, including such derivatives as AL-1095, diphemethoxidine, SCH-5472 and D2PM), and even mefloquine, 2-benzylpiperidine, rimiterol, enpiroline and DMBMPP, can also be considered structurally related, with the former ones also functionally so, as loosely analogous compounds. The acyl group has sometimes been replaced with similar length ketones to increase duration. Alternatively, the methoxycarbonyl has in some cases been replaced with an alkyl group.[4][5]
Dozens more phenidates and related compounds are known from the academic and patent literature, and molecular modelling and receptor binding studies have established that the aryl and acyl substituents in the phenidate series are functionally identical to the aryl and acyl groups in the phenyltropane series of drugs, suggesting that the central core of these molecules is primarily acting merely as a scaffold to correctly orientate the binding groups, and for each of the hundreds of phenyltropanes that are known, there may be a phenidate equivalent with a comparable activity profile. Albeit with the respective difference in their entropy of binding: cocaine being −5.6 kcal/mol and methylphenidate being −25.5 kcal/mol (Δs°, measured using [3H]GBR 1278 @ 25 °C).[a]
^Klare H, Neudörfl JM, Brandt SD, Mischler E, Meier-Giebing S, Deluweit K, Westphal F, Laussmann T. Analysis of six 'neuro-enhancing' phenidate analogs. Drug Test Anal. 2017 Mar;9(3):423-435. Klare H, Neudörfl JM, Brandt SD, Mischler E, Meier-Giebing S, Deluweit K, et al. (March 2017). "Analysis of six 'neuro-enhancing' phenidate analogs" (PDF). Drug Testing and Analysis. 9 (3): 423–435. doi:10.1002/dta.2161. PMID 28067464.
^Carlier J, Giorgetti R, Varì MR, Pirani F, Ricci G, Busardò FP. Use of cognitive enhancers: methylphenidate and analogs. Eur Rev Med Pharmacol Sci. 2019 Jan;23(1):3-15. Carlier J, Giorgetti R, Varì MR, Pirani F, Ricci G, Busardò FP (January 2019). "Use of cognitive enhancers: methylphenidate and analogs". European Review for Medical and Pharmacological Sciences. 23 (1): 3–15. doi:10.26355/eurrev_201901_16741. PMID 30657540. S2CID 58643522.
^Froimowitz M, Gu Y, Dakin LA, Nagafuji PM, Kelley CJ, Parrish D, et al. (January 2007). "Slow-onset, long-duration, alkyl analogues of methylphenidate with enhanced selectivity for the dopamine transporter". Journal of Medicinal Chemistry. 50 (2): 219–32. doi:10.1021/jm0608614. PMID 17228864.
^Misra M, Shi Q, Ye X, Gruszecka-Kowalik E, Bu W, Liu Z, Schweri MM, Deutsch HM, Venanzi CA (2010). "Quantitative structure-activity relationship studies of threo-methylphenidate analogs". Bioorg Med Chem. 18 (20): 7221–38. doi:10.1016/j.bmc.2010.08.034. PMID 20846865.
^Singh, Satendra; et al. (2000). "Chemistry, Design, and Structure-Activity Relationship of Cocaine Antagonists" (PDF). Chem. Rev. 100 (3): 925–1024. doi:10.1021/cr9700538. PMID 11749256.
Cite error: There are <ref group=lower-alpha> tags or {{efn}} templates on this page, but the references will not show without a {{reflist|group=lower-alpha}} template or {{notelist}} template (see the help page).
and 26 Related for: List of methylphenidate analogues information
This is a listofmethylphenidate (MPH or MPD) analogues, or Phenidates. The most well known compound from this family, methylphenidate, is widely prescribed...
continued to appear on the designer drug market. Berefrine Listofmethylphenidateanalogues Substituted benzofuran Substituted cathinone Substituted phenylmorpholine...
Methylphenidate, sold under the brand names Ritalin (/ˈrɪtəlɪn/ RIT-ə-lin) and Concerta (/kənˈsɜːrtə/ kən-SUR-tə) among others, is a potent central nervous...
a listof cocaine analogues. A cocaine analogue is an (usually) artificial construct of a novel chemical compound from (often the starting point of natural)...
functionality to the molecule: List of cocaine analoguesListof local anesthetics Listofmethylphenidateanalogues Singh, Satendra (2000). "Chem Inform Abstract:...
(relatively weak) Metaphit (irreversible; depletes dopamine) Methylphenidate (has a mild degree of selectivity for dopamine over norepinephrine reuptake inhibition...
Setola V, Treble R, et al. (2013). "The ketamine analogue methoxetamine and 3- and 4-methoxy analoguesof phencyclidine are high affinity and selective ligands...
about the efficacy ofmethylphenidate for reducing symptoms of ADHD. However, that meta-analysis used an idiosyncratic application of the Cochrane RoB for...
ketamine analogue to sell, the government has placed countless other ketamine analogues into Class B and Schedule 1." On 10 June 2013, a total of 10 benzofuran...
Medical use ofmethylphenidate is predominantly for symptoms of attention deficit/hyperactivity disorder (ADHD). Consumption ofmethylphenidate in the U...
as amphetamines, cocaine or methylphenidate, but still produces psychoactive, euphoric, and subjective effects typical of classical stimulants. Narcolepsy...
controlled by it, the CSA also controls "analogues" of many listed controlled substances. The definition of what 'analogue' means is kept deliberately vague...
β-phenethylamine in its structure. Phenibut is closely related to a variety of other GABA analogues including baclofen (β-(4-chlorophenyl)-GABA), 4-fluorophenibut...
chemical class of organic compounds that are based upon the phenethylamine structure; the class is composed of all the derivative compounds of phenethylamine...
individuals. Methylphenidate – a benzylpiperidine derivative that may improve working memory, episodic memory, and inhibitory control, aspects of attention...
WA (1994). "IV pentazocine/methylphenidate abuse--the clinical toxicity of another Ts and blues combination". Journal of Toxicology. Clinical Toxicology...
exploration of modifications to known active drugs—such as their structural analogues, stereoisomers and derivatives—yields drugs that may differ significantly...
step, although such a definition would indicate that alkyllysergamide analogues would be uncontrolled. Where the derivatives are specified to be "structural...
Global Information