4F-MPH: Difference between revisions

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'''4-Fluoromethylphenidate''' (commonly known as '''4F-MPH''') is a novel synthetic [[psychoactive class::stimulant]] of the [[chemical class::~~substituted phenethylamine~~]] ~~and [[chemical~~ class~~::piperidine]] classes~~ that produces long-lasting [[Euphoria|euphoriant]], and [[stimulant|stimulating]] effects when [[Routes of administration|administered]]. It is a closely related structural analog of the commonly prescribed ADHD drug [[methylphenidate]] (known by the brand-names ''Ritalin'' and ''Concerta'').

'''4-Fluoromethylphenidate''' (commonly known as '''4F-MPH''') is a novel synthetic [[psychoactive class::stimulant]] of the [[chemical class::phenidate]] class that produces long-lasting [[Euphoria|euphoriant]], and [[stimulant|stimulating]] effects when [[Routes of administration|administered]]. It is a closely related structural analog of the commonly prescribed ADHD drug [[methylphenidate]] (known by the brand-names ''Ritalin'' and ''Concerta'').

The two substances are believed to have very similar pharmacological mechanisms as [[monoamine]] [[reuptake inhibitors]] but have been reported to display distinctive [[subjective effects index|subjective effects]], with 4F-MPH being considered significantly more euphoric and recreational. Anecdotal reports suggest that it is considerably more potent with fewer uncomfortable side effects such as [[anxiety]], [[muscle spasms]] and [[compulsive redosing]].<ref>http://www.bluelight.org/vb/threads/770658-4-Fluoromethylphenidate-(4F-MPH)</ref> This perhaps owes to the fact that it has been shown to act as a higher efficiency [[dopamine]] reuptake inhibitor than the parent compound methylphenidate.<ref>Deutsch, H. M., Shi, Q., Gruszecka-Kowalik, E., & Schweri, M. M. (1996). Synthesis and pharmacology of potential cocaine antagonists. 2. Structure-activity relationship studies of aromatic ring-substituted methylphenidate analogs. Journal of medicinal chemistry, 39(6), 1201-1209. https://www.doi.org/10.1021/jm950697c</ref><ref>Biochemical and behavioral characterization of novel methylphenidate analogs (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/11961053</ref><ref>Synthesis of methylphenidate analogues and their binding affinities at dopamine and serotonin transport sites (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/15026075</ref><ref>Quantitative structure-activity relationship studies of threo-methylphenidate analogs (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/20846865</ref><ref>Chemistry, Design, and Structure−Activity Relationship of Cocaine Antagonists | http://pubs.acs.org/doi/abs/10.1021/cr9700538</ref>

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==Chemistry==

4F-MPH is a synthetic molecule of the substituted phenethylamine and ~~piperidine~~ classes, and a fluorinated analog of methylphenidate. It contains a phenethylamine core featuring a phenyl ring bound to an amino -NH2 group through an ethyl chain. It is structurally similar to amphetamine, featuring a substitution at Rα which is incorporated into a piperidine ring ending at the terminal amine of the phenethylamine chain. Additionally, it contains a methyl acetate bound to R2 or its structure. 4F-MPH is structurally identical to methylphenidate with the exception of a single fluorine atom bound to the four position on the phenethylamine core.

4F-MPH is a synthetic molecule of the [[substituted phenethylamine]] and [[substituted phenidate]] classes, and a fluorinated analog of [[methylphenidate]]. It contains a phenethylamine core featuring a phenyl ring bound to an amino -NH2 group through an ethyl chain. It is structurally similar to [[amphetamine]], featuring a substitution at Rα which is incorporated into a [[piperidine]] ring ending at the terminal amine of the phenethylamine chain. Additionally, it contains a methyl acetate bound to R2 or its structure. 4F-MPH is structurally identical to methylphenidate with the exception of a single fluorine atom bound to the four position on the phenethylamine core.

With respect to nomenclature, the methyl- in methylphenidate regards the side chain of one carbon atom, while phen- indicates the phenyl ring. Id- is contracted from a piperidine ring, and -ate indicates the acetate group containing the oxygen atoms. Like its parent molecule, 4F-MPH is a chiral compound, presumably produced as a racemic mixture.

With respect to nomenclature, the methyl- in [[methylphenidate]] regards the side chain of one carbon atom, while phen- indicates the phenyl ring. Id- is contracted from a [[piperidine]] ring, and -ate indicates the acetate group containing the oxygen atoms. Like its parent molecule, 4F-MPH is a chiral compound, presumably produced as a racemic mixture.

Of note is the scientific finding that amphetamine analogs containing fluorine, chlorine, bromine and methyl groups are typically stronger than those without.{{Citation needed}}

Of note is the scientific finding that [[amphetamine]] analogs containing fluorine, chlorine, bromine and methyl groups are typically stronger than those without.{{Citation needed}}

==Pharmacology==

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 {{SubstanceBox/4F-MPH}}
-'''4-Fluoromethylphenidate''' (commonly known as '''4F-MPH''') is a novel synthetic [[psychoactive class::stimulant]] of the [[chemical class::substituted phenethylamine]] and [[chemical class::piperidine]] classes that produces long-lasting [[Euphoria|euphoriant]], and [[stimulant|stimulating]] effects when [[Routes of administration|administered]]. It is a closely related structural analog of the commonly prescribed ADHD drug [[methylphenidate]] (known by the brand-names ''Ritalin'' and ''Concerta'').
+'''4-Fluoromethylphenidate''' (commonly known as '''4F-MPH''') is a novel synthetic [[psychoactive class::stimulant]] of the [[chemical class::phenidate]] class that produces long-lasting [[Euphoria|euphoriant]], and [[stimulant|stimulating]] effects when [[Routes of administration|administered]]. It is a closely related structural analog of the commonly prescribed ADHD drug [[methylphenidate]] (known by the brand-names ''Ritalin'' and ''Concerta'').
 The two substances are believed to have very similar pharmacological mechanisms as [[monoamine]] [[reuptake inhibitors]] but have been reported to display distinctive [[subjective effects index|subjective effects]], with 4F-MPH being considered significantly more euphoric and recreational. Anecdotal reports suggest that it is considerably more potent with fewer uncomfortable side effects such as [[anxiety]], [[muscle spasms]] and [[compulsive redosing]].<ref>http://www.bluelight.org/vb/threads/770658-4-Fluoromethylphenidate-(4F-MPH)</ref> This perhaps owes to the fact that it has been shown to act as a higher efficiency [[dopamine]] reuptake inhibitor than the parent compound methylphenidate.<ref>Deutsch, H. M., Shi, Q., Gruszecka-Kowalik, E., & Schweri, M. M. (1996). Synthesis and pharmacology of potential cocaine antagonists. 2. Structure-activity relationship studies of aromatic ring-substituted methylphenidate analogs. Journal of medicinal chemistry, 39(6), 1201-1209. https://www.doi.org/10.1021/jm950697c</ref><ref>Biochemical and behavioral characterization of novel methylphenidate analogs (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/11961053</ref><ref>Synthesis of methylphenidate analogues and their binding affinities at dopamine and serotonin transport sites (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/15026075</ref><ref>Quantitative structure-activity relationship studies of threo-methylphenidate analogs (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/20846865</ref><ref>Chemistry, Design, and Structure−Activity Relationship of Cocaine Antagonists | http://pubs.acs.org/doi/abs/10.1021/cr9700538</ref>
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 ==Chemistry==
-F-MPH is a synthetic molecule of the substituted phenethylamine and piperidine classes, and a fluorinated analog of methylphenidate. It contains a phenethylamine core featuring a phenyl ring bound to an amino -NH2 group through an ethyl chain. It is structurally similar to amphetamine, featuring a substitution at Rα which is incorporated into a piperidine ring ending at the terminal amine of the phenethylamine chain. Additionally, it contains a methyl acetate bound to R2 or its structure. 4F-MPH is structurally identical to methylphenidate with the exception of a single fluorine atom bound to the four position on the phenethylamine core.
+F-MPH is a synthetic molecule of the [[substituted phenethylamine]] and [[substituted phenidate]] classes, and a fluorinated analog of [[methylphenidate]]. It contains a phenethylamine core featuring a phenyl ring bound to an amino -NH2 group through an ethyl chain. It is structurally similar to [[amphetamine]], featuring a substitution at Rα which is incorporated into a [[piperidine]] ring ending at the terminal amine of the phenethylamine chain. Additionally, it contains a methyl acetate bound to R2 or its structure. 4F-MPH is structurally identical to methylphenidate with the exception of a single fluorine atom bound to the four position on the phenethylamine core.
-With respect to nomenclature, the methyl- in methylphenidate regards the side chain of one carbon atom, while phen- indicates the phenyl ring. Id- is contracted from a piperidine ring, and -ate indicates the acetate group containing the oxygen atoms. Like its parent molecule, 4F-MPH is a chiral compound, presumably produced as a racemic mixture.
+With respect to nomenclature, the methyl- in [[methylphenidate]] regards the side chain of one carbon atom, while phen- indicates the phenyl ring. Id- is contracted from a [[piperidine]] ring, and -ate indicates the acetate group containing the oxygen atoms. Like its parent molecule, 4F-MPH is a chiral compound, presumably produced as a racemic mixture.
-Of note is the scientific finding that amphetamine analogs containing fluorine, chlorine, bromine and methyl groups are typically stronger than those without.{{Citation needed}}
+Of note is the scientific finding that [[amphetamine]] analogs containing fluorine, chlorine, bromine and methyl groups are typically stronger than those without.{{Citation needed}}
 ==Pharmacology==
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