 | |
| Clinical data | |
|---|---|
| Other names | Chinoin-175; Fludepryl; SR-96516-A; p-Fluoro-L-deprenyl |
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| CompTox Dashboard (EPA) | |
| Chemical and physical data | |
| Formula | C13H16FN |
| Molar mass | 205.276 g·mol−1 |
| 3D model (JSmol) | |
| Density | 1.024 ± 0.06 g/cm3 |
| Boiling point | 276.2 ± 25 °C (529.2 ± 45.0 °F) |
| |
| |
4-Fluoroselegiline, or p-fluoro-L-deprenyl, is a substituted amphetamine designer drug. It is the 4-fluorinated derivate of selegiline.
4-Fluoroselegiline is a selective and irreversible inhibitor of monoamine oxidase B and monoaminergic activity enhancer. [1] [2] [3]
A radiolabelled derivative incorporating 18F is used to study MAO-B inhibition in both in vivo and in vitro experiments. [4]
4-Fluoro-deprenyl is metabolized to 4-Fluoromethamphetamine and 4-Fluoroamphetamine, both of which are active. The levels of substituted amphetamine metabolites in the brain is three times higher following 4-fluoroselegiline administration compared to an equivalent dose of selegiline. [2]
Synonyms of 4-fluoroselegiline or 4-fluorodeprenyl (the racemic form) include Chinoin-175, Fludepryl, and SR-96516-A. [5]
Monoamine oxidase inhibitors (MAOIs) are a class of drugs that inhibit the activity of one or both monoamine oxidase enzymes: monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B). They are best known as effective antidepressants, especially for treatment-resistant depression and atypical depression. They are also used to treat panic disorder, social anxiety disorder, Parkinson's disease, and several other disorders.
Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace amine-associated receptor 1 (TAAR1) and inhibiting vesicular monoamine transporter 2 (VMAT2) in monoamine neurons. To a lesser extent, it also acts as a neurotransmitter in the human central nervous system. In mammals, phenethylamine is produced from the amino acid L-phenylalanine by the enzyme aromatic L-amino acid decarboxylase via enzymatic decarboxylation. In addition to its presence in mammals, phenethylamine is found in many other organisms and foods, such as chocolate, especially after microbial fermentation.
Selegiline, also known as L-deprenyl and sold under the brand names Eldepryl, Zelapar, and Emsam among others, is a medication which is used in the treatment of Parkinson's disease and major depressive disorder. It has also been studied and used off-label for a variety of other indications, but has not been formally approved for any other use. The medication, in the form licensed for depression, has modest effectiveness for this condition that is similar to that of other antidepressants. Selegiline is provided as a swallowed tablet or capsule or an orally disintegrating tablet (ODT) for Parkinson's disease and as a patch applied to skin for depression.
Deprenyl, also known by its developmental code name E-250 and as N-propargylmethamphetamine, is the racemic mixture of D-deprenyl and L-deprenyl (selegiline). It was discovered in 1961 in Hungary at Chinoin Pharmaceutical Company by Zoltan Ecseri and József Knoll, was patented in 1962, and was first described in the literature in 1964 or 1965.
Clorgiline (INN), or clorgyline (BAN), is a monoamine oxidase inhibitor (MAOI) structurally related to pargyline which is described as an antidepressant. Specifically, it is an irreversible and selective inhibitor of monoamine oxidase A (MAO-A). Clorgiline was never marketed, but it has found use in scientific research. It has been found to bind with high affinity to the σ1 receptor (Ki = 3.2 nM) and with very high affinity to the I2 imidazoline receptor (Ki = 40 pM).
Rasagiline, sold under the brand name Azilect among others, is a medication which is used in the treatment of Parkinson's disease. It is used as a monotherapy to treat symptoms in early Parkinson's disease or as an adjunct therapy in more advanced cases. The drug is taken by mouth.
Pargyline, sold under the brand name Eutonyl among others, is a monoamine oxidase inhibitor (MAOI) medication which has been used to treat hypertension but is no longer marketed. It has also been studied as an antidepressant, but was never licensed for use in the treatment of depression. The drug is taken by mouth.
(–)-Benzofuranylpropylaminopentane is an experimental drug related to selegiline which acts as a monoaminergic activity enhancer (MAE). It is orally active in animals.
1-Phenyl-2-propylaminopentane is an experimental drug related to selegiline which acts as a catecholaminergic activity enhancer (CAE).
Monoamine oxidase B (MAO-B) is an enzyme that in humans is encoded by the MAOB gene.
Levoamphetamine is a stimulant medication which is used in the treatment of certain medical conditions. It was previously marketed by itself under the brand name Cydril, but is now available only in combination with dextroamphetamine in varying ratios under brand names like Adderall and Evekeo. The drug is known to increase wakefulness and concentration in association with decreased appetite and fatigue. Pharmaceuticals that contain levoamphetamine are currently indicated and prescribed for the treatment of attention deficit hyperactivity disorder (ADHD), obesity, and narcolepsy in some countries. Levoamphetamine is taken by mouth.
Pheniprazine, formerly sold under the brand names Catron and Cavodil, is an irreversible and non-selective monoamine oxidase inhibitor (MAOI) of the hydrazine group that was used as an antidepressant to treat depression in the 1960s. It was also used in the treatment of angina pectoris and schizophrenia. Pheniprazine has been largely discontinued due to toxicity concerns such as jaundice, amblyopia, and optic neuritis.
d-Deprenyl, also known as or dextro-N-propargyl-N-methylamphetamine, is an MAO-B inhibitor that metabolizes into d-amphetamine and d-methamphetamine and is therefore also a norepinephrine–dopamine releasing agent. It is one of the two enantiomers of deprenyl and is the opposite enantiomer of l-deprenyl (selegiline).
Mofegiline (MDL-72,974) is a selective, irreversible inhibitor of monoamine oxidase B (MAO-B) and semicarbazide-sensitive amine oxidase (SSAO) which was under investigation for the treatment of Parkinson's disease and Alzheimer's disease, but was never marketed.
Monoaminergic activity enhancers (MAE), also known as catecholaminergic/serotonergic activity enhancers (CAE/SAE), are a class of drugs that enhance the action potential-evoked release of monoamine neurotransmitters in the nervous system. MAEs are distinct from monoamine releasing agents (MRAs) like amphetamine and fenfluramine in that they do not induce the release of monoamines from synaptic vesicles but rather potentiate only nerve impulse propagation-mediated monoamine release. That is, MAEs increase the amounts of monoamine neurotransmitters released by neurons per electrical impulse.
Desmethylselegiline (DMS), also known as norselegiline or as N-propargyl-L-amphetamine, is an active metabolite of selegiline, a medication used in the treatment of Parkinson's disease and depression.
The pharmacology of selegiline pertains to the pharmacodynamic and pharmacokinetic properties of the antiparkinsonian and antidepressant selegiline (L-deprenyl). Selegiline is available in a few different forms, including oral tablets and capsules, orally disintegrating tablets (ODTs), and transdermal patches. These forms have differing pharmacological properties.
Indolylpropylaminopentane (IPAP), also known as α,N-dipropyltryptamine (α,N-DPT), is a monoaminergic activity enhancer (MAE) that is closely related to benzofuranylpropylaminopentane (BPAP) and phenylpropylaminopentane (PPAP). It is a tryptamine derivative and the corresponding analogue of PPAP and BPAP with an indole ring instead of a benzene ring or benzofuran ring, respectively. IPAP is also a positional isomer of N,N-dipropyltryptamine (N,N-DPT).
(R)-1-Aminoindan ((R)-1-AI; developmental code name TVP-136 or TV-136), or (R)-1-aminoindane, is the major metabolite of the selective MAO-B inhibitor and antiparkinsonian agent rasagiline ((R)-N-propargyl-1-aminoindan). In contrast to rasagiline, it lacks significant monoamine oxidase inhibition. In addition, unlike selegiline and its amphetamine metabolites, it lacks monoamine reuptake-inhibiting and -releasing activities and associated amphetamine-like psychostimulant effects. However, (R)-1-aminoindan retains neuroprotective effects and certain other activities.
SU-11739 is an experimental monoamine oxidase inhibitor (MAOI) that was never marketed.
