Monoamine releasing agent explained

A monoamine releasing agent (MRA), or simply monoamine releaser, is a drug that induces the release of a monoamine neurotransmitter from the presynaptic neuron into the synapse, leading to an increase in the extracellular concentrations of the neurotransmitter. Many drugs induce their effects in the body and/or brain via the release of monoamine neurotransmitters, e.g., trace amines, many substituted amphetamines, and related compounds.

Types of MRAs

MRAs can be classified by the monoamines they mainly release, although these drugs lie on a spectrum.

MRAs must be distinguished from monoamine reuptake inhibitors and monoaminergic activity enhancers, which work via distinct mechanisms.

Endogenous MRAs

A number of endogenous compounds are known to act as MRAs. These include the monoamine neurotransmitters dopamine (an NDRA), norepinephrine (an NDRA), and serotonin (an SRA) themselves, as well as the trace amines phenethylamine (an NDRA),[1] [2] tryptamine (an SDRA or imbalanced SNDRA), and tyramine (an NDRA). Synthetic MRAs are substantially based on structural modification of these endogenous compounds, most prominently including the substituted phenethylamines and substituted tryptamines.[3] [4] [5]

Mechanism of action

MRAs cause the release of monoamine neurotransmitters by various complex mechanism of actions. They may enter the presynaptic neuron primarily via plasma membrane transporters, such as the dopamine transporter (DAT), norepinephrine transporter (NET), and serotonin transporter (SERT). Some, such as exogenous phenethylamine, amphetamine, and methamphetamine, can also diffuse directly across the cell membrane to varying degrees. Once inside the presynaptic neuron, they may inhibit the reuptake of monoamine neurotransmitters through vesicular monoamine transporter 2 (VMAT2) and release the neurotransmitters stores of synaptic vesicles into the cytoplasm by inducing reverse transport at VMAT2. MRAs can also bind to the intracellular receptor TAAR1 as agonists, which triggers a phosphorylation cascade via protein kinases that results in the phosphorylation of monoamine transporters located at the plasma membrane (i.e., the dopamine transporter, norepinephrine transporter, and serotonin transporter); upon phosphorylation, these transporters transport monoamines in reverse (i.e., they move monoamines from the neuronal cytoplasm into the synaptic cleft).[6] The combined effects of MRAs at VMAT2 and TAAR1 result in the release of neurotransmitters out of synaptic vesicles and the cell cytoplasm into the synaptic cleft where they bind to their associated presynaptic autoreceptors and postsynaptic receptors. Certain MRAs interact with other presynaptic intracellular receptors which promote monoamine neurotransmission as well (e.g., methamphetamine is also an agonist at σ1 receptor).

Some MRAs, like the amphetamines amphetamine and methamphetamine, as well as trace amines like phenethylamine, tryptamine, and tyramine, are additionally monoaminergic activity enhancers (MAEs).[7] [8] [9] That is, they induce the action potential-mediated release of monoamine neurotransmitters (in contrast to MRAs, which induced uncontrolled monoamine release independent of neuronal firing). They are usually active as MAEs at much lower concentrations than those at which they induce monoamine release. The MAE actions of MAEs may be mediated by TAAR1 agonism, which has likewise been implicated in monoamine-releasing actions.[10] [11] MAEs without concomitant potent monoamine-releasing actions, like selegiline (L-deprenyl), phenylpropylaminopentane (PPAP), and benzofuranylpropylaminopentane (BPAP), have been developed.

Effects and uses

MRAs can have a wide variety of effects depending upon their selectivity for inducing release of different monoamine neurotransmitters.

Selective SRAs such as fenfluramine and related compounds are described as dysphoric and lethargic in lower doses, and in higher doses some hallucinogenic effects have been reported.[12] [13] Less selective SRAs that also stimulate the release of dopamine, such as methylenedioxymethamphetamine (MDMA), are described as more pleasant, increasing energy, sociability, and elevating mood.[14] They have been used as appetite suppressants and as entactogens. They have also been proposed for use as more effective antidepressants and anxiolytics than selective serotonin reuptake inhibitors (SSRIs) owing to the fact that they can produce much larger increases in serotonin levels in comparison.[15]

DRAs, usually non-selective for both norepinephrine and dopamine, have psychostimulant effects, causing an increase in energy, motivation, elevated mood, and euphoria.[16] Other variables can significantly affect the subjective effects, such as infusion rate (increasing positive effects of DRAs) and psychological expectancy effects.[17] They are used in the treatment of attention deficit hyperactivity disorder (ADHD), as appetite suppressants, wakefulness-promoting agents, to improve motivation, and are drugs of recreational use and misuse.

Selective NRAs are minimally psychoactive, but as demonstrated by ephedrine, may be distinguished from placebo, and may trends towards liking.[18] They may also be performance-enhancing,[19] in contrast to reboxetine which is solely a norepinephrine reuptake inhibitor.[20] [21] In addition to their central effects, NRAs produce peripheral sympathomimetic effects like increased heart rate, blood pressure, and force of heart contractions. They are used as nasal decongestants and bronchodilators, but have also seen use as wakefulness-promoting agents, appetite suppressants, and antihypotensive agents. They have additionally seen use as performance-enhancing drugs, for instance in sports.

Selectivity

MRAs act to varying extents on serotonin, norepinephrine, and dopamine. Some induce the release of all three neurotransmitters to a similar degree, like methylenedioxymethamphetamine (MDMA), while others are more selective. As examples, amphetamine and methamphetamine are NDRAs but only very weak releasers of serotonin (~60- and 30-fold less than of dopamine, respectively) and MBDB is a fairly balanced SNRA but a weak releaser of dopamine (~6- and 10-fold lower of dopamine than of norepinephrine or serotonin, respectively). Even more selective include agents like fenfluramine, a selective SRA, and ephedrine, a selective NRA. The differences in selectivity of these agents is the result of different affinities as substrates for the monoamine transporters, and thus differing ability to gain access into monoaminergic neurons and induce monoamine neurotransmitter release via the TAAR1 and VMAT2 proteins.

As of present, no selective DRAs are known. This is because it has proven extremely difficult to separate DAT affinity from NET affinity and retain releasing efficacy at the same time.[22] Several selective SDRAs, including tryptamine, (+)-α-ethyltryptamine (αET), 5-chloro-αMT, and 5-fluoro-αET, are known. However, besides their serotonin release, these compounds additionally act as non-selective serotonin receptor agonists, including of the serotonin 5-HT2A receptor (with accompanying hallucinogenic effects), and some of them are known to act as monoamine oxidase inhibitors.

Activity profiles

Activity profiles of MRAs (EC50, nM)[23] [24]
Compound data-sort-type="number" !data-sort-type="number" !data-sort-type="number" !Type Class Ref
>100000 >100000 >100000
>100000 >100000 >100000 Phenethylamine
46.8 Cathinone
1937 16.1 24.2 NDRA [25]
218 18.3 33.3 NDRA Amphetamine
730–939 28.0–37 51.5–200 NDRA Amphetamine
53.2 4.8 1.7 NDRA [26]
53.4 22.2 44.1 SNDRA Amphetamine
271 Phenethylamine
4-Methylthiomethamphetamine21 Amphetamine [27]
SNDRA Aminorex
cis-4,4'-Dimethylaminorex17.7–18.5 11.8–26.9 8.6–10.9 SNDRA Aminorex [28]
trans-4,4'-Dimethylaminorex59.9 31.6 24.4 SNDRA Aminorex
28–104.8 13.3–79 12.9–173 SNDRA Amphetamine [29] [30]
(R)-5-(2-Aminopropyl)indole177 81 1062 SNRA Amphetamine
(S)-5-(2-Aminopropyl)indoleSNDRA Amphetamine
16 3434 54 SDRA
36.6 5334 150 SDRA Tryptamine
19 126 32 SNDRA Tryptamine
460 8900 1500 SNDRA Tryptamine [31]
>100000 >100000 >100000 Tryptamine
19.9 25.6 164.0 SNDRA Amphetamine
23.2 640 232 SDRA Tryptamine
21.7–68 79–112 78.6–180 SNDRA Tryptamine
>10000 >10000 >10000 [32]
193–414 15.1–26.4 9.1–49.4 SNDRA Aminorex [33]
NDRA Amphetamine
698–1765 6.6–7.2 5.8–24.8 NDRA Amphetamine [34]
NRA Amphetamine
β-Ketophenethylamine208 Phenethylamine
180 540 2,300 NDRA Amphetamine
≥6050 62–68 175–600 NDRA [35]
30.5 >10000 >10000 SRA Tryptamine
ButylamphetamineAmphetamine
NDRA Cathinone
-CathinoneNRA Cathinone
-Cathinone2366 12.4 18.5 NDRA Cathinone
30.9 >10000 2650 SRA Amphetamine
DMPP26 56 1207 SNRA Arylpiperazine
114 4166 >10000 SRA Tryptamine
>10000 66.2 86.9 NDRA Phenethylamine
>100000 >100000 >100000 Tryptamine
NDRA
-Ephedrine>10000 43.1–72.4 236–1350 NDRA Cathinol
-Ephedrine>10000 218 2104 NRA Cathinol
NDRA Phenethylamine
2118 99.3 >1000 NRA Cathinone
296 Amphetamine
79.3–108 739 >10000 SRA Amphetamine [36] [37]
51.7 302 >10000 SNRA Amphetamine
147 >10000 >10000 SRA Amphetamine [38]
540 3300 >100000 SNRA Amphetamine
28–38.1 ≥1400 63000 SRA Arylpiperazine [39]
160 108 190 SNDRA Amphetamine
(R)-MDA310 290 900 SNDRA Amphetamine
(S)-MDA100 50 98 SNDRA Amphetamine
47 2608 622 SNDRA Amphetamine
(R)-MDEA52 651 507 SNDRA Amphetamine
(S)-MDEA465 SRA Amphetamine
49.6–72 54.1–110 51.2–278 SNDRA Amphetamine [40]
(''R'')-MDMA340 560 3700 SNDRA Amphetamine
(''S'')-MDMA74 136 142 SNDRA Amphetamine
MDMARSNDRA Aminorex
cis-MDMAR43.9 14.8 10.2 SNDRA Aminorex
trans-MDMAR73.4 38.9 36.2 SNDRA Aminorex
118.3–122 58–62.7 49.1–51 SNDRA Cathinone
13 34 10 SNDRA Amphetamine
NDRA Amphetamine
736–1291.7 12.3–13.8 8.5–24.5 NDRA Amphetamine
4640 28.5 416 NRA Amphetamine
NDRA Cathinone
-MethcathinoneNRA Cathinone
-Methcathinone1772 13.1 14.8 NDRA Cathinone
234–242.1 140–152.3 117–133.0 SNDRA Cathinone
3.4 11.1 12.6 SNDRA Amphetamine [41]
NDRA Cathinol
-Norephedrine>10000 42.1 302 NDRA Cathinol [42]
-Norephedrine (phenylpropanolamine) >10000 137 1371 NRA Cathinol
>10000 164 869 NDRA Phenethylamine
104 168–170 1900–1925 SNRA Amphetamine
NDRA Cyclohexethylamine
NDRA Cathinol
-Norpseudoephedrine (cathine) >10000 15.0 68.3 NDRA Cathinol
>10000 30.1 294 NDRA Cathinol
175 39.1 296–542 SNDRA Arylpiperazine [43] [44]
PAL-73823 65 58 SNDRA
>100000 >10000 >10000 Phenylmorpholine [45]
39.5 NDRA Phenethylamine
7765 50.4 131 NDRA Phenylmorpholine
3511 39.4 262 NDRA Amphetamine
PhenylalaninolAmphetamine
-Phenylalaninol>10000 106 1355 NRA Amphetamine
-PhenylalaninolAmphetamine
225 Amphetamine
3200 1500 11000 SNRA Arylpiperazine
pNPP43 >10000 >10000 SRA Arylpiperazine
(1013) Amphetamine
NDRA Cyclohexethylamine
NDRA Cathinol
>10000 4092 9125 NDRA Cathinol
-Pseudoephedrine>10000 224 1988 NRA Cathinol
>10000 514 NRA Phenylmorpholine
561 >10000 >10000 SRA Tryptamine
44.4 >10000 >10000 SRA Tryptamine
TFMCPP33 >10000 >10000 SRA Arylpiperazine
121 >10000 SRA Arylpiperazine
16000 >100000 >100000 Amphetamine
32.6 716 164 SDRA Tryptamine [46] [47]
2775 40.6 119 NDRA Phenethylamine
Notes: The smaller the value, the more strongly the substance releases the neurotransmitter.

See also

Further reading

Notes and References

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