Monoamine releasing agent

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"Releasing agent" redirects here. For mold release agents, see Release agent.
Amphetamine, the prototypical monoamine releasing agent, which acts on norepinephrine and dopamine.

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 like on a spectrum.

Mechanism of action[]

Main article: Amphetamine § Pharmacodynamics

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).[1] 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).

Effects[]

Monoamine releasing agents can have a wide variety of effects depending upon their selectivity for monoamines. Selective serotonin releasing agents 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.[2][3] Less selective serotonergic agents that stimulate an efflux in dopamine, such as MDMA are described as more pleasant, increasing energy, sociability and elevating mood.[4] Dopamine releasing agents, usually selective for both norepinephrine and dopamine have psychostimulant effect, causing an increase in energy, and elevated mood.[5] Other variables can significantly affect the subjective effects, such as infusion rate(increasing positive effects of cocaine), and expectancy.[6] Selectively noradrenergic drugs are minimally psychoactive, but as demonstrated by ephedrine may be distinguished from placebo, and trends towards liking.[7] They may also be ergogenic,[8] in contrast to reboxetine which is solely a reuptake inhibitor.[9][10]

Selectivity[]

MRAs act to varying extents on serotonin, norepinephrine, and dopamine. Some induce the release of all three neurotransmitters to a similar degree, like 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 dopamine, respectively) and MBDB is a fairly balanced SNRA but a weak releaser of dopamine (~6- and 10-fold lower for dopamine than 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.[11] Several selective SDRAs are known however, though these compounds also act as non-selective serotonin receptor agonists.[12]

Activity profiles[]

See also: Monoamine reuptake inhibitor § Binding profiles
Activity profiles of MRAs (EC50, nM)[13][14]
Compound NE DA 5-HT Type Class Ref
2C-E >100000 >100000 >100000 IA Phenethylamine [15]
2C-I >100000 >100000 >100000 IA Phenethylamine [15]
3-Chloromethcathinone ND 46.8 ND ND Cathinone [16]
3-Fluoroamphetamine 16.1 24.2 1937 NDRA Amphetamine [17]
3-Methylamphetamine 18.3 33.3 218 NDRA Amphetamine [17]
4-Fluoroamphetamine 28.0–37 51.5–200 730–939 NDRA Amphetamine [17][15]
cis-4-Methylaminorex 4.8 1.7 53.2 NDRA Aminorex [18]
4-Methylamphetamine 22.2 44.1 53.4 SNDRA Amphetamine [17]
4-Methylphenethylamine ND 271 ND ND Phenethylamine [16]
ND ND 21 ND Amphetamine [19]
4,4'-Dimethylaminorex ND ND ND SNDRA Aminorex ND
   11.8–26.9 8.6–10.9 17.7–18.5 SNDRA Aminorex [18][20]
   31.6 24.4 59.9 SNDRA Aminorex [20]
5-(2-Aminopropyl)indole 13.3–79 12.9–173 28–104.8 SNDRA Amphetamine [12][21]
   81 1062 177 SNRA Amphetamine [12]
   ND ND ND SNDRA Amphetamine ND
5-Chloro-αMT 3434 54 16 SDRA Tryptamine [12]
5-Fluoro-αMT 126 32 19 SNDRA Tryptamine [12]
5-MeO-αMT 8900 1500 460 SNDRA Tryptamine [15]
5-MeO-DMT >100000 >100000 >100000 IA Tryptamine [15]
6-(2-Aminopropyl)indole 25.6 164.0 19.9 SNDRA Amphetamine [21]
Adderall ND ND ND NDRA Amphetamine ND
α-Methyltryptamine 79 180 68 SNDRA Tryptamine [15]
Amfepramone (diethylpropion) >10000 >10000 >10000 PD Cathinone [22]
Aminorex 15.1–26.4 9.1–49.4 193–414 SNDRA Aminorex [23][18]
Amphetamine ND ND ND NDRA Amphetamine ND
  D-Amphetamine 6.6–7.2 5.8–24.8 698–1765 NDRA Amphetamine [23][24]
  L-Amphetamine ND ND ND NRA Amphetamine ND
ND 208 ND ND Phenethylamine [16]
BDB 540 2,300 180 NDRA Amphetamine [15]
Benzylpiperazine 62–68 175–600 ≥6050 NDRA Arylpiperazine [15][25][14]
ND IA ND ND Amphetamine [16]
Cathinone ND ND ND NDRA Cathinone ND
   ND ND ND NRA Cathinone ND
   12.4 18.5 2366 NDRA Cathinone [26]
Chlorphentermine >10000 2650 30.9 SRA Amphetamine [23]
56 1207 26 SNRA Arylpiperazine [19]
Dopamine 66.2 86.9 >10000 NDRA Phenethylamine [23]
DPT >100000 >100000 >100000 IA Tryptamine [15]
Ephedrine ND ND ND NDRA Cathinol ND
   43.1–72.4 236–1350 >10000 NDRA Cathinol [23]
   218 2104 >10000 NRA Cathinol [23][26]
Epinephrine ND ND ND NDRA Phenethylamine ND
Ethcathinone 99.3 >1000 2118 NRA Cathinone [22]
Ethylamphetamine ND 296 ND ND Amphetamine [16]
Fenfluramine 739 >10000 79.3–108 SRA Amphetamine [23][27][28]
  D-Fenfluramine 302 >10000 51.7 SNRA Amphetamine [23][27]
  L-Fenfluramine >10000 >10000 147 SRA Amphetamine [27][29]
MBDB 3300 >100,000 540 SNRA Amphetamine [15]
mCPP ≥1400 63000 28–38.1 SRA Arylpiperazine [15][29][30]
MDA 108 190 160 SNDRA Amphetamine [28]
   290 900 310 SNDRA Amphetamine [28]
   50 98 100 SNDRA Amphetamine [28]
MDEA 2608 622 47 SNDRA Amphetamine [19]
   651 507 52 SNDRA Amphetamine [19]
   RI RI 465 SRA Amphetamine [19]
MDMA 54.1–110 51.2–278 49.6–72 SNDRA Amphetamine [23][31][21][28]
   560 3700 340 SNDRA Amphetamine [28]
   136 142 74 SNDRA Amphetamine [28]
ND ND ND SNDRA Aminorex ND
   14.8 10.2 43.9 SNDRA Aminorex [20]
   38.9 36.2 73.4 SNDRA Aminorex [20]
Mephedrone 58–62.7 49.1–51 118.3–122 SNDRA Cathinone [31][24]
Methamnetamine 34 10 13 SNDRA Amphetamine [19]
Methamphetamine ND ND ND NDRA Amphetamine ND
  D-Methamphetamine 12.3–13.8 8.5–24.5 736–1291.7 NDRA Amphetamine [23][31]
  L-Methamphetamine 28.5 416 4640 NRA Amphetamine [23]
Methcathinone ND ND ND NDRA Cathinone ND
   ND ND ND NRA Cathinone ND
   13.1 14.8 1772 NDRA Cathinone [26]
Methylone 140–152.3 117–133.0 234–242.1 SNDRA Cathinone [31][24]
Naphthylisopropylamine 11.1 12.6 3.4 SNDRA Amphetamine [32]
Norephedrine ND ND ND NDRA Cathinol ND
   42.1 302 >10000 NDRA Cathinol [26]
   (phenylpropanolamine) 137 1371 >10000 NRA Cathinol [26]
Norepinephrine 164 869 >10000 NDRA Phenethylamine [23]
Norfenfluramine 168–170 1900–1925 104 SNRA Amphetamine [27][28]
Norpropylhexedrine ND ND ND NDRA Cyclohexethylamine ND
   ND ND ND NRA Cyclohexethylamine ND
   ND ND ND NDRA Cyclohexethylamine ND
Norpseudoephedrine ND ND ND NDRA Cathinol ND
  D-Norpseudoephedrine (cathine) 15.0 68.3 >10000 NDRA Cathinol [26]
  L-Norpseudoephedrine 30.1 294 >10000 NDRA Cathinol [26]
oMPP 39.1 296–542 175 SNDRA Arylpiperazine [33][16]
65 58 23 SNDRA Phenylmorpholine [19]
Phenethylamine ND 39.5 ND NDRA Phenethylamine [16]
Phendimetrazine >10000 >10000 >100000 PD Phenylmorpholine [34]
Phenmetrazine 50.4 131 7765 NDRA Phenylmorpholine [34]
Phentermine 39.4 262 3511 NDRA Amphetamine [23]
ND ND ND ND Amphetamine ND
   106 1355 >10000 NRA Amphetamine [33]
   ND ND ND ND Amphetamine ND
Phenylisobutylamine ND 225 ND ND Amphetamine [16]
pMPP 1500 11000 3200 SNRA Arylpiperazine [15]
>10000 >10000 43 SRA Arylpiperazine [19]
Propylamphetamine ND RI (1013) ND ND Amphetamine [16]
Propylhexedrine ND ND ND NDRA Cyclohexethylamine ND
   ND ND ND NRA Cyclohexethylamine ND
  L-Propylhexedrine ND ND ND NDRA Cyclohexethylamine ND
Pseudoephedrine ND ND ND NDRA Cathinol ND
  D-Pseudoephedrine 4092 9125 >10000 NDRA Cathinol [26]
   224 1988 >10000 NRA Cathinol [26]
Pseudophenmetrazine 514 RI >10000 NRA Phenylmorpholine [34]
Psilocin >10000 >10000 561 SRA Tryptamine [19]
Serotonin >10000 >10000 44.4 SRA Tryptamine [23]
TFMPP ND >10000 121 SRA Arylpiperazine [25]
>10000 >10000 33 SRA Arylpiperazine [19]
Trimethoxyamphetamine >100000 >100000 16000 IA Amphetamine [15]
Tyramine 40.6 119 2775 NDRA Phenethylamine [23]
The smaller the value, the more strongly the substance activates or releases the neurotransmitter.

See also[]

References[]

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