Monoamine releasing agent

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Amphetamine, the prototypical monoamine releasing agent, which acts on norepinephrine and dopamine. Racemic amphetamine 2.svg
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.

Contents

Types of MRAs

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

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). [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

Activity profiles of MRAs (EC50, nM) [13] [14]
Compound 5-HT Tooltip Serotonin NE Tooltip Norepinephrine DA Tooltip DopamineTypeClassRef
2C-E >100000>100000>100000IA Phenethylamine [15]
2C-I >100000>100000>100000IAPhenethylamine [15]
3-Chloromethcathinone NDND46.8NDCathinone [16]
3-Fluoroamphetamine 193716.124.2NDRA Amphetamine [17]
3-Methylamphetamine 21818.333.3NDRAAmphetamine [17]
4-Fluoroamphetamine 730–93928.0–3751.5–200NDRAAmphetamine [17] [15]
cis-4-Methylaminorex 53.24.81.7NDRA Aminorex [18]
4-Methylamphetamine 53.422.244.1SNDRAAmphetamine [17]
4-Methylphenethylamine NDND271NDPhenethylamine [16]
4-Methylthiomethamphetamine 21NDNDNDAmphetamine [19]
4,4'-Dimethylaminorex NDNDNDSNDRAAminorexND
   ''cis''-4,4'-Dimethylaminorex 17.7–18.511.8–26.98.6–10.9SNDRAAminorex [18] [20]
   ''trans''-4,4'-Dimethylaminorex 59.931.624.4SNDRAAminorex [20]
5-(2-Aminopropyl)indole 28–104.813.3–7912.9–173SNDRAAmphetamine [12] [21]
   (''R'')-5-(2-Aminopropyl)indole 177811062SNRAAmphetamine [12]
   (''S'')-5-(2-Aminopropyl)indole NDNDNDSNDRAAmphetamineND
5-Chloro-αMT 16343454SDRA Tryptamine [12]
5-Fluoro-αMT 1912632SNDRATryptamine [12]
5-MeO-αMT 46089001500SNDRATryptamine [15]
5-MeO-DMT >100000>100000>100000IATryptamine [15]
6-(2-Aminopropyl)indole 19.925.6164.0SNDRAAmphetamine [21]
Adderall NDNDNDNDRAAmphetamineND
α-Methyltryptamine 6879180SNDRATryptamine [15]
Amfepramone (diethylpropion) >10000>10000>10000PD Cathinone [22]
Aminorex 193–41415.1–26.49.1–49.4SNDRAAminorex [23] [18]
Amphetamine NDNDNDNDRAAmphetamineND
   D-Amphetamine 698–17656.6–7.25.8–24.8NDRAAmphetamine [23] [24]
   L-Amphetamine NDNDNDNRAAmphetamineND
β-Ketophenethylamine NDND208NDPhenethylamine [16]
BDB 1805402,300NDRAAmphetamine [15]
Benzylpiperazine ≥605062–68175–600NDRA Arylpiperazine [15] [25] [14]
Butylamphetamine NDNDIANDAmphetamine [16]
Cathinone NDNDNDNDRACathinoneND
   D-Cathinone NDNDNDNRACathinoneND
   L-Cathinone 236612.418.5NDRACathinone [26]
Chlorphentermine 30.9>100002650SRAAmphetamine [23]
DMPP 26561207SNRAArylpiperazine [19]
Dopamine >1000066.286.9NDRAPhenethylamine [23]
DPT >100000>100000>100000IATryptamine [15]
Ephedrine NDNDNDNDRA Cathinol ND
   D-Ephedrine >1000043.1–72.4236–1350NDRACathinol [23]
   L-Ephedrine >100002182104NRACathinol [23] [26]
Epinephrine NDNDNDNDRAPhenethylamineND
Ethcathinone 211899.3>1000NRACathinone [22]
Ethylamphetamine NDND296NDAmphetamine [16]
Fenfluramine 79.3–108739>10000SRAAmphetamine [23] [27] [28]
   D-Fenfluramine 51.7302>10000SNRAAmphetamine [23] [27]
   L-Fenfluramine 147>10000>10000SRAAmphetamine [27] [29]
MBDB 5403300>100,000SNRAAmphetamine [15]
mCPP 28–38.1≥140063000SRAArylpiperazine [15] [29] [30]
MDA 160108190SNDRAAmphetamine [28]
   (''R'')-MDA 310290900SNDRAAmphetamine [28]
   (''S'')-MDA 1005098SNDRAAmphetamine [28]
MDEA 472608622SNDRAAmphetamine [19]
   (''R'')-MDEA 52651507SNDRAAmphetamine [19]
   (''S'')-MDEA 465RIRISRAAmphetamine [19]
MDMA 49.6–7254.1–11051.2–278SNDRAAmphetamine [23] [31] [21] [28]
  (''R'')-MDMA 3405603700SNDRAAmphetamine [28]
   (''S'')-MDMA 74136142SNDRAAmphetamine [28]
MDMAR NDNDNDSNDRAAminorexND
   ''cis''-MDMAR 43.914.810.2SNDRAAminorex [20]
   ''trans''-MDMAR 73.438.936.2SNDRAAminorex [20]
Mephedrone 118.3–12258–62.749.1–51SNDRACathinone [31] [24]
Methamnetamine 133410SNDRAAmphetamine [19]
Methamphetamine NDNDNDNDRAAmphetamineND
   D-Methamphetamine 736–1291.712.3–13.88.5–24.5NDRAAmphetamine [23] [31]
   L-Methamphetamine 464028.5416NRAAmphetamine [23]
Methcathinone NDNDNDNDRACathinoneND
   D-Methcathinone NDNDNDNRACathinoneND
   L-Methcathinone 177213.114.8NDRACathinone [26]
Methylone 234–242.1140–152.3117–133.0SNDRACathinone [31] [24]
Naphthylisopropylamine 3.411.112.6SNDRAAmphetamine [32]
Norephedrine NDNDNDNDRACathinolND
   D-Norephedrine >1000042.1302NDRACathinol [26]
   L-Norephedrine (phenylpropanolamine)>100001371371NRACathinol [26]
Norepinephrine >10000164869NDRAPhenethylamine [23]
Norfenfluramine 104168–1701900–1925SNRAAmphetamine [27] [28]
Norpropylhexedrine NDNDNDNDRACyclohexethylamineND
   D-Norpropylhexedrine NDNDNDNRACyclohexethylamineND
   L-Norpropylhexedrine NDNDNDNDRACyclohexethylamineND
Norpseudoephedrine NDNDNDNDRACathinolND
   D-Norpseudoephedrine (cathine)>1000015.068.3NDRACathinol [26]
   L-Norpseudoephedrine >1000030.1294NDRACathinol [26]
oMPP 17539.1296–542SNDRAArylpiperazine [33] [16]
PAL-738 236558SNDRA Phenylmorpholine [19]
Phenethylamine NDND39.5NDRAPhenethylamine [16]
Phendimetrazine >100000>10000>10000PDPhenylmorpholine [34]
Phenmetrazine 776550.4131NDRAPhenylmorpholine [34]
Phentermine 351139.4262NDRAAmphetamine [23]
Phenylalaninol NDNDNDNDAmphetamineND
   D-Phenylalaninol >100001061355NRAAmphetamine [33]
   L-Phenylalaninol NDNDNDNDAmphetamineND
Phenylisobutylamine NDND225NDAmphetamine [16]
pMPP 3200150011000SNRAArylpiperazine [15]
pNPP 43>10000>10000SRAArylpiperazine [19]
Propylamphetamine NDNDRI (1013)NDAmphetamine [16]
Propylhexedrine NDNDNDNDRACyclohexethylamineND
   D-Propylhexedrine NDNDNDNRACyclohexethylamineND
   L-Propylhexedrine NDNDNDNDRACyclohexethylamineND
Pseudoephedrine NDNDNDNDRACathinolND
   D-Pseudoephedrine >1000040929125NDRACathinol [26]
   L-Pseudoephedrine >100002241988NRACathinol [26]
Pseudophenmetrazine >10000514RINRAPhenylmorpholine [34]
Psilocin 561>10000>10000SRATryptamine [19]
Serotonin 44.4>10000>10000SRATryptamine [23]
TFMPP 121ND>10000SRAArylpiperazine [25]
TFMCPP 33>10000>10000SRAArylpiperazine [19]
Trimethoxyamphetamine 16000>100000>100000IAAmphetamine [15]
Tyramine 277540.6119NDRAPhenethylamine [23]
The smaller the value, the more strongly the substance activates or releases the neurotransmitter.

See also

Related Research Articles

<span class="mw-page-title-main">Norepinephrine reuptake inhibitor</span> Class of drug

A norepinephrine reuptake inhibitor or noradrenaline reuptake inhibitor or adrenergic reuptake inhibitor (ARI), is a type of drug that acts as a reuptake inhibitor for the neurotransmitters norepinephrine (noradrenaline) and epinephrine (adrenaline) by blocking the action of the norepinephrine transporter (NET). This in turn leads to increased extracellular concentrations of norepinephrine and epinephrine and therefore can increase adrenergic neurotransmission.

α-Ethyltryptamine Chemical compound

α-Ethyltryptamine, also known as etryptamine, is a psychedelic, stimulant, and entactogenic drug of the tryptamine class. It was originally developed and marketed as an antidepressant under the brand name Monase by Upjohn in the 1960s.

<span class="mw-page-title-main">Fenfluramine</span> Medication used to treat seizures

Fenfluramine, sold under the brand name Fintepla, is a serotonergic medication used for the treatment of seizures associated with Dravet syndrome and Lennox–Gastaut syndrome. It was formerly used as an appetite suppressant in the treatment of obesity, but was discontinued for this use due to cardiovascular toxicity before being repurposed for new indications. Fenfluramine was used for weight loss both alone under the brand name Pondimin and in combination with phentermine commonly known as fen-phen.

<span class="mw-page-title-main">Etilamfetamine</span> Chemical compound

Etilamfetamine is a stimulant drug of the phenethylamine and amphetamine chemical classes. It was invented in the early 20th century and was subsequently used as an anorectic or appetite suppressant in the 1950s, but was not as commonly used as other amphetamines such as amphetamine, methamphetamine, and benzphetamine, and was largely discontinued once newer drugs such as phenmetrazine were introduced. It most likely acts primarily as a dopamine releasing agent. Its activity as a norepinephrine or serotonin releasing agent is not known.

<span class="mw-page-title-main">Naphthylaminopropane</span> Chemical compound

Naphthylaminopropane (PAL-287) is an experimental drug under investigation as of 2007 for the treatment of alcohol and stimulant addiction.

<span class="mw-page-title-main">5-Fluoro-AMT</span> Chemical compound

5-Fluoro-α-methyltryptamine, also known as PAL-544, is a putative stimulant, entactogen, and psychedelic tryptamine derivative related to α-methyltryptamine (αMT). It has been found to act as a well-balanced serotonin-norepinephrine-dopamine releasing agent, a 5-HT2A receptor agonist, and a potent and specific MAO-A inhibitor. which suggests that 5-fluoro-αMT could be an active psychedelic in humans, although it is not known to have been tested in humans and could be dangerous due to its strong inhibition of MAO-A.

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<span class="mw-page-title-main">Reuptake inhibitor</span> Type of drug

Reuptake inhibitors (RIs) are a type of reuptake modulators. It is a drug that inhibits the plasmalemmal transporter-mediated reuptake of a neurotransmitter from the synapse into the pre-synaptic neuron. This leads to an increase in extracellular concentrations of the neurotransmitter and an increase in neurotransmission. Various drugs exert their psychological and physiological effects through reuptake inhibition, including many antidepressants and psychostimulants.

A serotonin releasing agent (SRA) is a type of drug that induces the release of serotonin into the neuronal synaptic cleft. A selective serotonin releasing agent (SSRA) is an SRA with less significant or no efficacy in producing neurotransmitter efflux at other types of monoamine neurons.

A serotonin–dopamine releasing agent (SDRA) is a type of drug which induces the release of serotonin and dopamine in the body and/or brain.

<span class="mw-page-title-main">4-Methylamphetamine</span> Stimulant and anorectic drug of the amphetamine class

4-Methylamphetamine is a stimulant and anorectic drug of the phenethylamine and amphetamine chemical classes.

<span class="mw-page-title-main">5-IT</span> Chemical compound

5-(2-Aminopropyl)indole is an indole and phenethylamine derivative with empathogenic effects. Its preparation was first reported by Albert Hofmann in 1962. It is a designer drug that has been openly sold as a recreational drug by online vendors since 2011.

<span class="mw-page-title-main">3-Methylamphetamine</span> Stimulant drug of the amphetamine class

3-Methylamphetamine is a stimulant drug from the amphetamine family. It is self-administered by mice to a similar extent to 4-fluoroamphetamine and has comparable properties as a monoamine releaser, although with a more balanced release of all three monoamines, as opposed to the more dopamine/noradrenaline selective fluoro analogues.

<span class="mw-page-title-main">3-Fluoroamphetamine</span> Stimulant drug

3-Fluoroamphetamine is a stimulant drug from the amphetamine family which acts as a monoamine releaser with similar potency to methamphetamine but more selectivity for dopamine and norepinephrine release over serotonin. It is self-administered by mice to a similar extent to related drugs such as 4-fluoroamphetamine and 3-methylamphetamine.

<span class="mw-page-title-main">Serotonin–dopamine reuptake inhibitor</span> Class of drug

A serotonin–dopamine reuptake inhibitor (SDRI) is a type of drug which acts as a reuptake inhibitor of the monoamine neurotransmitters serotonin and dopamine by blocking the actions of the serotonin transporter (SERT) and dopamine transporter (DAT), respectively. This in turn leads to increased extracellular concentrations of serotonin and dopamine, and, therefore, an increase in serotonergic and dopaminergic neurotransmission.

A monoamine reuptake inhibitor (MRI) is a drug that acts as a reuptake inhibitor of one or more of the three major monoamine neurotransmitters serotonin, norepinephrine, and dopamine by blocking the action of one or more of the respective monoamine transporters (MATs), which include the serotonin transporter (SERT), norepinephrine transporter (NET), and dopamine transporter (DAT). This in turn results in an increase in the synaptic concentrations of one or more of these neurotransmitters and therefore an increase in monoaminergic neurotransmission.

<span class="mw-page-title-main">Methamnetamine</span> Chemical compound

Methamnetamine is a triple monoamine releasing agent and N-methyl analog of the non-neurotoxic experimental drug naphthylaminopropane and the naphthalene analog of methamphetamine. It has been sold online as a designer drug.

<span class="mw-page-title-main">Substituted phenylmorpholine</span> Class of chemical compounds

Substituted phenylmorpholines, or substituted phenmetrazines alternatively, are chemical derivatives of phenylmorpholine or of the psychostimulant drug phenmetrazine. Most such compounds act as releasers of monoamine neurotransmitters, and have stimulant effects. Some also act as agonists at serotonin receptors, and compounds with an N-propyl substitution act as dopamine receptor agonists. A number of derivatives from this class have been investigated for medical applications, such as for use as anorectics or medications for the treatment of ADHD. Some compounds have also become subject to illicit use as designer drugs.

<span class="mw-page-title-main">PCP site 2</span>

PCP site 2 is a binding site that was identified as a high-affinity target for phencyclidine (PCP), an anesthetic and dissociative hallucinogen that acts primarily as an NMDA receptor antagonist. The site is distinct from the PCP binding site on the NMDA receptor and the common/main sites on the monoamine transporters. It is associated with monoamine reuptake inhibition, and it has been suggested that the site may be an allosteric/regulatory site of the monoamine transporters.

<i>ortho</i>-Methylphenylpiperazine Chemical compound

ortho-Methylphenylpiperazine (also known as oMPP, oMePP, 1-(2-methylphenyl)piperazine, 2-MPP, and 2-MePP) is a psychoactive designer drug of the phenylpiperazine group. It acts as a serotonin–norepinephrine–dopamine releasing agent (SNDRA), with EC50 values for induction of monoamine release of 175 nM for serotonin, 39.1 nM for norepinephrine, and 296–542 nM for dopamine. As such, it has about 4.5-fold preference for induction of norepinephrine release over serotonin, and about 7.6- to 13.9-fold preference for induction of norepinephrine release over dopamine.

References

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  24. 1 2 3 Baumann MH, Partilla JS, Lehner KR, Thorndike EB, Hoffman AF, Holy M, Rothman RB, Goldberg SR, Lupica CR, Sitte HH, Brandt SD, Tella SR, Cozzi NV, Schindler CW (2013). "Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive 'bath salts' products". Neuropsychopharmacology. 38 (4): 552–62. doi:10.1038/npp.2012.204. PMC   3572453 . PMID   23072836.
  25. 1 2 Baumann MH, Clark RD, Budzynski AG, Partilla JS, Blough BE, Rothman RB (2005). "N-substituted piperazines abused by humans mimic the molecular mechanism of 3,4-methylenedioxymethamphetamine (MDMA, or 'Ecstasy')". Neuropsychopharmacology. 30 (3): 550–60. doi: 10.1038/sj.npp.1300585 . PMID   15496938.
  26. 1 2 3 4 5 6 7 8 9 Rothman RB, Vu N, Partilla JS, Roth BL, Hufeisen SJ, Compton-Toth BA, Birkes J, Young R, Glennon RA (2003). "In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates". J. Pharmacol. Exp. Ther. 307 (1): 138–45. doi:10.1124/jpet.103.053975. PMID   12954796. S2CID   19015584.
  27. 1 2 3 4 Rothman RB, Clark RD, Partilla JS, Baumann MH (2003). "(+)-Fenfluramine and its major metabolite, (+)-norfenfluramine, are potent substrates for norepinephrine transporters". J. Pharmacol. Exp. Ther. 305 (3): 1191–9. doi:10.1124/jpet.103.049684. PMID   12649307. S2CID   21164342.
  28. 1 2 3 4 5 6 7 8 Setola V, Hufeisen SJ, Grande-Allen KJ, Vesely I, Glennon RA, Blough B, Rothman RB, Roth BL (2003). "3,4-methylenedioxymethamphetamine (MDMA, "Ecstasy") induces fenfluramine-like proliferative actions on human cardiac valvular interstitial cells in vitro". Mol. Pharmacol. 63 (6): 1223–9. doi:10.1124/mol.63.6.1223. PMID   12761331. S2CID   839426.
  29. 1 2 Rothman RB, Baumann MH (2002). "Therapeutic and adverse actions of serotonin transporter substrates". Pharmacol. Ther. 95 (1): 73–88. doi:10.1016/s0163-7258(02)00234-6. PMID   12163129.
  30. ↑ Rothman RB, Baumann MH (2002). "Serotonin releasing agents. Neurochemical, therapeutic and adverse effects". Pharmacol. Biochem. Behav. 71 (4): 825–36. doi:10.1016/s0091-3057(01)00669-4. PMID   11888573. S2CID   24296122.
  31. 1 2 3 4 Baumann MH, Ayestas MA, Partilla JS, Sink JR, Shulgin AT, Daley PF, Brandt SD, Rothman RB, Ruoho AE, Cozzi NV (2012). "The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue". Neuropsychopharmacology. 37 (5): 1192–203. doi:10.1038/npp.2011.304. PMC   3306880 . PMID   22169943.
  32. ↑ Rothman RB, Blough BE, Woolverton WL, Anderson KG, Negus SS, Mello NK, Roth BL, Baumann MH (June 2005). "Development of a rationally designed, low abuse potential, biogenic amine releaser that suppresses cocaine self-administration". The Journal of Pharmacology and Experimental Therapeutics. 313 (3): 1361–9. doi:10.1124/jpet.104.082503. PMID   15761112. S2CID   19802702.
  33. 1 2 Kohut SJ, Jacobs DS, Rothman RB, Partilla JS, Bergman J, Blough BE (2017). "Cocaine-like discriminative stimulus effects of "norepinephrine-preferring" monoamine releasers: time course and interaction studies in rhesus monkeys". Psychopharmacology. 234 (23–24): 3455–3465. doi:10.1007/s00213-017-4731-5. PMC   5747253 . PMID   28889212.
  34. 1 2 3 Rothman RB, Katsnelson M, Vu N, Partilla JS, Dersch CM, Blough BE, Baumann MH (2002). "Interaction of the anorectic medication, phendimetrazine, and its metabolites with monoamine transporters in rat brain". Eur. J. Pharmacol. 447 (1): 51–7. doi:10.1016/s0014-2999(02)01830-7. PMID   12106802.
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