Monoamine releasing agent

Short description: Class of compounds

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

* 1 Types of MRAs
* 2 Mechanism of action
* 3 Effects
* 4 Selectivity
* 5 Activity profiles
* 6 See also
* 7 References
* 8 External links

## Types of MRAs

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

* Selective for one neurotransmitter
* Serotonin releasing agent (SRA)
* Norepinephrine releasing agent (NRA)
* Dopamine releasing agent (DRA)
* Non-selective, releasing two or more neurotransmitters
* Norepinephrine–dopamine releasing agent (NDRA)
* Serotonin–norepinephrine releasing agent (SNRA)
* Serotonin–dopamine releasing agent (SDRA)
* Serotonin–norepinephrine–dopamine releasing agent (SNDRA)

## 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 | NE | DA | Type | Class | Ref

|
|
|
|
|
|

2C-E | >100000 | >100000 | >100000 | IA | Phenethylamine | [15]
2C-I | >100000 | >100000 | >100000 | IA | Phenethylamine | [15]
3-Chloromethcathinone | ND | ND | 46.8 | ND | Cathinone | [16]
3-Fluoroamphetamine | 1937 | 16.1 | 24.2 | NDRA | Amphetamine | [17]
3-Methylamphetamine | 218 | 18.3 | 33.3 | NDRA | Amphetamine | [17]
4-Fluoroamphetamine | 730–939 | 28.0–37 | 51.5–200 | NDRA | Amphetamine | [17][15]
cis-4-Methylaminorex | 53.2 | 4.8 | 1.7 | NDRA | Aminorex | [18]
4-Methylamphetamine | 53.4 | 22.2 | 44.1 | SNDRA | Amphetamine | [17]
4-Methylphenethylamine | ND | ND | 271 | ND | Phenethylamine | [16]
4-Methylthiomethamphetamine | 21 | ND | ND | ND | Amphetamine | [19]
4,4'-Dimethylaminorex | ND | ND | ND | SNDRA | Aminorex | ND
cis-4,4'-Dimethylaminorex | 17.7–18.5 | 11.8–26.9 | 8.6–10.9 | SNDRA | Aminorex | [18][20]
trans-4,4'-Dimethylaminorex | 59.9 | 31.6 | 24.4 | SNDRA | Aminorex | [20]
5-(2-Aminopropyl)indole | 28–104.8 | 13.3–79 | 12.9–173 | SNDRA | Amphetamine | [12][21]
(R)-5-(2-Aminopropyl)indole | 177 | 81 | 1062 | SNRA | Amphetamine | [12]
(S)-5-(2-Aminopropyl)indole | ND | ND | ND | SNDRA | Amphetamine | ND
5-Chloro-αMT | 16 | 3434 | 54 | SDRA | Tryptamine | [12]
5-Fluoro-αMT | 19 | 126 | 32 | SNDRA | Tryptamine | [12]
5-MeO-αMT | 460 | 8900 | 1500 | SNDRA | Tryptamine | [15]
5-MeO-DMT | >100000 | >100000 | >100000 | IA | Tryptamine | [15]
6-(2-Aminopropyl)indole | 19.9 | 25.6 | 164.0 | SNDRA | Amphetamine | [21]
Adderall | ND | ND | ND | NDRA | Amphetamine | ND
α-Methyltryptamine | 68 | 79 | 180 | SNDRA | Tryptamine | [15]
Amfepramone (diethylpropion) | >10000 | >10000 | >10000 | PD | Cathinone | [22]
Aminorex | 193–414 | 15.1–26.4 | 9.1–49.4 | SNDRA | Aminorex | [23][18]
Amphetamine | ND | ND | ND | NDRA | Amphetamine | ND
D-Amphetamine | 698–1765 | 6.6–7.2 | 5.8–24.8 | NDRA | Amphetamine | [23][24]
L-Amphetamine | ND | ND | ND | NRA | Amphetamine | ND
β-Ketophenethylamine | ND | ND | 208 | ND | Phenethylamine | [16]
BDB | 180 | 540 | 2,300 | NDRA | Amphetamine | [15]
Benzylpiperazine | ≥6050 | 62–68 | 175–600 | NDRA | Arylpiperazine | [15][25][14]
Butylamphetamine | ND | ND | IA | ND | Amphetamine | [16]
Cathinone | ND | ND | ND | NDRA | Cathinone | ND
D-Cathinone | ND | ND | ND | NRA | Cathinone | ND
L-Cathinone | 2366 | 12.4 | 18.5 | NDRA | Cathinone | [26]
Chlorphentermine | 30.9 | >10000 | 2650 | SRA | Amphetamine | [23]
DMPP | 26 | 56 | 1207 | SNRA | Arylpiperazine | [19]
Dopamine | >10000 | 66.2 | 86.9 | NDRA | Phenethylamine | [23]
DPT | >100000 | >100000 | >100000 | IA | Tryptamine | [15]
Ephedrine | ND | ND | ND | NDRA | Cathinol | ND
D-Ephedrine | >10000 | 43.1–72.4 | 236–1350 | NDRA | Cathinol | [23]
L-Ephedrine | >10000 | 218 | 2104 | NRA | Cathinol | [23][26]
Epinephrine | ND | ND | ND | NDRA | Phenethylamine | ND
Ethcathinone | 2118 | 99.3 | >1000 | NRA | Cathinone | [22]
Ethylamphetamine | ND | ND | 296 | ND | Amphetamine | [16]
Fenfluramine | 79.3–108 | 739 | >10000 | SRA | Amphetamine | [23][27][28]
D-Fenfluramine | 51.7 | 302 | >10000 | SNRA | Amphetamine | [23][27]
L-Fenfluramine | 147 | >10000 | >10000 | SRA | Amphetamine | [27][29]
MBDB | 540 | 3300 | >100,000 | SNRA | Amphetamine | [15]
mCPP | 28–38.1 | ≥1400 | 63000 | SRA | Arylpiperazine | [15][29][30]
MDA | 160 | 108 | 190 | SNDRA | Amphetamine | [28]
(R)-MDA | 310 | 290 | 900 | SNDRA | Amphetamine | [28]
(S)-MDA | 100 | 50 | 98 | SNDRA | Amphetamine | [28]
MDEA | 47 | 2608 | 622 | SNDRA | Amphetamine | [19]
(R)-MDEA | 52 | 651 | 507 | SNDRA | Amphetamine | [19]
(S)-MDEA | 465 | RI | RI | SRA | Amphetamine | [19]
MDMA | 49.6–72 | 54.1–110 | 51.2–278 | SNDRA | Amphetamine | [23][31][21][28]
(''R'')-MDMA | 340 | 560 | 3700 | SNDRA | Amphetamine | [28]
(''S'')-MDMA | 74 | 136 | 142 | SNDRA | Amphetamine | [28]
MDMAR | ND | ND | ND | SNDRA | Aminorex | ND
cis-MDMAR | 43.9 | 14.8 | 10.2 | SNDRA | Aminorex | [20]
trans-MDMAR | 73.4 | 38.9 | 36.2 | SNDRA | Aminorex | [20]
Mephedrone | 118.3–122 | 58–62.7 | 49.1–51 | SNDRA | Cathinone | [31][24]
Methamnetamine | 13 | 34 | 10 | SNDRA | Amphetamine | [19]
Methamphetamine | ND | ND | ND | NDRA | Amphetamine | ND
D-Methamphetamine | 736–1291.7 | 12.3–13.8 | 8.5–24.5 | NDRA | Amphetamine | [23][31]
L-Methamphetamine | 4640 | 28.5 | 416 | NRA | Amphetamine | [23]
Methcathinone | ND | ND | ND | NDRA | Cathinone | ND
D-Methcathinone | ND | ND | ND | NRA | Cathinone | ND
L-Methcathinone | 1772 | 13.1 | 14.8 | NDRA | Cathinone | [26]
Methylone | 234–242.1 | 140–152.3 | 117–133.0 | SNDRA | Cathinone | [31][24]
Naphthylisopropylamine | 3.4 | 11.1 | 12.6 | SNDRA | Amphetamine | [32]
Norephedrine | ND | ND | ND | NDRA | Cathinol | ND
D-Norephedrine | >10000 | 42.1 | 302 | NDRA | Cathinol | [26]
L-Norephedrine (phenylpropanolamine) | >10000 | 137 | 1371 | NRA | Cathinol | [26]
Norepinephrine | >10000 | 164 | 869 | NDRA | Phenethylamine | [23]
Norfenfluramine | 104 | 168–170 | 1900–1925 | SNRA | Amphetamine | [27][28]
Norpropylhexedrine | ND | ND | ND | NDRA | Cyclohexethylamine | ND
D-Norpropylhexedrine | ND | ND | ND | NRA | Cyclohexethylamine | ND
L-Norpropylhexedrine | ND | ND | ND | NDRA | Cyclohexethylamine | ND
Norpseudoephedrine | ND | ND | ND | NDRA | Cathinol | ND
D-Norpseudoephedrine (cathine) | >10000 | 15.0 | 68.3 | NDRA | Cathinol | [26]
L-Norpseudoephedrine | >10000 | 30.1 | 294 | NDRA | Cathinol | [26]
oMPP | 175 | 39.1 | 296–542 | SNDRA | Arylpiperazine | [33][16]
PAL-738 | 23 | 65 | 58 | SNDRA | Phenylmorpholine | [19]
Phenethylamine | ND | ND | 39.5 | NDRA | Phenethylamine | [16]
Phendimetrazine | >100000 | >10000 | >10000 | PD | Phenylmorpholine | [34]
Phenmetrazine | 7765 | 50.4 | 131 | NDRA | Phenylmorpholine | [34]
Phentermine | 3511 | 39.4 | 262 | NDRA | Amphetamine | [23]
Phenylalaninol | ND | ND | ND | ND | Amphetamine | ND
D-Phenylalaninol | >10000 | 106 | 1355 | NRA | Amphetamine | [33]
L-Phenylalaninol | ND | ND | ND | ND | Amphetamine | ND
Phenylisobutylamine | ND | ND | 225 | ND | Amphetamine | [16]
pMPP | 3200 | 1500 | 11000 | SNRA | Arylpiperazine | [15]
pNPP | 43 | >10000 | >10000 | SRA | Arylpiperazine | [19]
Propylamphetamine | ND | ND | RI (1013) | ND | Amphetamine | [16]
Propylhexedrine | ND | ND | ND | NDRA | Cyclohexethylamine | ND
D-Propylhexedrine | ND | ND | ND | NRA | Cyclohexethylamine | ND
L-Propylhexedrine | ND | ND | ND | NDRA | Cyclohexethylamine | ND
Pseudoephedrine | ND | ND | ND | NDRA | Cathinol | ND
D-Pseudoephedrine | >10000 | 4092 | 9125 | NDRA | Cathinol | [26]
L-Pseudoephedrine | >10000 | 224 | 1988 | NRA | Cathinol | [26]
Pseudophenmetrazine | >10000 | 514 | RI | NRA | Phenylmorpholine | [34]
Psilocin | 561 | >10000 | >10000 | SRA | Tryptamine | [19]
Serotonin | 44.4 | >10000 | >10000 | SRA | Tryptamine | [23]
TFMPP | 121 | ND | >10000 | SRA | Arylpiperazine | [25]
TFMCPP | 33 | >10000 | >10000 | SRA | Arylpiperazine | [19]
Trimethoxyamphetamine | 16000 | >100000 | >100000 | IA | Amphetamine | [15]
Tyramine | 2775 | 40.6 | 119 | NDRA | Phenethylamine | [23]
The smaller the value, the more strongly the substance activates or releases the neurotransmitter.

## See also

* Monoamine reuptake inhibitor
* Release modulator

## References

1. ↑ "The emerging role of trace amine-associated receptor 1 in the functional regulation of monoamine transporters and dopaminergic activity". Journal of Neurochemistry 116 (2): 164–76. January 2011. doi:10.1111/j.1471-4159.2010.07109.x. PMID 21073468.
2. ↑ Brust, John Calvin M. (2004). Neurological Aspects of Substance Abuse. Butterworth-Heinemann. pp. 117–. ISBN 978-0-7506-7313-6. https://books.google.com/books?id=fOfxoQm_a7MC&pg=PA117.
3. ↑ United States. Congress. Senate. Select Committee on Small Business. Subcommittee on Monopoly and Anticompetitive Activities (1976). Competitive problems in the drug industry: hearings before Subcommittee on Monopoly and Anticompetitive Activities of the Select Committee on Small Business, United States Senate, Ninetieth Congress, first session. U.S. Government Printing Office. pp. 2–. https://books.google.com/books?id=Rs1GAQAAMAAJ&pg=RA2-PA56.
4. ↑ Parrott, A. C.; Stuart, M. (1 September 1997). "Ecstasy (MDMA), amphetamine, and LSD: comparative mood profiles in recreational polydrug users" (in en). Human Psychopharmacology: Clinical and Experimental 12 (5): 501–504. doi:10.1002/(sici)1099-1077(199709/10)12:5<501::aid-hup913>3.3.co;2-m. ISSN 1099-1077.
5. ↑ "The drug effects questionnaire: psychometric support across three drug types". Psychopharmacology 227 (1): 177–92. May 2013. doi:10.1007/s00213-012-2954-z. PMID 23271193.
6. ↑ "Effect of rate of administration on subjective and physiological effects of intravenous cocaine in humans". Drug and Alcohol Dependence 82 (1): 19–24. March 2006. doi:10.1016/j.drugalcdep.2005.08.004. PMID 16144747.
7. ↑ "Pharmacodynamics and pharmacokinetics of single nasal (5 mg and 10 mg) and oral (50 mg) doses of ephedrine in healthy subjects". European Journal of Clinical Pharmacology 57 (6–7): 447–55. September 2001. doi:10.1007/s002280100317. PMID 11699608.
8. ↑ "Ephedra and its application to sport performance: another concern for the athletic trainer?". Journal of Athletic Training 36 (4): 420–4. October 2001. PMID 16558668.
9. ↑ "Central fatigue: the serotonin hypothesis and beyond". Sports Medicine 36 (10): 881–909. 1 January 2006. doi:10.2165/00007256-200636100-00006. PMID 17004850.
10. ↑ "Alterations in central fatigue by pharmacological manipulations of neurotransmitters in normal and high ambient temperature". Sports Medicine 40 (3): 229–46. March 2010. doi:10.2165/11533670-000000000-00000. PMID 20199121. https://www.researchgate.net/publication/41720970.
11. ↑ "Dual dopamine/serotonin releasers as potential medications for stimulant and alcohol addictions". The AAPS Journal 9 (1): E1–10. January 2007. doi:10.1208/aapsj0901001. PMID 17408232.
12. ↑ 12.0 12.1 12.2 12.3 12.4 "Abuse-related effects of dual dopamine/serotonin releasers with varying potency to release norepinephrine in male rats and rhesus monkeys". Exp Clin Psychopharmacol 22 (3): 274–284. 2014. doi:10.1037/a0036595. PMID 24796848.
13. ↑ "Monoamine transporters and psychostimulant drugs". Eur. J. Pharmacol. 479 (1–3): 23–40. 2003. doi:10.1016/j.ejphar.2003.08.054. PMID 14612135.
14. ↑ 14.0 14.1 "Therapeutic potential of monoamine transporter substrates". Current Topics in Medicinal Chemistry 6 (17): 1845–59. 2006. doi:10.2174/156802606778249766. PMID 17017961. https://zenodo.org/record/1235860.
15. ↑ 15.00 15.01 15.02 15.03 15.04 15.05 15.06 15.07 15.08 15.09 15.10 15.11 15.12 "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". Eur. J. Pharmacol. 559 (2–3): 132–7. 2007. doi:10.1016/j.ejphar.2006.11.075. PMID 17223101.
16. ↑ 16.0 16.1 16.2 16.3 16.4 16.5 16.6 16.7 16.8 "Behavioral, biological, and chemical perspectives on atypical agents targeting the dopamine transporter". Drug Alcohol Depend 147: 1–19. 2015. doi:10.1016/j.drugalcdep.2014.12.005. PMID 25548026.
17. ↑ 17.0 17.1 17.2 17.3 "Relationship between the serotonergic activity and reinforcing effects of a series of amphetamine analogs". The Journal of Pharmacology and Experimental Therapeutics 313 (2): 848–54. May 2005. doi:10.1124/jpet.104.080101. PMID 15677348.
18. ↑ 18.0 18.1 18.2 "Characterization of a novel and potentially lethal designer drug (±)-cis-para-methyl-4-methylaminorex (4,4'-DMAR, or 'Serotoni')". Drug Test Anal 6 (7–8): 684–95. 2014. doi:10.1002/dta.1668. PMID 24841869.
19. ↑ 19.0 19.1 19.2 19.3 19.4 19.5 19.6 19.7 19.8 19.9 "Studies of the biogenic amine transporters. 14. Identification of low-efficacy "partial" substrates for the biogenic amine transporters". J. Pharmacol. Exp. Ther. 341 (1): 251–62. 2012. doi:10.1124/jpet.111.188946. PMID 22271821.
20. ↑ 20.0 20.1 20.2 20.3 "Synthesis, characterization, and monoamine transporter activity of the new psychoactive substance 3',4'-methylenedioxy-4-methylaminorex (MDMAR)". Drug Test Anal 7 (7): 555–64. 2015. doi:10.1002/dta.1732. PMID 25331619.
21. ↑ 21.0 21.1 21.2 "The new psychoactive substances 5-(2-aminopropyl)indole (5-IT) and 6-(2-aminopropyl)indole (6-IT) interact with monoamine transporters in brain tissue". Neuropharmacology 101: 68–75. 2016. doi:10.1016/j.neuropharm.2015.09.004. PMID 26362361.
22. ↑ 22.0 22.1 "Uptake and release effects of diethylpropion and its metabolites with biogenic amine transporters". Bioorg. Med. Chem. 8 (12): 2689–92. 2000. doi:10.1016/s0968-0896(00)00210-8. PMID 11131159.
23. ↑ 23.00 23.01 23.02 23.03 23.04 23.05 23.06 23.07 23.08 23.09 23.10 23.11 23.12 23.13 23.14 "Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin". Synapse 39 (1): 32–41. January 2001. doi:10.1002/1098-2396(20010101)39:1<32::AID-SYN5>3.0.CO;2-3. PMID 11071707.
24. ↑ 24.0 24.1 24.2 "Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive 'bath salts' products". Neuropsychopharmacology 38 (4): 552–62. 2013. doi:10.1038/npp.2012.204. PMID 23072836.
25. ↑ 25.0 25.1 "N-substituted piperazines abused by humans mimic the molecular mechanism of 3,4-methylenedioxymethamphetamine (MDMA, or 'Ecstasy')". Neuropsychopharmacology 30 (3): 550–60. 2005. doi:10.1038/sj.npp.1300585. PMID 15496938.
26. ↑ 26.0 26.1 26.2 26.3 26.4 26.5 26.6 26.7 26.8 "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. 2003. doi:10.1124/jpet.103.053975. PMID 12954796.
27. ↑ 27.0 27.1 27.2 27.3 "(+)-Fenfluramine and its major metabolite, (+)-norfenfluramine, are potent substrates for norepinephrine transporters". J. Pharmacol. Exp. Ther. 305 (3): 1191–9. 2003. doi:10.1124/jpet.103.049684. PMID 12649307.
28. ↑ 28.0 28.1 28.2 28.3 28.4 28.5 28.6 28.7 "3,4-methylenedioxymethamphetamine (MDMA, "Ecstasy") induces fenfluramine-like proliferative actions on human cardiac valvular interstitial cells in vitro". Mol. Pharmacol. 63 (6): 1223–9. 2003. doi:10.1124/mol.63.6.1223. PMID 12761331.
29. ↑ 29.0 29.1 "Therapeutic and adverse actions of serotonin transporter substrates". Pharmacol. Ther. 95 (1): 73–88. 2002. doi:10.1016/s0163-7258(02)00234-6. PMID 12163129.
30. ↑ "Serotonin releasing agents. Neurochemical, therapeutic and adverse effects". Pharmacol. Biochem. Behav. 71 (4): 825–36. 2002. doi:10.1016/s0091-3057(01)00669-4. PMID 11888573. https://zenodo.org/record/1259765.
31. ↑ 31.0 31.1 31.2 31.3 "The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue". Neuropsychopharmacology 37 (5): 1192–203. 2012. doi:10.1038/npp.2011.304. PMID 22169943.
32. ↑ "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. June 2005. doi:10.1124/jpet.104.082503. PMID 15761112.
33. ↑ 33.0 33.1 "Cocaine-like discriminative stimulus effects of "norepinephrine-preferring" monoamine releasers: time course and interaction studies in rhesus monkeys". Psychopharmacology 234 (23–24): 3455–3465. 2017. doi:10.1007/s00213-017-4731-5. PMID 28889212.
34. ↑ 34.0 34.1 34.2 "Interaction of the anorectic medication, phendimetrazine, and its metabolites with monoamine transporters in rat brain". Eur. J. Pharmacol. 447 (1): 51–7. 2002. doi:10.1016/s0014-2999(02)01830-7. PMID 12106802. https://zenodo.org/record/1259577.

* "The Designer Methcathinone Analogs, Mephedrone and Methylone, are Substrates for Monoamine Transporters in Brain Tissue". Neuropsychopharmacology 37 (5): 1192–203. 2012. doi:10.1038/npp.2011.304. PMID 22169943.
* "Neurochemical profiles of some novel psychoactive substances". European Journal of Pharmacology 700 (1–3): 147–51. January 2013. doi:10.1016/j.ejphar.2012.12.006. PMID 23261499.

## External links

* v
* t
* e

Monoamine releasing agents

DRAs|

* Morpholines: Fenbutrazate
* Fenmetramide
* Morazone
* Morforex
* Phendimetrazine
* Phenmetrazine
* Pseudophenmetrazine

* Oxazolines: 4-MAR
* Aminorex
* Clominorex
* Cyclazodone
* Fenozolone
* Fluminorex
* Pemoline
* Thozalinone

* Phenethylamines: 2-OH-PEA
* 4-CAB
* 4-FA
* 4-FMA
* 4-MA
* 4-MMA
* Alfetamine
* Amfecloral
* Amfepentorex
* Amfepramone
* Amphetamine (Dextroamphetamine
* Levoamphetamine)
* Amphetaminil
* β-Me-PEA
* BDB
* BOH
* Benzphetamine
* Buphedrone
* Butylone
* Cathine
* Cathinone
* Clobenzorex
* Clortermine
* D-Deprenyl
* DMA
* DMMA
* Dimethylamphetamine
* Ephedrine
* Ethcathinone
* EBDB
* Ethylone
* Etilamfetamine
* Famprofazone
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* Phenpromethamine
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* Zylofuramine

* Piperazines: 2C-B-BZP
* BZP
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* Others: 2-ADN
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* Phenylbiguanide
* Propylhexedrine
* Levopropylhexedrine

NRAs|

* Morpholines: Fenbutrazate
* Fenmetramide
* Morazone
* Morforex
* Phendimetrazine
* Phenmetrazine
* Pseudophenmetrazine

* Oxazolines: 4-MAR
* Aminorex
* Clominorex
* Cyclazodone
* Fenozolone
* Fluminorex
* Pemoline
* Thozalinone

* Phenethylamines: 2-OH-PEA
* 4-CAB
* 4-FA
* 4-FMA
* 4-MA
* 4-MMA
* Alfetamine
* Amfecloral
* Amfepentorex
* Amfepramone
* Amphetamine
* Dextroamphetamine
* Levoamphetamine
* Amphetaminil
* β-Me-PEA
* BDB
* Benzphetamine
* BOH
* Buphedrone
* Butylone
* Cathine
* Cathinone
* Clobenzorex
* Clortermine
* Dimethylamphetamine
* DMA
* DMMA
* EBDB
* Ephedrine
* Ethcathinone
* Ethylone
* Etilamfetamine
* Famprofazone
* Fenethylline
* Fenproporex
* Flephedrone
* Fludorex
* Furfenorex
* Hordenine
* 4-Hydroxyamphetamine
* 5-APDI (IAP)
* Iofetamine (123I)
* Lisdexamfetamine
* Lophophine
* MBDB
* MDA (tenamfetamine)
* MDEA
* MDMA (midomafetamine)
* Metamfepramone
* MDMPEA
* MDOH
* MDPEA
* Mefenorex
* Mephedrone
* Mephentermine
* Methamphetamine
* Dextromethamphetamine
* Levomethamphetamine
* Methcathinone
* Methedrone
* Methylone
* Morforex
* Naphthylaminopropane
* Ortetamine
* pBA
* pCA
* Pentorex
* Phenethylamine
* Pholedrine
* Phenpromethamine
* Phentermine
* Phenylpropanolamine
* pIA
* Prenylamine
* Propylamphetamine
* Pseudoephedrine
* Selegiline (also D-Deprenyl)
* Tiflorex
* Tyramine
* Xylopropamine
* Zylofuramine

* Piperazines: 2C-B-BZP
* BZP
* MBZP
* mCPP
* MDBZP
* MeOPP
* oMPP
* pFPP

* Others: 2-ADN
* 2-AI
* 2-AT
* 2-BP
* 4-BP
* 5-IAI
* Clofenciclan
* Cyclopentamine
* Cypenamine
* Cyprodenate
* Feprosidnine
* Gilutensin
* Heptaminol
* Hexacyclonate
* Indanorex
* Isometheptene
* Methylhexanamine
* Octodrine
* Phthalimidopropiophenone
* Propylhexedrine (Levopropylhexedrine)
* Tuaminoheptane

SRAs|

* Aminoindanes: 5-IAI
* AMMI
* ETAI
* MDAI
* MDMAI
* MMAI
* TAI

* Aminotetralins: 6-CAT
* 8-OH-DPAT
* MDAT
* MDMAT

* Oxazolines: 4-Methylaminorex
* Aminorex
* Clominorex
* Fluminorex

* Phenethylamines: 2-Methyl-MDA
* 4-CAB
* 4-FA
* 4-FMA
* 4-HA
* 4-MTA
* 5-APDB
* 5-Methyl-MDA
* 6-APDB
* 6-Methyl-MDA
* AEMMA
* Amiflamine
* BDB
* BOH
* Brephedrone
* Butylone
* Chlorphentermine
* Cloforex
* Amfepramone
* Metamfepramone
* DCA
* Dexfenfluramine
* DFMDA
* DMA
* DMMA
* EBDB
* EDMA
* Ethylone
* Etolorex
* Fenfluramine
* Flephedrone
* Flucetorex
* IAP
* Iofetamine
* Levofenfluramine
* Lophophine
* MBDB
* MDA (tenamfetamine)
* MDEA
* MDHMA
* MDMA (midomafetamine)
* MDMPEA
* MDOH
* MDPEA
* Mephedrone
* Methedrone
* Methylone
* MMA
* MMDA
* MMDMA
* MMMA
* NAP
* Norfenfluramine
* 4-TFMA
* pBA
* pCA
* pIA
* PMA
* PMEA
* PMMA
* TAP

* Piperazines: 2C-B-BZP
* 3-MeOPP
* BZP
* DCPP
* MBZP
* mCPP
* MDBZP
* MeOPP
* Mepiprazole
* oMPP
* pCPP
* pFPP
* pTFMPP
* TFMPP

* Tryptamines: 4-Methyl-αET
* 4-Methyl-αMT
* 5-CT
* 5-MeO-αET
* 5-MeO-αMT
* 5-MT
* αET
* αMT
* DMT
* Tryptamine

* Others: Indeloxazine
* Viqualine

Others|

* Monoamine activity enhancers: BPAP
* PPAP

* DAT modulators: Agonist-like: SoRI-9804
* SoRI-20040; Antagonist-like: SoRI-20041

* Adrenergic release blockers: Bethanidine
* Bretylium
* Guanadrel
* Guanazodine
* Guanethidine
* Guanoxan

See also: Receptor/signaling modulators • Monoamine reuptake inhibitors • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins

* v
* t
* e

Human trace amine-associated receptor ligands

TAAR1|

| Agonists|

| Endogenous†|

* Classical monoamine neurotransmitters
* Dopamine
* Histamine
* Norepinephrine
* Serotonin
* Trace amines
* 3-Iodothyronamine
* 3-Methoxytyramine
* N-Methylphenethylamine
* N-Methyltyramine
* m-Octopamine
* p-Octopamine
* Phenethylamine
* Phenylethanolamine
* Synephrine
* Tryptamine
* m-Tyramine
* p-Tyramine

|

Synthetic‡|

* Amphetamine
* DOB
* DOET
* 4-Hydroxyamphetamine
* Isoprenaline
* MDA (tenamfetamine)
* MDMA (midomafetamine)
* 2-Methylphenethylamine
* 3-Methylphenethylamine
* 4-Methylphenethylamine
* β-Methylphenethylamine
* Methamphetamine
* 3-MMA
* Norfenfluramine
* Phentermine
* o-PIT
* Propylhexedrine
* RO5166017
* N,N-Dimethylphenethylamine

Neutral antagonists|

Inverse agonists|

* EPPTB (RO5212773)

TAAR2|

| Agonists‡|

|

Neutral antagonists|

TAAR5|

| Agonists‡|

* N,N-Dimethylethylamine
* Trimethylamine

|

Neutral antagonists|

Inverse agonists‡|

* 3-Iodothyronamine

† References for all endogenous human TAAR1 ligands are provided at List of trace amines

‡ References for synthetic TAAR1 agonists can be found at TAAR1 or in the associated compound articles. For TAAR2 and TAAR5 agonists and inverse agonists, see TAAR for references.

See also: Receptor/signaling modulators

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Original source: https://en.wikipedia.org/wiki/Monoamine releasing agent. Read more

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Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Monoamine_releasing_agent&oldid=3337820"
*[5-HT]: Serotonin
*[NE]: Norepinephrine
*[DA]: Dopamine
*[IA]: Inactive
*[ND]: No data
*[PD]: Prodrug
*[RI]: Reuptake inhibitor
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[DRAs]: Dopamine releasing agents
*[NRAs]: Norepinephrine releasing agents
*[SRAs]: Serotonin releasing agents