Monoamine neurotoxin

Oxidopamine (6-hydroxydopamine), a selective dopaminergic and noradrenergic neurotoxin.

A monoamine neurotoxin, or monoaminergic neurotoxin, is a drug that selectively damages or destroys monoaminergic neurons. ^[1] Monoaminergic neurons are neurons that signal via stimulation by monoamine neurotransmitters including serotonin, dopamine, and norepinephrine. ^[1]

Examples of monoamine neurotoxins include the serotonergic neurotoxins para-chloroamphetamine (PCA), methylenedioxymethamphetamine (MDMA), and 5,7-dihydroxytryptamine (5,7-DHT); ^[2] the dopaminergic neurotoxins oxidopamine (6-hydroxydopamine), MPTP, and methamphetamine; and the noradrenergic neurotoxins oxidopamine and DSP-4. ^[1]

In the case of serotonergic neurotoxins like MDMA, research suggests that simultaneous induction of serotonin and dopamine release, serotonin depletion, dopamine uptake and metabolism, hyperthermia, oxidative stress and antioxidant depletion, and/or drug metabolites may all be involved in the neurotoxicity. ^{[3] [4]} On the other hand, there is evidence that drug metabolites may not be involved. ^{[3] [4]} Some research suggests that serotonergic neurotoxicity might represent neuroadaptive mechanisms rather than neuronal damage per se. ^{[5] [6]}

Dopaminergic neurotoxins can induce a Parkinson's disease-like condition in animals and humans. ^{[1] [7]} Serotonergic neurotoxins have been associated with cognitive and memory deficits and psychiatric changes. ^{[8] [9] [10] [11]}

List of monoamine neurotoxins

Serotonergic neurotoxins

Phenethylamines

• 2,4-Dichloroamphetamine (2,4-DCA) ^[12]
• 2,4,5-Trihydroxyamphetamine (2,4,5-THA) ^[13]
• 2,4,5-Trihydroxymethamphetamine (2,4,5-THMA) ^[13]
• 3-Chloroamphetamine (3-CA) ^{[12] [14]}
• 3,4-Dichloroamphetamine (3,4-DCA) ^[12]
• 3,4-Dihydroxyamphetamine (HHA; 3,4-DHA; α-methyldopamine; α-Me-DA) ^[2]
• 3,4-Dihydroxymethamphetamine (HHMA; 3,4-DHMA; α-methylepinine; α,N-dimethyldopamine) ^[2]
• 3,4-Methylenedioxyamphetamine (MDA) ^{[1] [15] [2] [13]}
• 3,4-Methylenedioxyethylamphetamine (MDEA) ^{[15] [16]}
• 3,4-Methylenedioxymethamphetamine (MDMA) ^{[1] [2] [17] [18]}
• 4-Chlorophenylisobutylamine (4-CAB; 4-chloro-α-desmethyl-α-ethylamphetamine; α-ethyl-PCA) ^[15]
• 5-MAPB ^[19]
• Fenfluramine ^{[1] [20] [21] [22]}
• Mephedrone ^[23]
• Methamphetamine ^{[1] [18] [13]}
• Methylbenzodioxolylbutanamine (MBDB) ^{[15] [16]}
• Methylone ^[23]
• Norfenfluramine ^{[22] [24]}
• para-Bromoamphetamine (PBA; 4-bromoamphetamine; 4-BA) ^[25]
• para-Bromomethamphetamine (PBMA; 4-bromomethamphetamine; 4-BMA) ^{[26] [27]}
• para-Chloroamphetamine (PCA; 4-chloroamphetamine; 4-CA) ^{[1] [2] [16]}
• para-Chloromethamphetamine (PCMA; 4-chloromethamphetamine; 4-PCMA) ^{[12] [28]}
• para-Iodoamphetamine (PIA; 4-iodoamphetamine; 4-IA) ^{[15] [29]}

Tryptamines

• 4-Hydroxy-5-methoxytryptamine (4-HO-5-MeO-T) ^{[30] [31]}
• 4,5-Dihydroxytryptamine (4,5-DHT) ^{[32] [33] [31]}
• 5,6-Dihydroxytryptamine (5,6-DHT) ^{[34] [1] [2]}
• 5,7-Dihydroxytryptamine (5,7-DHT) ^{[34] [1] [2]}
• 6,7-Dihydroxytryptamine (6,7-DHT) ^{[32] [35]}
• α-Ethyltryptamine (αET) ^{[16] [36] [37]}

2-Aminoindans

• 5-Iodo-2-aminoindan (5-IAI) (weak) ^{[38] [16] [15]}
• 5-Methoxy-6-methyl-2-aminoindane (MMAI) (weak; alone and with amphetamine) ^{[39] [40] [41]}
• 5,6-Methylenedioxy-2-aminoindan (MDAI) (weak; alone and with amphetamine) ^{[42] [15] [43]}

MPTP-related

• 2′-NH₂-MPTP (2′-amino-MPTP) ^[1]
• Haloperidol ^{[1] [44]}
• HPP⁺ (haloperidol pyridinium) ^{[1] [44]}
• HPTP ^{[1] [45]}

Dopaminergic neurotoxins

Phenethylamines

• 2,4,5-Trihydroxyamphetamine (2,4,5-THA) ^[13]
• 2,4,5-Trihydroxymethamphetamine (2,4,5-THMA) ^[13]
• 3,4-Methylenedioxymethamphetamine (MDMA) (in mice but not in humans) ^{[18] [10]}
• 4-Methylmethamphetamine (4-MMA; mephedrine) ^{[46] [47]}
• 6-Hydroxydopa (6-OH-DOPA, 6-OHDOPA) ^{[1] [48] [49]}
• 6-Hydroxydopamine quinone (6-OHDA quinone; oxidopamine quinone) ^{[50] [51]}
• Amphetamine ^[1]
• Mephedrone ^[23]
• Methamphetamine ^{[1] [17] [18]}
• Methcathinone ^{[46] [47]}
• Methylone ^[23]
• Oxidopamine (6-hydroxydopamine; 6-OHDA) ^{[52] [53] [50]}

Dopamine and metabolites

• 3,4-Dihydroxyphenylacetaldehyde (DOPAL; dopamine aldehyde) ^{[54] [55]}
• 5-S-Cysteinyldopamine (5-S-CyS-DA) ^[56]
• DOPA quinone ^{[57] [58]}
• DOPAL quinone ^[59]
• Dopamine ^[60]
• Dopamine quinone ^{[57] [58]}
• N-Methylnorsalsolinol ^[61]
• Norsalsolinol ^[61]
• Salsolinol ^{[61] [62]}

Tryptamines

• 5,6-Dihydroxytryptamine (5,6-DHT) ^{[34] [63]}
• 6,7-Dihydroxytryptamine (6,7-DHT) ^{[32] [35]}

MPTP-related

• 2′-CH₃-MPTP (2′-methyl-MPTP) ^{[64] [65] [66] [67] [68]}
• Haloperidol ^{[1] [44]}
• HPP⁺ (haloperidol pyridinium) ^{[1] [44]}
• HPTP ^{[1] [45]}
• MPP⁺ (cyperquat) ^{[69] [70]}
• MPTP ^[69]

Pesticides

• Benomyl ^[71]
• Daidzin ^[71]
• Dieldrin ^[71]
• Fenpropathrin ^{[72] [73] [74]}
• Mancozeb ^[75]
• Maneb ^[75]
• Paraquat ^{[72] [75] [76]}
• Rotenone ^{[1] [72] [75] [77]}
• Ziram ^[71]

Others

• Aldehyde dehydrogenase (ALDH) inhibitors (e.g., disulfiram, methylmercury) ^{[71] [78] [79] [80]}

Noradrenergic neurotoxins

Phenethylamines and related

• 2,4,5-Trihydroxyamphetamine (2,4,5-THA) ^[13]
• 3,4-Methylenedioxyamphetamine (MDA) ^[13]
• 3,4-Dihydroxyphenylglycolaldehyde (DOPEGAL; norepinephrine/epinephrine aldehyde) ^[81]
• 6-Hydroxydopa (6-OH-DOPA, 6-OHDOPA) ^{[1] [48] [49]}
• DSP-4 ^{[82] [83]}
• Oxidopamine (6-hydroxydopamine; 6-OHDA) ^{[52] [50]}
• Xylamine ^[1]

Tryptamines and related

• 4,5-Dihydroxytryptamine (4,5-DHT) ^{[32] [33]}
• 5,6-Dihydroxytryptamine (5,6-DHT) ^{[34] [63]}
• 5,7-Dihydroxytryptamine (5,7-DHT) ^{[34] [63]}

MPTP-related

• 2′-NH₂-MPTP (2′-amino-MPTP) ^[1]

Unsorted or unknown

• 5-Hydroxyindoleacetaldehyde (5-HIAL) ^{[84] [85] [86]}
• RHPP^{+ [87] [45]}
• RHPTP ^{[88] [89] [90] [91]}

See also

• Monoamine-depleting agent

References

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