N,N-Dimethyl-4-methylthioamphetamine: Difference between revisions

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	'''''N'',''N''-Dimethyl-4-methylthioamphetamine''' ('''DMMTA''' or '''''N'',''N''-dimethyl-4-MTA'''; code name '''PAL-1062'''), also known as '''4-methylthio-''N'',''N''-dimethylamphetamine''' ('''4-MTDMA'''), is a ] (MRA) of the ] family related to ] (4-MTA) and ] (4-MTMA or NMMTA).<ref name="GuajardoVelásquezRaby2020">{{cite journal \| vauthors = Guajardo FG, Velásquez VB, Raby D, Núñez-Vivanco G, Iturriaga-Vásquez P, España RA, Reyes-Parada M, Sotomayor-Zárate R \| title = Pharmacological Characterization of 4-Methylthioamphetamine Derivatives \| journal = Molecules \| volume = 25 \| issue = 22 \| date = November 2020 \| page = 5310 \| pmid = 33203055 \| pmc = 7696343 \| doi = 10.3390/molecules25225310 \| doi-access = free \| url = }}</ref><ref name="Sotomayor-ZárateJaraAraos2014">{{cite journal \| vauthors = Sotomayor-Zárate R, Jara P, Araos P, Vinet R, Quiroz G, Renard GM, Espinosa P, Hurtado-Guzmán C, Moya PR, Iturriaga-Vásquez P, Gysling K, Reyes-Parada M \| title = Improving amphetamine therapeutic selectivity: N,N-dimethyl-MTA has dopaminergic effects and does not produce aortic contraction \| journal = Basic Clin Pharmacol Toxicol \| volume = 114 \| issue = 5 \| pages = 395–399 \| date = May 2014 \| pmid = 24314229 \| doi = 10.1111/bcpt.12168 \| url = }}</ref><ref name="GobbiFunicelloGerstbrein2008">{{cite journal \| vauthors = Gobbi M, Funicello M, Gerstbrein K, Holy M, Moya PR, Sotomayor R, Forray MI, Gysling K, Paluzzi S, Bonanno G, Reyes-Parada M, Sitte HH, Mennini T \| title = N,N-dimethyl-thioamphetamine and methyl-thioamphetamine, two non-neurotoxic substrates of 5-HT transporters, have scant in vitro efficacy for the induction of transporter-mediated 5-HT release and currents \| journal = J Neurochem \| volume = 105 \| issue = 5 \| pages = 1770–1780 \| date = June 2008 \| pmid = 18248615 \| pmc = 4502523 \| doi = 10.1111/j.1471-4159.2008.05272.x \| url = }}</ref>		'''''N'',''N''-Dimethyl-4-methylthioamphetamine''' ('''DMMTA''' or '''''N'',''N''-dimethyl-4-MTA'''; code name '''PAL-1062'''), also known as '''4-methylthio-''N'',''N''-dimethylamphetamine''' ('''4-MTDMA'''), is a ] (MRA) of the ] family related to ] (4-MTA) and ] (4-MTMA or NMMTA).<ref name="GuajardoVelásquezRaby2020">{{cite journal \| vauthors = Guajardo FG, Velásquez VB, Raby D, Núñez-Vivanco G, Iturriaga-Vásquez P, España RA, Reyes-Parada M, Sotomayor-Zárate R \| title = Pharmacological Characterization of 4-Methylthioamphetamine Derivatives \| journal = Molecules \| volume = 25 \| issue = 22 \| date = November 2020 \| page = 5310 \| pmid = 33203055 \| pmc = 7696343 \| doi = 10.3390/molecules25225310 \| doi-access = free \| url = }}</ref><ref name="Sotomayor-ZárateJaraAraos2014">{{cite journal \| vauthors = Sotomayor-Zárate R, Jara P, Araos P, Vinet R, Quiroz G, Renard GM, Espinosa P, Hurtado-Guzmán C, Moya PR, Iturriaga-Vásquez P, Gysling K, Reyes-Parada M \| title = Improving amphetamine therapeutic selectivity: N,N-dimethyl-MTA has dopaminergic effects and does not produce aortic contraction \| journal = Basic Clin Pharmacol Toxicol \| volume = 114 \| issue = 5 \| pages = 395–399 \| date = May 2014 \| pmid = 24314229 \| doi = 10.1111/bcpt.12168 \| url = }}</ref><ref name="GobbiFunicelloGerstbrein2008">{{cite journal \| vauthors = Gobbi M, Funicello M, Gerstbrein K, Holy M, Moya PR, Sotomayor R, Forray MI, Gysling K, Paluzzi S, Bonanno G, Reyes-Parada M, Sitte HH, Mennini T \| title = N,N-dimethyl-thioamphetamine and methyl-thioamphetamine, two non-neurotoxic substrates of 5-HT transporters, have scant in vitro efficacy for the induction of transporter-mediated 5-HT release and currents \| journal = J Neurochem \| volume = 105 \| issue = 5 \| pages = 1770–1780 \| date = June 2008 \| pmid = 18248615 \| pmc = 4502523 \| doi = 10.1111/j.1471-4159.2008.05272.x \| url = }}</ref>

	It has been described as an MRA of ] and ] that lacks induction of ] ] '']'' and hence may lack concomitant ] release (i.e., it may be a ] (SDRA)).<ref name="GuajardoVelásquezRaby2020">{{cite journal \| vauthors = Guajardo FG, Velásquez VB, Raby D, Núñez-Vivanco G, Iturriaga-Vásquez P, España RA, Reyes-Parada M, Sotomayor-Zárate R \| title = Pharmacological Characterization of 4-Methylthioamphetamine Derivatives \| journal = Molecules \| volume = 25 \| issue = 22 \| date = November 2020 \| page = 5310 \| pmid = 33203055 \| pmc = 7696343 \| doi = 10.3390/~~molecules25225310 \| doi-access = free \| url = }}</ref~~><ref name="Sotomayor-ZárateJaraAraos2014">{{cite journal \| vauthors = Sotomayor-Zárate R, Jara P, Araos P, Vinet R, Quiroz G, Renard GM, Espinosa P, Hurtado-Guzmán C, Moya PR, Iturriaga-Vásquez P, Gysling K, Reyes-Parada M \| title = Improving amphetamine therapeutic selectivity: N,N-dimethyl-MTA has dopaminergic effects and does not produce aortic contraction \| journal = Basic Clin Pharmacol Toxicol \| volume = 114 \| issue = 5 \| pages = 395–399 \| date = May 2014 \| pmid = 24314229 \| doi = 10.1111/~~bcpt.12168 \| url = }}</ref~~><ref name="GobbiFunicelloGerstbrein2008">{{cite journal \| vauthors = Gobbi M, Funicello M, Gerstbrein K, Holy M, Moya PR, Sotomayor R, Forray MI, Gysling K, Paluzzi S, Bonanno G, Reyes-Parada M, Sitte HH, Mennini T \| title = N,N-dimethyl-thioamphetamine and methyl-thioamphetamine, two non-neurotoxic substrates of 5-HT transporters, have scant in vitro efficacy for the induction of transporter-mediated 5-HT release and currents \| journal = J Neurochem \| volume = 105 \| issue = 5 \| pages = 1770–1780 \| date = June 2008 \| pmid = 18248615 \| pmc = 4502523 \| doi = 10.1111/~~j.1471-4159.2008.05272.x \| url = }}</ref~~> However, {{Abbr\|EC<sub>50</sub>\|half-maximal effective concentration}} values for monoamine release by 4-MTDMA were not reported.<ref name="Sotomayor-ZárateJaraAraos2014" /><ref name="GobbiFunicelloGerstbrein2008" /> 4-MTDMA is a ] of serotonin rather than a full releaser, with a ] for induction of serotonin release of either 25% or 50% relative to the full serotonin releasers ] or ] (PCA).<ref name="GobbiFunicelloGerstbrein2008" />		It has been described as an MRA of ] and ] that lacks induction of ] ] '']'' and hence may lack concomitant ] release (i.e., it may be a ] (SDRA)).<ref name="GuajardoVelásquezRaby2020"/><ref name="Sotomayor-ZárateJaraAraos2014"/><ref name="GobbiFunicelloGerstbrein2008"/> However, {{Abbr\|EC<sub>50</sub>\|half-maximal effective concentration}} values for monoamine release by 4-MTDMA were not reported.<ref name="Sotomayor-ZárateJaraAraos2014" /><ref name="GobbiFunicelloGerstbrein2008" /> 4-MTDMA is a ] of serotonin rather than a full releaser, with a ] for induction of serotonin release of either 25% or 50% relative to the full serotonin releasers ] or ] (PCA).<ref name="GobbiFunicelloGerstbrein2008" />

	In addition to its MRA activity, 4-MTDMA is a fairly ] ] (MAO-A) ], with an {{Abbrlink\|IC<sub>50</sub>\|half-maximal inhibitory concentration}} of 2,100{{nbsp}}nM.<ref name="Reyes-ParadaIturriaga-VasquezCassels2019">{{cite journal \| vauthors = Reyes-Parada M, Iturriaga-Vasquez P, Cassels BK \| title = Amphetamine Derivatives as Monoamine Oxidase Inhibitors \| journal = Front Pharmacol \| volume = 10 \| issue = \| pages = 1590 \| date = 2019 \| pmid = 32038257 \| pmc = 6989591 \| doi = 10.3389/fphar.2019.01590 \| doi-access = free \| url = }}</ref><ref name="Hurtado-GuzmánFierroIturriaga-Vásquez2003">{{cite journal \| vauthors = Hurtado-Guzmán C, Fierro A, Iturriaga-Vásquez P, Sepúlveda-Boza S, Cassels BK, Reyes-Parada M \| title = Monoamine oxidase inhibitory properties of optical isomers and N-substituted derivatives of 4-methylthioamphetamine \| journal = J Enzyme Inhib Med Chem \| volume = 18 \| issue = 4 \| pages = 339–47 \| date = August 2003 \| pmid = 14567549 \| doi = 10.1080/1475636031000118437 \| url = https://repositorio.uchile.cl/bitstream/handle/2250/119450/Hurtado_Guzman_Claudio.pdf }}</ref> Potent ] by amphetamines has been associated with dangerous and sometimes fatal ] in humans.<ref name="Reyes-ParadaIturriaga-VasquezCassels2019" /><ref name="Hurtado-GuzmánFierroIturriaga-Vásquez2003" />		In addition to its MRA activity, 4-MTDMA is a fairly ] ] (MAO-A) ], with an {{Abbrlink\|IC<sub>50</sub>\|half-maximal inhibitory concentration}} of 2,100{{nbsp}}nM.<ref name="Reyes-ParadaIturriaga-VasquezCassels2019">{{cite journal \| vauthors = Reyes-Parada M, Iturriaga-Vasquez P, Cassels BK \| title = Amphetamine Derivatives as Monoamine Oxidase Inhibitors \| journal = Front Pharmacol \| volume = 10 \| issue = \| pages = 1590 \| date = 2019 \| pmid = 32038257 \| pmc = 6989591 \| doi = 10.3389/fphar.2019.01590 \| doi-access = free \| url = }}</ref><ref name="Hurtado-GuzmánFierroIturriaga-Vásquez2003">{{cite journal \| vauthors = Hurtado-Guzmán C, Fierro A, Iturriaga-Vásquez P, Sepúlveda-Boza S, Cassels BK, Reyes-Parada M \| title = Monoamine oxidase inhibitory properties of optical isomers and N-substituted derivatives of 4-methylthioamphetamine \| journal = J Enzyme Inhib Med Chem \| volume = 18 \| issue = 4 \| pages = 339–47 \| date = August 2003 \| pmid = 14567549 \| doi = 10.1080/1475636031000118437 \| url = https://repositorio.uchile.cl/bitstream/handle/2250/119450/Hurtado_Guzman_Claudio.pdf }}</ref> Potent ] by amphetamines has been associated with dangerous and sometimes fatal ] in humans.<ref name="Reyes-ParadaIturriaga-VasquezCassels2019" /><ref name="Hurtado-GuzmánFierroIturriaga-Vásquez2003" />
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	==References==		==References==
	{{Reflist}}		{{Reflist}}


	{{Monoamine releasing agents}}		{{Monoamine releasing agents}}
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	{{Phenethylamines}}		{{Phenethylamines}}

	{{DEFAULTSORT:Dimethylthiomethamphetamine, N,N-}}		{{DEFAULTSORT:Dimethylthiomethamphetamine, N, N-}}

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Latest revision as of 05:13, 18 January 2025

Pharmaceutical compound

N,N-Dimethyl-4-methylthioamphetamine
Clinical data

Other names	DMMTA; N,N-Dimethyl-4-MTA; 4-Methylthio-N,N-dimethylamphetamine; 4-MTDMA; PAL-1062; PAL1062
Drug class	Monoamine releasing agent; Monoamine oxidase inhibitor; Entactogen
Identifiers
IUPAC name N,N-dimethyl-1-(4-methylsulfanylphenyl)propan-2-amine
PubChem CID	46882974
ChemSpider	24657499
ChEMBL	ChEMBL1078835
Chemical and physical data
Formula	C₁₂H₁₉NS
Molar mass	209.35 g·mol
3D model (JSmol)	Interactive image
SMILES CC(CC1=CC=C(C=C1)SC)N(C)C
InChI InChI=1S/C12H19NS/c1-10(13(2)3)9-11-5-7-12(14-4)8-6-11/h5-8,10H,9H2,1-4H3 Key:NFRBJBFYUNQIQP-UHFFFAOYSA-N

N,N-Dimethyl-4-methylthioamphetamine (DMMTA or N,N-dimethyl-4-MTA; code name PAL-1062), also known as 4-methylthio-N,N-dimethylamphetamine (4-MTDMA), is a monoamine releasing agent (MRA) of the amphetamine family related to 4-methylthioamphetamine (4-MTA) and 4-methylthiomethamphetamine (4-MTMA or NMMTA).

It has been described as an MRA of serotonin and dopamine that lacks induction of aortic contraction in vitro and hence may lack concomitant norepinephrine release (i.e., it may be a serotonin–dopamine releasing agent (SDRA)). However, EC₅₀ values for monoamine release by 4-MTDMA were not reported. 4-MTDMA is a partial releaser of serotonin rather than a full releaser, with a maximal efficacy for induction of serotonin release of either 25% or 50% relative to the full serotonin releasers MDMA or para-chloroamphetamine (PCA).

In addition to its MRA activity, 4-MTDMA is a fairly potent monoamine oxidase A (MAO-A) inhibitor, with an IC₅₀Tooltip half-maximal inhibitory concentration of 2,100 nM. Potent monoamine oxidase inhibition by amphetamines has been associated with dangerous and sometimes fatal toxicity in humans.

References

^ Guajardo FG, Velásquez VB, Raby D, Núñez-Vivanco G, Iturriaga-Vásquez P, España RA, et al. (November 2020). "Pharmacological Characterization of 4-Methylthioamphetamine Derivatives". Molecules. 25 (22): 5310. doi:10.3390/molecules25225310. PMC 7696343. PMID 33203055.
^ Sotomayor-Zárate R, Jara P, Araos P, Vinet R, Quiroz G, Renard GM, et al. (May 2014). "Improving amphetamine therapeutic selectivity: N,N-dimethyl-MTA has dopaminergic effects and does not produce aortic contraction". Basic Clin Pharmacol Toxicol. 114 (5): 395–399. doi:10.1111/bcpt.12168. PMID 24314229.
^ Gobbi M, Funicello M, Gerstbrein K, Holy M, Moya PR, Sotomayor R, et al. (June 2008). "N,N-dimethyl-thioamphetamine and methyl-thioamphetamine, two non-neurotoxic substrates of 5-HT transporters, have scant in vitro efficacy for the induction of transporter-mediated 5-HT release and currents". J Neurochem. 105 (5): 1770–1780. doi:10.1111/j.1471-4159.2008.05272.x. PMC 4502523. PMID 18248615.
^ Reyes-Parada M, Iturriaga-Vasquez P, Cassels BK (2019). "Amphetamine Derivatives as Monoamine Oxidase Inhibitors". Front Pharmacol. 10: 1590. doi:10.3389/fphar.2019.01590. PMC 6989591. PMID 32038257.
^ Hurtado-Guzmán C, Fierro A, Iturriaga-Vásquez P, Sepúlveda-Boza S, Cassels BK, Reyes-Parada M (August 2003). "Monoamine oxidase inhibitory properties of optical isomers and N-substituted derivatives of 4-methylthioamphetamine" (PDF). J Enzyme Inhib Med Chem. 18 (4): 339–47. doi:10.1080/1475636031000118437. PMID 14567549.

Monoamine releasing agents

DRAsTooltip Dopamine releasing agents

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 Fenethylline Fenproporex Flephedrone Fludorex Furfenorex Hordenine 4-Hydroxyamphetamine Iofetamine (123I) Lisdexamfetamine Lophophine Mefenorex Mephedrone Metamfepramone Methamphetamine Dextromethamphetamine Levomethamphetamine Methcathinone Methedrone MMDA MMDMA MBDB MDA (tenamfetamine) MDEA MDMA (midomafetamine) MDMPEA MDOH MDPEA Methylone Morforex Ortetamine pBA pCA pIA Pholedrine Phenethylamine Pholedrine Phenpromethamine Prenylamine Propylamphetamine Pseudoephedrine Tiflorex Tyramine Xylopropamine Zylofuramine
Piperazines: 2C-B-BZP BZP MBZP MDBZP MeOPP oMPP
Others: 2-ADN 2-AI 2-AT 4-BP 5-APDI 5-IAI Amineptine Clofenciclan Cyclopentamine Cypenamine Cyprodenate Feprosidnine Gilutensin Heptaminol Hexacyclonate Indanorex Isometheptene Methylhexanamine Naphthylaminopropane Octodrine Phthalimidopropiophenone Phenylbiguanide Propylhexedrine

NRAsTooltip Norepinephrine releasing agents

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 Tuaminoheptane

SRAsTooltip Serotonin releasing agents

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

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

Monoamine metabolism modulators

Non-specific

AAADTooltip Aromatic L-amino acid decarboxylase

Substrates→Products: L-DOPA (levodopa)→Dopamine
5-HTP→Serotonin
L-Histidine→Histamine
Phenylalanine→Phenethylamine
L-Tyrosine→Tyramine
Tryptophan→Tryptamine

MAOTooltip Monoamine oxidase

Substrates→Products (with ALDHTooltip Aldehyde dehydrogenase/ALRTooltip ALR): Epinephrine (adrenaline)→DHMA
Metanephrine→MHPG/VMA
Norepinephrine (noradrenaline)→DHMA
Normetanephrine→MHPG/VMA
Dopamine→DOPAC
3-Methoxytyramine→HVA
Serotonin→5-HIAA

Inhibitors: Non-selective: Benmoxin
Caroxazone
Echinopsidine
Furazolidone
Guineesine
Hydralazine
Indantadol
Iproclozide
Iproniazid
Isocarboxazid
Isoniazid
Linezolid
Mebanazine
Metfendrazine
Nialamide
Octamoxin
Paraxazone
Phenelzine
Pheniprazine
Phenoxypropazine
Pivhydrazine
Procarbazine
Safrazine
Tranylcypromine

Inhibitors: MAO-A-selective: Amiflamine
Bazinaprine
Befloxatone
Brofaromine
Cimoxatone
Clorgiline
CX157 (Tyrima)
Eprobemide
Esuprone
Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine)
Methylene blue
Metralindole
Minaprine
Moclobemide
Pirlindole
Sercloremine
Tetrindole
Toloxatone

Inhibitors: MAO-B selective: Adarigiline
Almoxatone
D-Deprenyl
Desmethylselegiline
Ethanol
Ladostigil
Lazabemide
Milacemide
Mofegiline
Nicotine
Pargyline
Rasagiline
Safinamide
Selegiline (L-Deprenyl)
Sembragiline
Tisolagiline
Vafidemstat

Phenethylamines
(dopamine, epinephrine,
norepinephrine)

PAHTooltip Phenylalanine hydroxylase	Substrates→Products: Phenylalanine→Tyrosine Inhibitors: 3,4-Dihydroxystyrene α-Methylphenylalanine
THTooltip Tyrosine hydroxylase	Substrates→Products: Tyrosine→L-DOPA (levodopa) Inhibitors: 2-Hydroxyestradiol 2-Hydroxyestrone 3-Iodotyrosine α-Methyl-5-hydroxytryptophan (α-Me-5-HTP) α-Methylphenylalanine Aquayamycin Bulbocapnine Methyldopa (α-methyl-L-DOPA) Metirosine (α-methyl-p-tyrosine) Oudenone
DBHTooltip Dopamine beta-hydroxylase	Substrates→Products: Dopamine→Norepinephrine (Noradrenaline) Inhibitors: Bupicomide Disulfiram Dopastin Etamicastat Fusaric acid Nepicastat Phenopicolinic acid Tropolone Zamicastat
PNMTTooltip Phenylethanolamine N-methyltransferase	Substrates→Products: Norepinephrine (noradrenaline)→Epinephrine (adrenaline) Inhibitors: CGS-19281A SKF-64139 SKF-7698
COMTTooltip Catechol-O-methyl transferase	Substrates→Products: Dopamine→3-Methoxytyramine DOPAC→Homovanillic acid Norepinephrine→Normetanephrine Epinephrine→Metanephrine DOPEG→MOPEG DOMA→VMA 2-Hydroxyestradiol→2-Methoxyestradiol 2-Hydroxyestrone→2-Methoxyestrone 4-Hydroxyestradiol→4-Methoxyestradiol 4-Hydroxyestrone→4-Methoxyestrone Inhibitors: 2-Hydroxyestradiol 2-Hydroxyestrone Entacapone Nebicapone Neluxicapone Nitecapone Opicapone Quinalizarin Tolcapone

Tryptamines
(serotonin, melatonin)

TPHTooltip Tryptophan hydroxylase

Substrates→Products: Tryptophan→5-HTP

AANATTooltip Serotonin N-acetyl transferase

Substrates→Products: Serotonin→N-Acetylserotonin

ASMTTooltip Acetylserotonin O-methyltransferase

Substrates→Products: N-Acetylserotonin→Melatonin

Histamine

HDCTooltip Histidine decarboxylase

Substrates→Products: L-Histidine→Histamine

HNMTTooltip Histamine N-methyltransferase

Substrates→Products: Histamine→N-Methylhistamine

DAOTooltip Diamine oxidase

Substrates→Products: Histamine→Imidazole acetic acid

Inhibitors: Pimagedine (aminoguanidine)

See also: Receptor/signaling modulators • Adrenergics • Dopaminergics • Melatonergics • Serotonergics • Monoamine reuptake inhibitors • Monoamine releasing agents • Monoamine neurotoxins

v t e Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine Phenpromethamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-AL 3C-BZ 3C-E 3C-MAL 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA ZDCM-04 Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L-Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DiFMDA Selegiline (also D-Deprenyl)
Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine
Cathinones	Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone
Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D-DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L-DOPA (Levodopa) L-DOPS (Droxidopa) L-Phenylalanine L-Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101 Venlafaxine

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