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3-Methoxy-4-methylamphetamine

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From Wikipedia, the free encyclopedia

Entactogen and psychedelic drug of the phenethylamine and amphetamine classes

Not to be confused withmeta-Methoxyamphetamine.

Pharmaceutical compound

MMA
Clinical data

Routes of administration	Oral
ATC code	None
Legal status
Legal status	DE: NpSG (Industrial and scientific use only) UK: Class A US: Schedule I (isomer of PMMA)
Identifiers
IUPAC name 1-(3-methoxy-4-methylphenyl)propan-2-amine
CAS Number	24160-29-0^Y
PubChemCID	91253
ChemSpider	82402^Y
UNII	BHS67KQE5Q
ChEMBL	ChEMBL47696^Y
CompTox Dashboard(EPA)	DTXSID401007386
Chemical and physical data
Formula	C₁₁H₁₇NO
Molar mass	179.263 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES COc1cc(CC(N)C)ccc1C
InChI InChI=1S/C11H17NO/c1-8-4-5-10(6-9(2)12)7-11(8)13-3/h4-5,7,9H,6,12H2,1-3H3^Y Key:XDXMRSBXBOXSQW-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)

3-Methoxy-4-methylamphetamine (MMA) is anentactogen andpsychedelic drug of thephenethylamine andamphetamine classes.^[1]^[2] It was firstsynthesized in 1970^[1] and was encountered as astreet drug inItaly in the same decade.^[3] MMA was largely forgotten until being reassayed byDavid E. Nichols as a non-neurotoxic MDMA analogue in 1991,^[2] and has subsequently been sold as adesigner drug on the internet since the late 2000s.^{[citation needed]}

In animal studies, MMA fully substitutes forMDMA andMBDB, partially substitutes forLSD, and does not substitute foramphetamine in rodentdrug discrimination tests.^[2] However, in another study, MMA fully substituted fordextroamphetamine in such tests.^[4] Additionally, it has been shown to be apotent and highlyselective serotonin releasing agent (SSRA) and does not produceserotonergic neurotoxicity in rodents.^[5]^[2]^[6] These data appear to confer a profile of MMA as aselective serotonin releasing agent (SSRA) andserotonin 5-HT_2A receptor agonist.^[2]

In humans, MMA has been reported to behallucinogenic, "quitedypshoric", and long-lasting.^[7] The active doses have been reported to be 40 to 60 mg.^[7]Capsules containing 140 mg have been encountered as a designer drug inItaly in the 1980s.^[7]

The2-aminoindane analogue of MMA is5-methoxy-6-methyl-2-aminoindane (MMAI).^[8]^[6]

References

[edit]

^^a ^bHo BT, McIsaac WM, An R, Tansey LW, Walker KE, Englert LF, Noel MB (January 1970). "Analogs of alpha-methylphenethylamine (amphetamine). I. Synthesis and pharmacological activity of some methoxy and/or methyl analogs".Journal of Medicinal Chemistry.13 (1):26–30.doi:10.1021/jm00295a007.PMID 5412110.
^^a ^b ^c ^d ^eJohnson MP, Frescas SP, Oberlender R, Nichols DE (May 1991). "Synthesis and pharmacological examination of 1-(3-methoxy-4-methylphenyl)-2-aminopropane and 5-methoxy-6-methyl-2-aminoindan: similarities to 3,4-(methylenedioxy)methamphetamine (MDMA)".Journal of Medicinal Chemistry.34 (5):1662–1668.doi:10.1021/jm00109a020.PMID 1674539.
^de Zorzi C, Cavalli A (1974). "Un nuovo allucinogeno: la MMA (p-metil-m-metossi anfetamina)" [A new hallucinogen: MMA (p-methyl-m-methoxy amphetamine)].Zacchia (in Italian).49 (1):58–68.
^Glennon RA, Young R, Hauck AE (May 1985). "Structure-activity studies on methoxy-substituted phenylisopropylamines using drug discrimination methodology".Pharmacol Biochem Behav.22 (5):723–729.doi:10.1016/0091-3057(85)90520-9.PMID 3839309.
^Johnson MP, Conarty PF, Nichols DE (July 1991). "[3H]monoamine releasing and uptake inhibition properties of 3,4-methylenedioxymethamphetamine and p-chloroamphetamine analogues".Eur J Pharmacol.200 (1):9–16.doi:10.1016/0014-2999(91)90659-e.PMID 1685125.
^^a ^bRudnick G, Wall SC (February 1993). "Non-neurotoxic amphetamine derivatives release serotonin through serotonin transporters".Molecular Pharmacology.43 (2):271–276.doi:10.1016/S0026-895X(25)13609-2.PMID 8429828.
^^a ^b ^cShulgin A, Shulgin A (1991).Pihkal: A Chemical Love Story. Transform Press.ISBN 0-9630096-0-5.Some years ago a report appeared in the forensic literature of Italy, of the seizure of a small semi-transparent capsule containing 141 milligrams of a white powder that was stated to be a new hallucinogenic drug. This was shown to contain an analogue of DOM, 3-methoxy-4-methylamphetamine, or MMA. The Italian authorities made no mention of the net weight contained in each dosage unit, but it has been found that the active level of MMA in man is in the area of 40-60 milligrams. The compound can apparently be quite dysphoric, and long lived.
^Nichols DE, Marona-Lewicka D, Huang X, Johnson MP (1993)."Novel serotonergic agents".Drug des Discov.9 (3–4):299–312.PMID 8400010.

Entactogens

Phenethylamines

Non-ring-extended	Amphetamines:3-CMA 4-FA (PAL-303) 4-FMA 4-MA (PAL-313; Aptrol; normephedrine) 4-MMA (mephedrine) 4-MTA 4-MTMA (NMMTA; PAL-1063) MMA MMMA PMA PMEA PMMA Phenylisobutylamines:4-CAB (AEPCA) Cathinones:3-CMC (clophedrone; βk-3-CMA) 3-MMC (metaphedrone; βk-3-MMA) 4-EMC (βk-4-EMA) Brephedrone (4-BMC; βk-4-BMA) Flephedrone (4-FMC; βk-4-FMA) Mephedrone (4-MMC; 4-methylephedrone; βk-4-MMA) Methedrone (PMMC; βk-PMMA)
Benzodioxoles (methylenedioxy- or MDxx)	Phenethylamines:Lophophine (MMDPEA) Amphetamines:2-Methyl-MDA 3,4-MDA (tenamfetamine) 5-Methyl-MDA 6-Methyl-MDA DFMDA EIDA Lys-MDA MDEA (MDE) MDMA (midomafetamine; ecstasy) (R)-MDMA (EMP-01; MM-402) MDMA/citalopram MDMOH (FLEA; MDHMA) MDOH (MDH) MMDA (5-methoxy-MDA) MMDMA (5-methoxy-MDMA) N-t-BOC-MDMA Phenylisobutylamines:BDB (J) EBDB (Ethyl-J) MBDB (Methyl-J) Phentermines:MDMP MDPH Cathinones:5-Methoxymethylone (2-A1MP; βk-MMDMA) 5-Methylethylone (5-methyl-βk-MDEA) Butylone (βk-MBDB) Dimethylone (βk-MDDMA) Ethylone (MDEC; βk-MDEA) Eutylone (βk-EBDB) Methylenedioxycathinone (MDC; βk-MDA) Methylone (MDMC; βk-MDMA) Putylone (βk-PBDB)
Benzodioxines (ethylenedioxy-)	Amphetamines:EDA EDMA Cathinones:EDMC
Benzofurans	Amphetamines:4-APB 5-APB 5-EAPB 5-MAPB 6-APB 6-EAPB 6-MAPB 7-APB Phenylisobutylamines:5-MBPB (5-MABB) 6-MBPB (6-MABB) Cathinones:BK-5-MAPB BK-6-MAPB
Dihydrobenzofurans	Amphetamines:5-APDB (EMA-4) 5-MAPDB 6-APDB (EMA-3) 6-MAPDB IBF5MAP (5-MAPP)
Benzothiophenes	Amphetamines:4-APBT 5-APBT 5-MAPBT(MY400) 6-APBT 6-MAPBT (MY300) 7-APBT Cathinones:BK-5-MAPBT
Benzothiazoles	Amphetamines:5-BZT-MDA 5-BZT-MDMA 6-BZT-MDA 6-BZT-MDMA
Benzoxathioles	Amphetamines:MY100 MY101 MY200
Indanes	Amphetamines:5-APDI (IAP) 5-MAPDI (IMP)
Indoles	Amphetamines:5-API (5-IT; PAL-571) 6-API (6-IT)
Naphthalenes	Amphetamines:Ethylnaphthylaminopropane (ENAP; PAL-1045) Methamnetamine (MNAP; PAL-1046; MY-10) Naphthylaminopropane (NAP; PAL-287)
Tetralins	Amphetamines:6-APT (TAP) Cathinones:TH-PVP
Others	Amphetamines:ODMA SeDMA TDMA Unknown:MYCO-002 MYCO-006 MYCO-007

Cyclized
phenethylamines

2-Aminoindanes	5-IAI BFAI ETAI MDAI MDMAI MEAI (5-MeO-AI; CMND-100) MMAI TAI
1-Aminomethylindanes	AMMI
2-Aminotetralins	6-CAT MDAT MDMAT
Aminorexes	4,4'-DMAR MDMAR

Tryptamines

α-Alkyltryptamines	4-Methyl-αET 5-Chloro-αMT (PAL-542) 5-Fluoro-αET (PAL-545) 5-Fluoro-αMT (PAL-212, PAL-544) αET (etryptamine; Monase; PAL-125) αMT (Indopan; PAL-17; 3-API; 3-IT) β-Ketotryptamines:BK-NM-AMT BK-5Br-NM-AMT BK-5Cl-NM-AMT BK-5F-NM-AMT

Others

Benzofurans	2-APB 2-MAPB 3-APB
Benzothiophenes	2-APBT 3-APBT (SKF-6678)
Indolizines	1Z2MAP1O
Isotryptamines	isoAMT (PAL-569; 1-API; 1-IT)
Others	Borax combo (Blue Bliss, Pink Star) MDM1EA (α,N-DMMDBA) UnknownTACT411 TACT833 Atypical:2C-B 5-MeO-DiPT 5-MeO-MiPT

Psychedelics

Tryptamines

No ring subs.	CYB004 (deuDMT) DALT DBT DET (T-9) DiPT DMT DPT EiPT EPT iPALT (ALiPT) MALT MET MiPT MPT NBoc-DMT NMT PALT PiPT Tryptamine (T)
4-Hydroxytryptamines	4-HO-DALT (daltocin) 4-HO-DBT 4-HO-DET (ethocin; CZ-74) 4-HO-DiPT (iprocin) 4-HO-DPT (deprocin) 4-HO-EPT (eprocin) 4-HO-MALT (maltocin) 4-HO-McPT 4-HO-MET (metocin) 4-HO-MiPT (miprocin) 4-HO-MPT (meprocin) 4-HO-NALT 4-HO-NBnT 4-HO-NET 4-HO-NiPT 4-HO-NPT 4-HO-T 4-HO-TMT 4-HO-5-MeO-DMT 4-MeO-DMT CYB003 (deupsilocin) Psilocin (4-HO-DMT; CX-59) 4-Phosphoryloxytryptamines:Aeruginascin (4-PO-TMT) Baeocystin (4-PO-NMT) Ethocybin (4-PO-DET; CEY-19) Norbaeocystin (4-PO-T) Psilocybin (4-PO-DMT; CY-39) 4-Acetoxytryptamines:4-AcO-DALT (daltacetin) 4-AcO-DET (ethacetin) 4-AcO-DiPT (ipracetin) 4-AcO-DMT (psilacetin) 4-AcO-DPT (depracetin) 4-AcO-MALT 4-AcO-MET (metacetin) 4-AcO-MiPT (mipracetin) 4-GO-DMT (RE-109) 4-PrO-DiPT 4-PrO-DMT Luvesilocin (4-GO-DiPT; RE-104, FT-104)
5-Hydroxytryptamines	Bufotenin (5-HO-DMT) Serotonin (5-HT; 5-HO-T) 5-Acetoxytryptamines:O-Acetylbufotenine (5-AcO-DMT) O-Pivalylbufotenine (5-t-BuCO-DMT)
5-Methoxytryptamines	4-HO-5-MeO-DMT 5-MeO-2,N,N-TMT 5-MeO-DALT 5-MeO-DBT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT (mebufotenin) 5-MeO-DPT 5-MeO-EiPT 5-MeO-MALT 5-MeO-MET 5-MeO-MiPT 5-MeO-NiPT 5-MeO-NMT ASR-3001 (5-MeO-iPALT)
Other ring subs.	2,N,N-TMT 5-Bromo-DMT 5-Chloro-DMT 5-Fluoro-DMT 5-N,N-TMT 7,N,N-TMT 5-MeO-2,N,N-TMT 6-Fluoro-DMT 6-Hydroxy-DET (6-HO-DET) Bretisilocin (GM-2505; 5-fluoro-MET)
α-Alkyltryptamines	4-HO-AMT 4-Methyl-AMT 5-Fluoro-AMT 6-Fluoro-AMT AMT (Indopan) α-Methylserotonin (5-HO-αMT) α,N,N-TMT (α-Me-DMT; Alpha-N) N-Hydroxy-AMT 5-Methoxy-α-alkyltryptamines:5-MeO-AET 5-MeO-AMT (α,O-DMS; Alpha-O) α,N,O-TMS (5-MeO-α,N-DMT) α,N,N,O-TeMS (5-MeO-α,N,N-TMT)
Others	N-DEAOP-Ts (e.g.,N-DEAOP-NET,N-DEAOP-NMT,5-MeO-N-DEAOP-NMT,5-MeO-N-DEAOP-NET) Structure undisclosed:CT-4201 EB-002 (EB-373) MSP-1014 MYCO-004
Cyclized	Ergolines/lysergamides (e.g.,LSD) β-Carbolines andHarmala alkaloids (e.g.,harmine,harmaline,6-methoxyharmalan) Iboga alkaloids (e.g.,18-MAC,18-MC,coronaridine,ibogaine,ibogamine,ME-18-MC,noribogaine,tabernanthine,voacangine) Ibogalogs (e.g.,ibogainalog) O-Methylnordehydrobufotenine Partial ergolines (e.g.,NDTDI,RU-28306,CT-5252) Piperidinylethylindoles (e.g.,pip-T) Pyrrolidinylethylindoles (e.g.,pyr-T,5-MeO-pyr-T) Pyrrolidinylmethylindoles (e.g.,MPMI,4-HO-MPMI (lucigenol),5-MeO-MPMI) Tetrahydropyridinylindoles (e.g.,RU-28253 (5-MeO-THPI),NEtPhOH-THPI)
Bioisosteres	Benzofurans (e.g.,5-MeO-DiBF,dimemebfe (5-MeO-BFE),mebfap) Benzothiophenes (e.g.,3-APBT) Indazolethylamines (e.g.,AL-38022A,O-methyl-AL-34662) Indenylethylamines (e.g.,C-DMT) Isotryptamines (e.g.,6-MeO-isoDMT,Ro60-0175) MYCO-005 Quinolinylethylamines (e.g.,mefloquine)

Phenethylamines

Scalines	2-Bromomescaline 3-TE 3-TM 4-Desoxymescaline (DESOXY) 4-TE 4-TM Allylescaline Beta-D Cyclopropylmescaline Difluoroescaline Difluoromescaline N,N-Diformylmescaline Escaline Fluoroescaline Fluoroproscaline N-Formylmescaline Isobuscaline Isoproscaline Jimscaline Mescaline (3,4,5-TMPEA) Metadifluoromescaline (MDFM) Metaescaline Methallylescaline N-Methylmescaline (M-M) NBOMe-escaline NBOMe-mescaline Proscaline Thioproscaline Tomscaline Trichocereine (N,N-dimethylmescaline; MM-M) Trifluoroescaline Trifluoromescaline
2C-x	2C-B 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-H 2C-I 2C-iBu 2C-iP 2C-N 2C-NH2 2C-P 2C-Se 2C-Se-TFM 2C-tBu 2C-TFE 2C-TFM 2C-YN 2C-V 2C-T-x: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 CYB210010 (2C-T-TFM, 2C-T-36) 2C-O-x:2C-O 2C-O-2 2C-O-4 Others:2C-B-AN 2C-DB 2C-G-x (e.g.,2C-G-3,2C-G-5) β-Keto-2C-B (βk-2C-B) β-Keto-2C-I (βk-2C-I) β-Methyl-2C-B (BMB) BOx (e.g.,BOB,BOD,BOH-2C-B) HOT-x (e.g.,HOT-2,HOT-7,HOT-17) N-Ethyl-2C-B TWEETIOs (e.g.,2CD-2-ETO,2CD-5-ETO,2CE-5-ETO,2CE-5iPrO,2CT2-5-ETO,ASR-2001 (2CB-5PrO))
3C-x	3C-AL 3C-BZ 3C-DFE 3C-E 3C-MAL 3C-P TMA (3C-M)
DOx	DOAM DOB DOBU DOC DOEF DOET DOH (2,5-DMA) DOI DOIB DOIP DOM DON DOPR DOTFM DOYN Aleph-x (DOT-x):Aleph (DOT) Aleph-2 Aleph-4 Aleph-6 Aleph-7 TMA-2 and derivatives (Mxx):MALM MEM MDFEM MFEM MIPM MMALM MPM MTFEM TMA-2 Others:DODB DODC DOM-NBOMe DOTMA Ganeshas (G-x) (e.g.,Ganesha (G, G-0) N-Hydroxy-DOM
4C-x	4C-B 4C-C 4C-D (Ariadne) 4C-E 4C-I 4C-N 4C-P 4C-T-2
Ψ-PEA	Ψ-2C-DFMO (ψ-2C-O-35) Ψ-2C-T-4 Ψ-DODFMO Ψ-DOM TMA-6 (Ψ-TMA-2)
MDxx	5-Methyl-MDA 6-Methyl-MDA DMMDA DMMDA-2 EIDA EMDA-2 IDA Lophophine (MMDPEA) Lys-MDA MDA (tenamfetamine) MDHMA MDMA (midomafetamine; ecstasy) MDOH MMDA MMDA-2 MMDA-3a MMDA-3b MMDMA N-t-BOC-MDMA (R)-MDMA
FLY	2C-B-FLY 2C-B-BUTTERFLY 2C-B-DragonFLY 2C-B-DragonFLY-NBOH 2C-B-FLY-NB2EtO5Cl 2CB-5-hemifly 2CBFly-NBOMe Bromo-DragonFLY DOB-FLY DOH-FLY TFMFly
25x-NB (NBOMes)	25x-NBOMe:25B-NBOMe 25C-NBOMe 25CN-NBOMe 25D-NBOMe 25E-NBOMe 25F-NBOMe 25G-NBOMe 25H-NBOMe 25I-NBOMe 25iP-NBOMe 25N-NBOMe 25O-NBOMe 25P-NBOMe 25T-NBOMe 25T2-NBOMe 25T4-NBOMe 25T7-NBOMe 25TFM-NBOMe 25x-NBOH:25B-NBOH 25C-NBOH 25CN-NBOH 25D-NBOH 25E-NBOH 25I-NBOH 25P-NBOH Others:25B-NB (N-benzyl-2C-B) 2C-B-AN 2C2-NBOMe 2CBCB-NBOMe 2CBFly-NBOMe DOM-NBOMe NBOMe-escaline NBOMe-mescaline TGF-8027
Others	2-TOET 2-TOM 25B-NAcPip 4-HA 5-TOET 5-TOM Benzofurans (e.g.,5-APB,5-APDB,6-APB,6-APDB,F,F-2,F-22) Benzothiophenes (e.g.,5-APBT,6-APBT) CT-5172 DMAs (e.g.,2,4-DMA,3,4-DMA) Fenfluramine MMA (3-MeO-4-MA) Norfenfluramine PEA-NDEPAs (e.g.,25D-NM-NDEAOP,DOB-NDEPA,DOI-NDEPA,DOM-NDEPA,DOTFM-NDEPA,M-NDEPA,TMA-2-NDEPA) PMA (4-MA) TMAs (e.g.,TMA-3,TMA-4,TMA-5) TOMSO ZDCM-04 Structure undisclosed:CYB005
Cyclized	1-Aminomethylindanes (e.g.,2CB-Ind,jimscaline) 2-Aminoindanes (e.g.,DOM-AI) 3-Benzazepines (e.g.,lorcaserin) 3-Phenylpiperidines (e.g.,LPH-5,LPH-48) Benzocyclobutenes (e.g.,2CBCB-NBOMe,TCB-2,tomscaline) Benzoxepins (e.g.,BBOX,IBOX,TFMBOX) DMBMPP (juncosamine) Ergolines/lysergamides (e.g.,LSD) Glaucine Partial ergolines (e.g.,NDTDI,DEIMDHPCA,DEMPDHPCA,DEMTMPDHPCA,DEMNDHPCA) Phenylcyclopropylamines (e.g.,DMCPA,TMT) Phenyloxazolamines (aminorexes) (e.g.,2C-B-aminorex) Pyridopyrroloquinoxalines (e.g.,IHCH-7113) Z3517967757 ZC-B

Lysergamides

1-Alkyllysergamides (prodrugs):Methysergide (1-methylmethylergonovine; UML-491)
MLA-74 (1-methyl-LAE)
MLD-41 (1-methyl-LSD)
MPD-75 (1-methyl-LPD)
OML-632 (1-hydroxymethyl-LSD)

Other ring system-substituted lysergamides:12-Hydroxy-LSD
12-Methoxy-LSD

Bioisosteres:JRT

Others

Arylpiperazines (e.g.,2C-B-PP,2-NP,mCPP,MK-212,ORG-12962,pCPP,pFPP,quipazine,TFMPP)
Dihydrobenzoxazines (e.g.,efavirenz)
Phenoxyethylamines (e.g.,CT-4719,ORG-37684)
Pyridopyrroloquinoxalines (e.g.,IHCH-7113)
Quinazolinylethylamines (e.g.,RH-34)

Natural sources

Cyclized tryptamines:Banisteriopsis caapi (yagé)
Peganum harmala (Syrian rue)
Silene undulata
Tabernanthe iboga (iboga)

Phenethylamines:Pachycereus pringlei (saguesa, elephant cactus, cardon)
Peyote (Lophophora williamsii; peyotl)
Echinopsis cacti (e.g.,San Pedro,Peruvian torch)

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 (alsoD-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 MMDA-3b 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

Serotonin receptor modulators

5-HT₁

5-HT_1A

Agonists:4-F-5-MeO-pyr-T 5-MeO-pip-T 5-MeO-pyr-T 8-OH-DPAT Adatanserin Amphetamine Antidepressants (e.g.,etoperidone,hydroxynefazodone,nefazodone,trazodone,triazoledione,vilazodone,vortioxetine) Atypical antipsychotics (e.g.,aripiprazole,asenapine,brexpiprazole,cariprazine,clozapine,lurasidone,quetiapine,ziprasidone) Azapirones (e.g.,buspirone,eptapirone,gepirone,perospirone,tandospirone) Bay R 1531 Befiradol BMY-14802 Cannabidiol Dimemebfe Dopamine Ebalzotan Eltoprazine Enciprazine Ergolines (e.g.,bromocriptine,cabergoline,dihydroergotamine,ergotamine,lisuride,LSD,methylergometrine (methylergonovine),methysergide,pergolide) F-11461 F-12826 F-13714 F-14679 F-15063 F-15599 Flesinoxan Flibanserin Flumexadol Hypidone Lesopitron LY-293284 LY-301317 mCPP MKC-242 Naluzotan NBUMP Osemozotan Oxaflozane Pardoprunox Piclozotan Rauwolscine Repinotan Roxindole RU-24969 S-14506 S-14671 S-15535 Sarizotan Serotonin (5-HT) SSR-181507 Sunepitron Tryptamines (e.g.,5-CT,5-MeO-DMT,5-MT,bufotenin,DMT,indorenate,N-Me-5-HT,psilocin,psilocybin) TGBA01AD TMU4142 U-92016-A Urapidil Vilazodone Xaliproden Yohimbine
Positive allosteric modulators:Oleamide
Antagonists:Atypical antipsychotics (e.g.,iloperidone,risperidone,sertindole) AV965 Beta blockers (e.g.,alprenolol,carteolol,cyanopindolol,iodocyanopindolol,isamoltane,oxprenolol,penbutolol,pindobind,pindolol,propranolol,tertatolol) BMY-7378 CSP-2503 Dotarizine Ergolines (e.g.,metergoline) FCE-24379 Flopropione GR-46611 Isamoltane Lecozotan Mefway Metitepine (methiothepin) MIN-117 (WF-516) MPPF NAN-190 Robalzotan S-15535 SB-649915 SDZ 216-525 Spiperone Spiramide Spiroxatrine UH-301 WAY-100135 WAY-100635 Xylamidine
Unknown/unsorted:Acetryptine Carvedilol Ergolines (e.g.,ergometrine (ergonovine))

5-HT_1B

Agonists:Anpirtoline AZ10419369 Benzofurans (e.g.,5-MAPB,6-MAPB,BK-5-MAPB,BK-6-MAPB) Benzothiophenes (e.g.,5-MAPBT,6-MAPBT,BK-5-MAPBT) CGS-12066A CP-93129 CP-94253 CP-122288 CP-135807 Eltoprazine Ergolines (e.g.,bromocriptine,dihydroergotamine,ergotamine,methylergometrine (methylergonovine),methysergide,pergolide) mCPP Methylenedioxyphenethylamines (e.g.,MDMA,methylone) PZKKN-94 RU-24969 Serotonin (5-HT) Triptans (e.g.,avitriptan,donitriptan,eletriptan,sumatriptan,zolmitriptan) TFMPP Tryptamines (e.g.,5-BT,5-CT,5-MT,DMT) Vortioxetine
Antagonists:AR-A000002 Beta blockers (e.g.,alprenolol,carteolol,isamoltane,oxprenolol,penbutolol,propranolol,tertatolol) Elzasonan Ergolines (e.g.,metergoline) GR-127935 Isamoltane LY-393558 Metitepine (methiothepin) SB-216641 SB-224289 SB-236057 Yohimbine
Unknown/unsorted:Ergolines (e.g.,cabergoline,ergometrine (ergonovine),lisuride)

5-HT_1D

Agonists:CP-122288 CP-135807 CP-286601 Ergolines (e.g.,bromocriptine,cabergoline,dihydroergotamine,ergotamine,LSD,methysergide) GR-46611 L-694247 L-772405 mCPP PNU-109291 PNU-142633 Serotonin (5-HT) TGBA01AD Triptans (e.g.,almotriptan,avitriptan,donitriptan,eletriptan,frovatriptan,naratriptan,rizatriptan,sumatriptan,zolmitriptan) Tryptamines (e.g.,5-BT,5-CT,5-Et-DMT,5-MT,5-(nonyloxy)tryptamine,DMT)
Antagonists:Alniditan BRL-15572 Elzasonan Ergolines (e.g.,metergoline) GR-127935 Ketanserin LY-310762 LY-367642 LY-393558 LY-456219 LY-456220 Metitepine (methiothepin) Mianserin Ritanserin Yohimbine Ziprasidone
Unknown/unsorted:Acetryptine Ergolines (e.g.,lisuride,lysergol,pergolide)

5-HT_1E

Agonists:BRL-54443 Ergolines (e.g.,methysergide) Serotonin (5-HT) Triptans (e.g.,eletriptan) Tryptamines (e.g.,tryptamine)
Antagonists:Metitepine (methiothepin)
Unknown/unsorted:Ergolines (e.g.,ergometrine (ergonovine),lysergol,methylergometrine (methylergonovine)

5-HT_1F

Agonists:BRL-54443 CP-122288 Ergolines (e.g.,bromocriptine,lysergol,methylergometrine (methylergonovine)methysergide) Lasmiditan LY-334370 LY-344864 Serotonin (5-HT) Triptans (e.g.,eletriptan,naratriptan,sumatriptan) Tryptamines (e.g.,5-MT)
Antagonists:Metitepine (methiothepin) Mianserin

5-HT₂

5-HT_2A

Agonists: 25H/NB series (e.g.,25I-NBF,25I-NBMD,25I-NBOH,25I-NBOMe,25B-NBOMe,25C-NBOMe,25TFM-NBOMe,2CBCB-NBOMe,25CN-NBOH,2CBFly-NBOMe) 2Cs (e.g.,2C-B,2C-E,2C-I,2C-T-2,2C-T-7,2C-T-21) 2C-B-FLY 2CB-Ind 5-Methoxytryptamines (5-MeO-DET,5-MeO-DiPT,5-MeO-DMT,5-MeO-DPT,5-MT) α-Alkyltryptamines (e.g.,5-Cl-αMT,5-Fl-αMT,5-MeO-αET,5-MeO-αMT,α-Me-5-HT,αET,αMT) AL-34662 AL-37350A Bromo-DragonFLY Dimemebfe DMBMPP DOx (e.g.,DOB,DOC,DOI,DOM) Efavirenz Ergolines (e.g.,1P-LSD,ALD-52,bromocriptine,cabergoline,ergine (LSA),ergometrine (ergonovine),ergotamine,lisuride,LA-SS-Az,LSB,LSD,LSD-Pip,LSH,LSP,methylergometrine (methylergonovine),pergolide) Flumexadol IHCH-7113 Jimscaline Lorcaserin MDxx (e.g.,MDA (tenamfetamine),MDMA (midomafetamine),MDOH,MMDA) O-4310 Oxaflozane PHA-57378 PNU-22394 PNU-181731 RH-34 SCHEMBL5334361 Phenethylamines (e.g.,lophophine,mescaline) Piperazines (e.g.,BZP,quipazine,TFMPP) Serotonin (5-HT) TCB-2 TFMFly Tryptamines (e.g.,5-BT,5-CT,bufotenin,DET,DiPT,DMT,DPT,psilocin,psilocybin,tryptamine)
Positive allosteric modulators:CTW0404 CTW0419 JPC0323 (R)-Glaucine Oleamide
Antagonists:5-I-R91150 5-MeO-NBpBrT AC-90179 Adatanserin Altanserin Antihistamines (e.g.,cyproheptadine,hydroxyzine,ketotifen,perlapine) AMDA Atypical antipsychotics (e.g.,amperozide,aripiprazole,asenapine,blonanserin,brexpiprazole,carpipramine,clocapramine,clorotepine,clozapine,fluperlapine,gevotroline,iloperidone,lurasidone,melperone,mosapramine,ocaperidone,olanzapine,paliperidone,quetiapine,risperidone,sertindole,zicronapine,ziprasidone,zotepine) Chlorprothixene Cinanserin CSP-2503 Deramciclane Dotarizine Eplivanserin Ergolines (e.g.,amesergide,LY-53857,LY-215840,mesulergine,metergoline,methysergide,sergolexole) Fananserin Flibanserin Glemanserin Irindalone Ketanserin KML-010 Landipirdine LY-393558 mCPP Medifoxamine Metitepine (methiothepin) MIN-117 (WF-516) Naftidrofuryl Nantenine Nelotanserin Opiranserin (VVZ-149) Pelanserin Phenoxybenzamine Pimavanserin Pirenperone Pizotifen Pruvanserin Rauwolscine Ritanserin Roluperidone S-14671 Sarpogrelate Serotonin antagonists and reuptake inhibitors (e.g.,etoperidone,hydroxynefazodone,lubazodone,mepiprazole,nefazodone,triazoledione,trazodone) SR-46349B TGBA01AD Teniloxazine Temanogrel Tetracyclic antidepressants (e.g.,amoxapine,aptazapine,esmirtazapine,maprotiline,mianserin,mirtazapine) Tricyclic antidepressants (e.g.,amitriptyline) Typical antipsychotics (e.g.,chlorpromazine,fluphenazine,haloperidol,loxapine,perphenazine,pimozide,pipamperone,prochlorperazine,setoperone,spiperone,spiramide,thioridazine,thiothixene,trifluoperazine) Volinanserin Xylamidine Yohimbine
Unknown/unsorted:Ergolines (e.g.,dihydroergotamine,nicergoline)

5-HT_2B

Agonists:4-Methylaminorex Aminorex Amphetamines (e.g.,chlorphentermine,cloforex,dexfenfluramine,fenfluramine,levofenfluramine,norfenfluramine) BW-723C86 DOx (e.g.,DOB,DOC,DOI,DOM) Ergolines (e.g.,cabergoline,dihydroergocryptine,dihydroergotamine,ergotamine,methylergometrine (methylergonovine),methysergide,pergolide) Lorcaserin MDxx (e.g.,MDA (tenamfetamine),MDMA (midomafetamine),MDOH,MMDA) Piperazines (e.g.,TFMPP) PNU-22394 Ro60-0175 Serotonin (5-HT) Tryptamines (e.g.,5-BT,5-CT,5-MT,α-Me-5-HT,bufotenin,DET,DiPT,DMT,DPT,psilocin,psilocybin,tryptamine)
Antagonists:Agomelatine Atypical antipsychotics (e.g.,amisulpride,aripiprazole,asenapine,brexpiprazole,cariprazine,clozapine,N-desalkylquetiapine (norquetiapine),N-desmethylclozapine (norclozapine),olanzapine,pipamperone,quetiapine,risperidone,ziprasidone) Cyproheptadine EGIS-7625 Ergolines (e.g.,amesergide,bromocriptine,lisuride,LY-53857,LY-272015,mesulergine) Ketanserin LY-393558 mCPP Metadoxine Metitepine (methiothepin) Pirenperone Pizotifen Propranolol PRX-08066 Rauwolscine Ritanserin RS-127445 Sarpogrelate SB-200646 SB-204741 SB-206553 SB-215505 SB-221284 SB-228357 SDZ SER-082 Tegaserod Tetracyclic antidepressants (e.g.,amoxapine,mianserin,mirtazapine) Trazodone Typical antipsychotics (e.g.,chlorpromazine) TIK-301 Yohimbine
Unknown/unsorted:Ergolines (e.g.,ergometrine (ergonovine))

5-HT_2C

Agonists:2Cs (e.g.,2C-B,2C-E,2C-I,2C-T-2,2C-T-7,2C-T-21) 5-Methoxytryptamines (5-MeO-DET,5-MeO-DiPT,5-MeO-DMT,5-MeO-DPT,5-MT) α-Alkyltryptamines (e.g.,5-Cl-αMT,5-Fl-αMT,5-MeO-αET,5-MeO-αMT,α-Me-5-HT,αET,αMT) A-372159 AL-38022A Alstonine CP-809101 Dimemebfe DOx (e.g.,DOB,DOC,DOI,DOM) Ergolines (e.g.,ALD-52,cabergoline,dihydroergotamine,ergine (LSA),ergotamine,lisuride,LA-SS-Az,LSB,LSD,LSD-Pip,LSH,LSP,pergolide) Flumexadol Lorcaserin MDxx (e.g.,MDA (tenamfetamine),MDMA (midomafetamine),MDOH,MMDA) MK-212 ORG-12962 ORG-37684 Oxaflozane PHA-57378 Phenethylamines (e.g.,lophophine,mescaline) Piperazines (e.g.,aripiprazole,BZP,mCPP,quipazine,TFMPP) PNU-22394 PNU-181731 Ro60-0175 Ro60-0213 Serotonin (5-HT) Tryptamines (e.g.,5-BT,5-CT,bufotenin,DET,DiPT,DMT,DPT,psilocin,psilocybin,tryptamine) Vabicaserin WAY-629 WAY-161503 YM-348
Positive allosteric modulators:CTW0415 CYD-1-79 JPC0323 Oleamide PNU-69176E VA012 VA240
Antagonists:Adatanserin Agomelatine Atypical antipsychotics (e.g.,asenapine,clorotepine,clozapine,fluperlapine,iloperidone,melperone,olanzapine,paliperidone,quetiapine,risperidone,sertindole,ziprasidone,zotepine) Captodiame CEPC Cinanserin Cyproheptadine Deramciclane Desmetramadol Dotarizine Eltoprazine Ergolines (e.g.,amesergide,bromocriptine,LY-53857,LY-215840,mesulergine,metergoline,methysergide,sergolexole) Etoperidone Fluoxetine FR-260010 Irindalone Ketanserin Ketotifen Latrepirdine (dimebolin) Medifoxamine Metitepine (methiothepin) Nefazodone Pirenperone Pizotifen Propranolol Ritanserin RS-102221 S-14671 SB-200646 SB-206553 SB-221284 SB-228357 SB-242084 SB-243213 SDZ SER-082 Tedatioxetine Tetracyclic antidepressants (e.g.,amoxapine,aptazapine,esmirtazapine,maprotiline,mianserin,mirtazapine) TIK-301 Tramadol Trazodone Tricyclic antidepressants (e.g.,amitriptyline,nortriptyline) Typical antipsychotics (e.g.,chlorpromazine,loxapine,pimozide,pipamperone,thioridazine) Xylamidine
Unknown/unsorted:Efavirenz Ergolines (e.g.,ergometrine (ergonovine),methylergometrine (methylergonovine))

5-HT₃_–7

5-HT₃

Agonists:Alcohols (e.g.,butanol,ethanol (alcohol),trichloroethanol) m-CPBG Phenylbiguanide Piperazines (e.g.,BZP,mCPP,quipazine) RS-56812 Serotonin (5-HT) SR-57227 SR-57227A Tryptamines (e.g.,2-Me-5-HT,5-CT,bufotenidine (5-HTQ)) Volatiles/gases (e.g.,halothane,isoflurane,toluene,trichloroethane) YM-31636
Positive allosteric modulators:5-Aminoindole 5-Chloroindole 5-Hydroxyindole Catechol Chloroform meta-Chlorophenylbiguanide (mCPBG) Colchicine Ethanol (alcohol) Halothane Indole Isoflurane TMPPAA
Antagonists:Alosetron Anpirtoline Arazasetron AS-8112 Atypical antipsychotics (e.g.,clozapine,olanzapine,quetiapine) Azasetron Batanopride Bemesetron (MDL-72222) Cilansetron CSP-2503 Dazopride Dolasetron Galanolactone Granisetron Lerisetron Memantine Ondansetron Palonosetron Ramosetron Renzapride Ricasetron Tedatioxetine Tetracyclic antidepressants (e.g.,amoxapine,mianserin,mirtazapine) Thujone Tropanserin Tropisetron Typical antipsychotics (e.g.,loxapine) Volatiles/gases (e.g.,nitrous oxide,sevoflurane,xenon) Vortioxetine Zacopride Zatosetron
Negative allosteric modulators:Bupropion Colchicine Hydroxybupropion
Unknown/unsorted:LY-53857 Piperazines (e.g.,naphthylpiperazine)

5-HT₄

Agonists:5-MT BIMU8 Capeserod Cinitapride Cisapride CJ-033466 Dazopride Metoclopramide Minesapride Mosapride Prucalopride PRX-03140 Renzapride RS-67333 RS-67506 Serotonin (5-HT) Tegaserod Usmarapride Velusetrag Zacopride
Antagonists:GR-113808 GR-125487 L-Lysine Piboserod RS-39604 RS-67532 SB-203186 SB-204070

5-HT_5A

Agonists:Ergolines (e.g.,2-Br-LSD (BOL-148),ergotamine,LSD) Serotonin (5-HT) Tryptamines (e.g.,5-CT) UCSF648 Valerenic acid
Antagonists:Asenapine Latrepirdine (dimebolin) Metitepine (methiothepin) Ritanserin SB-699551 Unknown/unsorted:Ergolines (e.g.,metergoline,methysergide) Piperazines (e.g.,naphthylpiperazine)

5-HT₆

Agonists:Ergolines (e.g.,dihydroergocryptine,dihydroergotamine,ergotamine,lisuride,LSD,mesulergine,metergoline,methysergide) Hypidone Serotonin (5-HT) Tryptamines (e.g.,2-Me-5-HT,5-BT,5-CT,5-MT,Bufotenin,E-6801,E-6837,EMD-386088,EMDT,LY-586713,N-Me-5-HT,ST-1936,tryptamine) WAY-181187 WAY-208466
Antagonists:ABT-354 Atypical antipsychotics (e.g.,aripiprazole,asenapine,clorotepine,clozapine,fluperlapine,iloperidone,olanzapine,tiospirone) AVN-101 AVN-211 AVN-322 AVN-397 BGC20-760 BVT-5182 BVT-74316 Cerlapirdine EGIS-12233 GW-742457 Idalopirdine Ketanserin Landipirdine Latrepirdine (dimebolin) Masupirdine Metitepine (methiothepin) MS-245 PRX-07034 PZKKN-94 Ritanserin Ro 04-6790 Ro 63-0563 SB-258585 SB-271046 SB-357134 SB-399885 SB-742457 Tetracyclic antidepressants (e.g.,amoxapine,mianserin) Tricyclic antidepressants (e.g.,amitriptyline,clomipramine,doxepin,nortriptyline) Typical antipsychotics (e.g.,chlorpromazine,loxapine)
Unknown/unsorted:Ergolines (e.g.,2-Br-LSD (BOL-148),bromocriptine,lergotrile,pergolide) Piperazines (e.g.,naphthylpiperazine)

5-HT₇

Agonists:8-OH-DPAT AS-19 Bifeprunox E-55888 Ergolines (e.g.,LSD) LP-12 LP-44 LP-211 RU-24969 Sarizotan Serotonin (5-HT) Triptans (e.g.,frovatriptan) Tryptamines (e.g.,5-CT,5-MT,bufotenin,N-Me-5-HT)
Antagonists:Atypical antipsychotics (e.g.,amisulpride,aripiprazole,asenapine,brexpiprazole,clorotepine,clozapine,fluperlapine,olanzapine,risperidone,sertindole,tiospirone,ziprasidone,zotepine) Butaclamol DR-4485 EGIS-12233 Ergolines (e.g.,2-Br-LSD (BOL-148),amesergide,bromocriptine,cabergoline,dihydroergotamine,ergotamine,LY-53857,LY-215840,mesulergine,metergoline,methysergide,sergolexole) JNJ-18038683 Ketanserin LY-215840 Metitepine (methiothepin) Ritanserin SB-258719 SB-258741 SB-269970 SB-656104 SB-656104A SB-691673 SLV-313 SLV-314 Spiperone SSR-181507 Tetracyclic antidepressants (e.g.,amoxapine,maprotiline,mianserin,mirtazapine) Tricyclic antidepressants (e.g.,amitriptyline,clomipramine,imipramine) Typical antipsychotics (e.g.,acetophenazine,chlorpromazine,chlorprothixene,fluphenazine,loxapine,pimozide) Vortioxetine
Negative allosteric modulators:Oleamide
Unknown/unsorted:Ergolines (e.g.,lisuride,pergolide) Piperazines (e.g.,naphthylpiperazine)

See also:Receptor/signaling modulators
Adrenergics
Dopaminergics
Melatonergics
Monoamine reuptake inhibitors andreleasing agents
Monoamine metabolism modulators
Monoamine neurotoxins

Phenethylamines

Entactogens:Lophophine
MDPEA
MDMPEA

Amphetamines

Phentermines

Entactogens:MDPH
MDMPH

Others:Cericlamine

Cathinones

Phenylisobutylamines
(and further-extended)

Stimulants:α-Propylphenethylamine
Hexapradol
Phenylisobutylamine (α-ethylphenethylamine)

Catecholamines
(and close relatives)

Cyclized
phenethylamines

Phenylalkylpyrrolidines	α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP Fluorolintane MOPPP MOPVP MPBP MPEP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
2-Benzylpiperidines (phenidates)	2-Benzylpiperidine 3-Bromomethylphenidate 3-Chloromethylphenidate 3-Methylmethylphenidate 3,4-Dichloro-2-benzylpiperidine 3,4-Dichloroethylphenidate 3,4-Dichloromethylphenidate 4-Bromoethylphenidate 4-Bromomethylphenidate 4-Chloromethylphenidate 4-Fluoroethylphenidate 4-Fluoroisopropylphenidate 4-Fluoromethylphenidate 4-Methyl-2-benzylpiperidine 4-Methylisopropylphenidate 4-Methylmethylphenidate 4-Nitromethylphenidate α-Acetyl-2-benzylpiperidine α-Keto-2-benzylpiperidine CPMBP Desoxypipradrol (2-DPMP) Difemetorex Ethylnaphthidate (HDEP-28) Ethylphenidate Isopropylnaphthidate Isopropylphenidate MDMPH Methylnaphthidate (HDMP-28) Methylphenidate Phacetoperane Pipradrol Propylphenidate Rimiterol Ritalinamide Ritalinic acid SCH-5472 Serdexmethylphenidate
Phenylmorpholines (phenmetrazines)	(2R,3R)-Hydroxybupropion 2-(2,5-Dimethoxy-4-bromophenyl)morpholine 2-Fluorophenmetrazine 2-Methylphenmetrazine 2-Phenylmorpholine 2-Phenyl-3,6-dimethylmorpholine 3-Chlorophenmetrazine (PAL-594) 3-Fluorophenetrazine 3-Fluorophenmetrazine (PAL-593) 3-Methoxyphenmetrazine 3-Methylphenmetrazine (PAL-773) 4-Fluorophenmetrazine (PAL-748) 4-Methylphendimetrazine 4-Methylphenmetrazine (PAL-747) 2C-B-morpholine Fenbutrazate Fenmetramide Flumexadol G-130 Isophenmetrazine Manifaxine Methylenedioxyphenmetrazine Morazone N-Ethylphenmetrazol Naphthylmetrazine (PAL-704) Naphthylmorpholine (PAL-678) Oxaflozane PDM-35 PF-219,061) Phendimetrazine Phenetrazine Phenmetetrazine Phenmetrazine Phenmetrazol Pseudophenmetrazine Radafaxine ((2S,3S)-hydroxybupropion)
Phenyloxazolamines (aminorexes)	3-Methylaminorex 4-Ethylaminorex (4-EAR) 4'-Fluoroaminorex 4-Methylaminorex (4-MAR) 4,4'-Dimethylaminorex (4,4'-DMAR) 2C-B-aminorex 2F-MAR 4B-MAR 4C-MAR 4F-MAR Aminorex Clominorex Cyclazodone Ephedroxane Fenozolone Fluminorex MDMAR Methylenedioxyaminorex (MDAR) N-Methylcyclazodone N,N-Dimethylaminorex Pemoline Thozalinone
Isoquinolines and tetrahydroisoquinolines	Anhalamine Anhalidine Anhalinine Anhalonidine Anhalonine Anhalotine Arizonine Calycotomine Carnegine (pectenine) Corypalline Debrisoquine Deglucopterocereine Deutetrabenazine Diclofensine DOB-CR DOM-CR Esproquin Gigantine Hedycarine Heliamine Hydrastinine Hydrocotarnine Hydrohydrastinine (MDMTHIQ; MDMA-CR) Isoanhalamine Isoanhalidine Isoanhalonidine Isocorypalline Isopellotine Isosalsoline Lemaireocereine Longimammamine Longimammatine Longimammidine Longimammosine Lophocerine Lophophorine Lophotine MDMA-CR Mescalotam N-Methylanhalinine N-Methylheliamine N-Methylisosalsoline N-Methyl-DOM-CR (Beatrice-CR) N-Methyl-THIQ (METH-CR) Nomifensine Norsalsolinol Nortehaunine Norweberine O-Methylanhalonidine O-Methylpellotine Pachycereine Pellotine Perafensine Peyoglutam Peyophorine Peyotine PMMA-CR Quinisocaine Reticuline Salsolidine Salsoline Salsolinol TDIQ (MDTHIQ, MDA-CR) Tehaunine TehaunineN-oxide Tepenine Tetrabenazine Tetrahydroisoquinoline (THIQ; AMPH-CR) Tetrahydropapaveroline Tilisolol Tretoquinol Uberine Valbenazine Weberidine Weberine Zelandopam
2-Aminoindanes	2-Aminoindane (2-AI) 5-IAI Aprindine BFAI BFMAI DHAI DOM-AI ETAI Indantadol MDAI MDMAI MEAI (5-MeO-AI) MMAI NM-2-AI PNU-99,194 Pyr-AI TAI
2-Aminotetralins	2-Aminotetralin (2-AT) 5-OH-DPAT 6-CAT 7-OH-DPAT 8-OH-DPAT AS-19 CHF-1024 DOM-AT MDAT MDMAT Nolomirole UH-232
Others / unsorted	1-Aminomethylindanes (e.g.,2CB-Ind,AMMI,bromojimscaline,jimscaline) 2-ADN 2-Benzhydrylpyrrolidine 2C-B-5-hemiFLY-α6 (BNAP) 2C-B-PYR 2CBecca 2CB7 2CJP 2CLisaB 2CLisaH 3-Benzazepines (e.g.,fenoldopam,lorcaserin,7-chlorolorcaserin,SCHEMBL5334361) 3-Benzhydrylmorpholine 3-Phenylpiperidines (e.g.,3-phenylpiperidine,3-PPP,OSU-6162 (PNU-96391),LPH-5,LPH-48,Z3517967757 (Z7757)) 6-AB AL-1095 Aminochromes (e.g.,adrenochrome,adrenolutin) Benzocyclobutenes (e.g.,2CBCB-NBOMe,bromotomscaline,S33005,TCB-2,tomscaline) Benzoxepins (e.g.,BBOX,IBOX,TFMBOX) Butyltolylquinuclidine Camfetamine Cypenamine (trans-2-phenylcyclopentylamine) Diphenidine Diphenylprolinol DMBMPP Ergolines (e.g.,LSD) Fencamfamin GYKI-52895 HDMP-29 Ivabradine Methoxphenidine Methylmorphenate Milnacipran MT-45 2-Naphthylamine Org 6582 Partial ergolines (e.g.,NDTDI,RU-27849,DEIMDHPCA,DEMPDHPCA,DEMPDHPCA-2C-D,RU-27251) PF-592,379 Phenylcyclopropylamines (e.g.,DMCPA,TMT,tranylcypromine) Phenylpiracetams (e.g.,phenylpiracetam,MRZ-9547,RGPU-95) Pyridopyrroloquinoxalines (e.g.,lumateperone,deulumateperone,IHCH-7079,IHCH-7086,IHCH-7113,ITI-1549) Tetrahydrobenzopyranylamines (e.g.,CT-5126) Tolazoline Tricyclics (e.g.,AMDA,AMDH,benzoctamine,dizocilpine,SpAMDA) ZC-B

Related compounds

2-Furylethylamine
2-Pyrrolylethylamine
3-Pyrrolylethylamine
3-Pyrrolylpropylamine
2-Tetrahydrofurylethylamine
4-Benzylpiperidine
7-AB
Alkylamines (e.g.,1,3-DMBATooltip 1,3-dimethylbutylamine,1,4-DMAATooltip 1,4-dimethylamylamine,heptaminol,iproheptine,isometheptene,methylhexanamine/1,3-DMAA,octodrine,oenethyl,tuaminoheptane)
Benzylamines (e.g.,benzylamine,α-methylbenzylamine,MDM1EA,ALPHA,M-ALPHA,pargyline)
Benzylpiperazines (e.g.,benzylpiperazine,MDBZP,fipexide)
Cyclohexylaminopropanes (e.g.,propylhexedrine,norpropylhexedrine)
Cyclopentylaminopropanes (e.g.,isocyclamine,cyclopentamine)
Phenoxyethylamines (e.g.,3,4,5-trimethoxyphenoxyethylamine,CT-4719,ORG-37684)
Phenylalkenylamines (e.g.,phenylbutenamine)
Phenylalkynylamines (e.g.,phenylbutynamine)
Phenylpiperazines (e.g.,1-phenylpiperazine,mCPPTooltip meta-chlorophenylpiperazine,TFMPPTooltip trifluoromethylphenylpiperazine,oMPPTooltip ortho-methylphenylpiperazine,pFPPTooltip para-fluorophenylpiperazine,pMeOPPTooltip para-methoxyphenylpiperazine)
Phenylpropylamines (e.g.,phenylpropylamine,homo-MDA,homo-MDMA)
Thienylaminopropanes (thiopropamines) (e.g.,thiopropamine,methiopropamine,thiothinone)

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