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2C-N

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Pharmaceutical compound

2C-N
Clinical data


Other names	25N; 2,5-Dimethoxy-4-nitrophenethylamine; 4-Nitro-2,5-dimethoxyphenethylamine
Routes of administration	Oral^[1]
Drug class	Serotonin;5-HT₂ receptor agonist;Serotonergic psychedelic;Hallucinogen
ATC code	None
Pharmacokinetic data
Onset of action	≤30 minutes^[1]
Duration of action	4–6 hours^[1]
Identifiers
IUPAC name 2-(2,5-dimethoxy-4-nitrophenyl)ethan-1-amine
CAS Number	261789-00-8^Y
PubChemCID	10036637
ChemSpider	8212202^Y
UNII	BB2B23B11H
CompTox Dashboard(EPA)	DTXSID80180798
Chemical and physical data
Formula	C₁₀H₁₄N₂O₄
Molar mass	226.232 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES [O-][N+](=O)c1cc(OC)c(cc1OC)CCN
InChI InChI=1S/C10H14N2O4/c1-15-9-6-8(12(13)14)10(16-2)5-7(9)3-4-11/h5-6H,3-4,11H2,1-2H3^Y Key:ZMUSDZGRRJGRAO-UHFFFAOYSA-N^Y
(verify)

2C-N, also known as4-nitro-2,5-dimethoxyphenethylamine, is apsychedelic drug of thephenethylamine and2C families.^[1] It is takenorally.^[1]

2C-N was firstsynthesized byAlexander Shulgin and was described in his 1991 bookPiHKAL (Phenethylamines I Have Known and Loved).^[1]

Use and effects

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In his bookPiHKAL (Phenethylamines I Have Known and Loved),Alexander Shulgin lists 2C-N's dose range as 100 to 150 mg or moreorally and aduration of 4 to 6 hours.^[1]^[2] It has an estimated typical dose of about 120 mg orally.^[2] Itsonset is within 30 minutes and peak effects occur after 1 hour.^[1] The effects of 2C-N have been reported to include somevisual changes, similarities toMDMA,lightheadedness,eye wiggling, easier conversation, andimproved mood.^[1] It was described as a "strange material, but okay".^[1]

Interactions

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2C drugs like 2C-N are known to bemetabolized by themonoamine oxidase (MAO)enzymes MAO-A andMAO-B.^[3]^[4]Monoamine oxidase inhibitors (MAOIs) such asphenelzine,tranylcypromine,moclobemide, andselegiline may potentiate the effects of 2C drugs like 2C-N.^[3]^[4]^[5] This may result inoverdose and serioustoxicity.^[5]^[3]

Pharmacology

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Pharmacodynamics

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2C-N activities
Target	Affinity (K_i, nM)
5-HT_1A	1,450–2,200
5-HT_1B	>10,000
5-HT_1D	832
5-HT_1E	676
5-HT_1F	ND
5-HT_2A	23.5–72.4 (K_i) 170 (EC₅₀Tooltip half-maximal effective concentration) 48% (E_maxTooltip maximal efficacy)
5-HT_2B	123 (K_i) 730 (EC₅₀) 74% (E_max)
5-HT_2C	162–370 (K_i) ND (EC₅₀) ND (E_max)
5-HT₃	>10,000
5-HT₄	ND
5-HT_5A	>10,000
5-HT₆	251
5-HT₇	>10,000
α_1A	>15,000
α_1B,α_1D	>10,000
α_2A	240–1,300
α_2B	2,240
α_2C	891
β₁–β₃	>10,000
D₁	19,000
D₂	6,100–>10,000
D₃	20,000
D₄,D₅	>10,000
H₁	>25,000
H₂	>10,000
H₃	5,500
H₄	>10,000
M₁–M₅	>10,000
I₁	ND
σ₁,σ₂	>10,000
ORs	>10,000
TAAR1Tooltip Trace amine-associated receptor 1	>20,000 (K_i) (mouse) 340 (K_i) (rat) 15,000 (EC₅₀) (mouse) 250 (EC₅₀) (rat) >10,000 (EC₅₀) (human) 28% (E_max) (mouse) 59% (E_max) (rat)
SERTTooltip Serotonin transporter	32,000 (K_i) 154,000 (IC₅₀Tooltip half-maximal inhibitory concentration) ND (EC₅₀)
NETTooltip Norepinephrine transporter	>30,000 (K_i) 287,000 (IC₅₀) ND (EC₅₀)
DATTooltip Dopamine transporter	>30,000 (K_i) >900,000 (IC₅₀) ND (EC₅₀)
MAO-ATooltip Monoamine oxidase A	ND (IC₅₀)
MAO-BTooltip Monoamine oxidase B	66,000 (IC₅₀)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified.Refs:^[6]^[7]^[8]^[9]^[10]^[11]

2C-N is a low-potency partial agonist of theserotonin 5-HT_2A,5-HT_2B, and5-HT_2C receptors.^[7]^[9]^[12]

Chemistry

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Properties

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Salts of 2C-N have a bright yellow to orange color due to the presence of thenitro group,^{[citation needed]} unlike all other members of the 2C family in which the salts are white.

Synthesis

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Thechemical synthesis of 2C-N has been described.^[1] It is synthesized by the mixed acid nitration of2C-H usingsulfuric acid andnitric acid.^[1]

Analogues

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Analogues of 2C-N includeDON,2C-CN, and25N-NBOMe, among others.

History

[edit]

2C-N was first described in thescientific literature by at least 1991.^[1]

Society and culture

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Legal status

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Canada

[edit]

As of October 31, 2016, 2C-N is a controlled substance (Schedule III) in Canada.^[13]

United Kingdom

[edit]

2C-N and most (possibly all) other compounds featured in PiHKAL are illegal drugs in the United Kingdom.

United States

[edit]

In the United States, 2C-N is a Schedule 1 controlled substance.^[14]

References

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^^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^mShulgin, Alexander;Shulgin, Ann (September 1991).PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press.ISBN 0-9630096-0-5.OCLC 25627628.2C-N Entry inPiHKAL
^^a ^bLuethi D, Liechti ME (October 2018)."Monoamine Transporter and Receptor Interaction Profiles in Vitro Predict Reported Human Doses of Novel Psychoactive Stimulants and Psychedelics".Int J Neuropsychopharmacol.21 (10):926–931.doi:10.1093/ijnp/pyy047.PMC 6165951.PMID 29850881.
^^a ^b ^cDean BV, Stellpflug SJ, Burnett AM, Engebretsen KM (June 2013)."2C or not 2C: phenethylamine designer drug review".J Med Toxicol.9 (2):172–178.doi:10.1007/s13181-013-0295-x.PMC 3657019.PMID 23494844.
^^a ^bTheobald DS, Maurer HH (January 2007). "Identification of monoamine oxidase and cytochrome P450 isoenzymes involved in the deamination of phenethylamine-derived designer drugs (2C-series)".Biochem Pharmacol.73 (2):287–297.doi:10.1016/j.bcp.2006.09.022.PMID 17067556.
^^a ^bHalman A, Kong G, Sarris J, Perkins D (January 2024)."Drug-drug interactions involving classic psychedelics: A systematic review".J Psychopharmacol.38 (1):3–18.doi:10.1177/02698811231211219.PMC 10851641.PMID 37982394.
^"Kᵢ Database".PDSP. 10 May 2025. Retrieved10 May 2025.
^^a ^bRickli A, Luethi D, Reinisch J, Buchy D, Hoener MC, Liechti ME (December 2015)."Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs)"(PDF).Neuropharmacology.99:546–553.doi:10.1016/j.neuropharm.2015.08.034.PMID 26318099.
^Wallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, Hennessey JJ, Bock HA, Anderson EI, Sherwood AM, Morris H, de Klein R, Klein AK, Cuccurazzu B, Gamrat J, Fannana T, Zauhar R, Halberstadt AL, McCorvy JD (December 2023)."Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential".Nat Commun.14 (1) 8221.Bibcode:2023NatCo..14.8221W.doi:10.1038/s41467-023-44016-1.PMC 10724237.PMID 38102107.
^^a ^bMoya PR, Berg KA, Gutiérrez-Hernandez MA, Sáez-Briones P, Reyes-Parada M, Cassels BK, Clarke WP (June 2007). "Functional selectivity of hallucinogenic phenethylamine and phenylisopropylamine derivatives at human 5-hydroxytryptamine (5-HT)2A and 5-HT2C receptors".J Pharmacol Exp Ther.321 (3):1054–61.doi:10.1124/jpet.106.117507.PMID 17337633.
^Wagmann L, Brandt SD, Stratford A, Maurer HH, Meyer MR (February 2019)."Interactions of phenethylamine-derived psychoactive substances of the 2C-series with human monoamine oxidases"(PDF).Drug Test Anal.11 (2):318–324.doi:10.1002/dta.2494.PMID 30188017.
^Simmler LD, Buchy D, Chaboz S, Hoener MC, Liechti ME (April 2016)."In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1"(PDF).J Pharmacol Exp Ther.357 (1):134–144.doi:10.1124/jpet.115.229765.PMID 26791601. Archived fromthe original(PDF) on 9 May 2025.
^Acuña-Castillo C, Villalobos C, Moya PR, Sáez P, Cassels BK, Huidobro-Toro JP (June 2002)."Differences in potency and efficacy of a series of phenylisopropylamine/phenylethylamine pairs at 5-HT(2A) and 5-HT(2C) receptors".Br J Pharmacol.136 (4):510–519.doi:10.1038/sj.bjp.0704747.PMC 1573376.PMID 12055129.
^"Canada Gazette – Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". 4 May 2016.
^"Lists of: Scheduling Actions, Controlled Substances, Regulated Chemicals"(PDF).Diversion Control Division. Drug Enforcement Administration. April 2022.

External links

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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)

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

Trace amine-associated receptor modulators

TAAR1Tooltip Trace amine-associated receptor 1

EPPTB (RO-5212773)

TAAR5Tooltip Trace amine-associated receptor 5

Agonists	N,N-Dimethylethylamine Trimethylamine
Inverse agonists	3-Iodothyronamine

Notes: (1) TAAR1 activity of ligands varies significantly between species. Some agents that are TAAR1 ligands in some species are not in other species. This navbox includes all TAAR1 ligands regardless of species. (2) See the individual pages for references, as well as theList of trace amines,TAAR, andTAAR1 pages.
See also:Receptor/signaling modulators

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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