Psychoactive phenethylamine drug
Pharmaceutical compound
Ariadne Trade names Dimoxamine (tentative) Other names ARIADNE; 4-Methyl-2,5-dimethoxy-α-ethylphenethylamine; 2,5-Dimethoxy-4-methyl-α-ethylphenethylamine; 4C-D; 4C-DOM; "Four-carbon DOM"; α-Et-2C-D; α-Ethyl-2C-D; BL-3912; BL3912; Dimoxamine Routes of Oral [ 1] [ 2] Drug class Serotonin 5-HT2A , 5-HT2B , and 5-HT2C receptor agonist ; Non-hallucinogenic serotonin 5-HT2A receptor agonist ; Antidepressant ; Stimulant ATC code Legal status
1-(2,5-dimethoxy-4-methylphenyl)butan-2-amine
CAS Number PubChem CID ChemSpider UNII CompTox Dashboard (EPA ) Formula C 13 H 21 N O 2 Molar mass −1 3D model (JSmol )
O(c1cc(c(OC)cc1C[C@H](N)CC)C)C
InChI=1S/C13H21NO2/c1-5-11(14)7-10-8-12(15-3)9(2)6-13(10)16-4/h6,8,11H,5,7,14H2,1-4H3
Y Key:MLYCFWZIAJAIGW-UHFFFAOYSA-N
Y (verify)
Ariadne , also known chemically as 4C-D or 4C-DOM , by its developmental code name BL-3912 , and by its former tentative brand name Dimoxamine , is a psychoactive drug of the phenethylamine , phenylisobutylamine (α-ethylphenethylamine), and 4C families.[ 3] [ 1] [ 2] [ 4] analogue of the psychedelic drugs 2C-D and DOM , with 2C-D having no substitution at the α carbon , DOM having an α-methyl group , and Ariadne having an α-ethyl group .[ 3] [ 1] [ 2] [ 4] orally .[ 1] [ 2]
The drug is a serotonin 5-HT2 receptor partial agonist , including of the serotonin 5-HT2A receptor , similarly to psychedelics.[ 3] hallucinogenic in humans, but is still psychoactive , producing antidepressant and mild stimulant effects such as feelings of well-being and mental alertness .[ 3] [ 1] [ 2] [ 5] dopaminergic actions in animals, such as increased motivation and reversal of parkinsonism , which may be mediated by serotonin 5-HT2A receptor activation-induced dopamine release in the brain.[ 3] [ 1] activational efficacy at the serotonin 5-HT2A receptor relative to psychedelics.[ 3]
Ariadne was first synthesized by Alexander Shulgin in 1968 and its psychoactive effects were discovered by Shulgin in 1969.[ 5] [ 3] [ 1] pharmaceutical drug at Bristol Laboratories , for instance as an antidepressant and for various other uses, and entered clinical trials around 1974.[ 5] [ 3] [ 4] [ 2] phase 3 trials prior to its development being shelved.[ 5] effectiveness or safety .[ 5] [ 3] psychiatric disorders .[ 3] controlled substance in the United States .[ 2]
In his 1991 book PiHKAL Alexander Shulgin reported human tests of Ariadne at doses of up to 32 mg, finding that it produced "the alert of a psychedelic, with none of the rest of the package".[ 1] psychoactive effects, but no hallucinations .[ 6] [ 3]
In his 2011 book The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds R )-Ariadne as increasing mental alertness and producing feelings of well-being at doses of 25 to 50 mg.[ 2] manic depression in psychotic individuals at doses of 50 to 100 mg and to improve symptoms of Parkinson's disease at a dosage of 100 mg/day.[ 2] [ 3] mg resulted in an altered state of consciousness but still no psychedelic effects.[ 3] [ 2] mg and psychedelic effects at doses of more than 3 mg.[ 3]
Ariadne, as the (R )- enantiomer , is active at doses as low as 25 mg and was tested in clinical trials at doses of 50 to 100 mg.[ 3] mg have been assessed, more than 10 times higher than the minimum reported active dose.[ 3] [ 3]
Ariadne activities
Target Affinity (Ki , nM)
5-HT1A >10,000 (Ki )EC50 Tooltip half-maximal effective concentration )Emax Tooltip maximal efficacy )
5-HT1B >10,000 (Ki )EC50 )Emax )
5-HT1D ND (Ki )EC50 )Emax )
5-HT1E ND (Ki )EC50 )Emax )
5-HT1F ND (Ki )EC50 )Emax )
5-HT2A 120 (Ki )EC50 )Emax )
5-HT2B >10,000 (Ki )EC50 )Emax )
5-HT2C ND (Ki )EC50 )Emax )
5-HT3 >10,000
5-HT4 ND (Ki )ND (EC50 )Emax )
5-HT5A ND (Ki )ND (EC50 )Emax )
5-HT6 ND (Ki )EC50 )Emax )
5-HT7 ND (Ki )ND (EC50 )Emax )
α1A >10,000
α1B , α1D ND
α2A >10,000
α2B , α2C ND
β1 , β2 >10,000
β3 ND
D1 , D2 >10,000
D3 –D5 ND
H1 , H2 >10,000
H3 , H4 ND
M1 –M3 >10,000
M4 , M5 ND
I1 ND
σ1 , σ2 ND
TAAR1 Tooltip Trace amine-associated receptor 1 ND
SERT Tooltip Serotonin transporter >10,000 (Ki )IC50 Tooltip half-maximal inhibitory concentration )ND (EC50 )
NET Tooltip Norepinephrine transporter >10,000 (Ki )ND (IC50 )ND (EC50 )
DAT Tooltip Dopamine transporter >10,000 (Ki )IC50 )ND (EC50 )
MAO-A Tooltip Monoamine oxidase A >10,000 (Ki )
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [ 7] [ 3] [ 8]
Ariadne is a potent and selective agonist of the serotonin 5-HT2 receptors , including of the serotonin 5-HT2A , 5-HT2B , and 5-HT2C receptors .[ 3] [ 8] efficacious in activating the serotonin 5-HT2A receptor, including the Gq , G11 , and β-arrestin2 signaling pathways, compared to the related drug DOM , and this weaker partial agonism may be responsible for its lack of psychedelic effects.[ 3] [ 8] 2 receptors, Ariadne is a lower-affinity agonist of the serotonin 5-HT1 receptors .[ 3] monoamine transporters .[ 3]
Ariadne shows a markedly attenuated head-twitch response , a behavioral proxy of psychedelic effects, in animals, although it does still significantly induce a weak head-twitch response.[ 3] [ 8] [ 9] drug discrimination tests, albeit with dramatically lower potency than DOx drugs like DOM itself, DOET , and DOB .[ 9] LSD [ 6] MDMA .[ 10] α-ethyltryptamine (αET).[ 10] [ 11] increase motivation , as it caused monkeys that had stopped running mazes to begin running them again.[ 1] animal model of Parkinson's disease , where it reversed motor deficits similarly to levodopa .[ 3]
Serotonin 5-HT2A receptor agonists have been found to increase dopamine levels in the nucleus accumbens and other mesolimbic areas .[ 3] 2A receptor agonists like Ariadne may produce this effect without causing psychedelic effects.[ 3] parkinsonism in animals and humans.[ 3]
Ariadne, also known as 4-methyl-2,5-dimethoxy-α-ethylphenethylamine, is a substituted phenethylamine and amphetamine derivative .[ 1] [ 2] analogue of 2,5-dimethoxy-4-methylamphetamine (DOM) in which the α -methyl group has been replaced with an α-ethyl group and is the analogue of 2,5-dimethoxy-4-methylphenethylamine (2C-D) with an ethyl group substituted at the α carbon.[ 3] [ 1] [ 2]
Other related compounds include the 4C derivatives 4C-B (the α-ethyl homologue of 2C-B and DOB ) and 4C-T-2 (the α-ethyl homologue of 2C-T-2 and Aleph-2 ).[ 1] [ 12]
Ariadne was first synthesized by Alexander Shulgin in 1968 and he discovered its psychoactive effects in 1969.[ 5] [ 3] [ 1] Bristol Laboratories as an antidepressant , in an anecdote where he was explaining how human testing is invaluable (compared to animal testing) on drugs that change the state of the mind. He said, "Before they launched into a full multi-clinic study to determine whether it's going to be worth the animal studies or not, every person on the board of directors took it."[ 4] The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds mental alertness in geriatric individuals, treating Parkinson's disease , and treating psychosis and manic depression .[ 2] [ 3] Dimoxamine .[ 2] R )-Ariadne was said to have completed phase 2 clinical trials and to have reached phase 3 trials, but the actual clinical data were never disclosed and further development was halted due to strategic economic reasons.[ 5] [ 3] Hamilton Morris , the United States Central Intelligence Agency (CIA) may have had involvement in the discontinuation of Ariadne's development.[ 13]
Society and culture [ edit ] Ariadne's alternative name 4C-DOM or 4C-D stands for "four-carbon DOM", whereas the name of 2C-D stands for "two-carbon DOM".[ 3] α-Et-2C-D , which stands for α-ethyl-2C-D.[ 9] Racemic Ariadne is additionally known by the former developmental code name BL-3912 , while the (R )-enantiomer of Ariadne (R )-Ariadne, is known by the former developmental code name BL-3912A .[ 3] [ 2]
Ariadne is not an explicitly controlled substance anywhere in the United States as of 2011.[ 2]
^ a b c d e f g h i j k l m Alexander T. Shulgin , Ann Shulgin (1991). "#8 ARIADNE; 4C-DOM; BL-3912; DIMOXAMINE; 1-(2,5- DIMETHOXY-4-METHYLPHENYL)-2-AMINOBUTANE; 2,5- DIMETHOXY-a-ETHYL-4-METHYLPHENETHYLAMINE" . PiHKAL: A Chemical Love Story 475– 480. ISBN 978-0-9630096-0-9 OCLC 25627628 .^ a b c d e f g h i j k l m n o p q Shulgin A, Manning T, Daley PF (2011). "#7. ARIADNE" . The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds 7– 9. ISBN 978-0-9630096-3-0 OCLC 709667010 . It was developed commercially by the Bristol-Myers Company to increase mental alertness in geriatric patients, and was patented in Germany, France, and the United States (Shulgin, 1974a, 1974b, 1977a). Its commercial name, Dimoxamine, does not have a classic female ring to it. [...] In normal human subjects, R-4C-DOM orally at 25—50 mg increased mental alertness and feelings of well-being. At 100 mg/day, the symptoms of Parkinson's disease went into remission. With psychotic patients there was a consistent relief of manic depression at doses of 50-100 mg (Shulgin, 1977a; Partyka et al., 1978). A single human oral ingestion of 270 mg produced a change of state of consciousness but evoked no psychedelic effects (Winter, 1980). ^ a b c d e f g h i j k l m n o p q r s t u v w x y z aa ab ac ad ae af ag Cunningham MJ, Bock HA, Serrano IC, Bechand B, Vidyadhara DJ, Bonniwell EM, et al. (January 2023). "Pharmacological Mechanism of the Non-hallucinogenic 5-HT2A Agonist Ariadne and Analogs" . ACS Chemical Neuroscience . 14 (1): 119– 135. doi :10.1021/acschemneuro.2c00597 . PMC 10147382 PMID 36521179 . ^ a b c d Shulgin A (2021). The Nature of Drugs . Berkeley, California: Transform Press. pp. 299– 300. ISBN 978-0-9995472-1-2 ^ a b c d e f g Shulgin AT (1987). "The "Social-Chemistry" of Pharmacological Discovery: Interview with Dr. Alexander T. Shulgin. January 26, 1986" . Social Pharmacology . 1 (3): 279– 290. ^ a b Winter JC (1980-05-01). "Effects of the phenethylamine derivatives, BL-3912, fenfluramine, and Sch-12679, in rats trained with LSD as a discriminative stimulus". Psychopharmacology . 68 (2): 159– 162. doi :10.1007/BF00432134 . PMID 6776559 . S2CID 12221170 . ^ Sharp T, Ippolito A (May 2025). "Neuropsychopharmacology of hallucinogenic and non-hallucinogenic 5-HT2A receptor agonists" . Br J Pharmacol . doi :10.1111/bph.70050 PMID 40405723 . ^ a b c d Wallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, et al. (December 2023). "Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential" . Nat Commun . 14 (1): 8221. doi :10.1038/s41467-023-44016-1 . PMC 10724237 PMID 38102107 . ^ a b c Halberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD (May 2020). "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species" . Neuropharmacology . 167 107933. doi :10.1016/j.neuropharm.2019.107933 . PMC 9191653 PMID 31917152 . ^ a b Glennon RA (October 1993). "MDMA-like stimulus effects of alpha-ethyltryptamine and the alpha-ethyl homolog of DOM". Pharmacology, Biochemistry, and Behavior . 46 (2): 459– 462. doi :10.1016/0091-3057(93)90379-8 . PMID 7903460 . S2CID 54356633 . ^ Oberlender RA (May 1989). "Stereoselective aspects of hallucinogenic drug action and drug discrimination studies of entactogens" . Purdue e-Pubs . Purdue University. The results of initial studies (Nichols et al., 1986) generally demonstrated the lack of LSD-Iike discriminative stimulus properties for the members of the entactogen drug class. This was confirmed and extended to other hallucinogens in tests with rats trained on entactogens. These results are summarized in Table 12. Table 12. Results of DD tests comparing entactogens and hallucinogens. [...] It seems clear that entactogen activity is distinct from that of hallucinogens. [...] ^ Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: Von der Struktur zur Funktion . Nachtschatten Verlag AG. p. 832. ISBN 978-3-03788-700-4 Das α-Ethylhomologon von 2C-B (6) trägt den Namen (303; auch 4C-B) und wurde von Rausch eingehender untersucht [140, 145]. Es vermochte eine ausgeprägte psychedelische Wirkung mit Bewusstseinsvertiefung, Euphorie und Sensationen besonders im Bereich des Tastsinns hervorzurufen (50—80mg, rund acht Stunden Wirkdauer). Visuelle Pseudohalluzinationen traten kaum auf. Das Iodoanalogon DOI-B (304) wurde nur bis zu einer Dosierung von 4mg geprüft und zeigte dabei keinerlei Wirkungen [8]. ^ Smith S (25 September 2025). "The Hidden Side of Psychedelic Research ft. Hamilton Morris" . YouTube . Vice News . Retrieved 29 September 2025 .
No ring subs. 4-Hydroxytryptamines 5-Hydroxytryptamines 5-Methoxytryptamines Other ring subs.
2,N ,N -TMT 4,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 5-MeO-4,N ,N -TMT 6-Fluoro-DMT Bretisilocin (GM-2505; 5-fluoro-MET) α-Alkyltryptamines
5-Methoxy-α-alkyltryptamines: 5-MeO-AET α,N ,N -TMT (α-Me-DMT; Alpha-N) 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
Ergolines /lysergamides (e.g., LSD )β-Carbolines and Harmala alkaloidsharmine , harmaline , 6-methoxyharmalan )Iboga alkaloids18-MAC , 18-MC , coronaridine , ibogaine , ibogamine , ME-18-MC , noribogaine , tabernanthine , voacangine )Ibogalogs (e.g., ibogainalog )O -MethylnordehydrobufoteninePartial 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 )
Benzofurans (e.g., 5-MeO-DiBF , dimemebfe (5-MeO-BFE) , mebfap )Benzothiophenes (e.g., 3-APBT )Indazolethylamines (e.g., AL-38022A , O -methyl-AL-34662Indenylethylamines (e.g., C-DMT )Isotryptamines (e.g., 6-MeO-isoDMT , Ro60-0175 )MYCO-005 Quinolinylethylamines (e.g., mefloquine )
Others: 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) BOB , BOD , BOH-2C-B )HOT-2 , HOT-7 , HOT-17 )N -Ethyl-2C-B2CD-2-ETO , 2CD-5-ETO , 2CE-5-ETO , 2CE-5iPrO , 2CT2-5-ETO , ASR-2001 (2CB-5PrO) ) 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 25D-NM-NDEAOP , DOB-NDEPA , DOI-NDEPA , DOM-NDEPA , DOTFM-NDEPA , M-NDEPA , TMA-2-NDEPA )PMA (4-MA) TMA-3 , TMA-4 , TMA-5 )TOMSO ZDCM-04
1-Aminomethylindanes (e.g., 2CB-Ind , jimscaline )2-Aminoindanes (e.g., DOM-AI )3-Phenylpiperidines (e.g., LPH-5 , LPH-48 )Benzazepines (e.g., lorcaserin )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
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
Tryptamines: Acacia spp.Acacia acuminata Acacia confusa Ayahuasca and vinho de Jurema (e.g., Psychotria viridis (chacruna)Dipolopterys cabrerana (chaliponga, chacruna)Mimosa tenuiflora (Mimosa hostilis ; jurema)Brosimum Brosimum acutifolium (takini)Hallucinogenic snuffs (e.g., Anadenanthera peregrina (yopo, jopo, cohoba, parica, ebene)Anadenanthera colubrina (vilca, cebil)Incilius alvarius (Bufo alvarius ; Colorado River toad, Sonoran Desert toad; bufo)Psilocybin-containing mushrooms (magic mushrooms, shrooms) (e.g., Psilocybe cubensis Psilocybe mexicana (teonanacatl)Lysergamides: Achnatherum robustum (sleepy grass)Epichloë spp.Ergot (Claviceps ) (e.g., Claviceps purpurea Claviceps paspali Morning glory (Convolvulaceae) seeds (e.g., Ipomoea tricolor (tlitliltzin, badoh negro; Ipomoea violacea )Ipomoea corymbosa (coaxihuitl, ololiúqui; Rivea Corymbosa , Turbina Corymbosa )Argyreia nervosa (Hawaiian baby woodrose; HBWR)Periglandula spp.Periglandula ipomoeae Periglandula clandestina
5-HT1
5-HT1A
Agonists: 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 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
5-HT1B
Agonists: Anpirtoline CGS-12066A CP-93129 CP-94253 CP-122288 CP-135807 Eltoprazine Ergolines (e.g., bromocriptine , dihydroergotamine , ergotamine , methylergometrine (methylergonovine) , methysergide , pergolide )mCPP 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
5-HT1D
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 )
5-HT1E
5-HT1F
5-HT2
5-HT2A
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 )
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
5-HT2B
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
5-HT2C
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
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
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
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
5-HT4
5-HT5A
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 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 )
5-HT7
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
Phenethylamines Amphetamines Phentermines Cathinones Phenylisobutylamines (and further-extended) Catecholamines (and close relatives) Cyclized
Phenylalkylpyrrolidines 2-Benzylpiperidines (phenidates ) Phenylmorpholines (phenmetrazines) Phenyloxazolamines (aminorexes) Isoquinolines andtetrahydroisoquinolines 2-Aminoindanes 2-Aminotetralins 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 2CJP 2CLisaB 2CLisaH 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 )Benzazepines (e.g., fenoldopam , lorcaserin , SCHEMBL5334361 )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-DMBA Tooltip 1,3-dimethylbutylamine , 1,4-DMAA Tooltip 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 , mCPP Tooltip meta-chlorophenylpiperazine , TFMPP Tooltip trifluoromethylphenylpiperazine , oMPP Tooltip ortho-methylphenylpiperazine , pFPP Tooltip para-fluorophenylpiperazine , pMeOPP Tooltip para-methoxyphenylpiperazine )Phenylpropylamines (e.g., phenylpropylamine , homo-MDA , homo-MDMA )Thienylaminopropanes (thiopropamines) (e.g., thiopropamine , methiopropamine , thiothinone )
