Chemical compound
Pharmaceutical compound
Dipropyltryptamine (DPT ), also known as N ,N -dipropyltryptamineThe Light ", is a psychedelic drug of the tryptamine family related to dimethyltryptamine (DMT).[ 1] [ 3] orally or by other routes .[ 1]
The drug acts as a serotonin receptor modulator , including as a serotonin 5-HT2A receptor agonist .[ 4] [ 5] [ 6] [ 7] [ 8] homologue of DMT and diethyltryptamine (DET).[ 1] Derivatives of DPT include 4-HO-DPT and 5-MeO-DPT , among others.[ 1]
DPT was first described in the literature by 1959.[ 9] [ 10] [ 11] designer drug by 1968[ 12] alcoholism in 1973.[ 2] [ 3] [ 13] sacrament of the Temple of the True Inner Light , a New York City -based religious group.[ 1] [ 14] [ 15]
In his book TiHKAL Tryptamines I Have Known and Loved ), Alexander Shulgin lists DPT's dose range as 100 to 250 mg orally and its duration as 2 to 4 hours.[ 1] [ 2] mg dose was also reported, which was described as "exhausting" and as lasting 12 hours.[ 1] onset and time to peak effects were not given, but it was implied to have a fast onset.[ 1] smoking at a dose of 100 mg, by intramuscular injection at low doses of 15 to 30 mg, moderate doses of 30 to 70 mg, and "peak experience" doses of 75 to 125 mg, and by intravenous injection at 12 to 36 mg.[ 1] [ 16]
The effects of DPT have been reported to include visuals , being intensely visual at high doses, changes in time perception , feeling like one is in a different place like on a mountain in clouds or in a big castle, enhanced recall of memories and experiences, enhanced emotional expressiveness and self-exploration, entity encounters , and religious feelings.[ 1] [ 17] [ 13] nervousness , feeling light, and body rush.[ 1] [ 1] [ 17]
Other reports have stated effects of DPT including visual and auditory hallucinations , increased color intensity, flashes of light and sparkles, apparitions of faces, increased music appreciation, ego dissolution , stimulation , euphoria , relaxation , paranoia , psychosis , anxiety , nausea , dizziness , muscle tremors , and increased heart rate , among others.[ 2] [ 18] [ 19] [ 20] [ 18] [ 20]
Although tryptamines such as psilocybin and dimethyltryptamine (DMT) have relatively well‑characterized safety , synthetic analogues like DPT lack thorough toxicological evaluation and are mainly associated with anecdotal reports of intoxication and a few cases of fatal outcomes when used recreationally.[ 21] toxicity at controlled doses but a pronounced risk of acute adverse reactions, including agitation , tachycardia , hyperthermia , and serotonergic crisis , particularly in combination with monoamine oxidase inhibitors or other serotonergic substances.[ 21]
A meta-analysis of tryptamine psychedelics have further demonstrated cognitive effects through serotonin 5-HT2A receptor modulation but have not identified persistent neurotoxicity .[ 22] psychophysiological and behavioral disturbances rather than long‑term organ toxicity. Overall, DPT is a potent, short‑acting serotonergic hallucinogen with limited safety data and a toxicity profile comparable to related tryptamines such as DMT and 5-MeO-DMT .[ 21] [ 22]
DPT activities
Target Affinity (Ki , nM)Species
5-HT1A 31.8–1,641 (Ki )EC50 Tooltip half-maximal effective concentration )Emax Tooltip maximal efficacy )
Human
5-HT1B 854–8,081 (Ki )EC50 )
Human
5-HT1D 619
Human
5-HT1E 2,338
Human
5-HT2A 3.0–2,579 (Ki )a (EC50 )a –97% (Emax )
Human
5-HT2B 42
Human
5-HT2C 281–3,500 (Ki )a (EC50 )a (Emax )
Human
5-HT3 >10,000
Human
5-HT4 ND ND
5-HT5A 4,373
Human
5-HT6 4,543
Human
5-HT7 284
Human
D1 >10,000
Human
D2 9,249
Human
D3 1,361
Human
D4 2,014
Human
D5 >10,000
Human
α1A 881
Human
α1B 443
Human
α1D ND ND
α2A 458
Human
α2B 339
Human
α2C 514
Human
β1 –β2 >10,000
Human
H1 125
Human
H2 –H4 >10,000
Human
M1 –M5 >10,000
Human
I1 340
Human
σ1 397
Human
σ2 2,917
Human
SERT Tooltip Serotonin transporter 157–480 (Ki )IC50 Tooltip half-maximal inhibitory concentration )EC50 )
Human
NET Tooltip Norepinephrine transporter >10,000 (Ki )IC50 )EC50 )
Human
DAT Tooltip Dopamine transporter 1,500 (Ki )IC50 )EC50 )
Human
Notes: The smaller the value, the more avidly the drug binds to the site. Footnotes: a = Stimulation of IP1 Tooltip inositol phosphate formation. Refs: [ 4] [ 5] [ 6] [ 7] [ 8] [ 23] [ 24]
DPT produces the head-twitch response , a behavioral proxy of psychedelic -like effects, in rodents.[ 16] [ 25] selective 5-HT2A receptor antagonist blocks the behavioral actions of DPT strongly suggests that the 5-HT2A receptor is an important site of action for the drug, but the modulatory actions of a serotonin 5-HT1A receptor antagonist also imply a serotonin 5-HT1A receptor-mediated component to the actions of DPT.[ 25] tolerance in rodents.[ 26]
DPT hydrochloride powder. DPT, also known as N ,N -dipropyltryptamine, is a substituted tryptamine related to dimethyltryptamine (DMT).[ 1] crystalline hydrochloride salt or as an oily or crystalline base . The drug is synthetic and has not been found to occur endogenously .[ 17]
DPT changes Ehrlich's reagent violet and causes the marquis reagent to turn yellow.[ 27]
The chemical synthesis of DPT has been described.[ 1]
Analogues of DPT include dimethyltryptamine (DMT), diethyltryptamine (DET), diisopropyltryptamine (DiPT), diallyltryptamine (DALT), methylethyltryptamine (MET), methylpropyltryptamine (MPT), ethylpropyltryptamine (EPT), propylisopropyltryptamine (PiPT), propylallyltryptamine (PALT), 4-HO-DPT , 5-HO-DPT , and 5-MeO-DPT , among others.[ 1]
Cyclized tryptamine and partial ergoline derivatives of DPT include RU-28251 (4,α-methylene-DPT), Bay R 1531 (LY-197206; 4,α-methylene-5-MeO-DPT), LY-293284 (4,α-methylene-5-acetyl-DPT), and LY-178210 (LY-228729; 4,α-methylene-5-carboxamido-DPT).
A positional isomer of DPT with the side chain instead located at the 4 position is DPAI (2-desoxo-2-ene-ropinirole).[ 28] [ 29] [ 30]
DPT was first described in the scientific literature by 1959.[ 9] [ 10] [ 11] designer drug has been documented by law enforcement officials since as early as 1968.[ 12] alcoholism by Stanislav Grof and colleagues in 1973.[ 3] [ 2] [ 13] [ 31] anxiety associated with terminal cancer in the late 1970s.[ 31] [ 32]
Society and culture [ edit ] DPT is used as a religious sacrament by the Temple of the True Inner Light , a New York City offshoot of the Native American Church .[ 1] entheogens are physical manifestations of God .[ 1] [ 33]
DPT is not a controlled substance in Canada as of 2025.[ 34]
DPT is illegal in Sweden as of 26 January 2016.[ 35]
DPT is a Class A drug in the United Kingdom, making it illegal to possess or distribute.
DPT is not scheduled at the federal level in the United States,[ 36] 5-MeO-DiPT , DMT , or DET , in which case purchase, sale, or possession could be prosecuted under the Federal Analogue Act .
"DPT (N,N-Dipropyltryptamine)" is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida.[ 37]
DPT is a Schedule I controlled substance in the state of Maine making it illegal to buy, sell, or possess in Maine.
DPT has been found to completely prevent audiogenic seizures in mouse models of fragile X syndrome (FXS) at a 10 mg/kg dose, with its mechanism of action appearing to be independent of serotonin and sigma σ1 receptor activation.[ 38] agonist at several serotonin receptors in vitro anticonvulsant effects were not blocked by selective serotonin 5-HT2A , 5-HT1A , or 5-HT1B receptor antagonists nor by a selective sigma σ1 receptor antagonist in vivo [ 38] [ 38] anticonvulsant to proconvulsant action, indicating complex interactions.[ 38]
^ a b c d e f g h i j k l m n o p q r s t u Shulgin A , Shulgin A (September 1997). TiHKAL: The Continuation Berkeley, California : Transform Press . ISBN 0-9630096-9-9 OCLC 38503252 .^ a b c d e Tittarelli R, Mannocchi G, Pantano F, Romolo FS (January 2015). "Recreational use, analysis and toxicity of tryptamines" . Curr Neuropharmacol . 13 (1): 26– 46. doi :10.2174/1570159X13666141210222409 . PMC 4462041 PMID 26074742 . Dipropyl-tryptamine (DPT) was firstly synthesized in the 1950s [34], but it was firstly reported for use in the scientific literature only in 1973 [35], as an adjunct in psychotherapy of alcoholics. It is found either as its crystalline hydrochloride salt or as an oily or crystalline base and, as DET, it has not been found to occur naturally. There are few peer-reviewed experimental studies that try to explain the ways of interaction among DPT and serotonin receptors: Nagai revealed a strong inhibition of 5-HT reuptake in rat synaptosomes [16], and Thiagaraj also observed a moderate affinity partial agonism at the human 5-HT1A receptor [34]. Experiences related to DPT assumption are mostly psychedelic sensations, such as an increase of music and colors intensity, the vision of pleasant flashes of light and sparkles, a complete ego loss, and apparitions of faces. The dosage of DPT, for oral administration, is 100-250 mg and the duration of the psychoactive effects varies from 2 to 4 hours. ^ a b c Malaca S, Lo Faro AF, Tamborra A, Pichini S, Busardò FP, Huestis MA (December 2020). "Toxicology and Analysis of Psychoactive Tryptamines" . Int J Mol Sci . 21 (23): 9279. doi :10.3390/ijms21239279 PMC 7730282 PMID 33291798 . ^ a b Ray TS (February 2010). "Psychedelics and the human receptorome" . PLOS ONE . 5 (2) e9019. Bibcode :2010PLoSO...5.9019R . doi :10.1371/journal.pone.0009019 PMC 2814854 PMID 20126400 . ^ a b Kozell LB, Eshleman AJ, Swanson TL, Bloom SH, Wolfrum KM, Schmachtenberg JL, et al. (April 2023). "Pharmacologic Activity of Substituted Tryptamines at 5-Hydroxytryptamine (5-HT)2A Receptor (5-HT2A R), 5-HT2C R, 5-HT1A R, and Serotonin Transporter" . The Journal of Pharmacology and Experimental Therapeutics . 385 (1): 62– 75. doi :10.1124/jpet.122.001454 . PMC 10029822 PMID 36669875 . ^ a b Blough BE, Landavazo A, Decker AM, Partilla JS, Baumann MH, Rothman RB (October 2014). "Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes" . Psychopharmacology . 231 (21): 4135– 4144. doi :10.1007/s00213-014-3557-7 . PMC 4194234 PMID 24800892 . ^ a b Nagai F, Nonaka R, Satoh Hisashi Kamimura K (March 2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". European Journal of Pharmacology . 559 (2– 3): 132– 137. doi :10.1016/j.ejphar.2006.11.075 . PMID 17223101 . ^ a b Nelson DL, Lucaites VL, Audia JE, Nissen JS, Wainscott DB (June 1993). "Species differences in the pharmacology of the 5-hydroxytryptamine2 receptor: structurally specific differentiation by ergolines and tryptamines" . The Journal of Pharmacology and Experimental Therapeutics . 265 (3): 1272– 1279. doi :10.1016/S0022-3565(25)38269-8 . PMID 8510008 . Retrieved 11 December 2024 . ^ a b Barlow RB, Khan I (December 1959). "The use of the guinea-pig ileum preparation for testing the activity of substances which imitate or antagonize the actions of 5-hydroxytryptamine and tryptamine" . British Journal of Pharmacology and Chemotherapy . 14 (4): 553– 558. doi :10.1111/j.1476-5381.1959.tb00963.x . PMC 1481908 PMID 13796840 . ^ a b Barlow RB, Khan I (June 1959). "Actions of some analogues of 5-hydroxytryptamine on the isolated rat uterus and the rat fundus strip preparations" . British Journal of Pharmacology and Chemotherapy . 14 (2): 265– 272. doi :10.1111/j.1476-5381.1959.tb01397.x . PMC 1481803 PMID 13662587 . ^ a b Vane JR (March 1959). "The relative activities of some tryptamine analogues on the isolated rat stomach strip preparation" . British Journal of Pharmacology and Chemotherapy . 14 (1): 87– 98. doi :10.1111/j.1476-5381.1959.tb00933.x . PMC 1481817 PMID 13651584 . ^ a b "Microgram Journal Volume One No. 7" (PDF) . Microgram Journal . One (Seven). U.S DOJ , Bureau of Narcotics and Dangerous Drugs : 23. April 1968 [1968]. Retrieved 5 April 2021 .^ a b c Soskin RA, Grof S, Richards WA (June 1973). "Low doses of Dipropyltryptamine in psychotherapy". Arch Gen Psychiatry . 28 (6): 817– 821. doi :10.1001/archpsyc.1973.01750360047006 . PMID 4575167 . ^ DeKorne J (26 July 2011). Psychedelic Shamanism, Updated Edition: The Cultivation, Preparation, and Shamanic Use of Psychotropic Plants ISBN 978-1-58394-290-1 ^ Kaplan E (October 1987). "Still hippies, after all these years" . Spy Magazine (October 1987): 61. ^ a b 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" (PDF) . Neuropharmacology . 167 107933. doi :10.1016/j.neuropharm.2019.107933 . PMC 9191653 PMID 31917152 . Table 4 Human potency data for selected hallucinogens. [...] ^ a b c Pinchbeck D (2003). Breaking Open The Head: A Psychedelic Journey Into the Heart of Contemporary Shamanism . Broadway Books. pp. 262– 263, 265, 272, 275– 278. ISBN 978-0-7679-0743-9 ^ a b Dutta V (2012). "Repression of death consciousness and the psychedelic trip" . J Cancer Res Ther . 8 (3): 336– 342. doi :10.4103/0973-1482.103509 PMID 23174711 . Dipropyltryptamine (DPT), another psychedelic was also examined in two cancer studies in lieu of the LSD, since its properties were similar to LSD but was less time consuming.[38] It took about 1 ½ to 6 hours to act, and its effects too wore off easily unlike the LSD that demanded a considerable amount of time. Post-therapeutically DPT's benefits would mimic LSD. It was suggested to be a better alternative than LSD, but because of its quick onset, patients often found the sudden psychological upheaval overwhelming.[39] ^ Richards WA, Rhead JC, Dileo FB, Yensen R, Kurland AA (1977). "The Peak Experience Variable in DPT-Assisted Psychotherapy with Cancer Patients" Journal of Psychedelic Drugs . 9 (1): 1– 10. doi :10.1080/02791072.1977.10472020 . ISSN 0022-393X . Retrieved 8 November 2025 . ^ a b Richards WA, Rhead JC, Grof S, Goodman LE, Di Leo F, Rush L (1980). "DPT as an Adjunct in Brief Psychotherapy with Cancer Patients" OMEGA - Journal of Death and Dying . 10 (1): 9– 26. doi :10.2190/NGUB-V4RM-T7DC-XTH3 . ISSN 0030-2228 . Retrieved 8 November 2025 . ^ a b c Araújo AM, Carvalho F, Bastos M, Guedes de Pinho P, Carvalho M (August 2015). "The hallucinogenic world of tryptamines: an updated review". Archives of Toxicology . 89 (8): 1151– 1173. Bibcode :2015ArTox..89.1151A . doi :10.1007/s00204-015-1513-x . PMID 25877327 . ^ a b Castelhano J, Lima G, Teixeira M, Soares C, Pais M, Castelo-Branco M (2021). "The Effects of Tryptamine Psychedelics in the Brain: A meta-Analysis of Functional and Review of Molecular Imaging Studies" . Frontiers in Pharmacology . 12 739053. doi :10.3389/fphar.2021.739053 PMC 8511767 PMID 34658876 . ^ "PDSP Database" . UNC (in Zulu). Retrieved 11 December 2024 .^ Tyagi R, Saraf TS, Canal CE (October 2023). "The Psychedelic N ,N -Dipropyltryptamine Prevents Seizures in a Mouse Model of Fragile X Syndrome via a Mechanism that Appears Independent of Serotonin and Sigma1 Receptors" . ACS Pharmacology & Translational Science . 6 (10): 1480– 1491. doi :10.1021/acsptsci.3c00137 . PMC 10580393 PMID 37854624 . ^ a b Fantegrossi WE, Reissig CJ, Katz EB, Yarosh HL, Rice KC, Winter JC (January 2008). "Hallucinogen-like effects of N,N-dipropyltryptamine (DPT): possible mediation by serotonin 5-HT1A and 5-HT2A receptors in rodents" . Pharmacology, Biochemistry, and Behavior . 88 (3): 358– 365. doi :10.1016/j.pbb.2007.09.007 . PMC 2322878 PMID 17905422 . ^ Smith DA, Bailey JM, Williams D, Fantegrossi WE (December 2014). "Tolerance and cross-tolerance to head twitch behavior elicited by phenethylamine- and tryptamine-derived hallucinogens in mice" . J Pharmacol Exp Ther . 351 (3): 485– 491. doi :10.1124/jpet.114.219337 . PMC 4309922 PMID 25271256 . ^ Spratley T (2004). "Analytical Profiles for Five "Designer" Tryptamines" (PDF) . Microgram Journal . 3 (1– 2): 55. Retrieved 9 October 2013 . ^ Clemens, J. A., Kornfeld, E. C., Phebus, L. A., Shaar, C. J., Smalstig, E. B., Cassady, J. M., ... & Kelly, E. (1982). Dopaminergic Agents Related to Ergolines. In The Chemical Regulation of Biological Mechanisms: The Proceedings of the 1st Medicinal Chemistry Symposium, Cambridge, England, 27th-30 September 1981 (Vol. 42, p. 167). London: Royal Society of Chemistry. https://archive.org/details/chemicalregulati0000medi/page/167/mode/1up
^ David E. Nichols (29 June 1983). "The Development of Novel Dopamine Agonists" . Dopamine Receptors . Vol. 224. Washington, D.C.: American Chemical Society. pp. 201– 222. doi :10.1021/bk-1983-0224.ch009 . ISBN 978-0-8412-0781-3 ^ Clemens JA, Fuller RW, Phebus LA, Smalstig EB, Hynes MD, Cassady JM, et al. (March 1984). "Stimulation of presynaptic dopamine autoreceptors by 4-(2-di-n-propylaminoethyl) indole (DPAI)". Life Sci . 34 (11): 1015– 1022. doi :10.1016/0024-3205(84)90014-6 . PMID 6422174 . ^ a b Garcia-Romeu A, Kersgaard B, Addy PH (August 2016). "Clinical applications of hallucinogens: A review" . Exp Clin Psychopharmacol . 24 (4): 229– 268. doi :10.1037/pha0000084 . PMC 5001686 PMID 27454674 . Like other classic hallucinogens, research with DMT ceased with the passage of the Controlled Substances Act, and was never investigated as an aid in clinical treatment to the extent LSD was. However, research with dipropyltryptamine (DPT), a closely related synthetic analog of DMT, revealed some promise as an adjunct to psychotherapy both with alcoholics (Grof et al., 1973; Rhead et al., 1977; Soskin et al., 1973), and those with anxiety associated with a terminal cancer diagnosis (Richards et al., 1977; 1980; Richards, 1978). ^ Garcia-Romeu A, Richards WA (August 2018). "Current perspectives on psychedelic therapy: use of serotonergic hallucinogens in clinical interventions". Int Rev Psychiatry . 30 (4): 291– 316. doi :10.1080/09540261.2018.1486289 . PMID 30422079 . Others, like N, N-dipropyltryptamine (DPT), have been used in preliminary studies showing therapeutic potential (Grof et al., 1973; Richards, 1978; Richards, Rhead, DiLeo, Yensen, & Kurland, 1977; Richards et al., 1980), but have not been examined since. ^ "Temple of the True Inner Light" . tripod.com .^ "Controlled Drugs and Substances Act" . Department of Justice Canada . Retrieved 19 January 2026 .^ "31 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. November 2015.^ "SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I." CFR . Archived from the original on 27 August 2009. Retrieved 17 December 2014 .^ Florida Statutes – Chapter 893 – DRUG ABUSE PREVENTION AND CONTROL ^ a b c d Tyagi R, Saraf TS, Canal CE (October 2023). "The Psychedelic N ,N -Dipropyltryptamine Prevents Seizures in a Mouse Model of Fragile X Syndrome via a Mechanism that Appears Independent of Serotonin and Sigma1 Receptors" . ACS Pharmacology & Translational Science . 6 (10): 1480– 1491. doi :10.1021/acsptsci.3c00137 . PMC 10580393 PMID 37854624 .
No ring subs. 4-Hydroxytryptamines 5-Hydroxytryptamines 5-Methoxytryptamines Other ring subs. α-Alkyltryptamines Others
Ergolines /lysergamides (e.g., LSD )Ibogalogs (e.g., ibogainalog , tabernanthalog )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 , MSP-2020 )Tetrahydropyridinylindoles (e.g., RU-28253 (5-MeO-THPI) , NEtPhOH-THPI )
Benzofurans (e.g., 5-MeO-DiBF (1-oxa-5-MeO-DiPT) , dimemebfe (5-MeO-BFE; 1-oxa-5-MeO-DMT) , mebfap (5-MeO-3-APB; 1-oxa-5-MeO-AMT) )Benzothiophenes (e.g., 3-APBT (1-thia-AMT) )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-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) BOB , BOD , BOHB )HOT-2 , HOT-7 , HOT-17 )N -Ethyl-2C-B2CB-2-EtO , 2CD-2-EtO , 2CD-5-EtO , 2CE-5-EtO , 2CE-5iPrO , 2CT2-2-EtO , ASR-2001 (2CB-5-PrO) ) Others
25B-NAcPip 2-DM-DOM 4-HA 5-DM-DOM 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) Thio-2Cs (e.g., 2C-5-TOET )Thio-DOx (e.g., 2-TOM , 5-TOET , 5-TOM , TOMSO )TMA-3 , TMA-4 , TMA-5 )ZDCM-04 (DOC-fenethylline)
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
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: 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 (F-11440) , gepirone , perospirone , tandospirone )Bay R 1531 Befiradol (NLX-112; F-13640) 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 (NLX-101) Flesinoxan Flibanserin Flumexadol Hypidone Lesopitron LY-293284 LY-301317 mCPP Naluzotan NBUMP NLX-204 NLX-266 Osemozotan (MKC-242) 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
5-HT1B
Agonists: Alniditan 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-12066 (CGS-12066A, CGS-12066B) 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 )PGI-7043 PZKKN-94 RU-24969 Serotonin (5-HT) Triptans (e.g., avitriptan , donitriptan , eletriptan , IS-159 , sumatriptan , zolmitriptan )TFMPP Tryptamines (e.g., 5-BT , 5-CT , 5-MT , DMT )Vortioxetine
5-HT1D
Agonists: Alniditan CGS-12066 (CGS-12066A, CGS-12066B) 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 , IS-159 , 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 )Butanserin 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 LY03017 LY-393558 mCPP Medifoxamine Metitepine (methiothepin) Metrenperone MIN-117 (WF-516) MT-1207 Naftidrofuryl Nantenine Nelotanserin NH130 Opiranserin (VVZ-149) Pelanserin Phenoxybenzamine Pimavanserin Pirenperone Pizotifen Pruvanserin Rauwolscine Ritanserin Roluperidone S-14671 Sarpogrelate Seganserin Serotonin antagonists and reuptake inhibitors (e.g., etoperidone , hydroxynefazodone , lubazodone , mepiprazole , nefazodone , triazoledione , trazodone )Temanogrel Teniloxazine Tetracyclic antidepressants (e.g., amoxapine , aptazapine , esmirtazapine , maprotiline , mianserin , mirtazapine )TGBA01AD Trelanserin 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 ATHX-105 Centhaquine 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 PRX-00933 (BVT-933; GW-876167) Ro60-0175 Ro60-0213 Serotonin (5-HT) Tryptamines (e.g., 5-BT , 5-CT , bufotenin , DET , DiPT , DMT , DPT , psilocin , psilocybin , tryptamine )Vabicaserin VR-1065 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 FR260010 Irindalone Ketanserin Ketotifen Latrepirdine (dimebolin) LY03017 Medifoxamine Metitepine (methiothepin) Nefazodone Pirenperone Pizotifen Propranolol Ritanserin RS-102221 S-14671 SB-200646 SB-206553 SB-221284 SB-228357 SB-242084 SB-243213 SB-247853 SDZ SER-082 Seganserin 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 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 )
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
DAT Tooltip Dopamine transporter (DRIs Tooltip Dopamine reuptake inhibitors )
NET Tooltip Norepinephrine transporter (NRIs Tooltip Norepinephrine reuptake inhibitors )
Others: Antihistamines (e.g., brompheniramine , chlorphenamine , pheniramine , tripelennamine )Antipsychotics (e.g., loxapine , ziprasidone )Arylcyclohexylamines (e.g., ketamine , phencyclidine )Dopexamine Ephenidine Ginkgo biloba Indeloxazine Nefazodone Opioids (e.g., desmetramadol , methadone , pethidine (meperidine) , tapentadol , tramadol , levorphanol )
SERT Tooltip Serotonin transporter (SRIs Tooltip Serotonin reuptake inhibitors )
Others: A-80426 Amoxapine Antihistamines (e.g., brompheniramine , chlorphenamine , dimenhydrinate , diphenhydramine , mepyramine (pyrilamine) , pheniramine , tripelennamine )Antipsychotics (e.g., loxapine , ziprasidone )Arylcyclohexylamines (e.g., 3-MeO-PCP , esketamine , ketamine , methoxetamine , phencyclidine )Cyclobenzaprine Delucemine Dextromethorphan Dextrorphan Efavirenz Hypidone Medifoxamine Mesembrine Mifepristone MIN-117 (WF-516) N-Me-5-HT Opioids (e.g., dextropropoxyphene , methadone , pethidine (meperidine) , levorphanol , tapentadol , tramadol )Roxindole
VMATs Tooltip Vesicular monoamine transporters Others
Tryptamines
1-Methyl-DMT (1,N ,N -TMT, 1-TMT) 1-Methyl-T 2-HO-NMT 2-Methyl-DET 2-Methyl-DiPT 2-Methyl-iPALT (ASR-3002) 2,N ,N -TMT (2-methyl-DMT) 3-IAAR 4-Fluoro-DMT 4-Fluoro-T 4-Methyl-DMT 5-Bromo-DMT 5-Bromo-T 5-Chloro-DMT 5-Chloro-T 5-CT 5-Ethyl-DMT 5-Fluoro-DET 5-Fluoro-DMT 5-Fluoro-EPT 5-Fluoro-T 5-Me-MiPT 5-MeS-DMT 5-Methyl-DMT 5-Methyl-T 5-Nitro-T (Nitro-I) 6-Fluoro-DET 6-Fluoro-DMT 6-Fluoro-T 6-HO-DET 6-HO-DMT 6-HO-T (6-HT) 6-MeO-DMT 6-MeO-T 6-Methyl-DMT 6-Methyl-T 6,7-DHT 7-Chloro-T 7-HO-DMT 7-HO-T (7-HT) 7-MeO-DMT 7-MeO-T 7-Methyl-DMT 7-Methyl-T 7-Hydroxytryptophan Acetryptine (5-AT) Almotriptan Benzotript (4-CB-Trp) BGE Bretisilocin (5-fluoro-MET; GM-2505) Convolutindole A (2,4,6-TBr,1,7-DiMeO-DMT) DALT DAT DBT Desformylflustrabromine DET (T-9) DHT DiPT DMT DPT E-6801 E-6837 EB-003 EiPT EPT FGIN-127 FGIN-143 Idalopirdine iPALT (ALiPT; ASR-3003) Lespedamine (1-MeO-DMT) L-694247 MBT McPT MET MiPT MPT MsBT N -Benzyltryptamine (T-NB, NB-T)N -DEAOP-NETN -DEAOP-NMTNAT NBoc-DMT (NB-DMT) NET/NETP NHT NiPT NMT NsBT NtBT PALT (ASR-3004) PiPT Rizatriptan ST-1936 (2-Me-5-Cl-DMT) Sumatriptan TCS-1205 Tryptamine (T; indolylethylamine) Tryptophan (Trp) WAY-181187 Yuremamine Z2876442907 ZCZ-011 Zolmitriptan 4-Hydroxytryptamines esters /ethers 5-Hydroxy- and5-methoxytryptamines
2-Methyl-5-HT 2-Methyl-5-MeO-DALT 4-HO-5-MeO-T 4-F-5-MeO-DMT 4,5-DHP-DMT 4,5-DHT 4,5-MDO-DMT 4,5-MDO-DiPT 5-BT 5-Ethoxy-DMT 5-HO-DET 5-HO-DiPT 5-HO-DPT 5-HO-MET 5-HO-NiPT 5-HTP (oxitriptan )5-MeO-2-TMT 5-MeO-34MPEMT 5-MeO-7,N ,N -TMT 5-MeO-DALT 5-MeO-DBT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT (N ,N ,O -TMS; O -methylbufotenine) 5-MeO-DPT 5-MeO-EiPT 5-MeO-EPT 5-MeO-MALT 5-MeO-MBT 5-MeO-MET 5-MeO-MiPT 5-MeO-MsBT 5-MeO-NET 5-MeO-NiPT 5-MeO-NMT (O ,N -DMS) 5-MeO-NsBT 5-MeO-PiPT 5-MeO-NBpBrT 5-MeO-T (5-MT; mexamine; O -methylserotonin) 5-MeO-T-NBOMe 5-MeO-T-NB3OMe 5-MTP (cytoguardin) 5-NOT 5-PhO-T (OVT2) 5,6-DHT 5,6-MDO-DiPT 5,6-MDO-DMT 5,6-MDO-MiPT 5,6-MeO-MiPT 5,7-DHT Arachidonoyl serotonin ASR-3001 (5-MeO-iPALT) BAB Benanserin (BAS; SQ-4788) BGC20-761 Bufotenidine (5-HTQ; N ,N ,N -TMS) Bufotenin (5-HO-DMT; N ,N -DMS; mappine) Bufoviridine (5-SO-DMT) CP-132,484 Cqd 280 Cqd 285 Cqdd 280 Donitriptan EMDT (2-Et-5-MeO-DMT) HIOC Indorenate (TR-3369) IS-159 Isamide (N -CA-5-MT) L-741604 MS-245 N -DEAOP-5-MeO-NETN -DEAOP-5-MeO-NMTN -Feruloylserotonin (moschamine)NB-5-MeO-DALT NB-5-MeO-MiPT Norbufotenin (5-HO-NMT; NMS) O -Acetylbufotenine (5-AcO-DMT)O -Pivalylbufotenine (5-t -BuCO-DMT)Psilomethoxin (4-HO-5-MeO-DMT) Psilomethoxybin (4-PO-5-MeO-DMT) Serotonin (5-HT) N -Acetyltryptaminesα-Alkyltryptamines
5-Hydroxy- and 5-alkoxy-α-alkyltryptamines: 1-Pr-5-MeO-AMT 5-Allyloxy-AMT 5-Ethoxy-αMT 5-iPrO-αMT 5-MeO-αET 5-MeO-αMT (α,O -DMS; Alpha-O) α-Methyl-5-HTP α-Methylmelatonin α-Methylserotonin (5-HO-αMT; α-Me-5-HT) α,N ,O -TMS (5-MeO-α,N -DMT) α,N ,N ,O -TeMS (5-MeO-α,N ,N -TMT) AL-37350A (4,5-DHP-αMT) BW-723C86 α-Ketotryptamines Cyclized tryptamines
5-MeO-IsoqT Barettin BML-190 (indomethacin morpholinylamide) Cyclic 3-OHM Ergolines and lysergamides (e.g., LSD )Harmala alkaloidsβ-carbolines (e.g., 5-methoxyharmalan , 6-MeO-THH , 6-methoxyharmalan , 9-Me-BC , β-carboline (norharman) , fenharmane , harmaline , harmalol , harmane , harmine , LY-266,097 , pinoline , tetrahydroharmine , tryptoline )Iboga alkaloidsibogaine , ibogamine , noribogaine , tabernanthine )Ibogalogs (e.g., catharanthalog , fluorogainalog , ibogainalog , ibogaminalog (DM-506) , LS-22925 , noribogainalog , noribogaminalog , PHA-57378 , PNU-22394 , tabernanthalog )Imidazolylindoles (e.g., AGH-107 , AGH-192 , AH-494 )Metralindole Morpholinylethylindoles (e.g., mor-T , 5-MeO-mor-T )Partial ergolines and lysergamides (e.g., NDTDI , RU-27849 , RU-28251 , RU-28306 , FHATHBIN , LY-178210 , Bay R 1531 (LY-197206) , LY-293284 , 10,11-seco-LSD , 10,11-secoergoline (α,N -Pip-T) , CT-5252 )Pertines (e.g., alpertine , milipertine , oxypertine , solypertine )Piperidinylethylindoles (e.g., pip-T , 5-MeO-pip-T , indolylethylfentanyl )Pyrrolidinylethylindoles (e.g., pyr-T , 4-HO-pyr-T , 5-MeO-pyr-T , 4-F-5-MeO-pyr-T , L-760790 )Pyrrolidinylmethylindoles (e.g., MPMI , 4-HO-MPMI (lucigenol) , 5F-MPMI , 5-MeO-MPMI , CP-122288 , CP-135807 , eletriptan , MSP-2020 )Tetrahydrocarbazolamines (e.g., ciclindole , flucindole , frovatriptan , LY-344864 , ramatroban )Tetrahydropyridinylindoles (e.g., RS134-49 , RU-28253 , NEtPhOH-THPI )Tetrahydropyrroloquinolines (e.g., bufothionine , O -methylnordehydrobufoteninedehydrobufotenine )Yohimbans (e.g., yohimbine , rauwolscine , spegatrine , corynanthine , ajmalicine , reserpine , deserpidine , rescinnamine ) Isotryptamines Related compounds
2-Azapsilocin 2,3-Dihydro-L-tryptophan 2,3-Dihydrotryptamine 2,3-Dihydro-DMT 2,3-Dihydro-NMT 2,3-Dihydro-DET 4-Aza-5-MeO-DPT 5-Aza-4-MeO-DiPT 5-HIAA 5-HIAL 5-HITCA 5-MIAL 7-Aza-5-MeO-DiPT α-Carboline γ-Carbolines (pyridoindoles) (e.g., γ-carboline , alosetron , gevotroline , latrepirdine , lurosetron , mebhydrolin , tiflucarbine )Amedalin Benzindopyrine Benzofurans (e.g., 3-APB (1-oxa-AMT) , 5-MeO-DiBF (1-oxa-5-MeO-DiPT) , BPAP , 3-F-BPAP , dimemebfe (5-MeO-BFE; 1-oxa-5-MeO-DMT) , mebfap (5-MeO-3-APB; 1-oxa-5-MeO-AMT) , MiPBF (1-oxa-MiPT) , oxa-noribogaine )Benzothiophenes (e.g., S-DMT (1-thia-DMT) , 3-APBT (1-thia-AMT) )Carmoxirole CT-4436 Daledalin Gramine Histamine Homotryptamines (e.g., HT , DMHT )I-32 IAL IN-399 Indalpine Indazolethylamines (e.g., AL-34662 , AL-38022A , O -methyl-AL-34662VU6067416 , YM-348 )Indenylethylamines (e.g., C-DMT (1-carba-DMT) )Indolizinylethylamines (e.g., TACT908 (2ZEDMA) , 1ZP2MA , 1Z2MAP1O )Indolylaminopropanes (e.g., 1-API , 2-API , 4-API , 5-API (5-IT; PAL-571) , 6-API (6-IT) , 7-API )Iprindole Masupirdine Medmain Molindone Non-tryptamine triptans (e.g., avitriptan , LY-334370 , naratriptan )
Ondansetron Oxazinopyridoindoles (e.g., IHCH-8134 )Phenethylamines (e.g., phenethylamine , amphetamine )Piperidinylbenzimidazolines (e.g., benperidol , timiperone )Piperazinylbenzisothiazoles (e.g., lurasidone , perospirone , tiospirone , ziprasidone )Piperidinylbenzisoxazoles (e.g., iloperidone , milsaperidone , ocaperidone , paliperidone , risperidone )Piperidinylindoles (e.g., BRL-54443 , LY-334370 , naratriptan , sertindole , SN-22 )Pirlindole Pyridinylbenzimidazoles (e.g., droperidol )Pyridinylindoles (e.g., tepirindole )Pyridopyrroloquinoxalines (e.g., IHCH-7113 , IHCH-7079 , IHCH-7086 , lumateperone , deulumateperone , ITI-1549 )Pyrrolylethylamines (e.g., 2-pyrrolylethylamine (NEA) , 3-pyrrolylethylamine (3-NEA) , 3-pyrrolylpropylamine )Pyrrolopyridinylethylamines (e.g., WAY-208466 )Quinolinylethylamines (e.g., mefloquine )Ro60-0213 Selisistat Tetrahydropyridinylindoles (e.g., EMD-386088 , LY-367265 , RU-24,969 )Tetrahydropyridinylpyrrolopyridines (e.g., (R )-69 (3IQ) , (R )-70 , CP-93129 , CP-94253 )Tetrindole Tipindole Zilpaterol (RU-42173)
