- DPT
- N,N-Dipropyltryptamine
- 3-[2-(Dipropylamino)ethyl]indole
- Indole, 3-[2-(dipropylamino)ethyl]
- Tryptamine, N,N-dipropyl
Faillace, LA; Vourlekis, A; Szara, S. Clinical evaluation of some hallucinogenic tryptamine derivatives J. Nerv. Ment. Dis., 1 Jan 1967, 145 (4), 306–313. 635 kB. #DPT
Szara, S. DMT (N,N-dimethyltryptamine) and homologues: Clinical and pharmacological considerations In Psychotomimetic Drugs; Efron, DH, Ed., Raven Press, New York, 1 Jan 1970; pp 275–286. 1.9 MB. #DPT
Cozzi, NV; Gopalakrishnan, A; Anderson, LL; Feih, JT; Shulgin, AT; Daley, PF; Ruoho, AE. Dimethyltryptamine and other hallucinogenic tryptamines exhibit substrate behavior at the serotonin uptake transporter and the vesicle monoamine transporter J. Neural Transm., 1 Dec 2009, 116 (12), 1591–1599. 420 kB. https://doi.org/10.1007/s00702-009-0308-8
Toad. DPT Primer Erowid, 15 Nov 1998.
Cozzi, NV; Shulgin, AT; Daley, PF; Gopalakrishnan, A; Anderson, LL; Feih, JT; Ruoho, AE. Psychoactive N,N-dialkyltryptamines modulate serotonin transport by at least two mechanisms Soc. Neurosci. Abs., 1 Jan 2008, 536.17. 52 kB.
Ray, TS. Psychedelics and the human receptorome PLOS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. https://doi.org/10.1371/journal.pone.0009019
Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens Neuropharmacology, 1 Sep 2011, 61 (3), 364–381. 817 kB. https://doi.org/10.1016/j.neuropharm.2011.01.017
Meyers-Riggs, B. N-Alkylated tryptamines countyourculture, countyourculture: rational exploration of the underground, 10 Mar 2012.
Chen, B; Liu, J; Chen, W; Chen, H; Lin, C. A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation Talanta, 15 Jan 2008, 74 (4), 512–517. 486 kB. https://doi.org/10.1016/j.talanta.2007.06.012 MS
Brandt, SD; Tirunarayanapuram, SS; Freeman, S; Dempster, N; Barker, SA; Daley, PF; Cozzi, NV; Martins, CPB. Microwave-accelerated synthesis of psychoactive deuterated N,N-dialkylated-[α,α,β,β-d4]-tryptamines J. Labelled Compd. Radiopharm., 1 Nov 2008, 51 (14), 423–429. 169 kB. https://doi.org/10.1002/jlcr.1557 #19 MS,NMR
Brandt, SD; Freeman, S; Fleet, IA; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part III. Characterisation of the Speeter and Anthony route to N,N-dialkylated tryptamines using CI-IT-MS-MS Analyst, 1 Jan 2005, 130 (9), 1258–1262. 250 kB. https://doi.org/10.1039/b504001a #12a MS
Brandt, SD; Freeman, S; Fleet, IA; McGagh, P; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR Analyst, 21 Feb 2005, 130 (3), 330–344. 403 kB. https://doi.org/10.1039/b413014f #12a MS,NMR
Shulgin, AT. Abused substances Tech. Rev., 1 Jan 2005, August, 80–81. 415 kB.
Szara, S; Hearst, E; Putney, F. Metabolism and behavioural action of psychotropic tryptamine homologues Int. J. Neuropharmacol., 1 Nov 1962, 1 (1–3), 111–117. 1.1 MB. https://doi.org/10.1016/0028-3908(62)90015-1 #DPT
Spratley, TK; Hays, PA; Geer, LC; Cooper, SD; McKibben, TD. Analytical profiles for five “designer” tryptamines Microgram J., 1 Jan 2005, 3 (1–2), 54–68. 473 kB. GC,LC,MS,NMR,IR,spot
Rodriguez-Cruz, SE. Analysis and characterization of designer tryptamines using electrospray ionization mass spectrometry (ESI-MS) Microgram J., 1 Jul 2005, 3 (3–4), 107–129. 1.6 MB. #5 MS
Blough, BE; Landavazo, A; Decker, AM; Partilla, JS; Baumann, MH; Rothman, RB. Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes Psychopharmacology, 1 Oct 2014, 231 (21), 4135-4144. 298 kB. https://doi.org/10.1007/s00213-014-3557-7 #21
Meyer, MR; Caspar, A; Brandt, SD; Maurer, HH. A qualitative/quantitative approach for the detection of 37 tryptamine-derived designer drugs, 5 β-carbolines, ibogaine, and yohimbine in human urine and plasma using standard urine screening and multi-analyte approaches Anal. Bioanal. Chem., 1 Jan 2014, 406 (1), 225–237. 457 kB. https://doi.org/10.1007/s00216-013-7425-9 #DPT LC,MS
Brandt, SD; Martins, CPB. Analytical methods for psychoactive N,N-dialkylated tryptamines Trends Anal. Chem., 1 Sep 2010, 29 (8), 858–869. 446 kB. https://doi.org/10.1016/j.trac.2010.04.008 #11
Chapman, SJ. PeakAL: Protons I Have Known and Loved, Too — Another Fifty Shades of Grey-Market Spectra BLOTTER, 1 Mar 2018, 3 (1). 1.2 MB. https://doi.org/10.16889/isomerdesign-5 #T15 NMR
Chapman, SJ. PeakAL: Protons I Have Known and Loved, Too — Another Fifty Shades of Grey-Market Spectra. Supplementary Data BLOTTER, 1 Mar 2018, 3 (1). 5.7 MB. https://doi.org/10.16889/isomerdesign-5-supp #T15 NMR
Nichols, DE. Psychedelics Pharmacol. Rev., 1 Apr 2016, 68 (2), 264-355. 1.9 MB. https://doi.org/10.1124/pr.115.011478 Updated with published correction to Figure 4 (the α-methyl group was missing in the original)
Halberstadt, AL; Geyer, MA. Effect of hallucinogens on unconditioned behavior In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 159-199. 879 kB. https://doi.org/10.1007/7854_2016_466
Bogenschutz, MP; Ross, S. Therapeutic applications of classic hallucinogens In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 361-391. 360 kB. https://doi.org/10.1007/7854_2016_464
Wang, Y; Chen, C. Synthesis of deuterium labeled tryptamine derivatives J. Chin. Chem. Soc., 1 Oct 2007, 54 (5), 1363-1368. 92 kB. https://doi.org/10.1002/jccs.200700194 #6 MS,NMR,IR
Shulgin, AT. Basic Pharmacology and Effects In Hallucinogens. A Forensic Drug Handbook; Laing, R; Siegel, JA, Eds., Academic Press, London, 24 Apr 2003; pp 67–137. 6.3 MB.
Shulgin, AT. Chemistry of psychotomimetics In Handbook of Experimental Pharmacology. Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs; Hoffmeister, F; Stille, G, Eds., Springer-Verlag, Berlin, 1 Jan 1982; Vol. 55 (3), pp 3–29. 928 kB. https://doi.org/10.1007/978-3-642-67770-0_1 #4c
Jacob, P; Shulgin, AT. Structure-activity relationships of the classic hallucinogens and their analogs In Hallucinogens: An update. NIDA Research Monograph 146; Lin, GC; Glennon, RA, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 1 Jan 1994; pp 74–91. 51 kB.
Shulgin, AT. Hallucinogens In Burger’s Medicinal Chemistry, 4th ed., Part III; Wolff, ME, Ed., John Wiley & Sons, Inc., 1 Jan 1981; pp 1109–1137. 4.7 MB. #29b
Shulgin, AT. Psychotomimetic agents In Psychopharmacological Agents; Gordon, M, Ed., Academic Press, New York, 1 Jan 1976; Vol. 4, pp 59–146. 3.1 MB. #XXII,XXVII
Taschwer, M; Ebner, E; Schmid, MG. Test purchase of new synthetic tryptamines via the Internet: Identity check by GC-MS and separation by HPLC J. Appl. Pharm. Sci., 1 Jan 2016, 6 (1), 028–034. 504 kB. https://doi.org/10.7324/JAPS.2016.600105 GC,LC,MS
Nagai, F; Nonaka, R; Kamimura, KSH. The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain Eur. J. Pharmacol., 22 Mar 2007, 559 (2), 132–137. 399 kB. https://doi.org/10.1016/j.ejphar.2006.11.075 #DPT
Takahashi, M; Nagashima, M; Suzuki, J; Seto, T; Yasuda, I; Yoshida, T. Creation and application of psychoactive designer drugs data library using liquid chromatography with photodiode array spectrophotometry detector and gas chromatography–mass spectrometry Talanta, 15 Feb 2009, 77 (4), 1245–1272. 1.2 MB. https://doi.org/10.1016/j.talanta.2008.07.062 #DPT GC,LC,MS,UV
Zamberlan, F; Sanz, C; Vivot, RM; Pallavicini, C; Erowid, F; Erowid, E; Tagliazucchi, E. The varieties of the psychedelic experience: A preliminary study of the association between the reported subjective effects and the binding affinity profiles of substituted phenethylamines and tryptamines Front. Integr. Neurosci., 8 Nov 2018, 12 (54). 5.0 MB. https://doi.org/10.3389/fnint.2018.00054 #DPT
Qu, S; Wang, G; Duan, W; Yao, S; Zuo, J; Tan, C; Zhu, D. Tryptamine derivatives as novel non-nucleosidic inhibitors against hepatitis B virus Bioorg. Med. Chem., 15 May 2011, 19 (10), 3120–3127. 692 kB. https://doi.org/10.1016/j.bmc.2011.04.004 #2c MS,NMR
McCorvy, JD. Mapping the binding site of the 5-HT2A receptor using mutagenesis and ligand libraries: Insights into the molecular actions of psychedelics Ph. D. Thesis, Purdue University, 1 Jan 2012. 3.9 MB. #DPT
Yasuoka, T; Muroi, H; Okazaki, R; Matsumoto, Y; Terauchi, Y; Sasatani, T. Analysis of tryptamine group compounds JCCL, 1 Jan 2003, (43), 63–69. 151 kB. #DPT Japanese, English abstract LC,MS,NMR,IR,UV
Halberstadt, AL; Chatha, M; Klein, AK; Wallach, J; Brandt, SD. Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species Neuropharmacology, 1 May 2020, 167, 107933. 2.4 MB. https://doi.org/10.1016/j.neuropharm.2019.107933 #DPT
Sexton, JD; Nichols, CD; Hendricks, PS. Population survey data informing the therapeutic potential of classic and novel phenethylamine, tryptamine, and lysergamide psychedelics Front. Psychiatry, 11 Feb 2020, 10 (896). 529 kB. https://doi.org/10.3389/fpsyt.2019.00896 #DPT
Barlow, RB; Khan, I. Actions of some analogues of tryptamine on the isolated rat uterus and on the isolated rat fundus strip preparations Br. J. Pharmacol., 1 Mar 1959, 14 (1), 99–107. 1.9 MB. https://doi.org/10.1111/j.1476-5381.1959.tb00934.x #3 other
Chadeayne, AR; Pham, DNK; Golen, JA; Manke, DR. Bis(4-hydroxy-N,N-di-n-propyltryptammonium) fumarate tetrahydrate IUCrData, 28 Nov 2019, 4 (11), x191469. 727 kB. https://doi.org/10.1107/S241431461901469X #DPT other
Palamar, JJ; Acosta, P. A qualitative descriptive analysis of effects of psychedelic phenethylamines and tryptamines Hum. Psychopharmacol. Clin. Exp., 1 Jan 2020, 35 (1), e2719. 764 kB. https://doi.org/10.1002/hup.2719 #DPT
Åstrand, A; Guerrieri, D; Vikingsson, S; Kronstrand, R; Green, H. In vitro characterization of new psychoactive substances at the μ-opioid, CB1, 5HT1A, and 5-HT2A receptors—On-target receptor potency and efficacy, and off-target effects Forensic Sci. Int., 1 Dec 2020, 317, 110553. 1.7 MB. https://doi.org/10.1016/j.forsciint.2020.110553 #DPT
Kikura-Hanajiri, R; Kawamura, M; Uchiyama, N; Ogata, J; Kamakura, H; Saisho, K; Goda, Y. Analytical data of designated substances (shitei-yakubutsu) controlled by the pharmaceutical affairs law in Japan, Part I: GC-MS and LC-MS Yakugaku Zasshi, 1 Jun 2008, 128 (6), 971–979. 1.4 MB. https://doi.org/10.1248/yakushi.128.971 #DPT Incorrect structures drawn. Corrected structures in errata page at end. GC,LC,MS,UV
Uchiyama, N; Kawamura, M; Kamakura, H; Kikura-Hanajiri, R; Goda, Y. Analytical data of designated substances (shitei-yakubutsu) controlled by the pharmaceutical affairs law in Japan, Part II: Color test and TLC Yakugaku Zasshi, 1 Jan 2008, 128 (6), 981–987. 406 kB. https://doi.org/10.1248/yakushi.128.981 #DPT TLC
Doi, K; Miyazawa, M; Fujii, H; Kojima, T. The analysis of the chemical drugs among structural isomer Yakugaku Zasshi, 1 Sep 2006, 126 (9), 815–823. 371 kB. https://doi.org/10.1248/yakushi.126.815 #DPT GC,LC,MS,NMR,IR,TLC
Mesley, RJ; Evans, WH. Infrared identification of some hallucinogenic derivatives of tryptamine and amphetamine J. Pharm. Pharmacol., 1 May 1970, 22 (5), 321–332. 775 kB. https://doi.org/10.1111/j.2042-7158.1970.tb08533.x #N,N-Di-n-propyltryptamine IR
Brimblecombe, RW; Pinder, RM. Hallucinogenic agents, Wright-Scientechnica, Bristol, UK, 1 Jan 1975. 46.2 MB. #4.9
Halberstadt, AL. Recent advances in the neuropsychopharmacology of serotonergic hallucinogens Behav. Brain Res., 15 Jan 2015, 277, 99–120. 4.1 MB. https://doi.org/10.1016/j.bbr.2014.07.016 #DPT
Shulgin, AT. Psychotomimetic agents related to the catecholamines J. Psychedelic Drugs, 1 Apr 1969, 2 (2), 14–19. 782 kB. https://doi.org/10.1080/02791072.1969.10524409 #VIIc
Glennon, RA; Rosecrans, JA. Indolealkylamine and phenalkylamine hallucinogens: A brief overview Neurosci. Biobehav. Rev., 1 Jan 1982, 6 (4), 489–497. 895 kB. https://doi.org/10.1016/0149-7634(82)90030-6 #4c
McKenna, DJ; Towers, HHN. Biochemistry and pharmacology of tryptamines and beta-carbolines: A minireview J. Psychoactive Drugs, 1 Jan 1984, 16 (4), 347–358. 10.8 MB. https://doi.org/10.1080/02791072.1984.10472305 #DPT
Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2.3 MB. #356 Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols. LC,MS,NMR,IR,UV,TLC,spot