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TiHKAL book II entry DPT

ChemSpider 5866
PubChem 6091
Wikidata Q2723010
Erowid DPT
Wikipedia Dipropyltryptamine
Blotter DPT
PsychonautWiki DPT
Trout’s Notes DPT. In Some Simple Tryptamines, 2nd ed., p. 44
Project Response DPT (1663-16)
bluelight.org DPT scraps
bluelight.org The Big & Dandy DPT Thread Part 3
bluelight.org The Big & Dandy DPT Thread Part 1
bluelight.org The Big & Dandy DPT Thread Part 2
Rhodium Psychedelic chemistry by M. V. Smith, chapter 3
bluelight.org DPT Effects and Ratings Survey Results
swgdrug.org DPT

TiHKAL #2 DBT · #20 4-HO-DPT · #27 MBT · #49 NET

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

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

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

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

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.

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.

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

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

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

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

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

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

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-HT_2A 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, 5HT_1A, and 5-HT2_A 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

N,N-Diisopropyltryptamine · DIPT

1-Ethyl-N,N-diethyltryptamine · 1-Ethyl-DET

N-Propyl-N-isopropyltryptamine · PIPT

N-Hexyltryptamine

1-Pentyl-AMT · 1-Pentyl-α-methyltryptamine

N-Pentyl-N-methyltryptamine · N-Pentyl-NMT

DPAI

2792

2PYCP · PYCP

3PYCP

4PYCP

N-Isopentyl-N-methyltryptamine · N-Isopentyl-NMT

N-Neopentyl-AMT · N-Neopentylt-α-methyltryptamine

5-tert-Butyl-N,N-dimethyltryptamine · 5-tert-Butyl-DMT

N-Ethyl-N-butyltryptamine · EBT

13767

c8-63: DPT: GC-MS
c8-83: DPT: Synthesis
c8-84: DPT: GC-MS
c8-85: DPT: GC-MS
p4-462: α-CP-2C-D; 2C-C; 4-HO-DET; 4-HO-DPT; 4-MeO-DET; 5,6-MDO-MIPT; BOAD; BOD; DMA; DOIB; DPT; ORTHO-MDA