Chemistry:DiPT
Diisopropyltryptamine (DiPT), also known as N,N-diisopropyltryptamine, is a psychedelic hallucinogenic drug of the tryptamine family that has a unique effect. While the majority of hallucinogens affect the visual sense, DiPT is primarily aural.[1]
Use and effects
Alexander Shulgin in TiHKAL gave a dose range of DiPT of 25 to 100 mg orally and a duration of 6 to 8 hours.[1] A wider recreational dose range for DiPT of 15 to 150 mg or more has also been reported.[2]
DiPT's effects are primarily aural. At lower doses, Alexander Shulgin reported effects similar to a flanging or a phase shift. At medium and higher dosages, the effect of DiPT is typically a radical shift downward in perceived pitch. This shift tends to be nonlinear, in that the shift downwards varies in relation to the initial pitch. This can produce bizarre sounds and render music disharmonious.[1] There has been an experiment involving subjects with perfect pitch, the goal of which was to determine whether the pitch difference is truly distortive or linear, the results of which indicated that there is no clear relationship between perceived pitch and actual pitch.[1] Aside from these, the most prevalent non-auditory effect is inner ear pressure (which has been painful in some instances, for example when combined with MDMA).[1]
Interactions
Pharmacology
Pharmacodynamics
| Target | Affinity (Ki, nM) |
|---|---|
| 5-HT1A | 121–538 |
| 5-HT1B | >10,000 |
| 5-HT1D | 3,742 |
| 5-HT1E | >10,000 |
| 5-HT1F | ND |
| 5-HT2A | 1,200–>10,000 (Ki) 240–1,411 (EC50) 89–117% (Emax) |
| 5-HT2B | 399 (Ki) 1,000–2,380 (EC50) 103–107% (Emax) |
| 5-HT2C | 290–>10,000 (Ki) 167–1,999 (EC50) 81–143% (Emax) |
| 5-HT3 | >10,000 |
| 5-HT4 | ND |
| 5-HT5A | >10,000 |
| 5-HT6 | >10,000 |
| 5-HT7 | 3,423 |
| α1A | >12,000 |
| α1B | >10,000 |
| α1D | ND |
| α2A | 3,600–>10,000 |
| α2B | 2,870 |
| α2C | 2,523 |
| β1 | >10,000 |
| β2 | >10,000 |
| β3 | ND |
| D1 | >25,000 |
| D2 | >25,000 |
| D3 | 3,321–>25,000 |
| D4 | >10,000 |
| D5 | >10,000 |
| H1 | 920–3,583 |
| H2 | >10,000 |
| H3 | ND |
| H4 | >10,000 |
| M1 | >10,000 |
| M2 | >10,000 |
| M3 | >10,000 |
| M4 | >10,000 |
| M5 | >10,000 |
| I1 | 356 |
| σ1 | 1,798 |
| σ2 | 2,702 |
| TAAR1 | >15,000 (Ki) (mouse) >15,000 (Ki) (rat) ND (EC50) (mouse) ND (EC50) (rat) ND (EC50) (human) ND (Emax) (mouse) ND (Emax) (rat) |
| SERT | 180–1,258 (Ki) 900 (IC50) IA (EC50) |
| NET | 8,900–>10,000 (Ki) 9,900 (IC50) IA (EC50) |
| DAT | 4,100–>10,000 (Ki) 35,000 (IC50) IA (EC50) |
| Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [3][4][5][6][7] | |
DiPT binds to serotonin receptors including the serotonin 5-HT1A, 5-HT2A, 5-HT2B, 5-HT2C receptors among others.[4][5] It is known to act as a full agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors.[4][5] It is also a weak serotonin reuptake inhibitor.[5] In contrast to many related drugs, DiPT does not interact with the rodent or human trace amine-associated receptor 1 (TAAR1).[7]
The discriminative stimulus properties of DiPT in rodent drug discrimination tests are partially blocked by the serotonin 5-HT2A receptor antagonist volinanserin and by the serotonin 5-HT2C receptor antagonist SB-242084.[6] This is in contrast to the case of the related psychedelic dimethyltryptamine (DMT), wherein volinanserin fully blocks its stimulus properties and SB-242084 has minimal influence.[6] Similarly to DMT and other psychedelics, DiPT produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents, and this effect is blocked by volinanserin.[6][8]
Chemistry
DiPT is a derivative of tryptamine formed by substituting isopropyl groups for the two hydrogen atoms attached to the non-aromatic nitrogen atom in the tryptamine molecule.
Analogues of DiPT include dimethyltryptamine (DMT), diethyltryptamine (DET), dipropyltryptamine (DPT), 5-MeO-DMT, 5-MeO-DPT, 5-MeO-AMT, 5-MeO-DiPT, 4-HO-DiPT (iprocin), 5-HO-DiPT, 4-AcO-DiPT (ipracetin), and 5,6-MDO-DiPT, among others.
Society and culture
Legal status
United Kingdom
As is the case with many psychedelic tryptamines and phenethylamines, it is Class A in the UK, making it illegal to possess or use.
United States
DiPT is not scheduled at the federal level in the United States,[9] but it could be considered an analog of 5-MeO-DiPT, in which case purchase, sale, or possession for human consumption or illicit use that is not for scientific or industrial purposes could be prosecuted under the Federal Analog Act. Some of the people arrested in Operation Web Tryp were selling DiPT, however the drug is not explicitly forbidden or outlawed.
However the US Drug Enforcement Agency (DEA) withdrew a proposal to ban five psychedelic substances including 4-Hydroxy-N,N-diisopropyltryptamine (4-OH-DiPT), N-Isopropyl-5-Methoxy-N-Methyltryptamine (5-MeO-MiPT) and N,N-Diisopropyltryptamine (DiPT). DEA withdrew the proposed listing as schedule 1 banned substance after a public hearing in 2022.[10]
Florida
"DiPT (N,N-Diisopropyltryptamine)" is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida.[11]
Sweden
Sweden's public health agency suggested classifying DiPT as a hazardous substance, on May 15, 2019.[12]
See also
References
- ↑ 1.0 1.1 1.2 1.3 1.4 Shulgin, Alexander (1997). TiHKAL: Tryptamines I Have Known and Loved. Berkeley, CA USA: Transform Press. pp. 403–406. ISBN 0-9630096-9-9. https://www.erowid.org/library/books_online/tihkal/tihkal04.shtml.
- ↑ "Monoamine Transporter and Receptor Interaction Profiles in Vitro Predict Reported Human Doses of Novel Psychoactive Stimulants and Psychedelics". Int J Neuropsychopharmacol 21 (10): 926–931. October 2018. doi:10.1093/ijnp/pyy047. PMID 29850881.
- ↑ "Kᵢ Database". 25 March 2025. https://pdsp.unc.edu/kidb2/kidb/web/kis-results/index?KisResultsSearch%5Binput_receptors%5D=&KisResultsSearch%5Binput_sources%5D=&KisResultsSearch%5Binput_species%5D=&KisResultsSearch%5Binput_hot_ligands%5D=&KisResultsSearch%5Binput_test_ligands%5D=&KisResultsSearch%5Binput_test_ligands%5D%5B%5D=12948&KisResultsSearch%5Binput_citations%5D=&KisResultsSearch%5BsearchType%5D=&KisResultsSearch%5Bki_val_from%5D=&KisResultsSearch%5Bki_val_to%5D=&KisResultsSearch%5Bcustom_ki_val%5D=.
- ↑ 4.0 4.1 4.2 "Psychedelics and the human receptorome". PLOS ONE 5 (2). February 2010. doi:10.1371/journal.pone.0009019. PMID 20126400. Bibcode: 2010PLoSO...5.9019R.
- ↑ 5.0 5.1 5.2 5.3 "Receptor interaction profiles of novel psychoactive tryptamines compared with classic hallucinogens". European Neuropsychopharmacology 26 (8): 1327–1237. August 2016. doi:10.1016/j.euroneuro.2016.05.001. PMID 27216487. https://psilosybiini.info/paperit/Receptor%20interaction%20profiles%20of%20novel%20psychoactive%20tryptamines%20compared%20with%20classic%20hallucinogens%20(Rickli%20et%20al.,%202016).pdf.
- ↑ 6.0 6.1 6.2 6.3 "The role of 5-HT2A, 5-HT 2C and mGlu2 receptors in the behavioral effects of tryptamine hallucinogens N,N-dimethyltryptamine and N,N-diisopropyltryptamine in rats and mice". Psychopharmacology (Berl) 232 (1): 275–284. January 2015. doi:10.1007/s00213-014-3658-3. PMID 24985890. "DiPT bound with moderate affinity to the 5-HT2C receptor (Ki= 290 ± 110 nM; Hill coefficient = −0.72 ± 0.05) and was a full agonist in the IP-1 formation assay (EC50 = 2380 ± 340 nM), producing 107.4 ± 2.5% of the maximal 5-HT effect.".
- ↑ 7.0 7.1 "In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1". J Pharmacol Exp Ther 357 (1): 134–144. April 2016. doi:10.1124/jpet.115.229765. PMID 26791601. https://d1wqtxts1xzle7.cloudfront.net/74120533/eae6c6e62565b82d46b4d111bbea0f77b9c2-libre.pdf?1635931703=&response-content-disposition=inline%3B+filename%3DIn_Vitro_Characterization_of_Psychoactiv.pdf&Expires=1746838268&Signature=Sy4fJ90yUhxs68314NxYsW5PAaNrBGePRu35WRR4PIF-3YC7Z~sLdnCn5wfqqbLg9bDEGdt~oW55ugMP3D3jgA0BoRI~~GOb0NQOwrtfUEQK1PQs1uuN9qg5Y1ct8z5NsABm44RgtukkwRMdU6fO7OlfIsQ68hOiFk129Ll7UYqldxD2f1xhE2fTTfsxSpb8cMCJzHn7-ItqLdwnAUPFK7WggDIjmY1kCnaHLwIxMwdJCAq8L6DYzSTg7pZkbR8qlou~GXbTPQt~gYpyZTJp5hgW-7V6K5wLlQ7Z2xE7B0f9wEfuc1W1QNafg125Tr-vvAe4LEGKXV58bnn1bpfWKw__&Key-Pair-Id=APKAJLOHF5GGSLRBV4ZA.
- ↑ "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species". Neuropharmacology 167. May 2020. doi:10.1016/j.neuropharm.2019.107933. PMID 31917152. PMC 9191653. http://usdbiology.com/cliff/Courses/Advanced%20Seminars%20in%20Neuroendocrinology/Serotonergic%20Psychedelics%2020/Halberstadt%2020%20Neuropharm%20potency%20of%20hallucinogens%20%20head-twitch.pdf.
- ↑ "21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I.". Drug Enforcement Administration (DEA). U.S. Department Of Justice. http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm.
- ↑ "Placement of 4-hydroxy-N,N-diisopropyltryptamine (4-OH-DiPT), 5-methoxy-alpha-methyltryptamine (5-MeO-AMT), 5-methoxy-N-methyl-N-isopropyltryptamine (5-MeO-MiPT), 5-methoxy-N,N-diethyltryptamine (5-MeO-DET), and N,N-diisopropyltryptamine (DiPT) in Schedule I; Withdrawal of Proposed Rule". 27 July 2022. https://www.federalregister.gov/documents/2022/07/27/2022-16102/schedules-of-controlled-substances-placement-of-4-hydroxy-nn-diisopropyltryptamine-4-oh-dipt.
- ↑ "Chapter 893 - Drug Abuse Prevention and Control". Florida Statutes. http://leg.state.fl.us/statutes/index.cfm?App_mode=Display_Statute&URL=0800-0899/0893/0893.html.
- ↑ "Folkhälsomyndigheten föreslår att 20 ämnen klassas som narkotika eller hälsofarlig vara" (in sv). Folkhälsomyndigheten. 15 May 2019. https://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2019/maj/folkhalsomyndigheten-foreslar-att-20-amnen-klassas-som-narkotika-eller-halsofarlig-vara/.
External links
- DiPT - Isomer Design
- DiPT - PsychonautWiki
- DiPT - Erowid
- The Big & Dandy DiPT Thread - Bluelight
- DIPT - TiHKAL - Erowid
- DIPT - TiHKAL - Isomer Design
- Forget the Visuals—Psychedelic DiPT Makes You Trip On Sound - Double Blind Magazine
- What Is DiPT? The Auditory Psychedelic - Tripsitter
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