Dipropyltryptamine

Last updated

Dipropyltryptamine
DPT.svg
DPT-3d-sticks.png
Clinical data
Other namesDPT; N,N-Dipropyltryptamine; "The Light"
Routes of
administration 		Oral, smoking, intramuscular injection, intravenous injection [1]
Drug class Serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
Pharmacokinetic data
Onset of action Oral: Fast [1]
Injection: 10–15 minutes [1]
Duration of action 2–4 hours (but up to 12 hours at very high doses) [1] [2]
Identifiers
  • N-[2-(1H-indol-3-yl)]ethyl-N-propylpropan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C16H24N2
Molar mass 244.382 g·mol−1
3D model (JSmol)
Melting point 174.5 to 178 °C (346.1 to 352.4 °F)
  • CCCN(CCC)CCC1=CNC2=C1C=CC=C2
  • InChI=1S/C16H24N2/c1-3-10-18(11-4-2)12-9-14-13-17-16-8-6-5-7-15(14)16/h5-8,13,17H,3-4,9-12H2,1-2H3 Yes check.svgY
  • Key:BOOQTIHIKDDPRW-UHFFFAOYSA-N Yes check.svgY
   (verify)

Dipropyltryptamine (DPT), also known as N,N-dipropyltryptamine or as "The Light", is a psychedelic drug of the tryptamine family related to dimethyltryptamine (DMT). [1] [3] It is taken orally or by other routes. [1]

Contents

The drug acts as a serotonin receptor modulator, including as a serotonin 5-HT2A receptor agonist. [4] [5] [6] [7] [8] It is a close structural 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] It was encountered as a novel designer drug by 1968 [12] and was reported as a possible treatment for alcoholism in 1973. [2] [3] [13] The drug is the sacrament of the Temple of the True Inner Light, a New York City-based religious group. [1] [14] [15]

Use and effects

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] A 500 mg dose was also reported, which was described as "exhausting" and as lasting 12 hours. [1] The onset and time to peak effects were not given, but it was implied to have a fast onset. [1] In addition to oral administration, DPT has been assessed by 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] Other effects included trouble talking, feeling uncomfortable, nervousness, feeling light, and body rush. [1] Given at a high dose intravenously, it was described as every bit as powerful as a psychedelic as DMT. [1] According to one account however, DPT and DMT, despite their chemical similarity, "reveal completely different worlds". [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] Its duration is described as much shorter than those of certain other psychedelics like LSD, which can be advantageous in a clinical setting. [18] [19] [20] However, it is also said to have a rapid onset that can be psychologically overwhelming. [18] [20]

Side effects

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] The pharmacological similarity of DPT to DMT suggests a generally low intrinsic 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] The main safety concerns are acute 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]

Interactions

Pharmacology

Pharmacodynamics

DPT activities
Target Affinity (Ki, nM)Species
5-HT1A 31.8–1,641 (Ki)
274–>10,000 (EC50 Tooltip half-maximal effective concentration)
99% (Emax Tooltip maximal efficacy)		Human
Human
Human
5-HT1B 854–8,081 (Ki)
1,210 (EC50)		Human
Human
5-HT1D 619Human
5-HT1E 2,338Human
5-HT2A 3.0–2,579 (Ki)
26.1–943a (EC50)
85a–97% (Emax)		Human
Human
Human
5-HT2B 42Human
5-HT2C 281–3,500 (Ki)
444a (EC50)
93%a (Emax)		Human
Human
Human
5-HT3 >10,000Human
5-HT4 NDND
5-HT5A 4,373Human
5-HT6 4,543Human
5-HT7 284Human
D1 >10,000Human
D2 9,249Human
D3 1,361Human
D4 2,014Human
D5 >10,000Human
α1A 881Human
α1B 443Human
α1D NDND
α2A 458Human
α2B 339Human
α2C 514Human
β1–β2 >10,000Human
H1 125Human
H2–H4 >10,000Human
M1–M5 >10,000Human
I1 340Human
σ1 397Human
σ2 2,917Human
SERT Tooltip Serotonin transporter157–480 (Ki)
157–23,000 (IC50 Tooltip half-maximal inhibitory concentration)
>100,000 (EC50)		Human
Human
Rat
NET Tooltip Norepinephrine transporter>10,000 (Ki)
2,900–3,202 (IC50)
>100,000 (EC50)		Human
Human
Rat
DAT Tooltip Dopamine transporter1,500 (Ki)
2,218–9,100 (IC50)
>100,000 (EC50)		Human
Human
Rat
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] Studies on rodents have found that the effectiveness with which a 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]

Chemistry

DPT hydrochloride powder. N,N-Dipropyltryptamine.jpg
DPT hydrochloride powder.

DPT, also known as N,N-dipropyltryptamine, is a substituted tryptamine related to dimethyltryptamine (DMT). [1] It is found either as a crystalline hydrochloride salt or as an oily or crystalline base. The drug is synthetic and has not been found to occur endogenously. [17]

Detection

DPT changes Ehrlich's reagent violet and causes the marquis reagent to turn yellow. [26]

Synthesis

The chemical synthesis of DPT has been described. [1]

Analogues

Analogues of DPT include dimethyltryptamine (DMT), diethyltryptamine (DET), diisopropyltryptamine (DiPT), diallyltryptamine (DALT), methylethyltryptamine (MET), methylpropyltryptamine (MPT), ethylpropyltryptamine (EPT), propylisopropyltryptamine (PiPT), 4-HO-DPT, 5-HO-DPT, and 5-MeO-DPT, among others. [1]

History

DPT was first described in the scientific literature by 1959. [9] [10] [11] Use of DPT as a designer drug has been documented by law enforcement officials since as early as 1968. [12] It was described as a treatment for alcoholism by Stanislav Grof and colleagues in 1973. [3] [2] [13] [27] It was also studied for treatment of anxiety associated with terminal cancer in the late 1970s. [27] However, it was not further studied for such purposes after 1980. [28]

Society and culture

Religious use

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] The Temple believes DPT and other entheogens are physical manifestations of God. [1] [29]

Sweden

DPT is illegal in Sweden as of 26 January 2016. [30]

United Kingdom

DPT is a Class A drug in the United Kingdom, making it illegal to possess or distribute.

United States

DPT is not scheduled at the federal level in the United States, [31] but it could be considered an analog of 5-MeO-DiPT, DMT, or DET, in which case purchase, sale, or possession could be prosecuted under the Federal Analogue Act.

Florida

"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. [32]

Maine

DPT is a Schedule I controlled substance in the state of Maine making it illegal to buy, sell, or possess in Maine.

Research

Fragile X syndrome

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. [33] While DPT is an agonist at several serotonin receptors in vitro, its 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. [33] The drug's beneficial effects may be mediated by non-serotonergic pathways, possibly involving direct auditory processing modulation. [33] At higher doses, DPT switched from anticonvulsant to proconvulsant action, indicating complex interactions. [33]

See also

References

  1. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN   0-9630096-9-9. OCLC   38503252.
  2. 1 2 3 4 5 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.
  3. 1 2 3 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.
  4. 1 2 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.
  5. 1 2 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-HT2AR), 5-HT2CR, 5-HT1AR, and Serotonin Transporter". The Journal of Pharmacology and Experimental Therapeutics. 385 (1): 62–75. doi:10.1124/jpet.122.001454. PMC   10029822 . PMID   36669875.
  6. 1 2 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.
  7. 1 2 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.
  8. 1 2 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.
  9. 1 2 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.
  10. 1 2 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.
  11. 1 2 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.
  12. 1 2 "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.
  13. 1 2 3 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.
  14. ↑ DeKorne J (26 July 2011). Psychedelic Shamanism, Updated Edition: The Cultivation, Preparation, and Shamanic Use of Psychotropic Plants. North Atlantic Books. p. 81. ISBN   978-1-58394-290-1.
  15. ↑ Kaplan E (October 1987). "Still hippies, after all these years". Spy Magazine (October 1987): 61.
  16. 1 2 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. [...]
  17. 1 2 3 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.
  18. 1 2 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]
  19. ↑ 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.
  20. 1 2 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.
  21. 1 2 3 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.
  22. 1 2 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.
  23. ↑ "PDSP Database". UNC (in Zulu). Retrieved 11 December 2024.
  24. ↑ 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.
  25. 1 2 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.
  26. ↑ Spratley T (2004). "Analytical Profiles for Five "Designer" Tryptamines" (PDF). Microgram Journal. 3 (1–2): 55. Retrieved 9 October 2013.
  27. 1 2 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).
  28. ↑ 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.
  29. ↑ "Temple of the True Inner Light". tripod.com.
  30. ↑ "31 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. November 2015.
  31. ↑ "SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I." CFR. Archived from the original on 27 August 2009. Retrieved 17 December 2014.
  32. ↑ Florida Statutes – Chapter 893 – DRUG ABUSE PREVENTION AND CONTROL
  33. 1 2 3 4 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.
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