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Dipropyltryptamine

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(Redirected fromN,N-Dipropyltryptamine)
Chemical compound

Pharmaceutical compound
Dipropyltryptamine
Clinical data
Other namesDPT;N,N-Dipropyltryptamine; "The Light"
Routes of
administration
Oral,smoking,intramuscular injection,intravenous injection[1]
Drug classSerotonin receptor agonist;Serotonin5-HT2A receptoragonist;Serotonergic psychedelic;Hallucinogen
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Onset of actionOral: Fast[1]
Injection: 10–15 minutes[1]
Duration of action2–4 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
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC16H24N2
Molar mass244.382 g·mol−1
3D model (JSmol)
Melting point174.5 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 checkY
  • Key:BOOQTIHIKDDPRW-UHFFFAOYSA-N checkY
  (verify)

Dipropyltryptamine (DPT), also known asN,N-dipropyltryptamine or as "The Light", is apsychedelic drug of thetryptamine family related todimethyltryptamine (DMT).[1][3] It is takenorally or by otherroutes.[1]

The drug acts as aserotonin receptor modulator, including as aserotonin5-HT2A receptoragonist.[4][5][6][7][8] It is a close structuralhomologue of DMT anddiethyltryptamine (DET).[1]Derivatives of DPT include4-HO-DPT and5-MeO-DPT, among others.[1]

DPT was first described in the literature by 1959.[9][10][11] It was encountered as a noveldesigner drug by 1968[12] and was reported as a possible treatment foralcoholism in 1973.[2][3][13] The drug is thesacrament of theTemple of the True Inner Light, aNew York City-based religious group.[1][14][15]

Use and effects

[edit]

In his bookTiHKAL (Tryptamines I Have Known and Loved),Alexander Shulgin lists DPT's dose range as 100 to 250 mgorally and itsduration 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] Theonset 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 bysmoking at a dose of 100 mg, byintramuscular 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 byintravenous injection at 12 to 36 mg.[1][16]

The effects of DPT have been reported to includevisuals, being intensely visual at high doses, changes intime perception, feeling like one is in a different place like on a mountain in clouds or in a big castle, enhancedrecall of memories and experiences, enhanced emotional expressiveness and self-exploration,entity encounters, andreligious 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 includingvisual andauditory 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 increasedheart 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

[edit]

Althoughtryptamines such aspsilocybin anddimethyltryptamine (DMT) have relatively well‑characterizedsafety,syntheticanalogues like DPT lack thoroughtoxicological evaluation and are mainly associated withanecdotal 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 intrinsictoxicity at controlled doses but a pronounced risk of acute adverse reactions, includingagitation,tachycardia,hyperthermia, andserotonergic crisis, particularly in combination withmonoamine oxidase inhibitors or otherserotonergic substances.[21]

Ameta-analysis of tryptamine psychedelics have further demonstrated cognitive effects throughserotonin5-HT2A receptor modulation but have not identified persistentneurotoxicity.[22] The main safety concerns are acutepsychophysiological 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 and5-MeO-DMT.[21][22]

Interactions

[edit]
See also:Psychedelic drug § Interactions, andTrip killer § Serotonergic psychedelic antidotes

Pharmacology

[edit]

Pharmacodynamics

[edit]
DPT activities
TargetAffinity (Ki, nM)Species
5-HT1A31.8–1,641 (Ki)
274–>10,000 (EC50Tooltip half-maximal effective concentration)
99% (EmaxTooltip maximal efficacy)
Human
Human
Human
5-HT1B854–8,081 (Ki)
1,210 (EC50)
Human
Human
5-HT1D619Human
5-HT1E2,338Human
5-HT2A3.0–2,579 (Ki)
26.1–943a (EC50)
85a–97% (
Emax)
Human
Human
Human
5-HT2B42Human
5-HT2C281–3,500 (Ki)
444a (EC50)
93%a (
Emax)
Human
Human
Human
5-HT3>10,000Human
5-HT4NDND
5-HT5A4,373Human
5-HT64,543Human
5-HT7284Human
D1>10,000Human
D29,249Human
D31,361Human
D42,014Human
D5>10,000Human
α1A881Human
α1B443Human
α1DNDND
α2A458Human
α2B339Human
α2C514Human
β1β2>10,000Human
H1125Human
H2H4>10,000Human
M1M5>10,000Human
I1340Human
σ1397Human
σ22,917Human
SERTTooltip Serotonin transporter157–480 (Ki)
157–23,000 (IC50Tooltip half-maximal inhibitory concentration)
>100,000 (EC50)
Human
Human
Rat
NETTooltip Norepinephrine transporter>10,000 (Ki)
2,900–3,202 (IC50)
>100,000 (
EC50)
Human
Human
Rat
DATTooltip 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 ofIP1Tooltip inositol phosphate formation.Refs:[4][5][6][7][8][23][24]

DPT produces thehead-twitch response, a behavioral proxy ofpsychedelic-like effects, in rodents.[16][25] Studies on rodents have found that the effectiveness with which aselective5-HT2A receptorantagonist 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 serotonin5-HT1A receptor antagonist also imply a serotonin 5-HT1A receptor-mediated component to the actions of DPT.[25]

Chemistry

[edit]
DPT HCl Powder
DPThydrochloride powder.

DPT, also known asN,N-dipropyltryptamine, is asubstituted tryptamine related todimethyltryptamine (DMT).[1] It is found either as acrystallinehydrochloridesalt or as an oily or crystallinebase. The drug issynthetic and has not been found to occurendogenously.[17]

Detection

[edit]

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

Synthesis

[edit]

Thechemical synthesis of DPT has been described.[1]

Analogues

[edit]

Analogues of DPT includedimethyltryptamine (DMT),diethyltryptamine (DET),diisopropyltryptamine (DiPT),diallyltryptamine (DALT),methylethyltryptamine (MET),methylpropyltryptamine (MPT),ethylpropyltryptamine (EPT),propylisopropyltryptamine (PiPT),propylallyltryptamine (PALT),4-HO-DPT,5-HO-DPT, and5-MeO-DPT, among others.[1]

History

[edit]

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

Society and culture

[edit]

Religious use

[edit]

DPT is used as areligioussacrament by theTemple of the True Inner Light, aNew York City offshoot of theNative American Church.[1] The Temple believes DPT and otherentheogens are physical manifestations ofGod.[1][29]

Legal status

[edit]

Sweden

[edit]

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

United Kingdom

[edit]

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

United States

[edit]

DPT is not scheduled at the federal level in the United States,[31] but it could be considered an analog of5-MeO-DiPT,DMT, orDET, in which case purchase, sale, or possession could be prosecuted under theFederal Analogue Act.

Florida
[edit]

"DPT (N,N-Dipropyltryptamine)" is a Schedule Icontrolled substance in the state ofFlorida making it illegal to buy, sell, or possess in Florida.[32]

Maine
[edit]

DPT is a Schedule Icontrolled substance in the state ofMaine making it illegal to buy, sell, or possess in Maine.

Research

[edit]

Fragile X syndrome

[edit]

DPT has been found to completely preventaudiogenicseizures inmouse models offragile X syndrome (FXS) at a 10 mg/kg dose, with itsmechanism of action appearing to be independent ofserotonin andsigmaσ1 receptor activation.[33] While DPT is anagonist at several serotonin receptorsin vitro, itsanticonvulsant effects were not blocked byselectiveserotonin5-HT2A,5-HT1A, or5-HT1B receptorantagonists nor by a selective sigma σ1 receptor antagonistin 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 fromanticonvulsant toproconvulsant action, indicating complex interactions.[33]

See also

[edit]

References

[edit]
  1. ^abcdefghijklmnopqrstuShulgin A,Shulgin A (September 1997).TiHKAL: The Continuation.Berkeley, California:Transform Press.ISBN 0-9630096-9-9.OCLC 38503252.
  2. ^abcdeTittarelli 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. ^abcMalaca 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. ^abRay 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. ^abKozell 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. ^abBlough 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. ^abNagai 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. ^abNelson 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. Retrieved11 December 2024.
  9. ^abBarlow 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. ^abBarlow 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. ^abVane 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. ^ab"Microgram Journal Volume One No. 7"(PDF).Microgram Journal.One (Seven). U.S DOJ,Bureau of Narcotics and Dangerous Drugs: 23. April 1968 [1968]. Retrieved5 April 2021.
  13. ^abcSoskin 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. ^abHalberstadt 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. ^abcPinchbeck 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. ^abDutta 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. Retrieved8 November 2025.
  20. ^abRichards 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. Retrieved8 November 2025.
  21. ^abcAraújo 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. ^abCastelhano 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). Retrieved11 December 2024.
  24. ^Tyagi R, Saraf TS, Canal CE (October 2023)."The PsychedelicN,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. ^abFantegrossi 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. Retrieved9 October 2013.
  27. ^abGarcia-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 fromthe original on 27 August 2009. Retrieved17 December 2014.
  32. ^Florida Statutes – Chapter 893 – DRUG ABUSE PREVENTION AND CONTROL
  33. ^abcdTyagi R, Saraf TS, Canal CE (October 2023)."The PsychedelicN,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.

External links

[edit]
Tryptamines
No ring subs.
4-Hydroxytryptamines
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Other ring subs.
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DATTooltip Dopamine transporter
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