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| Other names | DPT;N,N-Dipropyltryptamine |
| Routes of administration | Oral,inhalation (smoking),intravenous orintramuscular injection[1] |
| Drug class | Serotonin receptor agonist;Serotonin5-HT2A receptoragonist;Serotonergic psychedelic;Hallucinogen |
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| Pharmacokinetic data | |
| Onset of action | Injection: 10–15 minutes[1] |
| Duration of action | 2–4 hours[1] |
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| 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) |
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N,N-Dipropyltryptamine (DPT) is apsychedelic drug andentheogen belonging to thetryptamine family.[1] Use as adesigner drug has been documented by law enforcement officials since as early as 1968.[2] However, potential therapeutic use was not investigated until the 1970s.[3] It is found either as acrystallinehydrochloridesalt or as an oily or crystallinebase. It has not been found to occurendogenously. It is a close structuralhomologue ofdimethyltryptamine (DMT) anddiethyltryptamine (DET).
Dose ranges of DPT of 100 to 250 mg (but up to 500 mg)orally, 100 mgsmoked, 15 to 125 mgintramuscularly, and 12 to 36 mgintravenously have been described.[1][4] Itsduration is 2 to 4 hours orally but can last up to 12 hours with high doses.[1]
While DPT is chemically similar todimethyltryptamine (DMT), its psychoactive effects have been said to be qualitatively markedly different.[5] On the other hand, others have reported similarities to DMT, for instance in terms of intensity.[1]
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.[6] 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.[6]
Ameta-analysis of tryptamine psychedelics have further demonstrated cognitive effects throughserotonin5-HT2A receptor modulation but have not identified persistentneurotoxicity.[7] 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.[6][7]
| Target | Affinity (Ki, nM) | Species |
|---|---|---|
| 5-HT1A | 31.8–1,641 (Ki) 274–>10,000 (EC50Tooltip half-maximal effective concentration) 99% (EmaxTooltip maximal efficacy) | Human Human Human |
| 5-HT1B | 854–8,081 (Ki) 1,210 (EC50) | Human Human |
| 5-HT1D | 619 | Human |
| 5-HT1E | 2,338 | Human |
| 5-HT2A | 3.0–2,579 (Ki) 26.1–943 (EC50) 85–97% (Emax) | Human Human Human |
| 5-HT2B | 42 | Human |
| 5-HT2C | 281–3,500 (Ki) 444 (EC50) 93% (Emax) | Human Human Human |
| 5-HT3 | >10,000 | Human |
| 5-HT4 | ND | ND |
| 5-HT5A | 4,373 | Human |
| 5-HT6 | 4,543 | Human |
| 5-HT7 | 284 | Human |
| D1 | >10,000 | Human |
| D2 | 9,249 | Human |
| D3 | 1,361 | Human |
| D4 | 2,014 | Human |
| D5 | >10,000 | Human |
| α1A | 881 | Human |
| α1B | 443 | Human |
| α1D | ND | ND |
| α2A | 458 | Human |
| α2B | 339 | Human |
| α2C | 514 | Human |
| β1–β2 | >10,000 | Human |
| H1 | 125 | Human |
| H2–H4 | >10,000 | Human |
| M1–M5 | >10,000 | Human |
| I1 | 340 | Human |
| σ1 | 397 | Human |
| σ2 | 2,917 | Human |
| SERTTooltip Serotonin transporter | 157 (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 transporter | 1,500 (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.Refs:[8][9][10][11][12][13][14] | ||
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.[15]
DPT produces thehead-twitch response, a behavioral proxy ofpsychedelic-like effects, in rodents.[4]
DPT changesEhrlich's reagent violet and causes the marquis reagent to turn yellow.[16]
Analogues of DPT includedimethyltryptamine (DMT),diethyltryptamine (DET),diisopropyltryptamine (DiPT),diallyltryptamine (DALT),methylpropyltryptamine (MPT),ethylpropyltryptamine (EPT),propylisopropyltryptamine (PiPT),4-HO-DPT,5-HO-DPT, and5-MeO-DPT, among others.
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DPT was first described in thescientific literature by 1959.[17][18][19]
DPT is used as areligioussacrament by theTemple of the True Inner Light, aNew York City offshoot of theNative American Church. The Temple believes DPT and otherentheogens are physical manifestations ofGod.[20]
DPT is illegal in Sweden as of 26 January 2016.[21]
DPT is a Class A drug in the United Kingdom, making it illegal to possess or distribute.
DPT is not scheduled at the federal level in the United States,[22] 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.
"DPT (N,N-Dipropyltryptamine)" is a Schedule Icontrolled substance in the state ofFlorida making it illegal to buy, sell, or possess in Florida.[23]
DPT is a Schedule Icontrolled substance in the state ofMaine making it illegal to buy, sell, or possess in Maine.
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.[24] 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.[24] The drug's beneficial effects may be mediated by non-serotonergic pathways, possibly involving direct auditory processing modulation.[24] At higher doses, DPT switched fromanticonvulsant toproconvulsant action, indicating complex interactions.[24]
Table 4 Human potency data for selected hallucinogens. [...]
