Dipropyltryptamine

N,N-Dipropyltryptamine (DPT) is a psychedelic drug and entheogen belonging to the tryptamine family.^[1] Use as a designer 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 a crystalline hydrochloride salt or as an oily or crystalline base. It has not been found to occur endogenously. It is a close structural homologue of dimethyltryptamine (DMT) and diethyltryptamine (DET).

Dipropyltryptamine

Clinical data
Other names	DPT; N,N-Dipropyltryptamine
Routes of administration	Oral, inhalation (smoking), intravenous or intramuscular 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	Injection: 10–15 minutes[1]
Duration of action	2–4 hours[1]
Identifiers
IUPAC name N-[2-(1H-indol-3-yl)]ethyl-N-propylpropan-1-amine
CAS Number	61-52-9 Y
PubChem CID	6091
ChemSpider	5866 Y
UNII	S7272VWU50
CompTox Dashboard (EPA)	DTXSID30209847
Chemical and physical data
Formula	C16H24N2
Molar mass	244.382 g·mol−1
3D model (JSmol)	Interactive image
Melting point	174.5 to 178 °C (346.1 to 352.4 °F)
SMILES CCCN(CCC)CCC1=CNC2=C1C=CC=C2
InChI 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 Y Key:BOOQTIHIKDDPRW-UHFFFAOYSA-N Y
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Use and effects

Dose ranges of DPT of 100 to 250 mg (but up to 500 mg) orally, 100 mg smoked, 15 to 125 mg intramuscularly, and 12 to 36 mg intravenously have been described.^[1][4] Its duration is 2 to 4 hours orally but can last up to 12 hours with high doses.^[1]

While DPT is chemically similar to dimethyltryptamine (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]

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.^[6] 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.^[6]

A meta-analysis of tryptamine psychedelics have further demonstrated cognitive effects through serotonin 5-HT_2A receptor modulation but have not identified persistent neurotoxicity.^[7] 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.^[6][7]

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

Pharmacodynamics

DPT activities

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 a selective 5-HT_2A receptor antagonist blocks the behavioral actions of DPT strongly suggests that the 5-HT_2A receptor is an important site of action for the drug, but the modulatory actions of a serotonin 5-HT_1A receptor antagonist also imply a serotonin 5-HT_1A receptor-mediated component to the actions of DPT.^[15]

DPT produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents.^[4]

Chemistry

DPT hydrochloride powder.

Detection

DPT changes Ehrlich's reagent violet and causes the marquis reagent to turn yellow.^[16]

Analogues

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

History

DPT was first described in the scientific literature by 1959.^[17][18][19]

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. The Temple believes DPT and other entheogens are physical manifestations of God.^[20]

Legal status

Sweden

DPT is illegal in Sweden as of 26 January 2016.^[21]

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,^[22] 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.^[23]

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.^[24] While DPT is an agonist at several serotonin receptors in vitro, its anticonvulsant effects were not blocked by selective serotonin 5-HT_2A, 5-HT_1A, or 5-HT_1B receptor antagonists nor by a selective sigma σ₁ receptor antagonist in 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 from anticonvulsant to proconvulsant action, indicating complex interactions.^[24]

See also

• Substituted tryptamine