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 and diethyltryptamine.

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

Doses 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 markedly different.^[5] On the other hand, others have reported similarities to DMT, for instance in terms of intensity.^[1]

Side effects

Side effects of DET may include nausea, numbness of the tongue or throat, pupil dilation, increased heart rate, dizziness, anxiety, panic, confusion, paranoia, delusions, and seizures (uncommon).^{[citation needed]}

The use of DPT has been implicated in at least one death due to seizures,^[6] although details are lacking and the drug has not officially been established as the sole cause of death.

Interactions

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

Pharmacology

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
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
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: [7][8][9][10][11][12][13]

Studies on rodents have found that the effectiveness with which a selective 5-HT_2A receptor antagonist blocks the behavioral actions of this compound strongly suggests that the 5-HT_2A receptor is an important site of action for DPT, but the modulatory actions of a 5-HT_1A receptor antagonist also imply a 5-HT_1A-mediated component to the actions of DPT.^[14]

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

Chemistry

DPT HCl Powder

DPT changes Ehrlich's reagent violet and causes the marquis reagent to turn yellow.^[15]

History

DPT was first described in the scientific literature by 1959.^[16][17][18]

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.^[19]

Legal status

Sweden

DPT is illegal in Sweden as of 26 January 2016.^[20]

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,^[21] 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.^[22]

Maine

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