DiPT

"DIPT" redirects here. For other uses, see DIPT (disambiguation).

Diisopropyltryptamine (DiPT), also known as N,N-diisopropyltryptamine, is a psychedelic hallucinogenic drug of the tryptamine family that has a unique effect. While the majority of hallucinogens affect the visual sense, DiPT is primarily aural.^[1]

DiPT

Clinical data
Pronunciation	/ˌdaɪˌaɪsoʊˌproʊpɪlˈtrɪptəmiːn/
Other names	Diisopropyltryptamine; N,N-Diisopropyltryptamine; DiPT; DIPT; Dipt; Dipsy
Routes of administration	Oral[1]
Drug class	Serotonin receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code	None
Legal status
Legal status	AU: Unscheduled CA: Unscheduled DE: NpSG (Industrial and scientific use only) UK: Class A US: Unscheduled UN: Unscheduled
Pharmacokinetic data
Duration of action	6–8 hours[1]
Identifiers
IUPAC name 3-[2-(Diisopropylamino)ethyl]indole
CAS Number	14780-24-6 Y
PubChem CID	26903
ChemSpider	25060 Y
UNII	E352B01VMH
ChEBI	CHEBI:48286 Y
CompTox Dashboard (EPA)	DTXSID80163804
Chemical and physical data
Formula	C16H24N2
Molar mass	244.382 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(C)N(CCc1c[nH]c2ccccc12)C(C)C
InChI InChI=1S/C16H24N2/c1-12(2)18(13(3)4)10-9-14-11-17-16-8-6-5-7-15(14)16/h5-8,11-13,17H,9-10H2,1-4H3 Y Key:ZRVAAGAZUWXRIP-UHFFFAOYSA-N Y
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Dosage

Alexander Shulgin in TiHKAL gave a dosage range of DiPT of 25 to 100 mg orally and a duration of 6 to 8 hours.^[1] A wider recreational dose range for DiPT of 15 to 150 mg or more has also been reported.^[2]

Effects

DiPT's effects are primarily aural. At lower doses, Alexander Shulgin reported effects similar to a flanging or a phase shift. At medium and higher dosages, the effect of DiPT is typically a radical shift downward in perceived pitch. This shift tends to be nonlinear, in that the shift downwards varies in relation to the initial pitch. This can produce bizarre sounds and render music disharmonious.^[1] There has been an experiment involving subjects with perfect pitch, the goal of which was to determine whether the pitch difference is truly distortive or linear, the results of which indicated that there is no clear relationship between perceived pitch and actual pitch.^[1] Aside from these, the most prevalent non-auditory effect is inner ear pressure (which has been painful in some instances, for example when combined with MDMA).^[1]

Interactions

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

Pharmacology

Pharmacodynamics

DiPT activities

Target	Affinity (Ki, nM)
5-HT1A	121–538
5-HT1B	>10,000
5-HT1D	3,742
5-HT1E	>10,000
5-HT1F	ND
5-HT2A	1,200–>10,000 (Ki) 240–1,411 (EC50Tooltip half-maximal effective concentration) 89–117% (EmaxTooltip maximal efficacy)
5-HT2B	399 (Ki) 1,000–2,380 (EC50) 103–107% (Emax)
5-HT2C	290–>10,000 (Ki) 167–1,999 (EC50) 81–143% (Emax)
5-HT3	>10,000
5-HT4	ND
5-HT5A	>10,000
5-HT6	>10,000
5-HT7	3,423
α1A	>12,000
α1B	>10,000
α1D	ND
α2A	3,600–>10,000
α2B	2,870
α2C	2,523
β1	>10,000
β2	>10,000
β3	ND
D1	>25,000
D2	>25,000
D3	3,321–>25,000
D4	>10,000
D5	>10,000
H1	920–3,583
H2	>10,000
H3	ND
H4	>10,000
M1	>10,000
M2	>10,000
M3	>10,000
M4	>10,000
M5	>10,000
I1	356
σ1	1,798
σ2	2,702
TAAR1Tooltip Trace amine-associated receptor 1	>15,000 (Ki) (mouse) >15,000 (Ki) (rat) ND (EC50) (mouse) ND (EC50) (rat) ND (EC50) (human) ND (Emax) (mouse) ND (Emax) (rat)
SERTTooltip Serotonin transporter	180–1,258 (Ki) 900 (IC50Tooltip half-maximal inhibitory concentration) IA (EC50)
NETTooltip Norepinephrine transporter	8,900–>10,000 (Ki) 9,900 (IC50) IA (EC50)
DATTooltip Dopamine transporter	4,100–>10,000 (Ki) 35,000 (IC50) IA (EC50)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [3][4][5][6][7]

DiPT binds to serotonin receptors including the serotonin 5-HT_1A, 5-HT_2A, 5-HT_2B, 5-HT_2C receptors among others.^[4][5] It is known to act as a full agonist of the serotonin 5-HT_2A, 5-HT_2B, and 5-HT_2C receptors.^[4][5] It is also a weak serotonin reuptake inhibitor.^[5] In contrast to many related drugs, DiPT does not interact with the rodent or human trace amine-associated receptor 1 (TAAR1).^[7]

The discriminative stimulus properties of DiPT in rodent drug discrimination tests are partially blocked by the serotonin 5-HT_2A receptor antagonist volinanserin and by the serotonin 5-HT_2C receptor antagonist SB-242084.^[6] This is in contrast to the case of the related psychedelic dimethyltryptamine (DMT), wherein volinanserin fully blocks its stimulus properties and SB-242084 has minimal influence.^[6] Similarly to DMT and other psychedelics, DiPT produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents, and this effect is blocked by volinanserin.^[6][8]

Chemistry

DiPT is a derivative of tryptamine formed by substituting isopropyl groups for the two hydrogen atoms attached to the non-aromatic nitrogen atom in the tryptamine molecule.

Analogues of DiPT include dimethyltryptamine (DMT), diethyltryptamine (DET), dipropyltryptamine (DPT), 5-MeO-DMT, 5-MeO-DPT, 5-MeO-AMT, 5-MeO-DiPT, 4-HO-DiPT (iprocin), 5-HO-DiPT, 4-AcO-DiPT (ipracetin), and 5,6-MDO-DiPT, among others.

Legal status

United Kingdom

As is the case with many psychedelic tryptamines and phenethylamines, it is Class A in the UK, making it illegal to possess or use.

United States

DiPT is not scheduled at the federal level in the United States,^[9] but it could be considered an analog of 5-MeO-DiPT, in which case purchase, sale, or possession for human consumption or illicit use that is not for scientific or industrial purposes could be prosecuted under the Federal Analog Act. Some of the people arrested in Operation Web Tryp were selling DiPT, however the drug is not explicitly forbidden or outlawed.

However the US Drug Enforcement Agency (DEA) withdrew a proposal to ban five psychedelic substances including 4-Hydroxy-N,N-diisopropyltryptamine (4-OH-DiPT), N-Isopropyl-5-Methoxy-N-Methyltryptamine (5-MeO-MiPT) and N,N-Diisopropyltryptamine (DiPT). DEA withdrew the proposed listing as schedule 1 banned substance after a public hearing in 2022.^[10]

Florida

"DiPT (N,N-Diisopropyltryptamine)" is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida.^[11]

Sweden

Sweden's public health agency suggested classifying DiPT as a hazardous substance, on May 15, 2019.^[12]