4-HO-DiPT

4-HO-DiPT, also known as 4-hydroxy-N,N-diisopropyltryptamine or as iprocin, is a synthetic psychedelic drug of the tryptamine family. It is a higher homologue of psilocin and 4-HO-DET and is a positional isomer of 4-HO-DPT.

4-HO-DiPT

Clinical data
Other names	4-OH-DiPT; 4-Hydroxy-N,N-diisopropyltryptamine; Iprocin
Routes of administration	Oral
Legal status
Legal status	DE: NpSG (Industrial and scientific use only) UK: Class A US: Unscheduled
Pharmacokinetic data
Duration of action	2–3 hours[1]
Identifiers
IUPAC name 3-[2-(diisopropylamino)ethyl]-1H-indol-4-ol
CAS Number	132328-45-1 Y HCl: 63065-90-7 Y
ChemSpider	10579819 Y
UNII	YG9OUS518B HCl: KE76PMQ2P3 Y
CompTox Dashboard (EPA)	DTXSID50618836
ECHA InfoCard	100.214.853
Chemical and physical data
Formula	C16H24N2O
Molar mass	260.381 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(C)N(CCc1c[nH]c2cccc(O)c12)C(C)C
InChI InChI=1S/C16H24N2O/c1-11(2)18(12(3)4)9-8-13-10-17-14-6-5-7-15(19)16(13)14/h5-7,10-12,17,19H,8-9H2,1-4H3 Y Key:KBRYKXCBGISXQV-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Use and dosage

In TiHKAL, Alexander Shulgin reported that 4-HO-DiPT had a dose range of 15 to 20 mg orally and a duration of 2 to 3 hours.^[1][2] However, a wider recreational dose range of 3 to 30 mg or more orally has also been reported.^[3] The drug is active at around 3 mg and above, and its effects last for 2 to 3 hours.^[4] Shulgin has stated that 4-HO-DiPT has an especially steep dose–response curve and narrow dose range, with doses below 10 mg having few to no effects and there having been no trials above 20 mg due to the intensity of its effects.^[1]

Effects

The effects of 4-HO-DiPT are broadly comparable to those of other serotonergic psychedelics such as LSD and psilocin, but they are distinguished by their relative brevity. Shulgin "doubt[s] that there is another psychedelic drug, anywhere, that can match this one for speed, for intensity, for brevity, and sensitivity to dose, at least one that is active orally." An idiosyncratic effect of the drug, also noted by Shulgin, is its tendency to induce tremors.^[1][5][6]

Some users have reported a minor audio distortion with lower dosages. Higher dosages increase the polarity of the distortion. It is defined as being slightly lower in pitch and creating several different effects, such as pitch bend, volume distortion, and rate distortion. As with most DiPT psychedelics, music can become more dissonant and less harmonious. Users have also reported a visual distortion widely comparable to the hallucinogen LSD.

Interactions

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

Pharmacology

Pharmacodynamics

4-HO-DiPT activities

Target	Affinity (Ki, nM)
5-HT1A	5,700–>10,000 3,900 (EC50Tooltip half-maximal effective concentration) 36% (EmaxTooltip maximal efficacy)
5-HT1B	>10,000
5-HT1D	1,860
5-HT1E	>10,000
5-HT1F	ND
5-HT2A	120–922 (Ki) 6.82–334 (EC50) 74–106% (Emax)
5-HT2B	85 (Ki) 5.12–460 (EC50) 55–110% (Emax)
5-HT2C	2.8–>10,000 (Ki) 1,080–6,442 (EC50) 72–104% (Emax)
5-HT3	ND
5-HT4	ND
5-HT5A	>10,000
5-HT6	>10,000
5-HT7	>10,000
α1A	>12,000
α1B, α1D	ND
α2A	15,000
α2B, α2C	>10,000
β1–β3	ND
D1–D3	>25,000
D4, D5	>10,000
H1	9,800–>10,000
H2	>10,000
H3, H4	ND
M1–M3	ND
M4	1,725
M5	ND
I1	ND
σ1	816–1,063
σ2	2,215
TAAR1Tooltip Trace amine-associated receptor 1	>15,000 (Ki) (mouse) >15,000 (Ki) (rat) ND (EC50) (human)
SERTTooltip Serotonin transporter	419–1,800 (Ki) 163–2,400 (IC50Tooltip half-maximal inhibitory concentration) IA (EC50)
NETTooltip Norepinephrine transporter	11,000 (Ki) 46,000 (IC50) IA (EC50)
DATTooltip Dopamine transporter	>26,000 (Ki) >100,000 (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: [7][8][9][10][11][12][13]

4-HO-DiPT acts as an agonist of serotonin receptors, including the serotonin 5-HT_2A and 5-HT_2B receptors.^{[7][8][9][10][12]} It may also act as a serotonin reuptake inhibitor, although its potency is variable across studies.^{[7][8][9][10]} The drug appears to activate the serotonin 5-HT_2C receptor with low potency and much lower than for the serotonin 5-HT_2A receptor.^{[7][8][9][10]} Unlike many other tryptamines, 4-HO-DiPT is not a ligand of the rodent trace amine-associated receptor 1 (TAAR1).^[7][13]

Pharmacokinetics

The pharmacokinetics of 4-HO-DiPT have been studied.^[11]

Legal status

4-HO-DiPT powder.

Finland

Scheduled in government decree on psychoactive substances banned from the consumer market.^[14]

Germany

Scheduled in New Psychoactive Substances Act (NpSG). Use of covered substances is permitted only for industrial and scientific purposes.

Sweden

Sveriges riksdags health ministry Statens folkhälsoinstitut classified 4-HO-DiPT as "health hazard" under the act Lagen om förbud mot vissa hälsofarliga varor (translated Act on the Prohibition of Certain Goods Dangerous to Health) as of Mar 1, 2005, in their regulation SFS 2005:26 listed as 4-hydroxi-N,N-diisopropyltryptamin (4-HO-DIPT), making it illegal to sell or possess.^[15]

United States

4-HO-DiPT is not scheduled at the federal level in the United States,^[16] but it is possible that it could be considered an analog of 5-MeO-DiPT, in which case purchase, sale, or possession could be prosecuted under the Federal Analog Act.

Florida

"4-Hydroxy-N,N-diisopropyltryptamine" is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida.^[17]

Research

[[File:FT-104 structure.svg|200px|thumb|right|FT-104 ]

Luvesilocin (RE-104, FT-104; O-glutaryl-4-HO-DiPT), a prodrug to 4-HO-DiPT, has entered double blind, randomized, placebo controlled, phase 1 clinical trials in healthy volunteers at the Royal Adelaide Hospital in Australia for the treatment of postpartum depression and treatment-resistant depression. ^[18][19][20]