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| Other names | 4-OH-DPT; 4-Hydroxy-N,N-dipropyltryptamine; Deprocin |
| Routes of administration | Oral[1] |
| Drug class | Non-selectiveserotonin receptor agonist;Serotonin5-HT2A receptoragonist;Serotonergic psychedelic;Hallucinogen |
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| Pharmacokinetic data | |
| Onset of action | 15–45 minutes[2] |
| Duration of action | 5–8 hours[2] |
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| Chemical and physical data | |
| Formula | C16H24N2O |
| Molar mass | 260.381 g·mol−1 |
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4-HO-DPT, also known as4-hydroxy-N,N-dipropyltryptamine or asdeprocin, is apsychedelic drug of thetryptamine and4-hydroxytryptamine families related topsilocin (4-HO-DMT).[1][2] It is takenorally.[1][2]
The drug acts as anon-selectiveserotonin receptor agonist, including of theserotonin5-HT2A receptor.[3] It produces psychedelic-like effects in animals.[3] The drug is closelystructurally related to other psychedelic tryptamines such asdipropyltryptamine (DPT),5-MeO-DPT, and psilocin (4-HO-DMT), among others.[1]
4-HO-DPT was first described in thescientific literature byDavid Repke and colleagues in 1977.[4][5][3][6] It was encountered as a noveldesigner drug in 2012.[7][8][9][3] A presumedprodrug,4-AcO-DPT, is also known, and has likewise been encountered as a designer drug.[3]
According toAlexander Shulgin in his bookTiHKAL (Tryptamines I Have Known and Loved) and other publications, the dose andduration of 4-HO-DPT are unknown.[1] At a dose of 20 mgorally, there were possibly threshold effects and nothing more.[1][10] Per Shulgin, there were not enough observations to know what dose would result in activity or what the effects would be.[1] However, the occurrence of threshold effects at a dose of 20 mg was suggestive that "something is nearby".[1]
Subsequently, 4-HO-DPT and its presumedprodrug4-AcO-DPT have been encountered as noveldesigner drugs, substantiating the notion that more significant effects do indeed occur with 4-HO-DPT at sufficiently high doses.[7][8][9][3] Based on user reports, 4-HO-DPT has anonset of 15 to 45 minutes, aduration of 5 to 8 hours, and produceshallucinogenic effects includingpsychedelic visuals among others.[2]
| Target | Affinity (Ki, nM) |
|---|---|
| 5-HT2A | 1.6 (EC50Tooltip half-maximal effective concentration) 103% (EmaxTooltip maximal efficacy) |
| 5-HT2B | 2.2 (EC50) 94% (Emax) |
| 5-HT2C | 212 (EC50) 83% (Emax) |
| Notes: The smaller the value, the more avidly the drug interacts with the site.Sources:[3] | |
4-HO-DPT acts as a high-efficacypartial agonist tofull agonist of theserotonin5-HT2A,5-HT2B, and5-HT2C receptors.[3] It has more than two orders of magnitude greaterpotency as anagonist of the serotonin 5-HT2A and 5-HT2B receptors than as an agonist of the serotonin 5-HT2C receptor.[3] Hence, it shows considerableselectivity for the serotonin 5-HT2A receptor over the serotonin 5-HT2C receptor.[3]
Compared topsilocin (4-HO-DMT), 4-HO-DPT has about the same potency and efficacy as a serotonin 5-HT2A receptor agonist, has about the same potency but is much more efficacious as a serotonin 5-HT2B receptor agonist (EmaxTooltip maximal efficacy = 39% vs. 94%, respectively), and has about the same efficacy but approximately 10-fold lower potency as a serotonin 5-HT2C receptor agonist.[3]
4-HO-DPT produces thehead-twitch response, a behavioral proxy ofpsychedelic effects, in rodents.[3] Its potency for inducing the head-twitch response in mice is about 4- or 5-fold lower than that of psilocin.[3]
Themetabolism of 4-HO-DPT has not been studied.[11][12]
4-HO-DPT, also known as 4-hydroxy-N,N-dipropyltryptamine, is asubstituted tryptamine and4-hydroxytryptaminederivative related topsilocin (4-HO-DMT).[1]
Thechemical synthesis of 4-HO-DPT has been described.[1][4] It is said to be difficult to make.[1]
In 2019, Chadeayne and colleagues solved thecrystal structure of thefumaratesalt of 4-HO-DPT.[13] The authors describe the structure as follows: "The asymmetric unit contains one 4-HO-DPT cation, protonated at the dipropylamine N atom. There are also two independent water molecules, and half of a fumarate ion present."[13]
Analogues of 4-HO-DPT includedipropyltryptamine (DPT),5-MeO-DPT,psilocin (4-HO-DMT),4-HO-DET,4-HO-DiPT,4-HO-MPT,4-HO-EPT,4-HO-PiPT, and5-HO-DPT, among others.[1]4-AcO-DPT is a presumedprodrug of 4-HO-DPT.[3]
4-HO-DPT was first described in thescientific literature byDavid Repke and colleagues in 1977.[4][5][3][6] Subsequently, it was described in further detail byAlexander Shulgin in his 1997 bookTiHKAL (Tryptamines I Have Known and Loved).[1] The drug was encountered as a noveldesigner drug inEurope in 2012.[7][8][9][3]
4-HO-DPT is controlled inGermany under theNeue-psychoaktive-Stoffe-Gesetz (NpSG; New Psychoactive Substances Act) as of July 2019.[14][15][16][17]
4-HO-DPT is classified as a "dangerous substance"Sweden, which means that it cannot be legally bought or sold without a special permit, though it is still not yet an illegal drug.[18]
4-HO-DPT is a controlled substance inSwitzerland as of 2020.[19]
4-HO-DPT is aClass A drug in theUnited Kingdom, as a result of the tryptamine catch-all clause.[20]
4-HO-DPT is not an explicitlycontrolled substance in theUnited States. However, the drug is a closeanalogue ofpsilocin (4-HO-DMT), which is aSchedule I controlled substance in this country, and hence sale for intended human consumption could be illegal under theFederal Analogue Act.[citation needed]
4-OH-DPT is the 4-hydroxylated DPT derivative first synthesized by Shulgin et al. [82]. 4-OH-DPT is a light beige or white powder [54] that acts as a 5-HT2A partial agonist. 4-OH-DPT also shares structural similarity with psilocin [83]. Effects are dose dependent, with onset at 15–45 min and duration of 5–8 h. According to user reports, synthetic 4-OH-DPT produces visual effects and hallucinatory states [84].
Repke synthesized several other psilocin homologues, including 4-hydroxy-N-methyl-N-ethyltryptamine (4-HO-MET), 4-hydroxy-N-methyl-N-isopropyltryptamine (4-HO-MIPT), 4-hydroxy-N,N-dipropyltryptamine (4-HO-DPT), and 4-hydroxy-N,N-diisopropyltryptamine (4-HO-DIPT).63,64
