5-MeO-DiPT

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Template:Short description Template:Infobox drug

5-MeO-DiPT, also known as 5-methoxy-N,N-diisopropyltryptamine and sometimes as foxy methoxy or simply foxy, is an atypical psychedelic drug of the tryptamine and 5-methoxytryptamine families.<ref name="TiHKAL">Template:CiteTiHKAL https://www.erowid.org/library/books_online/tihkal/tihkal37.shtml</ref><ref name="AraújoCarvalhoBastos2015">Template:Cite journal</ref><ref name="PalamarAcosta2020">Template:Cite journal</ref> It has unique and distinct effects from other serotonergic tryptamines, including some stimulant- and entactogen-like effects, robust tactile and sexual enhancement, and only light hallucinogenic effects.<ref name="TiHKAL" /><ref name="ShulginCarter1980" /><ref name="PalamarAcosta2020" /><ref name="Aipsin" /><ref name="MeatherallSharma2003" /> The drug is usually taken orally, but may also be used by other routes.<ref name="TiHKAL" /><ref name="ShulginCarter1980" /><ref name="AraújoCarvalhoBastos2015" /><ref name="Aipsin" /><ref name="MalacaLoFaroTamborra2020">Template:Cite journal</ref>

It acts as a non-selective serotonin receptor agonist, including of the serotonin 5-HT1A and 5-HT2A receptors among others.<ref name="Ray2010" /><ref name="RickliMoningHoener2016" /><ref name="BloughLandavazoDecker2014" /><ref name="KozellEshlemanSwanson2023" /><ref name="PuigsesllosesNadal-GratacósKetsela2024" /> Uniquely among most tryptamines, the drug has been found to produce serotonergic neurotoxicity and associated cognitive deficits in rodents reminiscent of but distinct from those observed with MDMA.<ref name="AraújoCarvalhoBastos2015" /><ref name="ComptonDietrichSelinger2011" /><ref name="SkeltonSchaeferHerring2009">Template:Cite journal</ref> Various severe and/or fatal intoxications associated with 5-MeO-DiPT have been reported in humans.<ref name="AraújoCarvalhoBastos2015" /><ref name="KozellEshlemanSwanson2023" /><ref name="PuigsesllosesNadal-GratacósKetsela2024" /> It is the 5-methoxy derivative of diisopropyltryptamine (DiPT) and is an analogue of other psychedelic tryptamines like 4-HO-DiPT, 5-MeO-DMT, and 5-MeO-MiPT.<ref name="TiHKAL" />

5-MeO-DiPT was first described in the literature by Alexander Shulgin and colleagues in 1980.<ref name="PalamarAcosta2020" /><ref name="ZamberlanSanzMartinezVivot2018" /><ref name="TiHKAL" /><ref name="ShulginCarter1980" /> Subsequently, Shulgin described 5-MeO-DiPT in further detail in his 1997 book TiHKAL (Tryptamines I Have Known and Loved).<ref name="TiHKAL" /> The drug was first encountered as a novel designer drug in 1999.<ref name="AraújoCarvalhoBastos2015" /><ref name="Aipsin" /> It is used recreationally as a "party drug" and sexual enhancer, with notable use among gay men and transgender women as part of "chemsex", although its use in general has declined over time and is rare.<ref name="PalamarAcosta2020" /><ref name="Aipsin" /><ref name="AraújoCarvalhoBastos2015" /><ref name="ShanYuYang2018" /> 5-MeO-DiPT became a controlled substance in the United States in 2003.<ref name="AraújoCarvalhoBastos2015" /><ref name="DEA2003">Template:Cite journal</ref><ref name="DEA2004" /> The closely related drug 5-MeO-MiPT (moxy) has similar effects as 5-MeO-DiPT, remains legal in the United States and many other countries, and is often used as a substitute for 5-MeO-DiPT.<ref name="PalamarAcosta2020" /><ref name="TiHKAL" /><ref name="Carpenter2022">Template:Cite web</ref><ref name="Aragón2024">Template:Cite web</ref><ref name="Aipsin-5-MeO-MiPT">Template:Cite web</ref>

Use and effects

In his book TiHKAL (Tryptamines I Have Known and Loved) and other publications, Alexander Shulgin reported the dose of 5-MeO-DiPT to be 6 to 12Template:Nbspmg orally, its onset to be 20 to 30Template:Nbspminutes or within 1Template:Nbsphour, its time to peak effects to be 1 to 1.5Template:Nbsphours, and its duration to be 4 to 8Template:Nbsphours.<ref name="TiHKAL" /><ref name="ShulginCarter1980" /><ref name="Shulgin2003">Template:Cite book</ref><ref name="JacobShulgin1994">Template:Cite journal</ref><ref name="MeatherallSharma2003" /><ref name="Aipsin" /> However, in other publications besides TiHKAL he gave a dose range of 6 to 10Template:Nbspmg<ref name="ShulginCarter1980" /><ref name="MeatherallSharma2003" /> or a dose range of 8 to 12Template:Nbspmg.<ref name="Shulgin2003" /><ref name="JacobShulgin1994" /><ref name="MeatherallSharma2003" /> According to Shulgin, testing of 5-MeO-DiPT started at a dose of 0.1 mg and gradually titrated up in 10 human volunteers, with threshold effects occurring at a dose of 4Template:Nbspmg orally and full effects occurring at doses of 6Template:Nbspmg or more.<ref name="ShulginCarter1980" /><ref name="MeatherallSharma2003" /> The drug's has been described as "fast-acting" and its duration has also been reported to be "short-lived" and as brief as 3 to 6Template:Nbsphours.<ref name="TiHKAL" /><ref name="ShulginCarter1980" /><ref name="PalamarAcosta2020" /><ref name="MeatherallSharma2003" /><ref name="Aipsin" /> In addition to oral administration, 5-MeO-DiPT has been reported to be used less commonly by smoking, insufflation, or intravenous injection.<ref name="Aipsin" /><ref name="AraújoCarvalhoBastos2015" /><ref name="MalacaLoFaroTamborra2020" /> Forms known to be used include powder, tablets, and capsules.<ref name="Aipsin" />

The psychedelic or perceptual effects of 5-MeO-DiPT have been reported to include colors on edges of eyesight, color contrasts and sparkle, altered facial perception, sensory distortion, few if any visual enhancements, some closed-eye imagery but only at high doses, feelings of strangeness, objects having special significance, some musical sound distortions reminiscent of those of DiPT, music sounding strange and fake, time dilation, having only mild hallucinogenic effects, outgoing rather than inwardly reflective intellectual activation, lack of intuitive leaps, and a wave-like experience wherein the effects "waved in and out".<ref name="TiHKAL" /><ref name="ShulginCarter1980" /><ref name="PalamarAcosta2020" /><ref name="Aipsin" /><ref name="MeatherallSharma2003" /> Affective and behavioral effects have included stimulation, some entactogen-like effects, talkativeness, disinhibition, emotional enhancement, opening of affect, easy emotional expression, easy communication with others, reduced guards and reservations, relaxation, feeling happy, mild euphoria, and mellowness.<ref name="TiHKAL" /><ref name="ShulginCarter1980" /><ref name="PalamarAcosta2020" /><ref name="Aipsin" /><ref name="MeatherallSharma2003" /> In addition, the drug has been reported to produce tactile or sensual enhancement, one's body feeling alive and alert, feeling like waves are passing back and forth over one's body, awareness of vibrations, feeling sexually aroused, and "dramatic" erotic or sexual enhancement.<ref name="TiHKAL" /><ref name="ShulginCarter1980" /><ref name="PalamarAcosta2020" /><ref name="Aipsin" /><ref name="MeatherallSharma2003" />

Negative emotional and behavioral effects have included uncomfortableness, agitation, feeling unnerved, paranoia, and social avoidance, but no hangover.<ref name="TiHKAL" /><ref name="ShulginCarter1980" /><ref name="MeatherallSharma2003">Template:Cite journal</ref> 5-MeO-DiPT has been described as having minimal physical side effects and as being relatively free of autonomic side effects and indicators of toxicity.<ref name="TiHKAL" /><ref name="ShulginCarter1980" /> Reported physical side effects have included body load and discomfort, slight pupil dilation, mild nausea, some muscular hyperreflexia, muscle contractions and spasms, gastrointestinal disturbances, hypertension, and little change in appetite or sleep disruption.<ref name="TiHKAL" /><ref name="ShulginCarter1980" /><ref name="MeatherallSharma2003" /> The effects of 5-MeO-DiPT have been described as either being "positive" or a "mixed bag".<ref name="TiHKAL" /><ref name="ShulginCarter1980" /> User responses are said to vary dramatically, with some people finding it appealing, sexual, invigorating, interesting, and enjoyable, and others finding it nauseating, annoying, diarrhea-inducing, and generally unpleasant.<ref name="Aipsin" />

5-MeO-DiPT has been described as LSD-like in some ways but as being quite different from other psychedelics.<ref name="TiHKAL" /><ref name="ShulginCarter1980" /><ref name="PalamarAcosta2020" /> Descriptions have included the drug never being psychedelic in the way of classical psychedelics like LSD and psilocybin, there being an absence of intense sensory disturbances or hallucinogenic effects as with other psychedelics like dimethyltryptamine (DMT) and psilocybin, never feeling as though one was having a psychedelic experience, and being able to function normally on a social level including at public events even at high doses.<ref name="TiHKAL" /><ref name="ShulginCarter1980" /><ref name="PalamarAcosta2020" /> However, one user who took a high dose described reaching a "plus-three" on the Shulgin Rating Scale in a very LSD-like manner but without the visuals.<ref name="TiHKAL" /> Higher doses may produce more psychedelic effects, but the drug is still described as not that psychedelic even at such doses.<ref name="PalamarAcosta2020" /> Despite its lack of robust hallucinogenic effects at typical doses, 5-MeO-DiPT is described as nonetheless producing quite profound emotional and intellectual modifications.<ref name="ShulginCarter1980" />

5-MeO-DiPT is reported to differ in its subjective effects from the structurally related DiPT in most respects but to share some auditory effects with this drug.<ref name="ShulginCarter1980" /><ref name="TiHKAL" /> In terms of these effects, whereas DiPT caused harmonic distortion of heard sounds, 5-MeO-DiPT caused changes in musical character and interpretation without apparent changes in harmonic structure.<ref name="TiHKAL" /> As such, while both produced auditory effects, DiPT and 5-MeO-DiPT caused different distortions of musical interpretation.<ref name="TiHKAL" /> 5-MeO-DiPT has been described as a "psychedelic stimulant" and has a reputation as a "sexual enhancer" or "aphrodisiac".<ref name="PalamarAcosta2020" /><ref name="Aipsin">Template:Cite web</ref> Among its effects, the pro-sexual effects of 5-MeO-DiPT have been especially highlighted, with these effects being present at low doses.<ref name="TiHKAL" /> Users have remarked that it took them to a "marvelous sexy place", that "everything [was] shaded with eroticism", that the "erotic world was fantastic, explosive, almost scary", and that the drug may vie with 2C-B as a sexual enhancer or that it left 2C-B "in the dust" in this regard.<ref name="TiHKAL" /><ref name="PalamarAcosta2020" />

5-MeO-DiPT has been described as having effects similar to those of 5-MeO-MiPT and these drugs as having unique and distinct effects from those of other psychedelic tryptamines.<ref name="PalamarAcosta2020" /><ref name="Aipsin-5-MeO-MiPT" /> They are reported to be very pro-sexual, much more stimulant, and more like party drugs than other tryptamines.<ref name="PalamarAcosta2020" /><ref name="AraújoCarvalhoBastos2015" /><ref name="Aipsin-5-MeO-MiPT" /> While 5-MeO-DiPT and 5-MeO-MiPT are described as pro-sexual, they may not be innately aphrodisiac but instead may produce tactile enhancement in a way that lends itself to sex.<ref name="PalamarAcosta2020" /> The tactile enhancement and "body high" with 5-MeO-DiPT and 5-MeO-MiPT may in part be why they have been compared to entactogens like MDMA.<ref name="PalamarAcosta2020" /> 5-MeO-DiPT has been described as being closer to MDMA in its effects than to psychedelic tryptamines and that the effects are a "body high kind of thing".<ref name="PalamarAcosta2020" /> The drug is also known to be combined with other drugs such as MDMA.<ref name="Noworyta-SokołowskaKamińskaKreiner2016" />

Side effects

Flashbacks have been reported with 5-MeO-DiPT.<ref name="Nichols2016" /><ref name="IkedaSekiguchiFujita2005">Template:Cite journal</ref> There is a report of a prolonged delusional state associated with 5-MeO-DiPT.<ref name="Fuse-NagaseNishikawa2013">Template:Cite journal</ref>

Overdose

Excessive doses or overdose have caused clinical intoxication, characterized by nausea, vomiting, agitation, hypotension, mydriasis, tachycardia, and hallucinations, in a number of young adults. A number of these overdoses are attributed to the drug's delayed onset of action, where first time users, who were unfamiliar with the drug, administered a second dose after initially feeling no effects. Rhabdomyolysis and renal failure occurred in one young man and another one died 3 to 4Template:Nbsphours after an apparent rectal overdose.<ref name="Baselt2008">Template:Cite book</ref> There have been a number of published cases of severe and/or fatal intoxication with 5-MeO-DiPT.<ref name="AraújoCarvalhoBastos2015" /><ref name="KozellEshlemanSwanson2023" /><ref name="PuigsesllosesNadal-GratacósKetsela2024" /><ref name="MeatherallSharma2003" /><ref name="WilsonMcGeorgeSmolinske2005">Template:Cite journal</ref><ref name="SmolinskeRastogiSchenkel2005">Template:Cite journal</ref><ref name="TanakaKamataKatagi2006">Template:Cite journal</ref><ref name="AlatrashMajhailPile2006">Template:Cite journal</ref><ref name="ItokawaIwataTakahashi2007">Template:Cite journal</ref>

Interactions

Template:See also

The effects of 5-MeO-DiPT may be potentiated when used in combination with cannabis.<ref name="MeatherallSharma2003" /><ref name="TiHKAL" />

Pharmacology

Pharmacodynamics

Template:Nowrap
Target Affinity (Ki, nM)
5-HT1A 16–170 (Ki)
56–>10,000 (Template:Abbrlink)
44–94% (Template:Abbrlink)
5-HT1B 5,137–>10,000 (Ki)
85–170 (Template:Abbr)
100–134% (Template:Abbr)
5-HT1D 293–1,718 (Ki)
41–126 (Template:Abbr)
92–104% (Template:Abbr)
5-HT1E >10,000 (Ki)
407–2,190 (Template:Abbr)
67–86% (Template:Abbr)
5-HT1F Template:Abbr (Ki)
871–3,240 (Template:Abbr)
53–83% (Template:Abbr)
5-HT2A 162–>10,000 (Ki)
6.2–946 (Template:Abbr)
99–124% (Template:Abbr)
5-HT2B 35–163 (Ki)
20–56 (Template:Abbr)
80–110% (Template:Abbr)
5-HT2C 1,740–>10,000 (Ki)
30–393 (Template:Abbr)
71–100% (Template:Abbr)
5-HT3 >10,000
5-HT4 Template:Abbr
5-HT5A >10,000 (Ki)
>10,000 (Template:Abbr)
Template:Abbr (Template:Abbr)
5-HT6 2,190–>10,000 (Ki)
324 (Template:Abbr)
87% (Template:Abbr)
5-HT7 1,231–>10,000 (Ki)
>10,000 (Template:Abbr)
Template:Abbr (Template:Abbr)
α1A, α1B >10,000
α1D Template:Abbr
α2A >10,000
α2B 5,293–>10,000
α2C 2,865–3,081
β1, β2 >10,000
β3 Template:Abbr
D1–D5 >10,000
H1–H4 >10,000
M1–M5 >10,000
I1 760
σ1 9,443–>10,000
σ2 291–3,002
Template:Abbrlink Template:Abbr
Template:Abbrlink 874–>10,000 (Ki)
239–24,215 (Template:Abbrlink)
>100,000 (Template:Abbr) (rat)
Template:Abbrlink >10,000 (Ki)
8,200–>10,000 (Template:Abbr)
>100,000 (Template:Abbr) (rat)
Template:Abbrlink >10,000 (Ki)
65,000 (Template:Abbr)
>100,000 (Template:Abbr) (rat)
Notes: The smaller the value, the more avidly the drug interacts with the site. All proteins are human unless otherwise specified. Refs: <ref name="PDSPKiDatabase">Template:Cite web</ref><ref name="JainGumpperSlocum2025" /><ref name="Ray2010">Template:Cite journal</ref><ref name="RickliMoningHoener2016">Template:Cite journal</ref><ref name="FantegrossiHarringtonKiessel2006" /><ref name="FantegrossiMurnaneReissig2008">Template:Cite journal</ref>
<ref name="BloughLandavazoDecker2014">Template:Cite journal</ref><ref name="NagaiNonakaKamimura2007">Template:Cite journal</ref><ref name="KozellEshlemanSwanson2023">Template:Cite journal</ref><ref name="PuigsesllosesNadal-GratacósKetsela2024">Template:Cite journal</ref><ref name="SimmlerBuchyChaboz2016">Template:Cite journal</ref>

5-MeO-DiPT acts as a non-selective serotonin receptor agonist, including of the serotonin 5-HT1A, 5-HT1B, 5-HT1D, 5-HT2A, 5-HT2B, and 5-HT2C receptors, among others.<ref name="JainGumpperSlocum2025">Template:Cite journal</ref><ref name="Ray2010" /><ref name="RickliMoningHoener2016" /><ref name="BloughLandavazoDecker2014" /><ref name="KozellEshlemanSwanson2023" /><ref name="PuigsesllosesNadal-GratacósKetsela2024" /> It has shown variably strong preference for the serotonin 5-HT1A receptor in terms of binding affinity, with 2-fold, 25-fold, >76-fold, and 161-fold higher for this receptor over the serotonin 5-HT2A receptor in different studies.<ref name="JainGumpperSlocum2025" /><ref name="Ray2010" /><ref name="PuigsesllosesNadal-GratacósKetsela2024" /><ref name="FantegrossiHarringtonKiessel2006" /><ref name="FantegrossiMurnaneReissig2008" /><ref name="Nichols2016" /><ref name="AraújoCarvalhoBastos2015" /> However, in terms of receptor activation, 5-MeO-DiPT showed similar potency at the serotonin 5-HT1A receptor and the serotonin 5-HT2A receptor and had several-fold preference for these receptors over the serotonin 5-HT2C receptor.<ref name="KozellEshlemanSwanson2023" />

In addition to its direct serotonin receptor interactions, 5-MeO-DiPT is a serotonin reuptake inhibitor with potency ranging from similar to its serotonin 5-HT2A receptor agonism to very low in different studies.<ref name="KozellEshlemanSwanson2023" /><ref name="HaginoHallUhl2021">Template:Cite journal</ref><ref name="SogawaSogawaTagawa2007">Template:Cite journal</ref><ref name="PuigsesllosesNadal-GratacósKetsela2024" /> Conversely, it does not significantly affect dopamine or norepinephrine reuptake and shows no activity as a monoamine releasing agent.<ref name="BloughLandavazoDecker2014" /><ref name="PuigsesllosesNadal-GratacósKetsela2024" /><ref name="NakagawaKaneko2008" /><ref name="NagaiNonakaKamimura2007" /><ref name="SogawaSogawaTagawa2007" /> The drug can block the serotonin release induced by methamphetamine in vitro.<ref name="NakagawaKaneko2008" /><ref name="SogawaSogawaTagawa2007" /> 5-MeO-DiPT can elevate brain serotonin levels in rodents, presumably via its serotonin reuptake inhibition.<ref name="Noworyta-SokołowskaKamińskaKreiner2016">Template:Cite journal</ref><ref name="LiLiChen2025a">Template:Cite journal</ref> The elevations in serotonin levels caused by 5-MeO-DiPT may be limited by its concomitant serotonin 5-HT1A receptor agonism, as serotonin 5-HT1A receptors serve as inhibitory autoreceptors that limit serotonin release.<ref name="HaginoHallUhl2021" /> By an unknown mechanism, but possibly serotonin 5-HT2A receptor agonism, 5-MeO-DiPT may also elevate brain dopamine levels in rodents, including in the prefrontal cortex, striatum, and/or nucleus accumbens, although findings are mixed.<ref name="Noworyta-SokołowskaKamińskaKreiner2016" /><ref name="HaginoHallUhl2021" /><ref name="LiLiChen2025a" /> The mechanism of action of the psychedelic effects of 5-MeO-DiPT is thought to be serotonin 5-HT2A receptor agonism, but its full mechanism of action is unclear and additional mechanisms may also be involved.<ref name="NakagawaKaneko2008" /><ref name="FantegrossiHarringtonKiessel2006" /><ref name="NagaiNonakaKamimura2007" />

5-MeO-DiPT produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents.<ref name="HalberstadtGeyer2018">Template:Cite book</ref><ref name="Nichols2016">Template:Cite journal</ref><ref name="AraújoCarvalhoBastos2015" /><ref name="HalberstadtGeyer2011">Template:Cite journal</ref><ref name="PuigsesllosesNadal-GratacósKetsela2024" /><ref name="LiLiChen2025b">Template:Cite journal</ref><ref name="FantegrossiHarringtonKiessel2006">Template:Cite journal</ref> As with many other psychedelics, this follows an inverted U-shaped dose–response curve.<ref name="HalberstadtGeyer2011" /><ref name="FantegrossiHarringtonKiessel2006" /> The head-twitch response induced by 5-MeO-DiPT is blocked by serotonin 5-HT2A receptor antagonists such as volinanserin.<ref name="HalberstadtGeyer2011" /><ref name="FantegrossiHarringtonKiessel2006" /> 5-MeO-DiPT's head-twitch response is described as robust but also weak and much lower in magnitude than that produced by other serotonergic psychedelics such as 5-MeO-DMT or DOM.<ref name="FantegrossiMurnaneReissig2008" /><ref name="FantegrossiHarringtonKiessel2006" /><ref name="PuigsesllosesNadal-GratacósKetsela2024" /> The serotonin 5-HT1A receptor agonism of 5-MeO-DiPT may inhibit its serotonin 5-HT2A receptor-mediated head-twitch response.<ref name="FantegrossiHarringtonKiessel2006" /> 5-MeO-DiPT partially substitutes for LSD in rodent drug discrimination tests, with 52% responding at 1Template:Nbspmg/kg, 75% responding at 3Template:Nbspmg/kg, and behavioral disruption at higher doses.<ref name="FantegrossiHarringtonKiessel2006" /> In addition, it substitutes for DOM in rodent drug discrimination tests.<ref name="FantegrossiHarringtonKiessel2006" /><ref name="GlennonYoungJacyno1983">Template:Cite journal</ref> The stimulus properties of 5-MeO-DiPT in LSD substitution tests are completely and insurmountably blocked by the serotonin 5-HT2A receptor antagonist volinanserin.<ref name="FantegrossiMurnaneReissig2008" /><ref name="FantegrossiHarringtonKiessel2006" /> Conversely, they are partially and surmountably blocked by the serotonin 5-HT1A receptor antagonist WAY-100635.<ref name="FantegrossiMurnaneReissig2008" /><ref name="FantegrossiHarringtonKiessel2006" /> Besides psychedelic-like effects, 5-MeO-DiPT also produces hypolocomotion and hypothermia in rodents and potentiates the forepaw treading induced by the serotonin 5-HT1A receptor agonist 8-OH-DPAT.<ref name="PuigsesllosesNadal-GratacósKetsela2024" /><ref name="LiLiChen2025b" /><ref name="WilliamsHerringSchaefer2007">Template:Cite journal</ref><ref name="Noworyta-SokołowskaKamińskaKreiner2016" />

5-MeO-DiPT has been reported to produce neurotoxicity in rodents.<ref name="Gołembiowska2022">Template:Cite book</ref><ref name="NakagawaKaneko2008">Template:Cite journal</ref><ref name="Noworyta-SokołowskaKamińskaKreiner2016" /><ref name="Noworyta-SokołowskaKamińskaRzemieniec2019">Template:Cite journal</ref><ref name="AraújoCarvalhoBastos2015" /> Administration of 5-MeO-DiPT to adolescent rodents produced marked decreases in spatial navigation performance in adulthood that were suggestive of deficits in cognitive flexibility, attention, and/or perseveration as well as other cognitive deficits.<ref name="AraújoCarvalhoBastos2015" /><ref name="ComptonSelingerTesta2006">Template:Cite journal</ref><ref name="ComptonDietrichSelinger2011" /><ref name="Noworyta-SokołowskaGórskaGołembiowska2018">Template:Cite journal</ref> This was associated with serotonergic neurotoxicity and substantial 26 to 49% reductions in cortical and hippocampal serotonin levels that were analogous to those occurring with MDMA.<ref name="AraújoCarvalhoBastos2015" /><ref name="ComptonDietrichSelinger2011">Template:Cite journal</ref> However, the neurotoxic effects of 5-MeO-DiPT are described as less severe than and distinct from those of MDMA.<ref name="ComptonDietrichSelinger2011" /><ref name="SkeltonSchaeferHerring2009" /> The drug has also been reported to produce cytotoxicity as well as neurotoxic effects on serotonergic neurons ex vivo.<ref name="NakagawaKaneko2008" /><ref name="Noworyta-SokołowskaKamińskaRzemieniec2019">Template:Cite journal</ref> The mechanisms underlying the serotonergic neurotoxicity of 5-MeO-DiPT are unknown.<ref name="NakagawaKaneko2008" /><ref name="ComptonDietrichSelinger2011" /> The drug might also produce prolonged dopaminergic adaptations or dopaminergic neurotoxicity in rodents as evidenced by long-lasting decreases in dopamine levels.<ref name="Noworyta-SokołowskaKamińskaKreiner2016" /><ref name="Noworyta-SokołowskaKamińskaRzemieniec2019" /> In addition, it has been associated with marked genotoxicity or oxidative DNA damage, which has also been seen with MDMA and methamphetamine.<ref name="Noworyta-SokołowskaKamińskaKreiner2016" /><ref name="Noworyta-SokołowskaKamińskaRzemieniec2019" /> It is said to be the first known tryptamine to be associated with such toxicity.<ref name="Noworyta-SokołowskaKamińskaKreiner2016" />

Pharmacokinetics

The pharmacokinetics and metabolism of 5-MeO-DiPT have been studied.<ref name="MeyerMaurer2010">Template:Cite journal</ref><ref name="AraújoCarvalhoBastos2015" /><ref name="Yu2008">Template:Cite journal</ref><ref name="KamataKatagiKamata2006">Template:Cite journal</ref><ref name="HarimatsuYonemotoSaito2006">Template:Cite journal</ref>

Chemistry

Properties

The log P of 5-MeO-DiPT is 3.68.<ref name="PuigsesllosesNadal-GratacósKetsela2024" />

Synthesis

The chemical synthesis of 5-MeO-DiPT has been described.<ref name="TiHKAL" />

Analogues

Analogues of 5-MeO-DiPT include diisopropyltryptamine (DiPT), 4-HO-DiPT (iprocin), 4-AcO-DiPT (ipracetin), 4-MeO-DiPT, 5-HO-DiPT, 5-MeO-DMT, 5-MeO-DET, 5-MeO-DPT, 5-MeO-DALT, 5-MeO-MiPT, 5-MeO-EiPT, 5-MeO-PiPT, 5-MeO-iPALT (ASR-3001), and 5-MeO-DiBF, among others.<ref name="TiHKAL" />

Positional isomers

4-MeO-DiPT, 6-MeO-DiPT, and 7-MeO-DiPT are known positional isomers of 5-MeO-DiPT.<ref name="TiHKAL" /><ref name="JacobShulgin1994" /> 6-MeO-DiPT and 7-MeO-DiPT have been described by Alexander Shulgin as being inactive at doses of up to 50Template:Nbspmg and 70Template:Nbspmg orally, respectively, whereas 4-MeO-DiPT was not assessed.<ref name="TiHKAL" /><ref name="JacobShulgin1994" />

History

5-MeO-DiPT was discovered in the 1970s and was first described by Alexander Shulgin and Michael Carter in 1980.<ref name="PalamarAcosta2020" /><ref name="ZamberlanSanzMartinezVivot2018">Template:Cite journal</ref><ref name="TiHKAL" /><ref name="ShulginCarter1980">Template:Cite journal</ref> Shulgin tested it and discovered its effects starting in 1975.<ref name="Shulgin1975a">https://isomerdesign.com/pihkal/notebooks/transcripts/p1/p1.176.pdf</ref><ref name="Shulgin1975b">https://isomerdesign.com/pihkal/notebooks/transcripts/p1/p1.176.pdf</ref> The drug started to be encountered as a novel recreational and designer drug in 1999.<ref name="AraújoCarvalhoBastos2015" /><ref name="Aipsin" /> 5-MeO-DiPT became a temporarily controlled substance in the United States in 2003 and a permanently controlled substance in 2004.<ref name="AraújoCarvalhoBastos2015" /><ref name="DEA2003" /><ref name="DEA2004">Template:Cite journal</ref> The recreational use of 5-MeO-DiPT appears to have declined over time and its use is described as being not very prevalent.<ref name="Aipsin" /><ref name="PalamarAcosta2020" /><ref name="AraújoCarvalhoBastos2015" />

Society and culture

Recreational use

File:5meodipt.jpg
5-MeO-DiPT tablets seized from Salem, Oregon.

Use of 5-MeO-DiPT has been found to be particularly prevalent among gay men who use drugs as part of chemsex.<ref name="AraújoCarvalhoBastos2015" /><ref name="HidakaIchikawaKoyano2006">Template:Cite journal</ref><ref name="KuwaharaNakakuraOda2008">Template:Cite journal</ref> It is also seen in transgender women.<ref name="ShanYuYang2018">Template:Cite journal</ref><ref name="XuChangChen2024">Template:Cite journal</ref> The drug is described as a stimulant, sexual enhancer, party drug, and light psychedelic.<ref name="PalamarAcosta2020" /> 5-MeO-DiPT has been associated with increased risk of HIV diagnosis in multiple studies in Asia, perhaps due to risky sexual behavior involving the drug.<ref name="PalamarAcosta2020" /><ref name="KuwaharaNakakuraOda2008" /><ref name="TogariInoueTakaku2016">Template:Cite journal</ref><ref name="ShanYuYang2018" />

Canada

5-MeO-DiPT is not scheduled in Canada.<ref>Template:Cite web</ref>

China

As of October 2015, 5-MeO-DiPT is a controlled substance in China.<ref>Template:Cite web</ref>

Denmark

Illegal since February 2004.Template:Citation needed

Germany

Illegal since September 1999.Template:Citation needed

Greece

Illegal since February 2003.Template:Citation needed

Japan

Illegal since April 2005.<ref name="AraújoCarvalhoBastos2015" />

Singapore

Illegal since early 2006.Template:Citation needed

Sweden

Sveriges riksdags health ministry Statens folkhälsoinstitut classified 5-MeO-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 Oct 1, 2004, in their regulation SFS 2004:696 listed as 5-metoxi-N,N-diisopropyltryptamin (5-MeO-DIPT), making it illegal to sell or possess.<ref>Template:Cite web</ref>

United States

On April 4, 2003, the United States DEA added both 5-MeO-DiPT and α-methyltryptamine (AMT) to Schedule I of the Controlled Substances Act under "emergency scheduling" procedures.<ref name="AraújoCarvalhoBastos2015" /> The drugs were officially placed into Schedule I on September 29, 2004.<ref name="AraújoCarvalhoBastos2015" /> Prior to its prohibition in the U.S., 5-MeO-DiPT was sold online alongside psychoactive analogues such as diisopropyltryptamine (DiPT), and dipropyltryptamine (DPT), neither of which have yet been expressly outlawed.

See also

References

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Template:Psychedelics Template:Entactogens Template:Stimulants Template:Serotonin receptor modulators Template:Monoamine reuptake inhibitors Template:Monoaminergic neurotoxins Template:Tryptamines

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