Movatterモバイル変換


[0]ホーム

URL:


Jump to content
WikipediaThe Free Encyclopedia
Search

5-MeO-MiPT

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
5-MeO-MiPT
Clinical data
Other names5-Methoxy-N-methyl-N-isopropyltryptamine; Moxy; Moxie; MSD-001; MSD001
Routes of
administration
Oral,smoking[1]
Drug classNon-selectiveserotonin receptor agonist;Serotonin5-HT2A receptoragonist;Serotonergic psychedelic;Hallucinogen;Entactogen
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Onset of actionOral: 30 min (15–45 min)[1][3]
Oral, peak: 1–2 hours[1][3]
Duration of actionOral: 4–6 hours[1] or 3–8 hours[4][5]
Smoked: 2–5 hours[6]
Identifiers
  • N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-methylpropan-2-amine
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.223.426Edit this at Wikidata
Chemical and physical data
FormulaC15H22N2O
Molar mass246.354 g·mol−1
3D model (JSmol)
  • O(c1cc2c(cc1)[nH]cc2CCN(C(C)C)C)C
  • InChI=1S/C15H22N2O/c1-11(2)17(3)8-7-12-10-16-15-6-5-13(18-4)9-14(12)15/h5-6,9-11,16H,7-8H2,1-4H3 checkY
  • Key:HEDOODBJFVUQMS-UHFFFAOYSA-N checkY
  (verify)

5-MeO-MiPT, also known as5-methoxy-N-methyl-N-isopropyltryptamine or by its nicknameMoxy, is an atypicalpsychedelic drug of thetryptamine and5-methoxytryptamine families.[1][4][3] It has unique and unusual effects compared to other psychedelic tryptamines.[1][4][7][3][6] At low doses, its effects includestimulation,tactile andsexual enhancement, someMDMA-likeentactogenic effects, andintrospective and mildperceptual changes with few or nopsychedelic visuals ortime dilation, whereas at higher doses, it produces5-MeO-DMT-likeclassical psychedelic effects.[1][4][7] It is usually takenorally orsmoked.[1]

The drug acts as anon-selectiveserotonin receptor agonist, including of theserotonin5-HT1A,5-HT2A, and5-HT2C receptors, among others.[8][9][10] It is closely related inchemical structure and effects to5-MeO-DiPT, and is also related to other tryptamines like 5-MeO-DMT,4-HO-MiPT, andMiPT.[1][4][7]

5-MeO-MiPT was first described in the literature byAlexander Shulgin andDavid Repke and colleagues in 1985.[4][6][11] It was later described by Shulgin in greater detail in his 1997 bookTiHKAL (Tryptamines I Have Known and Loved).[1]Recreational use of 5-MeO-MiPT is significant but relatively rare.[6] It is often used as a substitute for5-MeO-DiPT, which has similar effects but was became acontrolled substance in theUnited States in 2003.[6] TheDrug Enforcement Administration (DEA) proposed banning 5-MeO-MiPT as well in the 2020s, but later withdrew its proposal amid public opposition.[4] 5-MeO-MiPT, under the developmental code nameMSD-001, is being developed for the treatment ofpsychiatric disorders by Mindstate Design Labs and is inphase 1clinical trials for this purpose as of 2025.[3][12][13][14][15]

Use and effects

[edit]

In his bookTiHKAL (Tryptamines I Have Known and Loved),Alexander Shulgin lists the dose of 5-MeO-MiPT as 4 to 6 mgorally and 12 to 20 mgsmoked.[1][6] A widerrecreational dose range of 0.5 to 20 mg or more orally has also been reported however.[4][16][5] Oral doses of 1 to 3 mg have been described as light, 3 to 8 mg as common or moderate, and 8 to 12 mg as strong.[5] Itsonset of action when taken orally is described as very rapid, occurring within 15 to 45 minutes, peak effects appear to occur after around 1 to 2 hours, and itsduration as 4 to 6 hours.[1][6] However, other sources state its duration as 3 to 8 hours.[4][5] Aclinical trial confirmed that 5-MeO-MiPT has an onset of about 30 minutes and that peak effects occur after about 1.5 to 2 hours.[3] Its duration smoked is said to be 2 to 5 hours.[6]

5-MeO-MiPT has been described as having unique and unusual effects relative to other psychedelic tryptamines.[1][4][7] The effects of 5-MeO-MiPT differ depending on whether it is taken orally or smoked and are highlydose-dependent.[1][4] When taken orally at relatively low doses like 4 to 6 mg, it is usually described as not producingpsychedelic visuals or relatedsensory effects and as producing only hints oftime dilation.[1][4] However, it is said to produce astoned state that includes an ease ofinterpretive fantasy,dream-likeperception, intenseconceptual thought andphilosophical thinking, and mild perceptual effects like altereddepth perception, minor wave pattern in peripheral vision, and slightly enhanced auditory acuity.[1] Moreover, the drug is described as producingstimulation, greatly enhanced tactile sensation anderoticism, enhancedmusic appreciation,tingling,shakes, and mildmotor impairment.[1][4] Its head space is described as relatively "shallow", less confusing, and more easily tolerated compared to classical psychedelics.[4] Its effects have been described by users variably as both pleasant and negative.[1][4]

When smoked, 5-MeO-MiPT is described as having effects similar in many regards to those of5-MeO-DMT.[1] These effects of smoked 5-MeO-MiPT include a powerfulrush (but less intense than 5-MeO-DMT), loss ofcoherent thought, not much in the way of visuals,closed-eye visuals of moving and colored geometric patterns, intense waves ofmental imagery of emotionally infusedmemories, impressive recall of early memories, intensedepersonalization or disorientation of the normal sense of being a person in a body, loss of immediate contact with surroundings,emotional lability includinglaughing,crying, and vocal outbursts,groaning, writhing, shaking around, and generaldisorientation.[1] It is described as having a very rapid onset, with the peak phase lasting less than 30 minutes and waves continuing for up to a few hours.[1] It was described by one user as feeling like a hybrid betweendiethyltryptamine (DET) and 5-MeO-DMT.[1]

5-MeO-MiPT is also known by its nickname "Moxy"[4] and is closely related both in terms ofchemical structure and effects to5-MeO-DiPT (also known as "Foxy Methoxy").[1][7] These two serotonergic tryptamines at low doses have been described as veryaphrodisiac and much morestimulant-like andparty drugs than classical psychedelics.[7] However, they have been described as not innately aphrodisiac, but instead as enhancing tactile sensation in a way that lends itself tosex.[7]Matthew Baggott has described 5-MeO-MiPT as having someMDMA-likeentactogenic effects at low doses, including tactile enhancement and feelings ofempathy,intimacy, and closeness with others, and as producing classical psychedelic effects at higher doses.[17]

Mindstate Design Labs has described 5-MeO-MiPT as the "least psychedelic psychedelic that's psychoactive".[3] It is described as being quite psychoactive, but as lacking "hallucinations" and as not producing "mind-bending trips".[3] The drug was assessed at five different doses byoral administration in aphase 1clinical trial in 47 individuals.[3] Its effects included heightened emotions, associative thinking, enhanced imagination, and perceptual effects such as brighter colors.[3] However, there were no hallucinations,self-disintegration,oceanic boundlessness, or other typical features ofpsychedelic experiences.[3] Itsonset was 30 minutes and its peak of effects was 1.5 to 2 hours.[3] Mindstate Design Labs has hypothesized that a mild psychedelic experience, as with 5-MeO-MiPT, could still provide therapeutic benefits without overthallucinogenic effects.[3]

In addition to its use on its own, 5-MeO-MiPT, along with the related tryptamine psychedelic4-HO-MET, is employed as a component of the MDMA-mimickingBorax combo.[4][18][19][20]

Side effects

[edit]

Adverse effects of 5-MeO-MiPT includeloss of appetite andinsomnia.[1] Low-dose 5-MeO-MiPT did not cause any serious histopathological effects on the liver, kidney, and brain. High doses induce apoptotic cell death through caspase activity especially in some parts of the organs.[21] There is no known documentation of death attributed to the use of 5-MeO-MiPT alone.[4]

Interactions

[edit]
See also:Psychedelic drug § Interactions, andTrip killer § Serotonergic psychedelic antidotes

Pharmacology

[edit]

Pharmacodynamics

[edit]
5-MeO-MiPT activities
TargetAffinity (Ki, nM)
5-HT1A12–143 (Ki)
610–>10,000 (EC50Tooltip Half-maximal effective concentration)
109% (EmaxTooltip maximal efficacy)
5-HT1B303–728
5-HT1D23–103
5-HT1E3,496–>10,000
5-HT1FND
5-HT2A113–449 (Ki)
5.9–566 (EC50)
82–101% (
Emax)
5-HT2B53–59 (Ki)
1,500 (EC50)
12% (
Emax)
5-HT2C790–2,186 (Ki)
179 (EC50)
101% (
Emax)
5-HT3>10,000
5-HT4ND
5-HT5A953–>10,000
5-HT6130–281
5-HT720–122
α1A>12,000
α1B>10,000
α2A175–>10,000
α2B1,693–>10,000
α2C637–2174
β1β2>10,000
D1>25,000
D2>25,000
D32,470–>25,000
D41,422–6,331
D5>10,000
H13,900–>10,000
H2H4>10,000
I1879
TAAR1>15,000 (rat/mouse)
σ11,666–>10,000
σ290–918
SERTTooltip Serotonin transporter3,300–>10,000 (Ki)
2,680–29,768 (IC50Tooltip half-maximal inhibitory concentration)
>100,000 (EC50)
NETTooltip Norepinephrine transporter>22,000 (Ki)
84,000 (IC50)
>100,000 (
EC50)
DATTooltip Dopamine transporter>26,000 (Ki)
>100,000 (IC50)
>100,000 (
EC50)
Notes: The smaller the value, the more avidly the drug interacts with the site.Refs:[8][9][10][22][23][24][25]

Themechanism that produces thehallucinogenic andentheogenic effects of 5-MeO-MiPT is thought to result primarily fromserotonin5-HT2A receptoragonism, although additional mechanisms of action such asinhibition ofmonoamine oxidase (MAO) might also be involved.[11][22] In addition to the serotonin 5-HT2A receptor, 5-MeO-MiPT alsopotently binds to and/or activates otherserotonin receptors, such as the serotonin5-HT1A,5-HT2B, and5-HT2C receptors.[8][25]

In addition to the serotonin receptors, 5-MeO-MiPT has also been found to show significant affinity to theserotonin transporter (SERT) andnorepinephrine transporter (NET), thereby acting as a moderately potentserotonin–norepinephrine reuptake inhibitor (SNRI).[10] However, subsequent research contradicted the preceding findings and found that 5-MeO-MiPT did not significantly bind to or inhibit the humanmonoamine transporters.[8][25] The drug is also inactive as amonoamine releasing agent.[22]

5-MeO-MiPT itself does not appear to have been studied, but the closely related drug5-MeO-DiPT has been found to produceserotonergic neurotoxicity,genotoxicity, and associatedcognitive deficits in rodents.[26][27][28][29][30]

Pharmacokinetics

[edit]

Absorption and distribution

[edit]

Followingintraperitoneal administration of 5-MeO-MiPT at doses of 2.7 mg/kg in mice the compound was detectable inblood,kidney,liver, andbrain.[21] At lower doses of 0.27 mg/kg, concentrations of theparent compound remained below the limit of quantification in all samples.[21]

In one humancase report 5-MeO-MiPT concentrations were measured at 160 ng/mL in blood and 3,380 ng/mL inurine samples collected approximately one and two hours post-exposure, respectively.[31]

In silico ADMET predictions projected highjejunal permeability and very high kidney permeability inMDCK cells, which suggests efficientgastrointestinal absorption andrenal filtration.[32] The compound demonstrated nearly completeblood-brain barrier penetration (99% predicted), and was not predicted to be asubstrate forP-glycoprotein, ororganic anion transporters.[32] The predicted human percent unbound toblood plasmaproteins was 45.5%, compared to 31.6% in mice.[32] The predictedvolume of distribution (Vd) for 5-MeO-MiPT was 3.743 L/kg, lower than itsstructural analogue5-MeO-DiPT (4.219 L/kg) andDMT (4.396 L/kg).[32]

Metabolism

[edit]

5-MeO-MiPT undergoes extensivephase I hepatic metabolism, mediated bycytochrome P450 enzymes.In vitro experiments using pooled human livermicrosomes identified seven phase Imetabolites, of which five were foundin vivo.[31][33] The majormetabolic pathways includeO-demethylation,N-demethylation,hydroxylation, andN-oxide formation.[31][33] The metabolic profile of 5-MeO-MiPT shows similarity to the structurally related compound5-MeO-DiPT.[31]

In vivo analysis of forensic case sample identified five phase I metabolites in blood and seven in urine. The metabolites detected in both blood and urine included5-MeO-NiPT,5-HO-MiPT, 5-MeO-MiPT-N-oxide, and HO-5-MeO-MiPT.[31] Two additionalphase II metabolites (glucuronides) were found in mice andin vitro models, but not in human urine sample.[31][33][34]

In silico ADMET predicted the compound to be asubstrate but not an inhibitor for theCYP1A2 andCYP2C9enzymes, and a substrate forCYP2A6 andCYP2B6.[32] Additionally, the compound is predicted to be both substrate and inhibitor for theCYP2D6.[32]

Detection of multiple metabolites in human urine sample two hours post-exposure, along with measurable blood concentrations at one hour, suggest relatively rapid metabolism andelimination.[31] Renal excretion is likely a major route of elimination.[31]

Chemistry

[edit]

5-MeO-MiPT, also known as 5-methoxy-N-methyl-N-isopropyltryptamine, is in a class of compounds commonly known astryptamines, and is theN-methyl-N-isopropylhomologue of5-MeO-DMT.[1]

Synthesis

[edit]

Thechemical synthesis of 5-MeO-MiPT has been described.[1]

Analogues

[edit]

Analogues of 5-MeO-MiPT includemethylisopropyltryptamine (MiPT),4-HO-MiPT (miprocin),4-AcO-MiPT (mipracetin),5-MeO-DMT,5-MeO-DiPT,5-MeO-DALT,5-MeO-MET,5-MeO-MPT,5-MeO-EiPT,5-MeO-PiPT, and5-MeO-iPALT (ASR-3001), among others.[1]

Positional isomers

[edit]

6-MeO-MiPT and 7-MeO-MiPT arepositional isomers of 5-MeO-MiPT.[35] They have been described byAlexander Shulgin as being inactive at doses of up to 50 mg and 70 mgorally, respectively.[35] Another notable positional isomer is4-MeO-MiPT.[1][35]

Detection

[edit]

5-MeO-MiPT causes theehrlich reagent to turn purple then fade to faint blue. It causes the marquis reagent to go yellow through to black.[36]

History

[edit]

5-MeO-MiPT was first described in thescientific literature byAlexander Shulgin andDavid Repke and colleagues in 1985.[4][6][11] It was later described by Shulgin in greater detail in his 1997 bookTiHKAL (Tryptamines I Have Known and Loved).[1] TheUnited StatesDrug Enforcement Administration (DEA) proposed banning 5-MeO-MiPT in the 2020s, but this proposal was later withdrawn.[4] The effort to make 5-MeO-MiPT acontrolled substance was prominently opposed by the psychedelic community.[4]

Society and culture

[edit]

Legal status

[edit]
See also:Drug Enforcement Administration § Scheduling of psychedelic drugs, andConvention on Psychotropic Substances of 1971
Two tablets of 5-MeO-MiPT.

The legal status of 5-MeO-MiPT differs internationally. It is not scheduled inCanada but is illegal if is sold for human consumption or recreational use ,[37] and inLuxembourg it is not listed among prohibited substances, making it not illegal but a legal gray area there.[38] In theUnited States, it is unscheduled at the federal level,[39] but may be treated as an analog of5-MeO-DiPT under theFederal Analog Act therefore if is sold for human consumption and not for medical or scientific uses is illegal and persecuted. At the state level, "5-Methoxy-N-methyl-N-isopropyltryptamine" is classified as a Schedule Icontrolled substance inFlorida, prohibiting its purchase, consumption, sale, or possession.[40]

In other jurisdictions, control is stricter and could be punished by death or life imprisonment its sale for human use. As of September–October 2015, China lists 5-MeO-MiPT as a controlled substance.[41] Finland includes it in its decree banning certain psychoactive substances from the consumer market.[42] In theUnited Kingdom, it is classified as a Class A drug along with most ethers of ring-hydroxy tryptamines.[citation needed]

Research

[edit]

5-MeO-MiPT, under the developmental code name MSD-001, is being developed for the treatment ofpsychiatric disorders.[3][12][13][14][15] It is under development specifically by Mindstate Design Labs.[3][12][13][14][15] As of October 2025, the drug is inphase 1clinical trials in theUnited States andEuropean Union.[3][12][13][43][44][45] A phase 1 trial was completed in July 2025.[3][12] Mindstate Design Labs has developed anartificial intelligence (AI) platform known as Osmanthus to analyzetrip reports in order to identify relationships betweenreceptor interactions andpsychoactive effects.[46][47][48][49] Other research of this sort has also been conducted and published by other groups.[50] Mindstate Design Labs's platform has processed 70,000 online trip reports and led to the selection of 5-MeO-MiPT for development.[3][46][47][48][49] According to its developer, 5-MeO-MiPT is intended as a "neutral base compound" with mild effects on its own for use as a sort of "psychedelic tofu" in combination with other drugs to precisely modulate serotonin receptors and create various uniquealtered states of consciousness.[3][46][47][48][49]

See also

[edit]

References

[edit]
  1. ^abcdefghijklmnopqrstuvwxyzaaabacShulgin A,Shulgin A (September 1997).TiHKAL: The Continuation.Berkeley, California:Transform Press.ISBN 0-9630096-9-9.OCLC 38503252."5-MeO-MiPT".
  2. ^Anvisa (2023-07-24)."RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).Diário Oficial da União (published 2023-07-25).Archived from the original on 2023-08-27. Retrieved2023-08-27.
  3. ^abcdefghijklmnopqrsMullin E (24 September 2025)."A Startup Used AI to Make a Psychedelic Without the Trip".WIRED. Retrieved12 November 2025.
  4. ^abcdefghijklmnopqrstuAragón M (9 January 2024)."Meet Moxy: The Novel Psychedelic the DEA Tried To Ban".DoubleBlind Mag. Retrieved8 October 2025.
  5. ^abcdMalaca S, Lo Faro AF, Tamborra A, Pichini S, Busardò FP, Huestis MA (December 2020)."Toxicology and Analysis of Psychoactive Tryptamines".International Journal of Molecular Sciences.21 (23): 9279.doi:10.3390/ijms21239279.PMC 7730282.PMID 33291798.5-Methoxy-N-methyl-N-isopropyltryptamine (5-MeO-MiPT): 5-MeO-MiPT or "moxy" was marketed as a "plant fertilizer." Oral doses ranged from 1–3 mg (light), 3–8 mg (common) and 8–12 mg (strong), with typical 10–20 mg doses if inhaled [22,103]. The principal effects lasted 3–7 h and included a general heightening of awareness, mild euphoria, psychedelic visual effects, such as enhanced colors but also anxiety, nausea, confusion and paranoia. Repke et al. studied if the effects of the drug would differ depending upon the route of administration [104]. If ingested the effects were stimulating, with visual hallucinations prevailing. 5-MeO-MiPT metabolism studied by LC-HRMS/MS identified six phase I metabolites following N-demethylation, O-demethylation, demethylation and hydroxylation and N-oxide formation and hydroxylation of the parent compound and N-O-bis-demethylation of the metabolite 5-OH-MiPT [105].
  6. ^abcdefghi"5-MeO-MiPT".АИПСИН (in Russian). Retrieved13 November 2025.
  7. ^abcdefgPalamar JJ, Acosta P (January 2020)."A qualitative descriptive analysis of effects of psychedelic phenethylamines and tryptamines".Human Psychopharmacology.35 (1) e2719.doi:10.1002/hup.2719.PMC 6995261.PMID 31909513.5-Meo-DIPT, Foxy, or Moxy (5-Meo-MIPT) are tryptamines that are distinct. A lot of people I know that like them think they're very aphrodisiac and much more stimulant and a party drug. My opinion on 5-MeO-MIPT is that it was a very sexual chemical … it feels good to touch things, and that sort of sensation certainly lends itself to sex but I wouldn't call it innately an aphrodisiac.
  8. ^abcdRickli A, Moning OD, Hoener MC, Liechti ME (August 2016). "Receptor interaction profiles of novel psychoactive tryptamines compared with classic hallucinogens".European Neuropsychopharmacology.26 (8):1327–1337.doi:10.1016/j.euroneuro.2016.05.001.PMID 27216487.S2CID 6685927.
  9. ^abPuigseslloses P, Nadal-Gratacós N, Ketsela G, Weiss N, Berzosa X, Estrada-Tejedor R, et al. (August 2024)."Structure-activity relationships of serotonergic 5-MeO-DMT derivatives: insights into psychoactive and thermoregulatory properties".Molecular Psychiatry.29 (8):2346–2358.doi:10.1038/s41380-024-02506-8.PMC 11412900.PMID 38486047.
  10. ^abcRay TS (February 2010)."Psychedelics and the human receptorome".PLOS One.5 (2) e9019.Bibcode:2010PLoSO...5.9019R.doi:10.1371/journal.pone.0009019.PMC 2814854.PMID 20126400.
  11. ^abcRepke DB, Grotjahn DB, Shulgin AT (July 1985). "Psychotomimetic N-methyl-N-isopropyltryptamines. Effects of variation of aromatic oxygen substituents".Journal of Medicinal Chemistry.28 (7):892–896.doi:10.1021/jm00145a007.PMID 4009612.
  12. ^abcde"MSD 001".AdisInsight. 17 October 2025. Retrieved12 November 2025.
  13. ^abcdBayer M (13 March 2024)."After crunching 70k 'trip reports', Mindstate looks to test first AI-derived psychedelic on humans".Fierce Biotech. Retrieved10 November 2024.
  14. ^abc"Mindstate Design Labs AI-Designed Trial Gets FDA Approval".Microdose. 10 September 2024. Retrieved10 November 2024.
  15. ^abcMeissen A (20 September 2024)."Mindstate Uses AI to Design "Next-Gen" Psychedelics Combined With 5-MeO-MiPT".Lucid News - Psychedelics, Consciousness Technology, and the Future of Wellness. Retrieved10 November 2024.
  16. ^Luethi D, Liechti ME (October 2018)."Monoamine Transporter and Receptor Interaction Profiles in Vitro Predict Reported Human Doses of Novel Psychoactive Stimulants and Psychedelics".The International Journal of Neuropsychopharmacology.21 (10):926–931.doi:10.1093/ijnp/pyy047.PMC 6165951.PMID 29850881.
  17. ^Carpenter DE (2022-01-25)."DEA Proposes Adding Five Psychedelic Compounds to Schedule 1".Lucid News. Retrieved2022-01-26.
  18. ^Baggott M (23 June 2023).Beyond Ecstasy: Progress in Developing and Understanding a Novel Class of Therapeutic Medicine. PS2023 [Psychedelic Science 2023, June 19–23, 2023, Denver, Colorado]. Denver, CO:Multidisciplinary Association for Psychedelic Studies.
  19. ^Hamilton Morris (28 November 2023)."POD 92: Understanding and Improving MDMA with Dr. Matthew Baggott". The Hamilton Morris Podcast (Podcast). Patreon. Retrieved30 November 2024.
  20. ^"Borax Combo (Synonyms: Blue Bliss)".naddi.org. National Association of Drug Diversion Investigators (NADDI). 14 December 2022. Retrieved21 November 2024.
  21. ^abcAltuncı YA, Aydoğdu M, Açıkgöz E, Güven Ü, Düzağaç F, Atasoy A, et al. (January 2021)."New Psychoactive Substance 5-MeO-MiPT In vivo Acute Toxicity and Hystotoxicological Study".Balkan Medical Journal.38 (1):34–42.doi:10.4274/balkanmedj.galenos.2020.2019.11.68.PMC 8909217.PMID 32936075.
  22. ^abcNagai F, Nonaka R, Satoh Hisashi Kamimura K (March 2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain".European Journal of Pharmacology.559 (2–3):132–137.doi:10.1016/j.ejphar.2006.11.075.PMID 17223101.
  23. ^Blough BE, Landavazo A, Decker AM, Partilla JS, Baumann MH, Rothman RB (October 2014)."Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes".Psychopharmacology.231 (21):4135–4144.doi:10.1007/s00213-014-3557-7.PMC 4194234.PMID 24800892.
  24. ^Kozell LB, Eshleman AJ, Swanson TL, Bloom SH, Wolfrum KM, Schmachtenberg JL, et al. (April 2023)."Pharmacologic Activity of Substituted Tryptamines at 5-Hydroxytryptamine (5-HT)2A Receptor (5-HT2AR), 5-HT2CR, 5-HT1AR, and Serotonin Transporter".The Journal of Pharmacology and Experimental Therapeutics.385 (1):62–75.doi:10.1124/jpet.122.001454.PMC 10029822.PMID 36669875.
  25. ^abcGlatfelter GC, Clark AA, Cavalco NG, Landavazo A, Partilla JS, Naeem M, et al. (December 2024). "Serotonin 1A Receptors Modulate Serotonin 2A Receptor-Mediated Behavioral Effects of 5-Methoxy-N,N-dimethyltryptamine Analogs in Mice".ACS Chemical Neuroscience.15 (24):4458–4477.doi:10.1021/acschemneuro.4c00513.PMID 39636099.
  26. ^Araújo AM, Carvalho F, Bastos M, Guedes de Pinho P, Carvalho M (August 2015). "The hallucinogenic world of tryptamines: an updated review".Archives of Toxicology.89 (8):1151–1173.Bibcode:2015ArTox..89.1151A.doi:10.1007/s00204-015-1513-x.PMID 25877327.
  27. ^Compton DM, Dietrich KL, Selinger MC, Testa EK (May 2011). "5-methoxy-N,N-di(iso)propyltryptamine hydrochloride (Foxy)-induced cognitive deficits in rat after exposure in adolescence".Physiology & Behavior.103 (2):203–209.doi:10.1016/j.physbeh.2011.01.021.PMID 21295050.
  28. ^Skelton MR, Schaefer TL, Herring NR, Grace CE, Vorhees CV, Williams MT (June 2009)."Comparison of the developmental effects of 5-methoxy-N,N-diisopropyltryptamine (Foxy) to (+/-)-3,4-methylenedioxymethamphetamine (ecstasy) in rats".Psychopharmacology.204 (2):287–297.doi:10.1007/s00213-009-1459-x.PMC 2888297.PMID 19198809.
  29. ^Noworyta-Sokołowska K, Kamińska K, Kreiner G, Rogóż Z, Gołembiowska K (November 2016)."Neurotoxic Effects of 5-MeO-DIPT: A Psychoactive Tryptamine Derivative in Rats".Neurotoxicity Research.30 (4):606–619.doi:10.1007/s12640-016-9654-0.PMC 5047954.PMID 27461536.
  30. ^Noworyta-Sokołowska K, Kamińska K, Rzemieniec J, Wnuk A, Wojcieszak J, Górska AM, et al. (2019)."Effects of exposure to 5-MeO-DIPT during adolescence on brain neurotransmission and neurotoxicity in adult rats".Forensic Toxicology.37 (1):45–58.doi:10.1007/s11419-018-0433-x.PMC 6315008.PMID 30636982.
  31. ^abcdefghGrafinger KE, Hädener M, König S, Weinmann W (March 2018). "Study of the in vitro and in vivo metabolism of the tryptamine 5-MeO-MiPT using human liver microsomes and real case samples".Drug Testing and Analysis.10 (3):562–574.doi:10.1002/dta.2245.PMID 28677880.
  32. ^abcdefBassi M, Bilel S, Tirri M, Corli G, Di Rosa F, Gregori A, et al. (March 2024)."Pharmaco-toxicological effects of the novel tryptamine hallucinogen 5-MeO-MiPT on motor, sensorimotor, physiological, and cardiorespiratory parameters in mice-from a human poisoning case to the preclinical evidence".Psychopharmacology.241 (3):489–511.doi:10.1007/s00213-024-06526-8.PMC 10884077.PMID 38214743.
  33. ^abcWang Y, Zhong C, Chen J, Meng L (April 2024). "Biotransformation of 5-methoxy-N-isopropyl-N-methyltryptamine by zebrafish and human liver microsome with high-resolution mass spectrometry".Journal of Pharmaceutical and Biomedical Analysis.241 115987.doi:10.1016/j.jpba.2024.115987.PMID 38280235.
  34. ^Fabregat-Safont D, Barneo-Muñoz M, Martinez-Garcia F, Sancho JV, Hernández F, Ibáñez M (July 2017). "Proposal of 5-methoxy-N-methyl-N-isopropyltryptamine consumption biomarkers through identification of in vivo metabolites from mice".Journal of Chromatography. A.1508:95–105.doi:10.1016/j.chroma.2017.06.010.PMID 28602505.
  35. ^abcShulgin AT (2003)."Basic Pharmacology and Effects". In Laing RR (ed.).Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137.ISBN 978-0-12-433951-4. Archived fromthe original on 13 July 2025.
  36. ^Spratley T (2004)."Analytical Profiles for Five "Designer" Tryptamines"(PDF).Microgram Journal.3 (1–2): 55. Retrieved2013-10-09.
  37. ^"Controlled Drugs and Substances Act".Justice Laws Website. Government of Canada. RetrievedMarch 28, 2025.
  38. ^"Loi du 19 février 1973 concernant la vente de substances médicamenteuses et la lutte contre la toxicomanie" [Law of February 19, 1973 concerning the sale of medicinal substances and the fight against drug addiction].Journal officiel du Grand-Duché de Luxembourg [Official Journal of the Grand Duchy of Luxembourg] (in French).
  39. ^"21 CFR — Schedules of Controlled Substances §1308.11 Schedule I." Archived fromthe original on 2009-08-27. Retrieved2014-12-17.
  40. ^"Chapter 893 - Drug Abuse Prevention and Control".Florida Statutes.
  41. ^"关于印发《非药用类麻醉药品和精神药品列管办法》的通知" [Notice on Printing and Distributing the "Measures for the Scheduling of Non-Pharmaceutical Narcotic Drugs and Psychotropic Substances"] (in Chinese). China Food and Drug Administration. 27 September 2015. Archived fromthe original on 1 October 2015. Retrieved1 October 2015.
  42. ^"FINLEX ® - Säädökset alkuperäisinä: Valtioneuvoston asetus kuluttajamarkkinoilta… 1130/2014".www.finlex.fi. Retrieved11 July 2023.
  43. ^Ovalle D, Beard M (5 September 2024)."FDA gives an early nod to psychedelic research".The Washington Post. Retrieved7 August 2025.
  44. ^"Mindstate Design Labs AI-Designed Trial Gets FDA Approval".Microdose. 10 September 2024. Retrieved10 November 2024.
  45. ^Ducharme J (2 October 2024)."Safer Psychedelic Drugs May Be Coming".TIME. Retrieved7 August 2025.
  46. ^abcMeissen A (20 September 2024)."Mindstate Uses AI to Design "Next-Gen" Psychedelics Combined With 5-MeO-MiPT".Lucid News. Retrieved10 November 2024.
  47. ^abcNichols MR (20 June 2025)."The next era of psychedelics may be precision-designed".Big Think. Retrieved7 August 2025.
  48. ^abcDimitropoulos S (12 June 2025)."Science Has a Powerful New Tool to Unlock the Mysteries of Consciousness—And Even Help You Reach Transcendence".Popular Mechanics. Retrieved7 August 2025.Their first proprietary compound, MOXY, currently in a 52-person Phase I trial, is designed to be just that, says DiNardo: "A sort of 'psychedelic tofu,' a drug that allows moderate cognitive flexibility, but isn't likely to cause awe or ego dissolution." In other words, MOXY acts as a neutral base that's mild on its own, but intended to combine with other compounds to produce fine-tuned mental states.
  49. ^abcHouser K (28 May 2025)."Startups Are Trying to Hack Psychedelic Drugs to Make Them Safer".Futurism. Retrieved7 August 2025.
  50. ^Ballentine G, Friedman SF, Bzdok D (March 2022)."Trips and neurotransmitters: Discovering principled patterns across 6850 hallucinogenic experiences".Science Advances.8 (11) eabl6989.Bibcode:2022SciA....8L6989B.doi:10.1126/sciadv.abl6989.PMC 8926331.PMID 35294242.

External links

[edit]
Tryptamines
No ring subs.
4-Hydroxytryptamines
5-Hydroxytryptamines
5-Methoxytryptamines
Other ring subs.
α-Alkyltryptamines
Others
Cyclized
Bioisosteres
Phenethylamines
Scalines
2C-x
3C-x
DOx
4C-x
Ψ-PEA
MDxx
FLY
25x-NB (NBOMes)
Others
Cyclized
Lysergamides
  • Bioisosteres:JRT
Others
Natural sources
5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT37
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
Tryptamines
4-Hydroxytryptamines
andesters/ethers
5-Hydroxy- and
5-methoxytryptamines
N-Acetyltryptamines
α-Alkyltryptamines
Cyclized tryptamines
Isotryptamines
Related compounds
Retrieved from "https://en.wikipedia.org/w/index.php?title=5-MeO-MiPT&oldid=1323686467"
Categories:
Hidden categories:

[8]ページ先頭

©2009-2025 Movatter.jp