5-MeO-MiPT

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5-MeO-MiPT
5-MeO-MiPT.svg
5-MeO-MiPT 3D.png
Clinical data
Other namesMoxy; MSD-001; MSD001; 5-Methoxy-N-methyl-N-isopropyltryptamine
Legal status
Legal status
Identifiers
  • N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-methylpropan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.223.426 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C15H22N2O
Molar mass 246.354 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 Yes check.svgY
  • Key:HEDOODBJFVUQMS-UHFFFAOYSA-N Yes check.svgY
   (verify)

5-MeO-MiPT is a psychedelic and hallucinogen of the tryptamine family. It used by some as an entheogen. It has structural and pharmacodynamic properties similar to the drugs 5-MeO-DiPT, DiPT, and MiPT.

Contents

The drug acts as a non-selective serotonin receptor agonist, including of the serotonin 5-HT2A receptor. [2] [3] [4]

5-MeO-MiPT was first described in the scientific literature by Alexander Shulgin and colleagues in 1985. [5]

Dosage

Two tablets of 5-MeO-MiPT 5meomipt.jpg
Two tablets of 5-MeO-MiPT

Based on Shulgin's personal experience, [6] dosage for an adult male of approximately 200 lbs weight:

Dosage: 4–6 mg, orally; 12–20 mg, smoked

Duration: 4–6 hours

A wider recreational dosage range of 0.5 to 20 mg or more orally has also been reported. [7]

Effects

This is an analogue of the more popular drug 5-MeO-DiPT (nicknamed "foxy methoxy") and has the nickname "moxy". Some users report the tactile effects of 5-MeO-DiPT without some of the unwanted side effects. At higher doses it becomes much more psychedelic, sometimes being compared to 5-MeO-DMT. At doses of 4 to 10 mg, users find 5-MeO-MiPT to be a very euphoric and tactile chemical. [8] [9] Its energetic effects can be very strong at high doses, increasing normal heart rate considerably. Sounds can be amplified in perception to a point where synesthetic effects ("touching or/and tasting sounds") occur. [10]

Side effects

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. [11] There is no known documentation of death attributed to the use of 5-MeO-MiPT alone.

Interactions

Pharmacology

5-MeO-MiPT activities
TargetAffinity (Ki, nM)
5-HT1A 12–143 (Ki)
610–>10,000 (EC50 Tooltip Half-maximal effective concentration)
109% (Emax Tooltip maximal efficacy)
5-HT1B 303
5-HT1D 23
5-HT1E 3,496
5-HT1F ND
5-HT2A 113–449 (Ki)
5.9–566 (EC50)
82–101% (Emax)
5-HT2B 59 (Ki)
1,500 (EC50)
12% (Emax)
5-HT2C 790–2,186 (Ki)
179 (EC50)
101% (Emax)
5-HT3 >10,000
5-HT4 ND
5-HT5A 953
5-HT6 130
5-HT7 20
α1A >12,000
α1B >10,000
α2A 175–5,300
α2B 1,693
α2C 637
β1–β2 >10,000
D1 >25,000
D2 >25,000
D3 2,470–>25,000
D4 6,331
D5 >10,000
H1 3,900–4,819
H2–H4 >10,000
I1 879
TAAR1 >15,000 (rat/mouse)
σ1 >10,000
σ2 918
SERT Tooltip Serotonin transporter3,300–6,409 (Ki)
2,680–29,768 (IC50 Tooltip half-maximal inhibitory concentration)
>100,000 (EC50)
NET Tooltip Norepinephrine transporter>22,000 (Ki)
84,000 (IC50)
>100,000 (EC50)
DAT Tooltip Dopamine transporter>26,000 (Ki)
>100,000 (IC50)
>100,000 (EC50)
Notes: The smaller the value, the more avidly the drug binds to the site. Refs: [12] [4] [13] [2] [3] [14]

Pharmacodynamics

The mechanism that produces the hallucinogenic and entheogenic effects of 5-MeO-MiPT is thought to result primarily from serotonin 5-HT2A receptor agonism, although additional mechanisms of action such as inhibition of monoamine oxidase (MAO) might also be involved. [5] [12] In addition to the serotonin 5-HT2A receptor, 5-MeO-MiPT also potently binds to and/or activates other serotonin receptors, such as the serotonin 5-HT1A, 5-HT2B, and 5-HT2C receptors. [2]

In addition to the serotonin receptors, 5-MeO-MiPT has also been found to show significant affinity to the serotonin transporter (SERT) and norepinephrine transporter (NET), thereby acting as a moderately potent serotonin–norepinephrine reuptake inhibitor (SNRI). [4] These mechanisms might help explain anecdotal reports of antidepressant and anxiolytic effects from modest doses of this compound. For example, SNRIs such as venlafaxine are commonly prescribed to treat depression, and the serotonin 5-HT1A receptor agonist buspirone is prescribed primarily for treatment of anxiety. However, subsequent research contradicted the preceding findings and found that 5-MeO-MiPT did not significantly bind to or inhibit the human monoamine transporters. [2] The drug is also inactive as a monoamine releasing agent. [12]

Chemistry

5-MeO-MiPT is in a class of compounds commonly known as tryptamines, and is the N-methyl-N-isopropyl homologue of 5-MeO-DMT. The full name of the chemical is 5-methoxy-N-methyl-N-isopropyltryptamine.

Analogues

Analogues of 5-MeO-MiPT include MiPT, 5-MeO-DMT, 5-MeO-DiPT, and 5-MeO-MET, among others.

Detection

5-MeO-MiPT causes the ehrlich reagent to turn purple then fade to faint blue. It causes the marquis reagent to go yellow through to black. [15]

Exposing compounds to the reagents gives a colour change which is indicative of the compound under test. The following test results are from protestkit.

5-MeO-MiPT Marquis Mecke Mandelin Liebermann Ehrlich Hofmann Simon’s
FreebaseOrange to brownOrange redDeep greenish brownUnknownPurpleNo reactionNo reaction
HClOrange to brownRed to brownGreenish brownBrownViolet to purpleGreenUnknown

Society and culture

The legal status of 5-MeO-MiPT differs internationally. It is not scheduled in Canada, [16] and in Luxembourg it is not listed among prohibited substances, making it legal there. [17] In the United States, it is unscheduled at the federal level, [18] but may be treated as an analog of 5-MeO-DiPT under the Federal Analog Act. At the state level, “5-Methoxy-N-methyl-N-isopropyltryptamine” is classified as a Schedule I controlled substance in Florida, prohibiting its purchase, sale, or possession. [19]

In other jurisdictions, control is stricter. As of September–October 2015, China lists 5-MeO-MiPT as a controlled substance. [20] Finland includes it in its decree banning certain psychoactive substances from the consumer market. [21] In the United Kingdom, it is classified as a Class A drug along with most ethers of ring-hydroxy tryptamines.[ citation needed ]

Research

5-MeO-MiPT, under the developmental designation MSD-001, is being investigated for potential medical use. As of September 2024, it has received regulatory approval to begin Phase I clinical trials in healthy individuals in both the United States and the European Union. [22] [23] [24] [25] The compound is being developed by Mindstate Design Labs, which uses an AI platform named Osmanthus to analyze subjective experience reports and identify relationships between receptor targets and psychoactive effects. MSD-001 is being developed as a neutral psychoactive base intended for combination with other compounds selected based on biochemical insights derived from this analysis. [26] [27] [28] [29]

See also

References

  1. ↑ 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. Retrieved 2023-08-27.
  2. 1 2 3 4 Rickli A, Moning OD, Hoener MC, Liechti ME (August 2016). "Receptor interaction profiles of novel psychoactive tryptamines compared with classic hallucinogens" (PDF). European Neuropsychopharmacology. 26 (8): 1327–1337. doi:10.1016/j.euroneuro.2016.05.001. PMID   27216487. S2CID   6685927.
  3. 1 2 Puigseslloses 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.
  4. 1 2 3 Ray 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.
  5. 1 2 Repke 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.
  6. ↑ "#40 5-MEO-MIPT". Erowid Online Books: "TIHKAL". Retrieved 2021-06-01.
  7. ↑ 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.
  8. ↑ Carpenter DE (2022-01-25). "DEA Proposes Adding Five Psychedelic Compounds to Schedule 1". Lucid News. Retrieved 2022-01-26.
  9. ↑ Palamar 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.
  10. ↑ "5-MeO-MiPT". The Drug Classroom. Retrieved 2022-11-16.
  11. ↑ Altuncı YA, Aydoğdu M, Açıkgöz E, Düzağaç F, Atasoy A, Dağlıoğlu N, et al. (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.
  12. 1 2 3 Nagai 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.
  13. ↑ 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.
  14. ↑ 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.
  15. ↑ Spratley T (2004). "Analytical Profiles for Five "Designer" Tryptamines" (PDF). Microgram Journal. 3 (1–2): 55. Retrieved 2013-10-09.
  16. ↑ "Controlled Drugs and Substances Act". Justice Laws Website. Government of Canada. Retrieved March 28, 2025.
  17. ↑ "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).
  18. ↑ "21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2014-12-17.
  19. ↑ "Chapter 893 - Drug Abuse Prevention and Control". Florida Statutes.
  20. ↑ "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 from the original on 1 October 2015. Retrieved 1 October 2015.
  21. ↑ "FINLEX ® - Säädökset alkuperäisinä: Valtioneuvoston asetus kuluttajamarkkinoilta… 1130/2014". www.finlex.fi. Retrieved 11 July 2023.
  22. ↑ Ovalle D, Beard M (5 September 2024). "FDA gives an early nod to psychedelic research". The Washington Post. Retrieved 7 August 2025.
  23. ↑ NewsDesk M (10 September 2024). "Mindstate Design Labs AI-Designed Trial Gets FDA Approval". Microdose. Retrieved 10 November 2024.
  24. ↑ Ducharme J (2 October 2024). "Safer Psychedelic Drugs May Be Coming". TIME. Retrieved 7 August 2025.
  25. ↑ Bayer M (13 March 2024). "After crunching 70k 'trip reports', Mindstate looks to test first AI-derived psychedelic on humans". Fierce Biotech. Retrieved 10 November 2024.
  26. ↑ Meissen A (20 September 2024). "Mindstate Uses AI to Design "Next-Gen" Psychedelics Combined With 5-MeO-MiPT". Lucid News. Retrieved 10 November 2024.
  27. ↑ Nichols MR (20 June 2025). "The next era of psychedelics may be precision-designed". Big Think. Retrieved 7 August 2025.
  28. ↑ Dimitropoulos S (12 June 2025). "Science Has a Powerful New Tool to Unlock the Mysteries of Consciousness—And Even Help You Reach Transcendence". Popular Mechanics. Retrieved 7 August 2025.
  29. ↑ Houser K (28 May 2025). "Startups Are Trying to Hack Psychedelic Drugs to Make Them Safer". Futurism. Retrieved 7 August 2025.
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