5-MeO-MiPT

5-MeO-MiPT
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 InfoCard100.223.426 Edit 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 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. It is commonly used as a "substitute" for 5-MeO-DiPT because of the very similar structure and effects.

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

Chemistry

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

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.[5]

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. But at doses of 4-10 milligrams users find 5-MeO-MiPT to be a very euphoric and tactile chemical.[6][7] 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.[8]

Pharmacology

Pharmacodynamics

5-MeO-MiPT activities
Target Affinity (Ki, nM)
5-HT1A 12–143 (Ki)
610 (EC50Tooltip Half-maximal effective concentration)
5-HT1B 303
5-HT1D 23
5-HT1E 3,496
5-HT1F ND
5-HT2A 113–449 (Ki)
5.9–290 (EC50)
5-HT2B 59
5-HT2C 790–2,186 (Ki)
179 (EC50)
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
σ1 >10,000
σ2 918
SERTTooltip Serotonin transporter 3,300–6,409 (Ki)
2,680–29,768 (IC50Tooltip half-maximal inhibitory concentration)
NETTooltip Norepinephrine transporter >22,000 (Ki)
22,000 (IC50)
DATTooltip Dopamine transporter >26,000
>100,000 (IC50)
Notes: The smaller the value, the more avidly the drug binds to the site. Refs: [4][2][3][9]

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.[10][11] 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]

Dosage

Two tablets of 5-MeO-MiPT

Based on Shulgin's personal experience,[12] dosage for an adult male of approximately 6' and 200lbs:

DOSAGE: 4 - 6 mg, orally; 12 - 20 mg, smoked

DURATION : 4 - 6 hrs

Reagent results

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
Freebase Orange to brown Orange red Deep greenish brown Unknown Purple No reaction No reaction
HCl Orange to brown Red to brown Greenish brown Brown Violet to purple Green Unknown

Dangers

The toxicity of 5-MeO-MiPT is not known. There is no known documentation of death attributed to the use of 5-MeO-MiPT alone.

Canada

5-MeO-MiPT is not scheduled in Canada.[citation needed]

China

As of October 2015 5-MeO-MiPT is a controlled substance in China.[13]

Finland

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

Luxembourg

In Luxembourg, 5-MeO-MiPT is not cited in the list of prohibited substances.[15] Therefore, it is still a legal substance.

United Kingdom

5-MeO-MiPT is a Class A drug in the United Kingdom as are most ethers of ring-hydroxy tryptamines.[citation needed]

United States

5-MeO-MiPT is unscheduled at the federal level in the United States,[16] but it could be considered an analog of 5-MeO-DiPT, in which case purchase, sale, or possession with intent to consume could be prosecuted under the Federal Analog Act.

Florida

"5-Methoxy-N-methyl-N-isopropyltryptamine" is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in the state of Florida.[17]

Research

5-MeO-MiPT, under the developmental code name MSD-001, is being developed for potential medical use.[18][19][20] As of September 2024, it is in phase 1 clinical trials in healthy individuals in the United States and the European Union.[18][19][20] It is being developed by Mindstate Design Labs.[18][19][20] The drug was selected for development via artificial intelligence (AI)-assisted processing of 70,000 online trip reports that aimed to identify a psychedelic with unique subjective effects deemed promising for pharmaceutical development.[18]

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. ^ a b c d 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. ^ a b 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". Mol Psychiatry. 29 (8): 2346–2358. doi:10.1038/s41380-024-02506-8. PMC 11412900. PMID 38486047.
  4. ^ a b c 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. ^ Spratley T (2004). "Analytical Profiles for Five "Designer" Tryptamines" (PDF). Microgram Journal. 3 (1–2): 55. Retrieved 2013-10-09.
  6. ^ Carpenter DE (2022-01-25). "DEA Proposes Adding Five Psychedelic Compounds to Schedule 1". Lucid News. Retrieved 2022-01-26.
  7. ^ 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.
  8. ^ "5-MeO-MiPT". The Drug Classroom. Retrieved 2022-11-16.
  9. ^ 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". J Pharmacol Exp Ther. 385 (1): 62–75. doi:10.1124/jpet.122.001454. PMC 10029822. PMID 36669875.
  10. ^ 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.
  11. ^ 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.
  12. ^ "#40 5-MEO-MIPT". Erowid Online Books : "TIHKAL". Retrieved 2021-06-01.
  13. ^ "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.
  14. ^ "FINLEX ® - Säädökset alkuperäisinä: Valtioneuvoston asetus kuluttajamarkkinoilta… 1130/2014". www.finlex.fi. Retrieved 11 July 2023.
  15. ^ "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).
  16. ^ "21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2014-12-17.
  17. ^ "Chapter 893 - Drug Abuse Prevention and Control". Florida Statutes.
  18. ^ a b c d 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.
  19. ^ a b c Microdose NewsDesk (10 September 2024). "Mindstate Design Labs AI-Designed Trial Gets FDA Approval". Microdose. Retrieved 10 November 2024.
  20. ^ a b c Meissen 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. Retrieved 10 November 2024.

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