5-MeO-MiPT

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Summary sheet: 5-MeO-MiPT
5-MeO-MiPT
5-MeO-MiPT.svg
Chemical Nomenclature
Common names 5-MeO-MiPT, Moxy
Substitutive name 5-Methoxy-N-methyl-N-isopropyltryptamine
Systematic name N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-N-methylpropan-2-amine
Class Membership
Psychoactive class Psychedelic / Entactogen
Chemical class Tryptamine
Routes of Administration

WARNING: Always start with lower doses due to differences between individual body weight, tolerance, metabolism, and personal sensitivity. See responsible use section.


⇣ Smoked
Dosage
Threshold 5 mg
Light 5 - 10 mg
Common 10 - 15 mg
Strong 15 - 20 mg
Heavy 20 mg +
Duration
Total 5 - 8 hours
Onset 20 - 60 minutes
Peak 1 - 2 hours
Offset 1 - 2 hours
After effects 1 - 3 hours
⇣ Oral
Dosage
Threshold 3 mg
Light 3 - 7 mg
Common 7 - 15 mg
Strong 15 - 20 mg
Heavy 20 mg +
Duration
Total 5 - 8 hours
Onset 20 - 40 minutes
Come up 30 - 60 minutes
Peak 2 - 3 hours
Offset 2 - 3 hours
After effects 2 - 4 hours









DISCLAIMER: PW's dosage information is gathered from users and resources for educational purposes only. It is not a recommendation and should be verified with other sources for accuracy.

Interactions
2C-T-X
2C-X
Cannabis
DOx
MDMA
Mescaline
NBOMe
Amphetamines
Cocaine
DXM
Tramadol
aMT
MAOIs
PCP


5-Methoxy-N-methyl-N-isopropyltryptamine (also known as 5-MeO-MiPT and moxy) is a lesser-known psychedelic substance of the tryptamine class. 5-MeO-MiPT is chemically related to tryptamines like 5-MeO-DMT and 5-MeO-DiPT. It produces its psychoactive effects through activity at serotonin receptors in the brain.

The synthesis and pharmacology of 5-MeO-MiPT was first reported in 1985 by David Repke and Alexander Shulgin.[1] Its effects in humans was documented in Shulgin's book TiHKAL ("Tryptamines I Have Known and Loved").

Anecdotal reports describe 5-MeO-MiPT's effects as highly stimulating and mildly entactogenic, lacking in typical psychedelic visual distortions. Many users report strong physical and tactile effects that serve to enhance libido and sexual pleasure. An unpleasant "body load" is also often reported at common to high doses, marked by muscle tension and nausea.

Very little is known about the pharmacological properties, metabolism and toxicity of 5-MeO-MiPT, and it has a limited history of human use. It has been sold online as a research chemical. It is highly advised to use harm reduction practices when using this substance.

Chemistry

5-MeO-MiPT, or 5-methoxy-N-methyl-N-isopropyltryptamine, is a synthetic indole alkaloid molecule of the tryptamine class. Tryptamines share a core structure comprised of a bicylic indole heterocycle attached at R3 to an amino group via an ethyl side chain. 5-MeO-MiPT is substituted at R5 of its indole heterocycle with a methoxy (MeO) functional group CH3O−; it also contains a methyl group and an isopropyl chain bound to the terminal amine RN of its tryptamine backbone (MiPT).

5-MeO-MiPT is the N-substituted isopropyl homologue of 5-MeO-DMT.[2]

Pharmacology

Further information: Serotonergic psychedelic

5-MeO-MiPT's psychedelic effects are believed to come from its efficacy at the 5-HT2A receptor as a partial agonist[3][1] and additional mechanisms of action such as the inhibition of MAO (i.e. digestive enzymes in the stomach) have also been speculated upon, though this has yet to be demonstrated scientifically. While 5-MeO-MiPT binds most strongly to 5-HT1A receptors, it also shows fairly strong binding affinity to the SERT and NET, thereby acting as a moderately potent serotonin-norepinephrine reuptake inhibitor.[4] These mechanisms may help explain why there are many anecdotal reports of anti-depressant and anxiolytic effects from modest doses of this compound. For example, SNRIs such as venlafaxine are commonly prescribed to treat depression, and the 5-HT1A agonist buspirone is prescribed primarily for treatment of anxiety.

Subjective effects

5-MeO-MiPT can be taken via oral ingestion or it can be smoked. When ingested orally, the visual and sensory effects are reported to become more prominent. The experience can be broken up into two stages; the first half feels stimulating and entactogenic whilst the second half feels more similar to a traditional tryptamine psychedelic like psilocybin mushrooms or LSD. When smoked, the physically and cognitively stimulating effects become emphasized.

Disclaimer: The effects listed below cite the Subjective Effect Index (SEI), an open research literature based on anecdotal user reports and the personal analyses of PsychonautWiki contributors. As a result, they should be viewed with a healthy degree of skepticism.

It is also worth noting that these effects will not necessarily occur in a predictable or reliable manner, although higher doses are more liable to induce the full spectrum of effects. Likewise, adverse effects become increasingly likely with higher doses and may include addiction, severe injury, or death ☠.

Physical effects
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Visual effects
Eye.svg

Cognitive effects
User.svg

Auditory effects
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Experience reports

There are currently no anecdotal reports which describe the effects of this compound within our experience index. Additional experience reports can be found here:

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

Toxicity and harm potential

Further information: Research chemicals § Toxicity and harm potential, and Responsible use § Hallucinogens

Almost nothing is known about the long-term effects of 5-MeO-MiPT. Alongside of this, the exact toxic dosage is unknown. This is because 5-MeO-MiPT is a research chemical with very little history of human use.

A preliminary study on mice has shown that a normal dose of 5-MeO-MiPT (0.27 mg/kg) was unable to produce any measurable toxic effects.[5] However, doses of 5-MeO-MiPT way above the normal dosage range (2.7 mg/kg) have been shown to produce cell toxicity by triggering programmed cell death in the brain, liver and kidneys. The extent of the damage, if it occurs in other bodily tissues as well and how it is caused is not known yet.

Anecdotal evidence from people within the community who have tried 5-MeO-MiPT suggests that there are no negative health effects attributed to simply trying the drug by itself at low to moderate doses and using it very sparingly (but nothing can be completely guaranteed). Independent research should always be done to ensure that a combination of two or more substances is safe before consumption.

It is strongly recommended that one use harm reduction practices when using this drug.

Tolerance and addiction potential

5-MeO-MiPT is not habit-forming, and the desire to use it can actually decrease with use. It is most often self-regulating.

Tolerance to the effects of 5-MeO-MiPT is built almost immediately after ingestion. After that, it takes about 3 days for the tolerance to be reduced to half and 7 days to be back at baseline (in the absence of further consumption). 5-MeO-MiPT presents cross-tolerance with all psychedelics, meaning that after the consumption of 5-MeO-MiPT all psychedelics will have a reduced effect.

Dangerous interactions

Warning: Many psychoactive substances that are reasonably safe to use on their own can suddenly become dangerous and even life-threatening when combined with certain other substances. The following list provides some known dangerous interactions (although it is not guaranteed to include all of them).

Always conduct independent research (e.g. Google, DuckDuckGo, PubMed) to ensure that a combination of two or more substances is safe to consume. Some of the listed interactions have been sourced from TripSit.

  • 2C-T-X - Both classes of compounds can be unpredictable alone.
  • 2C-X - The 5-MeO psychedelics can interact unpredictably to potentiate other psychedelics.
  • Cannabis - May increase the risk of negative psychological effects such as anxiety, paranoia, and psychosis.
  • DOx - The 5-MeO class of tryptamines can be unpredictable in their interactions, particularly increasing the risk of unpleasant physical side effects.
  • MDMA - Some of the 5-MeO tryptamines are a bit unpredictable and should be mixed with MDMA with care.
  • Mescaline - The 5-MeO class of tryptamines can be unpredictable in their interactions.
  • NBOMe - The 5-MeO class of tryptamines can be unpredictable in their interactions and the NBOMes are known to be unpredictable even alone. This combination is best avoided.
  • Amphetamines - The anxiogenic and focusing effects of stimulants increase the chance of unpleasant thought loops. The combination is generally unnecessary because of the stimulating effects of psychedelics.
  • Cocaine - The anxiogenic and focusing effects of stimulants increase the chance of unpleasant thought loops. The combination is generally unnecessary because of the stimulating effects of psychedelics.
  • DXM - Little information exists about this combination.
  • Tramadol - Increased risk of serotonin syndrome.
  • aMT - Increased risk of serotonin syndrome.
  • MAOIs - Increased risk of serotonin syndrome.
  • PCP - Little information exists about this combination. May increase risk of psychosis and excessive stimulation.

There are no known deaths from 5-MeO-MiPT but, as a monoamine reuptake inhibitor (MRI)[3], injury could occur when excessive doses are taken or when it is taken with drugs such as MAOIs, RIMAs, stimulants and any substance which act as a releasing agent or reuptake inhibitor of neurotransmitters such as serotonin and dopamine.[6]

Legal status

  • Austria: 5-MeO-MiPT is illegal to possess, produce and sell under the NPSG (Neue Psychoaktive Substanzen Gesetz).[7] However, offenders with no intent to distribute will likely not have to face prosecution.
  • Brazil: 5-MeO-MiPT is illegal to produce, sell, or possess as it is listed on Portaria SVS/MS nº 344.[8]
  • China: 5-MeO-MiPT is controlled as a Category I psychotropic substance and is illegal to sell, buy, import, export, and manufacture.[9]
  • Finland: 5-MeO-MiPT was banned in Finland in December 2014.[10]
  • Germany: 5-MeO-MiPT is controlled under the NpSG[11] (New Psychoactive Substances Act) as of July 18, 2019.[12] Production and import with the aim to place it on the market, administration to another person, placing it on the market and trading is punishable. Possession is illegal but not punishable.[13][14] The legislator considers it possible that orders of 4-HO-MiPT are punishable as an incitement to place it on the market.[15]
  • Japan: 5-MeO-MiPT is controlled as a "Designated Substance" (Shitei-Yakubutsu) by the Pharmaceutical Affairs Law, making it illegal to possess or sell.[citation needed]
  • Latvia: 5-MeO-MiPT is a Schedule I drug in Latvia.[16]
  • Luxembourg: 5-MeO-MiPT is not cited in the list of prohibited substances[17]. Therefore, it is still a legal substance.
  • New Zealand: 5-MeO-MiPT is an analogue of DMT which makes it a Class C controlled drug in New Zealand.[18]
  • Romania: 5-MeO-MiPT and other derivatives are illegal in Romania, as of January 2011.[citation needed]
  • Switzerland: 5-MeO-MiPT is a controlled substance specifically named under Verzeichnis E.[19]
  • Turkey: 5-MeO-MiPT is classed as a drug and is illegal to possess, produce, supply, or import.[20]
  • United Kingdom: 5-MeO-MiPT is a Class A drug in the UK as it is an ether of the drug 5-HO-MiPT, which is a Class A drug as a result of the tryptamine catch-all clause.[21]
  • United States: 5-MeO-MiPT is unscheduled in the United States. It may be considered an analogue of 5-MeO-DiPT, a Schedule I drug under the Controlled Substances Act. As such, the sale for human consumption or the use for illicit non-medical or industrial intents and purposes could be prosecuted as crimes under the Federal Analogue Act.[22]
    • Florida: 5-MeO-MiPT is a Schedule I drug in Florida.[23]
    • Louisiana: 5-MeO-MiPT is a Schedule I drug (as of June 2013).[24]
    • Minnesota: Minnesota banned a series of drugs including 5-MeO-MiPT.[25]

See also

External links

Discussion

References

  1. ↑ 1.0 1.1 Repke, D. B.; Grotjahn, D. B.; Shulgin, A. T. (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. eISSN 1520-4804. ISSN 0022-2623. OCLC 39480771. PMID 4009612. 
  2. ↑ Shulgin, Alexander; Shulgin, Ann (1997). "#40. 5-MeO-MiPT". TiHKAL: The Continuation. United States: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. 
  3. ↑ 3.0 3.1 Nagai, F.; Nonaka, R.; Satoh, K.; Kamimura, H. (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. eISSN 1879-0712. ISSN 0014-2999. OCLC 01568459. PMID 17223101. 
  4. ↑ Ray, T. S. (4 March 2010). "Correction: Psychedelics and the Human Receptorome". PLoS ONE. 5 (3). doi:10.1371/annotation/e580a864-cf13-40c2-9bd9-b9687a6f0fe4. ISSN 1932-6203. 
  5. ↑ Altuncı YA, Aydoğdu M, Açıkgöz E, Güven Ü, Düzağaç F, Atasoy A, Dağlıoğlu N, Annette Akgür S. New Psychoactive Substance 5-MeO-MiPT In vivo Acute Toxicity and Hystotoxicological Study. Balkan Med J. 2021 Jan;38(1):34-42. doi:10.4274/balkanmedj.galenos.2020.2019.11.68 PMID: 32936075; PMCID: PMC8909217.
  6. ↑ Gillman, P. K. (2005). "Monoamine oxidase inhibitors, opioid analgesics and serotonin toxicity". British Journal of Anaesthesia. 95 (4): 434–441. doi:10.1093/bja/aei210. eISSN 1471-6771. ISSN 0007-0912. OCLC 01537271. 
  7. ↑ Gesamte Rechtsvorschrift für Neue-Psychoaktive-Substanzen-Gesetz (in german). Bundeskriminalamt Österreich. Retrieved April 13, 2023.
  8. ↑ "RESOLUÇÃO DA DIRETORIA COLEGIADA - RDC N° 130, DE 2 DE DEZEMBRO DE 2016" (in Portuguese). Agência Nacional de Vigilância Sanitária (ANVISA) [Brazilian Health Regulatory Agency (ANVISA)]. December 5, 2016. 
  9. ↑ "Erowid China Psychoactive Law Update: September 2015" (PDF). Erowid. Retrieved September 29, 2020. 
  10. ↑ "1130/2014: Valtioneuvoston asetus: kuluttajamarkkinoilta kielletyistä psykoaktiivisista aineista" (PDF). Suomen Säädöskokoelma (in Finnish). December 19, 2014. 
  11. ↑ "Anlage NpSG" (in German). Bundesamt für Justiz [Federal Office of Justice]. Retrieved December 10, 2019. 
  12. ↑ "Verordnung zur Änderung der Anlage des Neue-psychoaktive-Stoffe-Gesetzes und von Anlagen des Betäubungsmittelgesetzes" (PDF). Bundesgesetzblatt Jahrgang 2019 Teil I Nr. 27 (in German). Bundesanzeiger Verlag. July 17, 2019. pp. 1083–1094. ISSN 0341-1095. 
  13. ↑ "§ 4 NpSG" (in German). Bundesamt für Justiz [Federal Office of Justice]. Retrieved December 10, 2019. 
  14. ↑ "§ 3 NpSG" (in German). Bundesamt für Justiz [Federal Office of Justice]. Retrieved December 10, 2019. 
  15. ↑ "Gesetzentwurf der Bundesregierung: Entwurf eines Gesetzes zur Bekämpfung der Verbreitung neuer psychoaktiver Stoffe" (PDF) (in German). Deutscher Bundestag. May 30, 2016. p. 20. Drucksache 18/8579. 
  16. ↑ "Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem" (in Latvian). VSIA Latvijas Vēstnesis. November 10, 2005. Retrieved January 1, 2020. 
  17. ↑ Loi du 19 février 1973 concernant la vente de substances médicamenteuses et la lutte contre la toxicomanie. 
  18. ↑ "Schedule 1: Class A controlled drugs". Misuse of Drugs Act 1975. Parliamentary Counsel Office (PCO). Retrieved September 19, 2020. 
  19. ↑ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Bundeskanzlei [Federal Chancellery of Switzerland]. Retrieved January 1, 2020. 
  20. ↑ Bakanlar Kurulu Kararı Karar Sayısı : 2013/4827 | https://free-ankara.org/wp-content/uploads/2017/09/BKK_2013_4827_28688.pdf
  21. ↑ "Schedule 2: Part I: Class A Drugs". "Misuse of Drugs Act 1971". UK Government. Retrieved August 20, 2020. 
  22. ↑ https://www.law.cornell.edu/uscode/text/21/813
  23. ↑ "The 2015 Florida Statutes - Chapter 893". The Florida Legislature. Retrieved July 18, 2020. 
  24. ↑ "5-MeO-MIPT: Legal Status". Erowid. July 7, 2005. Retrieved September 29, 2020. 
  25. ↑ "2019 Minnesota Statutes". Office of the Revisor of Statutes. 2019. Retrieved September 29, 2020. 


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