5-MeO-MiPT

{{Drugbox

| Verifiedfields = verified

| Watchedfields = verified

| verifiedrevid = 477224982

| IUPAC_name = N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-methylpropan-2-amine

| image = 5-MeO-MiPT.svg

| width = 200px

| image2 = 5-MeO-MiPT 3D.png

| width2 = 200px

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| legal_BR = F2

| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-07-25}}

| legal_CA =

| legal_UK = Class A

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| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 96096-55-8

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| PubChem = 2763156

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 2043845

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 172139

| UNII_Ref= {{fdacite|correct|FDA}}

| UNII = L0P1807EUY

| synonyms = Moxy; MSD-001; MSD001; 5-Methoxy-N-methyl-N-isopropyltryptamine

| C=15 | H=22 | N=2 | O=1

| SMILES = O(c1cc2c(cc1)[nH]cc2CCN(C(C)C)C)C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = HEDOODBJFVUQMS-UHFFFAOYSA-N

}}

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-HT_2A receptor.

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

Dosage

Image:5meomipt.jpg

Based on Shulgin's personal experience,{{Cite web| work = Erowid Online Books : "TIHKAL" | title = #40 5-MEO-MIPT|url=https://www.erowid.org/library/books_online/tihkal/tihkal40.shtml|access-date=2021-06-01 }} dosage for an adult male of approximately 200{{nbsp}}lbs weight:

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

Duration: 4–6{{nbsp}}hours

A wider recreational dosage range of 0.5 to 20{{nbsp}}mg or more orally has also been reported.{{cite journal | vauthors = Luethi D, Liechti ME | title = Monoamine Transporter and Receptor Interaction Profiles in Vitro Predict Reported Human Doses of Novel Psychoactive Stimulants and Psychedelics | journal = Int J Neuropsychopharmacol | volume = 21 | issue = 10 | pages = 926–931 | date = October 2018 | pmid = 29850881 | pmc = 6165951 | doi = 10.1093/ijnp/pyy047 | url = https://bitnest.netfirms.com/external/10.1093/ijnp/pyy047}}

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 to 10{{nbsp}}mg, users find 5-MeO-MiPT to be a very euphoric and tactile chemical.{{Cite web| vauthors = Carpenter DE |date=2022-01-25|title=DEA Proposes Adding Five Psychedelic Compounds to Schedule 1|url=https://www.lucid.news/dea-proposes-five-psychedelic-compounds-schedule-1/|access-date=2022-01-26|website=Lucid News|language=en-US}}{{cite journal | vauthors = Palamar JJ, Acosta P | title = A qualitative descriptive analysis of effects of psychedelic phenethylamines and tryptamines | journal = Human Psychopharmacology | volume = 35 | issue = 1 | pages = e2719 | date = January 2020 | pmid = 31909513 | pmc = 6995261 | doi = 10.1002/hup.2719 }} 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.{{Cite web |title=5-MeO-MiPT |url=https://thedrugclassroom.com/video/5-meo-mipt/ |access-date=2022-11-16 |website=The Drug Classroom |language=en-US}}

Side effects

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.

Interactions

{{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}

Pharmacology

=Pharmacodynamics=

Target	Affinity (K_i, nM)
class="wikitable floatright" style="font-size:small;" \|+ 5-MeO-MiPT activities
5-HT_1A	12–143 (K_i) 610–>10,000 ({{Abbrlink\|EC₅₀\|Half-maximal effective concentration}}) 109% ({{Abbrlink\|E_max\|maximal efficacy}})
5-HT_1B	303
5-HT_1D	23
5-HT_1E	3,496
5-HT_1F	{{Abbr\|ND\|No data}}
5-HT_2A	113–449 (K_i) 5.9–566 ({{Abbr\|EC₅₀\|Half-maximal effective concentration}}) 82–101% ({{Abbr\|E_max\|maximal efficacy}})
5-HT_2B	59 (K_i) 1,500 ({{Abbr\|EC₅₀\|Half-maximal effective concentration}}) 12% ({{Abbr\|E_max\|maximal efficacy}})
5-HT_2C	790–2,186 (K_i) 179 ({{Abbr\|EC₅₀\|Half-maximal effective concentration}}) 101% ({{Abbr\|E_max\|maximal efficacy}})
5-HT₃	>10,000
5-HT₄	{{Abbr\|ND\|No data}}
5-HT_5A	953
5-HT₆	130
5-HT₇	20
α_1A	>12,000
α_1B	>10,000
α_2A	175–5,300
α_2B	1,693
α_2C	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
{{Abbrlink\|SERT\|Serotonin transporter}}	3,300–6,409 (K_i) 2,680–29,768 ({{Abbrlink\|IC₅₀\|half-maximal inhibitory concentration}}) >100,000 ({{Abbr\|EC₅₀\|half-maximal effective concentration}})
{{Abbrlink\|NET\|Norepinephrine transporter}}	>22,000 (K_i) 84,000 ({{Abbr\|IC₅₀\|half-maximal inhibitory concentration}}) >100,000 ({{Abbr\|EC₅₀\|half-maximal effective concentration}})
{{Abbrlink\|DAT\|Dopamine transporter}}	>26,000 (K_i) >100,000 ({{Abbr\|IC₅₀\|half-maximal inhibitory concentration}}) >100,000 ({{Abbr\|EC₅₀\|half-maximal effective concentration}})
class="sortbottom" \| colspan="2" style="width: 1px; background-color:#eaecf0; text-align: center;" \| Notes: The smaller the value, the more avidly the drug binds to the site. Refs: {{cite journal \| vauthors = Ray TS \| title = Psychedelics and the human receptorome \| journal = PLOS ONE \| volume = 5 \| issue = 2 \| pages = e9019 \| date = February 2010 \| pmid = 20126400 \| pmc = 2814854 \| doi = 10.1371/journal.pone.0009019 \| doi-access = free \| bibcode = 2010PLoSO...5.9019R \| url = }}{{cite journal \| vauthors = Blough BE, Landavazo A, Decker AM, Partilla JS, Baumann MH, Rothman RB \| title = Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes \| journal = Psychopharmacology (Berl) \| volume = 231 \| issue = 21 \| pages = 4135–4144 \| date = October 2014 \| pmid = 24800892 \| pmc = 4194234 \| doi = 10.1007/s00213-014-3557-7 \| url = }}{{cite journal \| vauthors = Rickli A, Moning OD, Hoener MC, Liechti ME \| title = Receptor interaction profiles of novel psychoactive tryptamines compared with classic hallucinogens \| journal = European Neuropsychopharmacology \| volume = 26 \| issue = 8 \| pages = 1327–1337 \| date = August 2016 \| pmid = 27216487 \| doi = 10.1016/j.euroneuro.2016.05.001 \| s2cid = 6685927 \| url = http://edoc.unibas.ch/53326/1/20170117174852_587e4af45b658.pdf }}{{cite journal \| vauthors = Puigseslloses P, Nadal-Gratacós N, Ketsela G, Weiss N, Berzosa X, Estrada-Tejedor R, Islam MN, Holy M, Niello M, Pubill D, Camarasa J, Escubedo E, Sitte HH, López-Arnau R \| title = Structure-activity relationships of serotonergic 5-MeO-DMT derivatives: insights into psychoactive and thermoregulatory properties \| journal = Mol Psychiatry \| volume = 29 \| issue = 8 \| pages = 2346–2358 \| date = August 2024 \| pmid = 38486047 \| doi = 10.1038/s41380-024-02506-8 \| pmc = 11412900 \| url = }}{{cite journal \| vauthors = Kozell LB, Eshleman AJ, Swanson TL, Bloom SH, Wolfrum KM, Schmachtenberg JL, Olson RJ, Janowsky A, Abbas AI \| title = Pharmacologic Activity of Substituted Tryptamines at 5-Hydroxytryptamine (5-HT)2A Receptor (5-HT2AR), 5-HT2CR, 5-HT1AR, and Serotonin Transporter \| journal = J Pharmacol Exp Ther \| volume = 385 \| issue = 1 \| pages = 62–75 \| date = April 2023 \| pmid = 36669875 \| doi = 10.1124/jpet.122.001454 \| pmc = 10029822 \| url = }}

The mechanism that produces the hallucinogenic and entheogenic effects of 5-MeO-MiPT is thought to result primarily from serotonin 5-HT_2A receptor agonism, although additional mechanisms of action such as inhibition of monoamine oxidase (MAO) might also be involved.{{cite journal | vauthors = Repke DB, Grotjahn DB, Shulgin AT | title = Psychotomimetic N-methyl-N-isopropyltryptamines. Effects of variation of aromatic oxygen substituents | journal = Journal of Medicinal Chemistry | volume = 28 | issue = 7 | pages = 892–896 | date = July 1985 | pmid = 4009612 | doi = 10.1021/jm00145a007 }}{{cite journal | vauthors = Nagai F, Nonaka R, Satoh Hisashi Kamimura K | title = The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain | journal = European Journal of Pharmacology | volume = 559 | issue = 2–3 | pages = 132–137 | date = March 2007 | pmid = 17223101 | doi = 10.1016/j.ejphar.2006.11.075 | url = https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=00665d67c36dcf1777989b70cc901c654420a0c7}} In addition to the serotonin 5-HT_2A receptor, 5-MeO-MiPT also potently binds to and/or activates other serotonin receptors, such as the serotonin 5-HT_1A, 5-HT_2B, and 5-HT_2C receptors.

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). 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-HT_1A 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. The drug is also inactive as a monoamine releasing agent.

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.

=Reagent results=

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.{{cite journal | title = Analytical Profiles for Five "Designer" Tryptamines | journal = Microgram Journal | date = 2004 | vauthors = Spratley T | volume = 3 | issue = 1–2 | pages = 55 | url = http://www.erowid.org/library/periodicals/microgram/microgram_journal_2005-1.pdf#page=54 | format = PDF | access-date = 2013-10-09 }}

Exposing compounds to the reagents gives a colour change which is indicative of the compound under test. The following test results are from [https://www.protestkit.eu/results/ protestkit].

class="wikitable"

! 5-MeO-MiPT

! Marquis

! Mecke

! Mandelin

! Liebermann

! Ehrlich

! Hofmann

! Simon’s

Freebase

| Orange to brown

| Orange red

| Deep greenish brown

| Unknown

| Purple

| No reaction

HCl

| Orange to brown

| Red to brown

| Greenish brown

| Brown

| Violet to purple

| Green

| Unknown

Society and culture

=Legal status=

==Canada==

5-MeO-MiPT is not scheduled in Canada.{{cite web |title=Controlled Drugs and Substances Act |url=https://laws-lois.justice.gc.ca/eng/acts/c-38.8/fulltext.html |website=Justice Laws Website |publisher=Government of Canada |access-date=March 28, 2025}}

==China==

As of October 2015 5-MeO-MiPT is a controlled substance in China.{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | trans-title = Notice on Printing and Distributing the "Measures for the Scheduling of Non-Pharmaceutical Narcotic Drugs and Psychotropic Substances" | publisher=China Food and Drug Administration | date=27 September 2015 | language=zh | access-date=1 October 2015 | archive-url=https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html | archive-date=1 October 2015 | url-status=dead }}

==Finland==

Scheduled in government decree on psychoactive substances banned from the consumer market.{{Cite web|url=https://www.finlex.fi/fi/laki/alkup/2014/20141130|title=FINLEX ® - Säädökset alkuperäisinä: Valtioneuvoston asetus kuluttajamarkkinoilta… 1130/2014|website=www.finlex.fi|accessdate=11 July 2023}}

==Luxembourg==

In Luxembourg, 5-MeO-MiPT is not cited in the list of prohibited substances.{{cite web | url = http://legilux.public.lu/eli/etat/leg/loi/1973/02/19/n1/jo | title = Loi du 19 février 1973 concernant la vente de substances médicamenteuses et la lutte contre la toxicomanie | trans-title = Law of February 19, 1973 concerning the sale of medicinal substances and the fight against drug addiction | language = fr | work = Journal officiel du Grand-Duché de Luxembourg | trans-work = Official Journal of the Grand Duchy of Luxembourg }} 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|date=January 2019}}

==United States==

5-MeO-MiPT is unscheduled at the federal level in the United States,{{Cite web |url=http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm |title=21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I. |access-date=2014-12-17 |archive-date=2009-08-27 |archive-url=https://web.archive.org/web/20090827043725/http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm |url-status=dead }} 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.{{cite web | url = http://leg.state.fl.us/statutes/index.cfm?App_mode=Display_Statute&URL=0800-0899/0893/0893.html | work = Florida Statutes | title = Chapter 893 - Drug Abuse Prevention and Control }}

Research

5-MeO-MiPT, under the developmental code name MSD-001, is being developed for potential medical use.{{cite web | last=Bayer | first=Max | title=After crunching 70k 'trip reports', Mindstate looks to test first AI-derived psychedelic on humans | website=Fierce Biotech | date=13 March 2024 | url=https://www.fiercebiotech.com/biotech/mindstates-first-ai-derived-psychedelic-heads-clinic | access-date=10 November 2024}}{{cite web | author=Microdose NewsDesk | title=Mindstate Design Labs AI-Designed Trial Gets FDA Approval | website=Microdose | date=10 September 2024 | url=https://microdose.buzz/news/mindstate-design-receives-fda-approval/ | access-date=10 November 2024}}{{cite web | last=Meissen | first=Andrew | title=Mindstate Uses AI to Design "Next-Gen" Psychedelics Combined With 5-MeO-MiPT | website=Lucid News - Psychedelics, Consciousness Technology, and the Future of Wellness | date=20 September 2024 | url=https://www.lucid.news/mindstate-uses-ai-to-design-next-gen-psychedelics-combined-with-5-meo-mipt/ | access-date=10 November 2024}} As of September 2024, it is in phase 1 clinical trials in healthy individuals in the United States and the European Union. It is being developed by Mindstate Design Labs. The drug was selected for development via artificial intelligence (AI)-assisted processing of 70,000{{nbsp}}online trip reports that aimed to identify a psychedelic with unique subjective effects deemed promising for pharmaceutical development.

References

External links

[https://isomerdesign.com/pihkal/explore/5040 5-MeO-MiPT - Isomer Design]
[https://psychonautwiki.org/wiki/5-MeO-MiPT 5-MeO-MiPT - PsychonautWiki]
[https://www.erowid.org/chemicals/5meo_mipt/5meo_mipt.shtml 5-MeO-MIPT - Erowid]
[http://www.erowid.org/library/books_online/tihkal/tihkal40.shtml 5-MeO-MiPT - TiHKAL - Erowid]
[http://tihkal.info/read.php?domain=tk&id=40 5-MeO-MiPT - TiHKAL - Isomer Design]
[https://tripsit.me/factsheets/5-meo-mipt 5-MeO-MiPT - TripSit]
[https://www.youtube.com/watch?v=3WHWmjwfKZM 5-MeO-MiPT: What We Know - The Drug Classroom - YouTube]
[https://doubleblindmag.com/what-is-moxy/ Meet Moxy: The Novel Psychedelic the DEA Tried To Ban - Double Blind Magazine]

Category:5-HT1A agonists

Category:5-HT2A agonists

Category:5-HT2B agonists

Category:5-HT2C agonists

Category:Designer drugs

Category:N,N-Dialkyltryptamines

Category:Experimental hallucinogens

Category:Isopropyl compounds

Category:5-Methoxytryptamines

Category:Psychedelic tryptamines

Category:Serotonin receptor agonists