Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 5-MeO-MiPT: Difference between pages

{{Short description|Chemical compound}}

| Verifiedfields = changed

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| verifiedrevid = 477224982

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

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

| width = 200px

| width2 = 200px

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| pregnancy_AU =

| pregnancy_US =

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| legal_AU =

| legal_BR = F2

| legal_BR_comment = <ref>{{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}}</ref>

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| legal_UK = Class A

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| CAS_number_Ref = {{cascite|changed|CAS}}

| CAS_number = 96096-55-8

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| UNII = L0P1807EUY

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

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

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[[Image:5meomipt.jpg|thumb|200px|right|Two tablets of 5-MeO-MiPT]]

'''5-MeO-MiPT''' is a [[psychedelic drug|psychedelic]] and [[hallucinogenic drug]], used by some as an [[entheogen]]. It has structural and pharmacodynamic properties similar to the drugs [[5-MeO-DiPT]], [[DiPT]], and [[N-Methyl-N-isopropyltryptamine|MiPT]]. It is commonly used as a "substitute" for 5-MeO-DiPT because of the very similar structure and effects.

==Chemistry==

5-MeO-MiPT is in a class of compounds commonly known as [[tryptamine]]s, and is the N-methyl-N-isopropyl [[homologous series|homologue]] of the psychedelic, [[5-MeO-DMT]]. The full name of the chemical is 5-[[methoxy]]-N-[[methyl]]-N-[[isopropyl]]tryptamine.

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.<ref name='microgram2005'>{{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 }}</ref>

==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.<ref>{{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}}</ref><ref>{{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 }}</ref> 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.<ref>{{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}}</ref>

==Pharmacodynamics==

{| class="wikitable"

|-

! Binding Sites

! Binding Affinity Ki (μM)<ref name="pmid27216487">{{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 }}</ref>

|-

| 5-HT_1A

| 0.058

|-

| 5-HT_2A

| 0.163

|-

| 5-HT_2C

| 1.3

|-

| D₁

| >25

|-

| D₂

| >25

|-

| D₃

| >25

|-

| α_1A

| >12

|-

| α_2A

| 5.3

|-

| TAAR₁

| >15

|-

| H₁

| 3.9

|-

| SERT

| 3.3

|-

| DAT

| >26

|-

| NET

| >22

|}

==Dosage==

Based on many anecdotal reports,<ref>{{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 }}</ref><ref>{{Cite web|title=5-MeO-MIPT (also 5-Methoxy-N,N-Methylisopropyltryptamine | work = Erowid Exp: Main Index|url=https://www.erowid.org/experiences/subs/exp_5MeOMIPT.shtml|access-date=2021-06-01 }}</ref> dosages can be classified as follows:

{| class="wikitable"

!

!Smoked

!Oral

|-

|Threshold

|5 mg

|3 mg

|-

|Light

|5 - 10 mg

|3 - 7 mg

|-

|Common

|10 - 15 mg

|7 - 15 mg

|-

|Strong

|15 - 20 mg

|15 - 20 mg

|-

|Heavy

|20 mg +

|20 mg +

|}

==Pharmacology==

The mechanism that produces the hallucinogenic and entheogenic effects of 5-MeO-MiPT is thought to result primarily from [[5-HT2A receptor|5-HT_2A receptor]] agonism, although additional mechanisms of action such as inhibition of [[Monoamine oxidase|MAO]] may be involved also.<ref name="pmid4009612">{{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 }}</ref><ref name="pmid17223101">{{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 }}</ref> 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.<ref>{{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 }}</ref> 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.

== 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 [https://www.protestkit.eu/results/ protestkit].

{| class="wikitable"

!5-MeO-MiPT

! [[Marquis reagent|Marquis]]

! [[Mecke reagent|Mecke]]

![[Mandelin reagent|Mandelin]]

! [[Liebermann reagent|Liebermann]]

![[Ehrlich's reagent|Ehrlich]]

!Hofmann

![[Simon's reagent|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.

==Legal status==

===Canada===

5-MeO-MiPT is not scheduled in [[Canada]].{{citation needed|date=January 2019}}

===China===

As of October 2015 5-MeO-MiPT is a controlled substance in China.<ref>{{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 }}</ref>

===Finland===

Scheduled in government decree on psychoactive substances banned from the consumer market.<ref>{{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}}</ref>

=== Luxembourg ===

In [[Luxembourg]], 5-MeO-MiPT is not cited in the list of prohibited substances.<ref>{{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 }}</ref> 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]],<ref name="PART 1308 — SCHEDULES OF CONTROLLED SUBSTANCES - 1308.11 Schedule I">{{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 }}</ref> 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.<ref name="Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL">{{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 }}</ref>

== See also ==

* [[N-Methyl-N-isopropyltryptamine|MIPT]]

* [[5-MeO-DMT]]

* [[5-MeO-DiPT]]

* [[5-MeO-MET]]

== References ==

{{reflist}}

== External links ==

* [http://www.erowid.org/library/books_online/tihkal/tihkal40.shtml 5-MeO-MiPT Entry in TIHKAL]

* [http://tihkal.info/read.php?domain=tk&id=40 5-MeO-MIPT Entry in TiHKAL • info]

{{Entactogens}}

{{Hallucinogens}}

{{Tryptamines}}

[[Category:Designer drugs]]

[[Category:Psychedelic tryptamines]]

[[Category:Methoxy compounds]]