PsychonautWiki Archive

4-HO-MET: Difference between revisions

← Older edit
>Agile
m →Pharmacology: Added information about SRI properties.
>Thomasdequincey
→Legal status: . Added a section for Canada and rearranged the list to be in alphabetical order.
 
(78 intermediate revisions by 15 users not shown)
Line 2: Line 2:
{{SubstanceBox/4-HO-MET}}
{{SubstanceBox/4-HO-MET}}


'''4-Hydroxy-N-methyl-N-ethyltryptamine''' (also known as '''"schleeb"''', '''"colour"''',<ref name="erowid">Erowid. (2011). Erowid 4-HO-MET Vault. Retrieved from https://erowid.org/chemicals/4_ho_met/4_ho_met.shtml</ref> '''"methylcybin"''',<ref name="erowid" /> '''"metocin"''',<ref name="erowid" /> and '''4-HO-MET''') is a lesser-known novel [[psychoactive class::psychedelic]] substance of the [[chemical class::tryptamine]] class.  
'''4-Hydroxy-N-methyl-N-ethyltryptamine''' (also known as '''colour''',<ref name="erowid">{{cite web|publisher=Erowid|title=4-HO-MET |work=The Vaults of Erowid|publication-date=August 18, 2011|access-date=August 27, 2020|url=https://erowid.org/chemicals/4_ho_met/4_ho_met.shtml}}</ref> '''methylcybin''',<ref name="erowid" /> '''metocin''',<ref name="erowid" /> and '''4-HO-MET''') is a lesser-known novel [[psychoactive class::psychedelic]] substance of the [[chemical class::tryptamine]] class.  
4-HO-MET is chemically similar to [[Psilocin]], the active ingredient in [[psilocybin mushrooms]] ('''"magic mushrooms"'''). Like other [[substituted tryptamines]], it produces its psychedelic effects by acting on [[serotonin]] [[receptors]] in the brain.  
4-HO-MET is structurally related to [[psilocin]], the active ingredient in [[psilocybin mushrooms]] ('''"magic mushrooms"'''). It is thought to produce its effects by binding to [[serotonin]] [[receptors]] in the brain.  


4-HO-MET was first synthesized by [[Alexander Shulgin]] and reported in his 1997 book [[TiHKAL]] ("Tryptamines I Have Known and Loved"). Reports of human use began to surface in the late 2000s following its appearance on the online [[research chemicals]] market. It has been sold alongside other psilocybin analogues such as [[4-AcO-DMT]] and [[4-HO-MiPT]].  
4-HO-MET was first synthesized by the American chemist [[Alexander Shulgin]], who documented it in his 1997 book [[TiHKAL]] ("Tryptamines I Have Known and Loved"). Reports of human use began to surface in the late 2000s, following its appearance on the online [[research chemical]] market. It has been sold alongside other psilocybin analogues such as [[4-AcO-DMT]] and [[4-HO-MiPT]].  


User reports typically describe 4-HO-MET as a more recreational version of [[psilocybin mushrooms]] or [[psilocin]] (4-HO-DMT) due to its less serious headspace and greater emphasis on visual effects. Notable effects include [[geometry|geometric visual hallucinations]], [[time distortion]], [[introspection|enhanced introspection]], and [[ego loss]].
[[Subjective effects]] include [[geometry|geometric visual hallucinations]], [[time distortion]], [[introspection|enhanced introspection]], and [[ego loss]]. Users typically describe 4-HO-MET as a more recreational version of [[psilocybin mushrooms]] or [[psilocin]] (4-HO-DMT) due to its less serious headspace and greater emphasis on visual effects. Its psychedelic visuals are reported to be vivid and colorful.  


Very little data exists about the pharmacological properties, metabolism, and toxicity of 4-HO-MET. It is assumed to have a similar risk and toxicity profile as psilocybin but there is no data to support this. It is highly advised to use [[harm reduction practices]] if using this substance.
Very little data exists about the pharmacological properties, metabolism, and toxicity of 4-HO-MET. It is assumed to have a similar risk and toxicity profile as psilocin and [[4-AcO-DMT]] but there is no data to support this. It is highly advised to use [[harm reduction practices]] if using this substance.


==Chemistry==
==Chemistry==
4-HO-MET, or 4-hydroxy-N-ethyl-N-methyltryptamine, is a synthetic indole alkaloid molecule of the [[tryptamine]] chemical class. Tryptamines share a core structure comprised of a bicyclic indole heterocycle attached at R<sub>3</sub> to an amino group via an ethyl side chain. 4-HO-MET is substituted at R<sub>4</sub> of its indole heterocycle with a hydroxyl functional group OH−. It also contains a methyl group and an ethyl chain bound to the terminal amine R<sub>N</sub> of its tryptamine backbone ([[MET]]).  
4-HO-MET, or 4-hydroxy-N-ethyl-N-methyltryptamine, is a synthetic indole alkaloid molecule of the [[tryptamine]] chemical class. Tryptamines share a core structure comprised of a bicyclic indole heterocycle attached at R<sub>3</sub> to an amino group via an ethyl side chain. 4-HO-MET is substituted at R<sub>4</sub> of its indole heterocycle with a hydroxyl functional group OH−. It also contains a methyl group and an ethyl chain bound to the terminal amine R<sub>N</sub> of its tryptamine backbone ([[MET]]).  


4-HO-MET is a 4-hydroxy homolog of [[4-AcO-MET]] and the N-substituted ethyl homolog of psilocin ([[4-HO-DMT]]).<ref>http://isomerdesign.com/PiHKAL/read.php?domain=tk&id=21</ref> It is also the 4-hydroxyl analog of the base tryptamine [[MET]].
4-HO-MET is a 4-hydroxy homolog of [[4-AcO-MET]] and the N-substituted ethyl homolog of psilocin ([[4-HO-DMT]]).<ref name="TiHKAL">{{cite book|title=TiHKAL: The Continuation|title-link=TiHKAL|last1=Shulgin|first1=Alexander|last2=Shulgin|first2=Ann|author-link1=Alexander Shulgin|year=1997|publisher=Transform Press|location=United States|isbn=0-9630096-9-9|oclc=38503252|chapter-url=https://erowid.org/library/books_online/tihkal/tihkal21.shtml|chapter=#21. 4-HO-MET}}</ref> It is also the 4-hydroxyl analog of the base tryptamine [[MET]].


==Pharmacology==
==Pharmacology==
{{Further|Serotonergic psychedelic}}
{{Further|Serotonergic psychedelic}}
4-HO-MET's [[psychedelic]] effects are believed to come from its activity at the [[Serotonin#The 5-HT system|5-HT<sub>2A</sub> receptor]] as a [[Agonist#Agonists|partial agonist]]. However, the role of these interactions and how they result in the [[psychedelic]] experience remains subject to on-going scientific investigation. In addition, 4-HO-MET is a strong serotonin reuptake inhibitor.
4-HO-MET's [[psychedelic]] effects are believed to come from its activity at the [[Serotonin#The 5-HT system|5-HT<sub>2A</sub> receptor]] as a [[Agonist#Agonists|partial agonist]]. However, the role of these interactions and how they result in the [[psychedelic]] experience remains subject to on-going scientific investigation.


{| class="wikitable"
{| class="wikitable"
|-
|-
!Binding Sites
!Binding Sites
!Binding Affinity Ki (µM)<ref name="pmid27216487">{{cite journal |author1=Rickli A. |author2=Moning O.D. |author3=Hoener M.C. |author4=Liechti M.E. |title=Receptor interaction profiles of novel psychoactive tryptamines compared with classic hallucinogens |pmid=27216487 |doi=10.1016/j.euroneuro.2016.05.001 |url=https://www.ncbi.nlm.nih.gov/pubmed/27216487}}</ref>
!Binding Affinity Ki (µM)<ref name="pmid27216487">{{cite journal|last1=Rickli|first1=A.|last2=Moning|first2=O.D.|last3=Hoener|first3=M. C.|last4=Liechti|first4=M. E.|title=Receptor interaction profiles of novel psychoactive tryptamines compared with classic hallucinogens|pmid=27216487|issn=0924-977X|oclc=795935172|volume=26|issue=8|pages=1327-1337doi=10.1016/j.euroneuro.2016.05.001|year=2016}}</ref>
|-
|-
|5-HT<sub>1A</sub>
|5-HT<sub>1A</sub>
Line 66: Line 66:


==Subjective effects==
==Subjective effects==
A large body of anecdotal reports suggests that the active dose can vary greatly. Some users report very heavy experiences with doses as low as 17mg, while others report light experiences with doses as high as 30 mg.<ref>https://www.erowid.org/chemicals/4_ho_met/4_ho_met_dose.shtml</ref>  
A large body of anecdotal reports suggests that the active dose can vary greatly. Some users report very heavy experiences with doses as low as 17mg, while others report light experiences with doses as high as 30 mg.<ref>{{cite web|publisher=Erowid|title=4-HO-MET: Dose|work=The Vaults of Erowid|publication-date=August 18, 2011|access-date=August 27, 2020|url=https://www.erowid.org/chemicals/4_ho_met/4_ho_met_dose.shtml}}</ref> Possible causes may be attributed to individual differences in neurochemistry and metabolism as well as variations in batch quality and physical forms (e.g. HCl vs. fumarate salt).
Possible causes for this observed effect may be attributed to individual differences in neurochemistry and metabolism as well as large variations in the quality of different batches and physical forms (e.g. the HCl vs. fumarate salt) that it has appeared in.
 
The experiences reported indicate hallucinatory states coming in waves of euphoria, swapping from moments of sobriety to intense visuals. Because 4-HO-MET is heavy on visuals and light on cognitive distress, it can be described as a recreational and practical alternative to psilocybin mushrooms, with thematic similarities in visual effects.


{{Preamble/SubjectiveEffects}}
{{Preamble/SubjectiveEffects}}
{{effects/base
{{effects/base


Line 105: Line 107:
*'''[[Effect::Scenery slicing]]'''
*'''[[Effect::Scenery slicing]]'''
*'''[[Effect::Symmetrical texture repetition]]'''
*'''[[Effect::Symmetrical texture repetition]]'''
*'''[[Effect::Environmental patterning]]'''
*'''[[Effect::Tracers]]'''
*'''[[Effect::Tracers]]'''


Line 135: Line 138:
*'''[[Effect::Increased sense of humor]]'''
*'''[[Effect::Increased sense of humor]]'''
**'''[[Effect::Laughter fits]]'''
**'''[[Effect::Laughter fits]]'''
*'''[[Effect::Novelty enhancement]]'''
*'''[[Effect::Personal bias suppression]]'''
*'''[[Effect::Personal bias suppression]]'''
*'''[[Effect::Thought acceleration]]'''
*'''[[Effect::Thought acceleration]]'''
Line 184: Line 186:
==Toxicity and harm potential==
==Toxicity and harm potential==
{{further|Research chemicals#Toxicity and harm potential|Responsible use #Hallucinogens}}
{{further|Research chemicals#Toxicity and harm potential|Responsible use #Hallucinogens}}
The toxicity and long-term health effects of recreational 4-HO-MET use do not seem to have been studied in any scientific context and the exact [[Toxicity::toxic dose is unknown]]. This is because 4-HO-MET is a [[research chemical]] with very little history of human usage. However, there are reports of very high doses leading to drug induced psychosis.<ref>Täljemark J, Johansson BA. (2012). Drug-induced acute psychosis in an adolescent first-time user of 4-HO-MET. Eur Child Adolesc Psychiatry. 21(9), 527-8. doi:10.1007/s00787-012-0282-9</ref>
The toxicity and long-term health effects of recreational 4-HO-MET use do not seem to have been studied in any scientific context and the exact [[Toxicity::toxic dose is unknown]]. This is because 4-HO-MET is a [[research chemical]] with very little history of human usage. However, there are reports of very high doses leading to drug induced psychosis.<ref>{{cite journal|last1=Täljemark|first1=J.|last2=Johansson|first2=B. A.|year=2012|pmid=22580963|title=Drug-induced acute psychosis in an adolescent first-time user of 4-HO-MET|journal=European Child & Adolescent Psychiatry|volume=21|issue=9|pages=527-528|doi=10.1007/s00787-012-0282-9|issn=1018-8827|eissn=1435-165X|oclc=26585556}}</ref>


Anecdotal evidence from those who have tried 4-HO-MET suggests that there are no negative health effects attributed to simply trying the substance by itself at low to moderate doses and using it very sparingly (but nothing can be completely guaranteed). [https://www.google.com/ Independent research] should always be done to ensure that a combination of two or more substances is safe before consumption.  
Anecdotal evidence from those who have tried 4-HO-MET suggests that there are no negative health effects attributed to simply trying the substance by itself at low to moderate doses and using it very sparingly (but nothing can be completely guaranteed). [https://www.google.com/ Independent research] should always be done to ensure that a combination of two or more substances is safe before consumption.  
Line 191: Line 193:


===Tolerance and addiction potential===
===Tolerance and addiction potential===
4-HO-MET is [[Addiction potential::not habit-forming]] and the desire to use it can actually decrease with use. It is most often self-regulating.  
4-HO-MET is [[Addiction potential::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 4-HO-MET are built [[Time to full tolerance::almost immediately after ingestion]]. After that, it takes about [[Time to half tolerance::3 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::7 days]] to be back at baseline (in the absence of further consumption). 4-HO-MET presents cross-tolerance with [[Cross-tolerance::all [[psychedelic]]s]], meaning that after the consumption of 4-HO-MET all psychedelics will have a reduced effect.
Tolerance to the effects of 4-HO-MET is built [[Time to full tolerance::almost immediately after ingestion]]. After that, it takes about [[Time to half tolerance::3 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::7 days]] to be back at baseline (in the absence of further consumption). 4-HO-MET presents cross-tolerance with [[Cross-tolerance::all [[psychedelic]]s]], meaning that after the consumption of 4-HO-MET all psychedelics will have a reduced effect.


===Dangerous interactions===
===Dangerous interactions===
Line 202: Line 204:


*'''Austria''': 4-HO-MET is illegal to possess, produce and sell under the NPSG (Neue-Psychoaktive-Substanzen-Gesetz Österreich). {{citation needed}}
*'''Austria''': 4-HO-MET is illegal to possess, produce and sell under the NPSG (Neue-Psychoaktive-Substanzen-Gesetz Österreich). {{citation needed}}
*'''Germany''': 4-HO-MET is controlled under the NpSG (New Psychoactive Substances Act) as of July 18, 2019.<ref>{{cite web|url=https://www.bundesgesundheitsministerium.de/fileadmin/Dateien/3_Downloads/Gesetze_und_Verordnungen/GuV/N/NPS_BtM_RegV_Bgbl.pdf|title=Verordnung zur Änderung der Anlage des Neue-psychoaktive-Stoffe-Gesetzes und von Anlagen des Betäubungsmittelgesetzes|publisher=Bundesanzeiger Verlag|access-date=December 10, 2019|language=de}}</ref><ref>{{cite web|url=https://www.gesetze-im-internet.de/npsg/anlage.html|title=Anlage NpSG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 10, 2019|language=de}}</ref> Production and import with the aim to place it on the market, administration to another person and trading is punishable. Possession is illegal but not penalized.<ref>{{cite web|url=https://www.gesetze-im-internet.de/npsg/__4.html|title=§ 4 NpSG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 10, 2019|language=de}}</ref>
*'''Canada''': 4-HO-MET is unscheduled in Canada.
*'''Sweden''': Sveriges Riksdag added 4-HO-MET to Schedule I ("substances, plant materials and fungi which normally do not have medical use") as narcotics in Sweden as of May 1, 2012.<ref>https://lakemedelsverket.se/upload/lvfs/LVFS_2012_6.pdf</ref>
*'''Germany''': 4-HO-MET is controlled under the NpSG<ref>{{cite web|url=https://www.gesetze-im-internet.de/npsg/anlage.html|title=Anlage NpSG|publisher=Bundesamt für Justiz [Federal Office of Justice]|access-date=December 10, 2019|language=de}}</ref> (''New Psychoactive Substances Act'') as of July 18, 2019.<ref>{{cite web|url=http://www.bgbl.de/xaver/bgbl/start.xav?startbk=Bundesanzeiger_BGBl&jumpTo=bgbl119s1083.pdf|title=Verordnung zur Änderung der Anlage des Neue-psychoaktive-Stoffe-Gesetzes und von Anlagen des Betäubungsmittelgesetzes|publisher=Bundesanzeiger Verlag|work=Bundesgesetzblatt Jahrgang 2019 Teil I Nr. 27|pages=1083-1094|publication-date=July 17, 2019|language=de|issn=0341-1095}}</ref> 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.<ref>{{cite web|url=https://www.gesetze-im-internet.de/npsg/__4.html|title=§ 4 NpSG|publisher=Bundesamt für Justiz [Federal Office of Justice]|access-date=December 10, 2019|language=de}}</ref><ref>{{cite web|url=https://www.gesetze-im-internet.de/npsg/__3.html|title=§ 3 NpSG|publisher=Bundesamt für Justiz [Federal Office of Justice]|access-date=December 10, 2019|language=de}}</ref> The legislator considers it possible that orders of 4-HO-MET are punishable as an incitement to place it on the market.<ref>{{cite web|url=http://dip21.bundestag.de/dip21/btd/18/085/1808579.pdf|title=Gesetzentwurf der Bundesregierung: Entwurf eines Gesetzes zur Bekämpfung der Verbreitung neuer psychoaktiver Stoffe|page=20|date=May 30, 2016|id=Drucksache 18/8579|publisher=Deutscher Bundestag|language=de}}</ref>
*'''United Kingdom''': 4-HO-MET is a Class A drug in the United Kingdom as a result of the tryptamine catch-all clause.<ref>Misuse of Drugs Act 1971 (Legislation.gov.uk) |http://www.legislation.gov.uk/ukpga/1971/38/schedule/2/part/I#reference-M_F_c7632653-ddad-4420-f307-e3da1e36d30e</ref>
*'''Japan''': 4-HO-MET is a controlled substance in Japan effective March 25th, 2015.<ref>[https://www.mhlw.go.jp/stf/houdou/0000078803.html "危険ドラッグの成分１６物質を新たに指定薬物に指定"] (in Japanese). 厚生労働省 [Ministry of Health, Labour and Welfare (MHLW)]. Retrieved May 2, 2022.</ref>
*'''Poland:''' 4-HO-MET is illegal to posses, manufacture and sell under "Wykaz środków odurzających i substancji psychotropowych" (Group I-P) <ref>{{Citation | year=2022 | language=polish | title=Wykaz środków odurzających i substancji psychotropowych | url=https://pl.wikipedia.org/wiki/Wykaz_%C5%9Brodk%C3%B3w_odurzaj%C4%85cych_i_substancji_psychotropowych#Grupa_I-P}}</ref>
*'''Sweden''': Sveriges Riksdag added 4-HO-MET to Schedule I ("substances, plant materials and fungi which normally do not have medical use") as narcotics in Sweden as of May 1, 2012.<ref>{{cite web|url=https://lakemedelsverket.se/upload/lvfs/LVFS_2012_6.pdf|archive-url=https://web.archive.org/web/20181031222225/https://lakemedelsverket.se/upload/lvfs/LVFS_2012_6.pdf|archive-date=October 31, 2018|title=Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 2011:10) om förteckningar över narkotika|date=April 20, 2012|id=LVFS 2012:6|publication-date=April 30, 2012|issn=1101-5225|publisher=Läkemedelsverket [Medical Products Agency ]|language=sv}}</ref>
*'''Switzerland''': 4-HO-MET is a controlled substance specifically named under Verzeichnis E.<ref>{{cite web|url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html|title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien|publisher=Bundeskanzlei [Federal Chancellery of Switzerland]|access-date=January 1, 2020|language=de}}</ref>
*'''United Kingdom''': 4-HO-MET is a Class A drug in the United Kingdom as a result of the tryptamine catch-all clause.<ref>{{cite web|title=Schedule 2: Part I: Class A Drugs|url=http://www.legislation.gov.uk/ukpga/1971/38/schedule/2/part/I|work="Misuse of Drugs Act 1971"|access-date=August 20, 2020|publisher=UK Government}}</ref>
*'''United States''': 4-HO-MET is unscheduled in the United States. It may be considered an analogue of [[psilocin]] (''4-HO-DMT''), 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.{{citation needed}}
*'''United States''': 4-HO-MET is unscheduled in the United States. It may be considered an analogue of [[psilocin]] (''4-HO-DMT''), 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.{{citation needed}}


Retrieved from "https://psy.st/wiki/4-HO-MET"