4-HO-MET: Difference between revisions
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{{SubstanceBox/4-HO-MET}} | {{SubstanceBox/4-HO-MET}} | ||
'''4-Hydroxy-N-methyl-N-ethyltryptamine''' (also known as ''' | '''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 | 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]] | 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]]. | ||
[[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 | 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> | 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== | ||
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{| class="wikitable" | {| class="wikitable" | ||
|- | |- | ||
! Binding Sites | !Binding Sites | ||
! Binding Affinity Ki (µM)<ref name="pmid27216487">{{cite journal | | !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> | ||
| 0.228 | |0.228 | ||
|- | |- | ||
| 5-HT<sub>2A</sub> | |5-HT<sub>2A</sub> | ||
| 0.057 | |0.057 | ||
|- | |- | ||
| 5-HT<sub>2C</sub> | |5-HT<sub>2C</sub> | ||
| 0.141 | |0.141 | ||
|- | |- | ||
| D<sub>1</sub> | |D<sub>1</sub> | ||
| >25 | |>25 | ||
|- | |- | ||
| D<sub>2</sub> | |D<sub>2</sub> | ||
| 4 | |4 | ||
|- | |- | ||
| D<sub>3</sub> | |D<sub>3</sub> | ||
| 6.7 | |6.7 | ||
|- | |- | ||
| α<sub>1A</sub> | |α<sub>1A</sub> | ||
| 9.7 | |9.7 | ||
|- | |- | ||
| α<sub>2A</sub> | |α<sub>2A</sub> | ||
| 2.4 | |2.4 | ||
|- | |- | ||
| TAAR<sub>1</sub> | |TAAR<sub>1</sub> | ||
| 3.1 | |3.1 | ||
|- | |- | ||
| H<sub>1</sub> | |H<sub>1</sub> | ||
| 0.82 | |0.82 | ||
|- | |- | ||
| SERT | |SERT | ||
| 0.2 | |0.2 | ||
|- | |- | ||
| DAT | |DAT | ||
| >26 | |>26 | ||
|- | |- | ||
| NET | |NET | ||
| 13 | |13 | ||
|} | |} | ||
==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 | |||
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 | ||
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*'''[[Effect::Scenery slicing]]''' | *'''[[Effect::Scenery slicing]]''' | ||
*'''[[Effect::Symmetrical texture repetition]]''' | *'''[[Effect::Symmetrical texture repetition]]''' | ||
*'''[[Effect::Environmental patterning]]''' | |||
*'''[[Effect::Tracers]]''' | *'''[[Effect::Tracers]]''' | ||
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*'''[[Effect::Increased sense of humor]]''' | *'''[[Effect::Increased sense of humor]]''' | ||
**'''[[Effect::Laughter fits]]''' | **'''[[Effect::Laughter fits]]''' | ||
*'''[[Effect::Personal bias suppression]]''' | *'''[[Effect::Personal bias suppression]]''' | ||
*'''[[Effect::Thought acceleration]]''' | *'''[[Effect::Thought acceleration]]''' | ||
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}} | }} | ||
===Combination effects=== | ===Combination effects=== | ||
*'''[[Cannabis]]''' - When used in conjunction with cannabis, both the visual and cognitive effects of 4-HO-MET can be intensified and extended with extreme efficacy. This should be used with extreme caution, however, especially if one is not experienced with psychedelics as this can also amplify the [[anxiety]], [[confusion]] and [[psychosis]] producing aspects of cannabis significantly. | |||
*'''[[Cannabis]]''' - When used in conjunction with cannabis, both the visual and cognitive effects of 4-HO-MET can be intensified and extended with extreme efficacy. This should be used with extreme caution, however, especially if one is not experienced with psychedelics as this can also amplify the [[anxiety]], [[confusion]] and [[psychosis]] producing aspects of cannabis significantly. | |||
*'''[[Dissociatives]]''' - When used in combination with dissociatives, the geometry, euphoria, dissociation and hallucinatory effects are often greatly enhanced. Dissociative-induced [[Visual_disconnection#Holes.2C_spaces_and_voids|holes, spaces, and voids]] while under the influence of 4-HO-MET can result in significantly more vivid visuals than dissociatives alone present, along with more intense [[internal hallucinations]], [[confusion]], [[delusions]] and chances of a [[psychosis|psychotic reaction]]. | *'''[[Dissociatives]]''' - When used in combination with dissociatives, the geometry, euphoria, dissociation and hallucinatory effects are often greatly enhanced. Dissociative-induced [[Visual_disconnection#Holes.2C_spaces_and_voids|holes, spaces, and voids]] while under the influence of 4-HO-MET can result in significantly more vivid visuals than dissociatives alone present, along with more intense [[internal hallucinations]], [[confusion]], [[delusions]] and chances of a [[psychosis|psychotic reaction]]. | ||
*'''[[MDMA]]''' - When used in conjunction with MDMA, the physical and cognitive effects of MDMA are amplified. The visual, physical and cognitive effects of 4-HO-MET are also intensified with an overwhelming euphoric pleasure manifested through uniquely pleasurable body highs and headspaces, and uniquely colorful and awe-inspiring visuals. The synergy between these substances is unpredictable, and it is best to start with markedly lower dosages than one would take for both substances individually. | *'''[[MDMA]]''' - When used in conjunction with MDMA, the physical and cognitive effects of MDMA are amplified. The visual, physical and cognitive effects of 4-HO-MET are also intensified with an overwhelming euphoric pleasure manifested through uniquely pleasurable body highs and headspaces, and uniquely colorful and awe-inspiring visuals. The synergy between these substances is unpredictable, and it is best to start with markedly lower dosages than one would take for both substances individually. | ||
*'''[[Alcohol]]''' - This interaction is not typically recommended due to alcohol’s ability to cause [[dehydration]], which can negatively affect a trip if taken in high dosages. This combination is, however, reasonably safe in low doses and when used responsibly, this can often "take the edge off the trip" as well as dull its psychedelic effects in a fashion somewhat similar to benzodiazepines, albeit more in a more stressful way on the body. | *'''[[Alcohol]]''' - This interaction is not typically recommended due to alcohol’s ability to cause [[dehydration]], which can negatively affect a trip if taken in high dosages. This combination is, however, reasonably safe in low doses and when used responsibly, this can often "take the edge off the trip" as well as dull its psychedelic effects in a fashion somewhat similar to benzodiazepines, albeit more in a more stressful way on the body. | ||
*'''[[Benzodiazepines]]''' - When used in combination with benzodiazepines, benzodiazepines can, depending on the dosage, slightly to completely reduce the intensity of the cognitive, physical and visual effects of a 4-HO-MET trip. With higher doses, they are very efficient at stopping [[bad trip|"bad trips"]] at the cost of reduced trip intensity and in the worst case, amnesia and blacking out. Caution is advised when acquiring them for this purpose, however, due to the very high addiction potential that benzodiazepines possess. It is generally advised to refrain from intending to use them at all unless the trip suddenly becomes completely overwhelming. | *'''[[Benzodiazepines]]''' - When used in combination with benzodiazepines, benzodiazepines can, depending on the dosage, slightly to completely reduce the intensity of the cognitive, physical and visual effects of a 4-HO-MET trip. With higher doses, they are very efficient at stopping [[bad trip|"bad trips"]] at the cost of reduced trip intensity and in the worst case, amnesia and blacking out. Caution is advised when acquiring them for this purpose, however, due to the very high addiction potential that benzodiazepines possess. It is generally advised to refrain from intending to use them at all unless the trip suddenly becomes completely overwhelming. | ||
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{{#ask: [[Category:4-HO-MET]][[Category:Experience]]|format=ul|Columns=1}} | {{#ask: [[Category:4-HO-MET]][[Category:Experience]]|format=ul|Columns=1}} | ||
Additional experience reports can be found here: | Additional experience reports can be found here: | ||
* [https://www.erowid.org/experiences/subs/exp_4HOMET.shtml Erowid Experience Vaults: 4-HO-MET] | |||
*[https://www.erowid.org/experiences/subs/exp_4HOMET.shtml Erowid Experience Vaults: 4-HO-MET] | |||
==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 | 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. | ||
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===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 | 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=== | ||
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==Legal status== | ==Legal status== | ||
*'''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= | *'''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> | *'''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}} | ||
==See also== | ==See also== | ||
*[[Responsible use]] | *[[Responsible use]] | ||
*[[Research chemical]] | *[[Research chemical]] | ||
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==External links== | ==External links== | ||
*[https://en.wikipedia.org/wiki/4-HO-MET 4-HO-MET (Wikipedia)] | *[https://en.wikipedia.org/wiki/4-HO-MET 4-HO-MET (Wikipedia)] | ||
*[https://erowid.org/chemicals/4_ho_met/4_ho_met.shtml 4-HO-MET (Erowid Vault)] | *[https://erowid.org/chemicals/4_ho_met/4_ho_met.shtml 4-HO-MET (Erowid Vault)] | ||
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===Discussion=== | ===Discussion=== | ||
*[http://www.bluelight.org/vb/threads/250897-The-Big-amp-Dandy-4-HO-MET-Thread The Big & Dandy 4-HO-MET Thread (Bluelight)] | *[http://www.bluelight.org/vb/threads/250897-The-Big-amp-Dandy-4-HO-MET-Thread The Big & Dandy 4-HO-MET Thread (Bluelight)] | ||