2C-H: Difference between revisions

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'''2,5-Dimethoxyphenethylamine''' (also known as '''2C-H''' and '''DMPEA''') is a lesser-known psychoactive substance of the [[chemical class::phenethylamine]] class. 2C-H belongs to the [[2C-x]] family of substituted phenethylamines. However, it does not have psychedelic properties and is primarily used as a precursor in the synthesis of other phenethylamines such as 2C-B, 2C-I, and 2C-N.
'''2,5-Dimethoxyphenethylamine''' (also known as '''2C-H''' and '''DMPEA''') is a lesser-known psychoactive substance of the [[chemical class::phenethylamine]] class. 2C-H belongs to the [[2C-x]] family of substituted phenethylamines. However, it does not have psychedelic properties and is primarily used as a precursor in the synthesis of other phenethylamines such as 2C-B, 2C-I, and 2C-N.


2C-H was first synthesized in 1932 by Johannes S. Buck.<ref>Buck, J. S. (1932). HYDROXY-AND DIHYDROXYPHENYLETHYLMETHYLAMINES AND THEIR ETHERS. Journal of the American Chemical Society, 54(9), 3661-3665. https://doi.org/10.1021/ja01348a024.</ref> Its effects in humans were explored in the 1970s by [[Alexander Shulgin]], who published his findings in the book [[PiHKAL|PiHKAL (Phenethylamines I Have Known and Loved)]].  
2C-H was first synthesized in 1932 by Johannes S. Buck.<ref>{{cite journal|last1=Buck|first1=J. S.|year=1932|title=Hydroxy- And Dihydroxyphenylethylmethylamines And Their Ethers|journal=Journal of the American Chemical Society|volume=54|issue=9|pages=3661-3665|doi=10.1021/ja01348a024|issn=0002-7863|eissn=1520-5126|oclc=01226990}}</ref> Its effects in humans were explored in the 1970s by [[Alexander Shulgin]], who published his findings in the book [[PiHKAL|PiHKAL (Phenethylamines I Have Known and Loved)]].  


In PiHKAL, Shulgin lists both the dosage and duration as unknown, commenting that 2C-H is likely easily broken down by MAO enzymes in the liver and is thus probably inactive. However, there have since been some anecdotal reports that suggest it may be active when taken [[sublingually]].<ref>So Happy, Very Happy 2C-H by PandaDoom (Erowid) | https://erowid.org/experiences/exp.php?ID=80334</ref> It is theorized to be [[orally]] active if taken in combination with a [[MAOI]]. However, it is unknown whether this would result in typical 2C-x psychedelic effects.
In PiHKAL, Shulgin lists both the dosage and duration as unknown, commenting that 2C-H is likely easily broken down by MAO enzymes in the liver and is thus probably inactive. However, there have since been some anecdotal reports that suggest it may be active when taken [[sublingually]].<ref>{{cite web|title=So Happy, Very Happy 2C-H|author="PandaDoom"|publisher=Erowid|url=https://erowid.org/experiences/exp.php?ID=80334|date=August 3, 2009|id=exp80334|work=Experience Vaults}}</ref> It is theorized to be [[orally]] active if taken in combination with a [[MAOI]]. However, it is unknown whether this would result in typical 2C-x psychedelic effects.


Very little data exists about the pharmacological properties, metabolism, and toxicity of 2C-H. It is highly advised to use [[harm reduction practices]] when using this substance.
Very little data exists about the pharmacological properties, metabolism, and toxicity of 2C-H. It is highly advised to use [[harm reduction practices]] when using this substance.
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==Pharmacology==
==Pharmacology==
There is no record of 2C-H trials in humans, as it would likely be destroyed by monoamine oxidase enzymes before causing any significant psychoactive effects.<ref>[[Alexander Shlulgin|Shulgin, Alexander]]; [[Ann Shulgin]] (September 1991). [https://www.erowid.org/library/books_online/pihkal/pihkal023.shtml PiHKAL: A Chemical Love Story.] Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.</ref> Very little data exists about the pharmacological properties, metabolism, and toxicity of 2C-H. However, it has been shown to have binding affinity towards [[Serotonin#The_5-HT_system|5-HT2C]] and [[Serotonin#The_5-HT_system|5-HT2A]] [[receptor]]s in rats.<ref>2C-H BioAssay Results (PubChem) | https://pubchem.ncbi.nlm.nih.gov/compound/76632#section=BioAssay-Results</ref> 2C-H has been shown to inhibit MAO-B activity by over 50% in experiments.<ref name="WagmannBrandt2019">{{cite journal|last1=Wagmann|first1=Lea|last2=Brandt|first2=Simon D.|last3=Stratford|first3=Alexander|last4=Maurer|first4=Hans H.|last5=Meyer|first5=Markus R.|title=Interactions of phenethylamine-derived psychoactive substances of the 2C-series with human monoamine oxidases|journal=Drug Testing and Analysis|volume=11|issue=2|year=2019|pages=318–324|issn=19427603|doi=10.1002/dta.2494}}</ref>
There is no record of 2C-H trials in humans, as it would likely be destroyed by monoamine oxidase enzymes before causing any significant psychoactive effects.<ref name="PiHKAL">{{cite book|title=PiHKAL: A Chemical Love Story|title-link=PiHKAL|author-link1=Alexander Shulgin|author1=Alexander Shulgin|author2=Ann Shulgin|year=1991|publisher=Transform Press|location=United States|isbn=0963009605|oclc=1166889264|chapter-url=https://erowid.org/library/books_online/pihkal/pihkal032.shtml|chapter=#32. 2C-H}}</ref> Very little data exists about the pharmacological properties, metabolism, and toxicity of 2C-H. However, it has been shown to have binding affinity towards [[Serotonin#The_5-HT_system|5-HT2C]] and [[Serotonin#The_5-HT_system|5-HT2A]] [[receptor]]s in rats.<ref>{{cite web|title=2,5-Dimethoxyphenethylamine (compound): Biological Test Results|publisher=PubChem|url=https://pubchem.ncbi.nlm.nih.gov/compound/76632#section=Biological-Test-Results|access-date=October 11, 2020}}</ref> 2C-H has been shown to inhibit MAO-B activity by over 50% in experiments.<ref name="WagmannBrandt2019">{{cite journal|last1=Wagmann|first1=Lea|last2=Brandt|first2=Simon D.|last3=Stratford|first3=Alexander|last4=Maurer|first4=Hans H.|last5=Meyer|first5=Markus R.|title=Interactions of phenethylamine-derived psychoactive substances of the 2C-series with human monoamine oxidases|pmid=30188017|journal=Drug Testing and Analysis|volume=11|issue=2|year=2019|pages=318–324|issn=1942-7603|doi=10.1002/dta.2494|eissn=1942-7611|oclc=231680670}}</ref>


==Subjective effects==
==Subjective effects==
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===Dangerous interactions===
===Dangerous interactions===
{{DangerousInteractions/Intro}}
{{DangerousInteractions/Intro}}
 
{{DangerousInteractions/Psychedelics}}
*'''[[DangerousInteraction::Tramadol]]''' - Tramadol lowers the seizure threshold<ref>Talaie, H., Panahandeh, R., Fayaznouri, M. R., Asadi, Z., & Abdollahi, M. (2009). Dose-independent occurrence of seizure with tramadol. Journal of medical toxicology, 5(2), 63-67. doi:10.1007/BF03161089</ref> and [[psychedelics]] may act as triggers for seizures, particularly in those who are predisposed to them.{{citation needed}}
*'''[[DangerousInteraction::Stimulants]]''' - Stimulants affect many parts of the brain. Combined with psychedelics, stimulation can turn into uncontrollable [[anxiety]], [[Panic attacks|panic]], [[thought loops]] and [[paranoia]]. This interaction may cause elevated risk of psychosis.{{citation needed}}
*'''[[DangerousInteraction::Lithium]]''' - Lithium is often used as treatment for bipolar disorder. It may possibly cause elevated risk of seizures and psychosis due to its [[Glutamate|glutaminergic]] and [[GABA|GABAergic]] effects.{{citation needed}}


==Legal status==
==Legal status==
*'''Austria''': 2C-H is illegal to possess, produce and sell under the NPSG (Neue-Psychoaktive-Substanzen-Gesetz Österreich).{{citation needed}}
*'''Austria''': 2C-H is illegal to possess, produce and sell under the NPSG (Neue-Psychoaktive-Substanzen-Gesetz Österreich).{{citation needed}}
*'''Canada''': As of October 31st, 2016, 2C-H is a controlled substance (Schedule III) in Canada, and is thus illegal to possess, produce and sell.<ref>http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php</ref>
*'''Canada''': As of October 31st, 2016, 2C-H is a controlled substance (Schedule III) in Canada, and is thus illegal to possess, produce and sell.<ref>{{cite journal|url=http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php|title=Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)|id=SOR/2016-72|issn=0045-4206|work=Canada Gazette Part II|volume=150|issue=9|publication-date=May 4, 2016|date=April 15, 2016|}}</ref>
*'''Germany''': 2C-H is controlled under the NpSG (''New Psychoactive Substances Act'')<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> as of November 26, 2016.<ref>{{cite web|url=http://www.bgbl.de/xaver/bgbl/start.xav?startbk=Bundesanzeiger_BGBl&jumpTo=bgbl116s2615.pdf|title=Gesetz zur Bekämpfung der Verbreitung neuer psychoaktiver Stoffe|publisher=Bundesanzeiger Verlag|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>
*'''Germany''': 2C-H 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 November 26, 2016.<ref>{{cite web|url=http://www.bgbl.de/xaver/bgbl/start.xav?startbk=Bundesanzeiger_BGBl&jumpTo=bgbl116s2615.pdf|title=Gesetz zur Bekämpfung der Verbreitung neuer psychoaktiver Stoffe|pages=2615-2622|issn=0341-1095|oclc=1004462279|publisher=Bundesanzeiger Verlag|date=November 21, 2016|publication-date=November 25, 2016|language=de|work=Bundesgesetzblatt Jahrgang 2016 Teil I Nr. 55}}</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 2C-H 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>
*'''Switzerland''': 2C-H can be considered a controlled substance as a defined derivative of Phenethylamine under Verzeichnis E point 130. It is legal when used for scientific or industrial use.<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>
*'''Switzerland''': 2C-H can be considered a controlled substance as a defined derivative of Phenethylamine under Verzeichnis E point 130. It is legal when used for scientific or industrial use.<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>
*'''Turkey:''' 2C-H is a classed as drug and is illegal to possess, produce, supply, or import.<ref name="Bakanlar Kurulu Kararı - Karar Sayısı : 2013/5742">https://resmigazete.gov.tr/eskiler/2014/01/20140125-3.htm</ref> <ref name="List of illegal substances for law"> https://resmigazete.gov.tr/eskiler/2014/01/20140125-3-1.pdf</ref>
*'''Turkey:''' 2C-H is a classed as drug and is illegal to possess, produce, supply, or import.<ref>{{cite web|title=Bakanlar Kurulu Kararı - Karar Sayısı : 2013/5742|url=https://resmigazete.gov.tr/eskiler/2014/01/20140125-3.htm|publisher=Başbakanlık Mevzuatı Geliştirme ve Yayın Genel Müdürlüğü [General Directorate of Legislation Development and Publication]|publication-date=January 25, 2014|date=December 16, 2013|language=tr}}</ref><ref>{{cite web|title=Kararnamenin Eki: Liste|url=https://resmigazete.gov.tr/eskiler/2014/01/20140125-3-1.pdf|publisher=Başbakanlık Mevzuatı Geliştirme ve Yayın Genel Müdürlüğü [General Directorate of Legislation Development and Publication]|publication-date=January 25, 2014|date=December 16, 2013|language=tr|id=2013/5742|work=Resmî Gazete, Sayı: 28893}}</ref>
*'''United Kingdom''': 2C-H is a Class A drug in the United Kingdom as a result of the phenethylamine catch-all clause.<ref>United Kingdom. (1977). Misuse of Drugs Act 1971 (S.I. 1977/1243). London: The Stationery Office Limited. Retrieved July 5, 2017, from http://www.legislation.gov.uk/uksi/1977/1243/made</ref>
*'''United Kingdom''': 2C-H is a Class A drug in the United Kingdom as a result of the phenethylamine 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''': As of July 9, 2012, 2C-H is a Schedule I controlled substance in the United States, under the Synthetic Drug Abuse Prevention Act of 2012.<ref>https://www.deadiversion.usdoj.gov/fed_regs/rules/2013/fr0104.htm</ref>
*'''United States''': As of July 9, 2012, 2C-H is a Schedule I controlled substance in the United States, under the Synthetic Drug Abuse Prevention Act of 2012.<ref>{{cite magazine|url=https://www.deadiversion.usdoj.gov/fed_regs/rules/2013/fr0104.htm|title=Establishment of Drug Codes for 26 Substances|work=Federal Register|volume=78|issue=3|publisher=Diversion Control Devision|pages=664-666|id=FR Doc No: 2012-31698|publication-date=January 4, 2013}}</ref><ref>{{cite web|url=http://www.govtrack.us/congress/bills/112/s3187/text|title=S. 3187 (112<sup>th</sup>): Food and Drug Administration Safety and Innovation Act|date=June 27, 2012|access-date=October 10, 2020|publisher=GovTrack}}</ref>


==See also==
==See also==
Retrieved from "http://psy.st/wiki/2C-H"