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25C-NBOH: Difference between revisions

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'''25C-NBOH''' (also known as '''2C-C-NBOH''' and '''NBOH-2C-C''') is novel synthetic [[Psychoactive class::psychedelic]] substance of the [[chemical class::phenethylamine]] chemical class that produces an array of visually-dominant and [[stimulating]] [[psychedelic]] effects when [[Routes of administration|administered]]. It is a closely related analog of [[25B-NBOMe]] and is reported to share most of its properties with the exception of a moderately reduced potency and a shorter duration.
'''25C-NBOH''' (also known as '''2C-C-NBOH''' and '''NBOH-2C-C''') is novel synthetic [[Psychoactive class::psychedelic]] substance of the [[chemical class::phenethylamine]] chemical class that produces an array of visually-dominant and [[stimulating]] [[psychedelic]] effects when [[Routes of administration|administered]]. It is a closely related analog of [[25B-NBOMe]] and is reported to share most of its properties with the exception of a moderately reduced potency and a shorter duration.


The name 25C-NBOH, which is short-hand for 2C-C-NBOH, is a derivative of the phenethylamine psychedelic [[2C-C]]. It was first synthesized and documented in 2011 by Martin Hansen at the University of Copenhagen.<ref>Martin Hansen (2011). "Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain." University of Copenhagen. Retrieved 27 June 2015.</ref>
The name 25C-NBOH, which is short-hand for 2C-C-NBOH, is a derivative of the phenethylamine psychedelic [[2C-C]]. It was first synthesized and documented in 2011 by Martin Hansen at the University of Copenhagen.<ref>{{cite book | vauthors=((Hansen, M.)) | date= 2010 | title=Design and synthesis of selective serotonin receptor agonists for positron emission tomography imaging of the brain: PhD thesis | publisher=Faculty of Pharmaceutical Sciences, University of Copenhagen | isbn=9788792719003}}</ref>


It is worth noting that compounds of the NBOH family are not [[orally]] active and should be administered [[sublingual|sublingually]] by placing and holding it into one's mouth and allowing it to absorb over a period of 15-25 minutes.
It is worth noting that compounds of the NBOH family are not [[orally]] active and should be administered [[sublingual|sublingually]] by placing and holding it into one's mouth and allowing it to absorb over a period of 15-25 minutes.


Extremely little is known about the pharmacological properties, metabolism, and toxicity of 25C-NBOH in humans. It has no history of human use before being sold online as a [[designer drug]] in 2011.{{citation needed}} It is closely related to members of the [[25x-NBOMe]] series, which have been associated with many hospitalizations and deaths.<ref name="25Ifatal">25I-NBOMe (2C-I-NBOMe) Fatalities / Deaths by Erowid | https://www.erowid.org/chemicals/2ci_nbome/2ci_nbome_death.shtml</ref><ref name="25Cfatal">25C-NBOMe (2C-C-NBOMe) Fatalities / Deaths by Erowid | https://www.erowid.org/chemicals/2cc_nbome/2cc_nbome_death.shtml</ref><ref name="25Xfatal">Other or Unknown NBOMe Compound Fatalities / Deaths by Erowid | https://www.erowid.org/chemicals/nbome/nbome_death.shtml</ref> Anecdotal reports suggest that this substance may be difficult to use safely due to its highly sensitive dose-response and unpredictable effects.
Extremely little is known about the pharmacological properties, metabolism, and toxicity of 25C-NBOH in humans. It has no history of human use before being sold online as a [[designer drug]] in 2011.{{citation needed}} It is closely related to members of the [[25x-NBOMe]] series, which have been associated with many hospitalizations and deaths.<ref name="25Ifatal">{{Citation | title=Erowid 25I-NBOMe (2C-I-NBOMe) Vault : Fatalities / Deaths | url=https://www.erowid.org/chemicals/2ci_nbome/2ci_nbome_death.shtml}}</ref><ref name="25Cfatal">{{Citation | title=Erowid 2C-C-NBOMe (25C-NBOMe) Vault : Fatalities / Deaths | url=https://www.erowid.org/chemicals/2cc_nbome/2cc_nbome_death.shtml}}</ref><ref name="25Xfatal">{{Citation | title=Erowid NBOMe (Other or Unknown NBOMe-Compound) Vault : Fatalities / Deaths | url=https://www.erowid.org/chemicals/nbome/nbome_death.shtml}}</ref> Anecdotal reports suggest that this substance may be difficult to use safely due to its highly sensitive dose-response and unpredictable effects.


==Chemistry==
==Chemistry==
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25C-NBOH has efficacy at the [[serotonin#The 5-HT system|5-HT<sub>2A</sub> receptor]] where it acts as a potent [[Agonist#Agonists|agonist]].  
25C-NBOH has efficacy at the [[serotonin#The 5-HT system|5-HT<sub>2A</sub> receptor]] where it acts as a potent [[Agonist#Agonists|agonist]].  


This compound is pharmacologically unique when compared to other psychedelics due to the unusually high selectivity it displays for various [[serotonin]] receptors. It is notable as one of the most selective agonist ligands for the 5-HT<sub>2A</sub> receptor with a pEC<sub>50</sub> value of 9.43<ref>Silva, M. E., Heim, R., Strasser, A., Elz, S., & Dove, S. (2011). Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor. Journal of Computer-aided Molecular Design, 25(1), 51-66. https://doi.org/10.1007/s10822-010-9400-2</ref>
This compound is pharmacologically unique when compared to other psychedelics due to the unusually high selectivity it displays for various [[serotonin]] receptors. It is notable as one of the most selective agonist ligands for the 5-HT<sub>2A</sub> receptor with a pEC<sub>50</sub> value of 9.43<ref>{{cite journal | vauthors=((Silva, M. E.)), ((Heim, R.)), ((Strasser, A.)), ((Elz, S.)), ((Dove, S.)) | journal=Journal of Computer-Aided Molecular Design | title=Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor | volume=25 | issue=1 | pages=51–66 | date= January 2011 | url=http://link.springer.com/10.1007/s10822-010-9400-2 | issn=0920-654X | doi=10.1007/s10822-010-9400-2}}</ref>


It acts as a potent [[serotonin]] [[receptor]] [[agonist]] with similar affinity to the better-known compound [[25C-NBOMe]] at 5-HT<sub>2A</sub> and 5-HT<sub>2C</sub> receptors with pKis values of 9.4 and 7.8, respectively.<ref>Hansen, M., Phonekeo, K., Paine, J. S., Leth-Petersen, S., Begtrup, M., Bräuner-Osborne, H., & Kristensen, J. L. (2014). Synthesis and structure–activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists. ACS Chemical Neuroscience, 5(3), 243-249. https://doi.org/10.1021/cn400216u</ref>
It acts as a potent [[serotonin]] [[receptor]] [[agonist]] with similar affinity to the better-known compound [[25C-NBOMe]] at 5-HT<sub>2A</sub> and 5-HT<sub>2C</sub> receptors with pKis values of 9.4 and 7.8, respectively.<ref>{{cite journal | vauthors=((Hansen, M.)), ((Phonekeo, K.)), ((Paine, J. S.)), ((Leth-Petersen, S.)), ((Begtrup, M.)), ((Bräuner-Osborne, H.)), ((Kristensen, J. L.)) | journal=ACS Chemical Neuroscience | title=Synthesis and Structure–Activity Relationships of N -Benzyl Phenethylamines as 5-HT 2A/2C Agonists | volume=5 | issue=3 | pages=243–249 | date=19 March 2014 | url=https://pubs.acs.org/doi/10.1021/cn400216u | issn=1948-7193 | doi=10.1021/cn400216u}}</ref>


However, the role of these interactions and how they result in the [[psychedelic]] experience continues to remain elusive.
However, the role of these interactions and how they result in the [[psychedelic]] experience continues to remain elusive.
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25C-NBOH is a relatively new substance, and little is known about its toxicity or interaction with other substances. It is assumed to pose similar acute health risks as 25C-NBOMe and other members of 25x-NBOMe series. The [[LD50|LD<sub>50</sub>]] has not yet been determined although it is likely to be [[Toxicity::potentially fatal at heavy dosages]].  
25C-NBOH is a relatively new substance, and little is known about its toxicity or interaction with other substances. It is assumed to pose similar acute health risks as 25C-NBOMe and other members of 25x-NBOMe series. The [[LD50|LD<sub>50</sub>]] has not yet been determined although it is likely to be [[Toxicity::potentially fatal at heavy dosages]].  


25C-NBOH's extreme potency means it should not be [[insufflated]] (snorted) as this method of administration has been associated with many deaths and hospitalizations with closely related members of the [[25x-NBOMe]] series.<ref name="25Ifatal">25I-NBOMe (2C-I-NBOMe) Fatalities / Deaths by Erowid | https://www.erowid.org/chemicals/2ci_nbome/2ci_nbome_death.shtml</ref><ref name="25Cfatal">25C-NBOMe (2C-C-NBOMe) Fatalities / Deaths by Erowid | https://www.erowid.org/chemicals/2cc_nbome/2cc_nbome_death.shtml</ref><ref name="25Xfatal">Other or Unknown NBOMe Compound Fatalities / Deaths by Erowid | https://www.erowid.org/chemicals/nbome/nbome_death.shtml</ref>
25C-NBOH's extreme potency means it should not be [[insufflated]] (snorted) as this method of administration has been associated with many deaths and hospitalizations with closely related members of the [[25x-NBOMe]] series.<ref name="25Ifatal"/><ref name="25Cfatal"/><ref name="25Xfatal"/>


===Tolerance and addiction potential===
===Tolerance and addiction potential===
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{{DangerousInteractions/Psychedelics}}
{{DangerousInteractions/Psychedelics}}


==Legality==
==Legal status==
{{legalStub}}
{{legalStub}}


*'''Brazil''' - As of December 10, 2018, 25C-NBOH has been added to Portaria SVS/MS nº 344. Possession, distribution and use of this substance is now considered illegal.<ref>List of controlled substances: Portaria SVS/MS nº 344 (Portuguese) | http://portal.anvisa.gov.br/lista-de-substancias-sujeitas-a-controle-especial</ref>
*'''Brazil''': As of December 10, 2018, 25C-NBOH has been added to Portaria SVS/MS nº 344. Possession, distribution and use of this substance is now considered illegal.<ref>List of controlled substances: Portaria SVS/MS nº 344 (Portuguese) | http://portal.anvisa.gov.br/lista-de-substancias-sujeitas-a-controle-especial</ref>
*'''United Kingdom''' - 25C-NBOH is a Class A drug in the United Kingdom as a result of the N-benzylphenethylamine catch-all clause.<ref>United Kingdom. (2014). Misuse of Drugs Act 1971 (S.I. 2014/1106). London: The Stationery Office Limited. Retrieved July 5, 2017, from http://www.legislation.gov.uk/uksi/2014/1106/made</ref>
*'''Germany''': 25C-NBOH is controlled under the NpSG (New Psychoactive Substances Act) as of November 26, 2016.<ref>{{cite web|url=https://www.bgbl.de/xaver/bgbl/start.xav?startbk=Bundesanzeiger_BGBl&jumpTo=bgbl116s2615.pdf#__bgbl__%2F%2F*%5B%40attr_id%3D%27bgbl116s2615.pdf%27%5D__1576017393518|title=Gesetz zur Bekämpfung der Verbreitung neuer psychoaktiver Stoffe|publisher=Bundesanzeiger Verlag|access-date=December 11, 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 11, 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 11, 2019|language=de}}</ref>
*'''Sweden:''' The Riksdag added 25C-NBOH to Narcotic Drugs Punishments Act under swedish schedule I ("substances, plant materials and fungi which normally do not have medical use") as of August 18, 2015, published by Medical Products Agency (MPA) in regulation HSLF-FS 2015:12<ref>https://lakemedelsverket.se/upload/lvfs/HSLF_FS_2015_12.pdf</ref>
*'''Sweden''': The Riksdag added 25C-NBOH to Narcotic Drugs Punishments Act under swedish schedule I ("substances, plant materials and fungi which normally do not have medical use") as of August 18, 2015, published by Medical Products Agency (MPA) in regulation HSLF-FS 2015:12<ref>https://lakemedelsverket.se/upload/lvfs/HSLF_FS_2015_12.pdf</ref>
*'''Germany:''' 25C-NBOH is not a controlled substance under the BtMG.<ref>https://www.gesetze-im-internet.de/btmg_1981/anlage_i.html</ref> It is legal, as long as it is not sold for human consumption, according to §2 AMG<ref>https://www.gesetze-im-internet.de/amg_1976/__2.html</ref>
*'''Switzerland''': 25C-NBOH 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''': 25C-NBOH is a Class A drug in the United Kingdom as a result of the N-benzylphenethylamine catch-all clause.<ref>{{Citation | year=2014 | title=Misuse of Drugs Act 1971 (S.I. 2014/1106) | publisher=London: The Stationery Office Limited | url=https://www.legislation.gov.uk/uksi/2014/1106/made | access-date=5 July 2017}}</ref>


==See also==
==See also==
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==References==
==References==
<references />
<references />
[[Category:Psychoactive substance]]
[[Category:Psychoactive substance]]
[[Category:Psychedelic]]
[[Category:25x-NBOH]]
[[Category:Research chemical]]
[[Category:Research chemical]]
[[Category:Phenethylamine]]
 
[[Category:Hallucinogen]]
[[Category:Psychedelic]]
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{{#set:Featured=true
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