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25C-NBOH: Difference between revisions

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{{Headerpanel|{{Warning/25C-NBOH}}}}
{{Headerpanel|{{Warning/25C-NBOH}}}}
{{SummarySheet}}
{{SummarySheet}}
{{SubstanceBox/25C-NBOH}}
{{SubstanceBox/25C-NBOH}}
'''25C-NBOH''' (also known as '''2C-C-NBOH''' and '''NBOH-2CC''') 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>
'''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>{{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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*'''[[Effect::Muscle cramps]]'''
*'''[[Effect::Muscle cramps]]'''
*'''[[Effect::Muscle tension]]'''
*'''[[Effect::Muscle tension]]'''
*'''[[Effect::Gustatory hallucinations]]'''
*'''[[Effect::Gustatory hallucination]]'''
*'''[[Effect::Vasoconstriction]]'''  
*'''[[Effect::Vasoconstriction]]'''  
*'''[[Effect::Appetite suppression]]'''
*'''[[Effect::Appetite suppression]]'''
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*'''[[Effect::Transformations]]'''
*'''[[Effect::Transformations]]'''
*'''[[Effect::Machinescapes]]''' - This component is an uncommon effect that typically only occurs at very strong to heavy doses. It also tends to be accompanied by overwhelming if not dangerous physical and cognitive effects.
*'''[[Effect::Machinescapes]]''' - This component is an uncommon effect that typically only occurs at very strong to heavy doses. It also tends to be accompanied by overwhelming if not dangerous physical and cognitive effects.
*'''[[Effect::Internal hallucinations]]''' - (''[[effect::settings, sceneries, and landscapes]]''; ''[[effect::alterations in perspective]]'' and ''[[effect::scenarios and plots]]''). These are more common within dark environments and can be described as lucid in believability, interactive in style and almost exclusively of a personal, religious, spiritual, science-fiction, fantasy, surreal, nonsensical or transcendental nature in their overall theme.
*'''[[Effect::Internal hallucination]]''' - (''[[effect::settings, sceneries, and landscapes]]''; ''[[effect::perspective hallucinations]]'' and ''[[effect::scenarios and plots]]''). These are more common within dark environments and can be described as lucid in believability, interactive in style and almost exclusively of a personal, religious, spiritual, science-fiction, fantasy, surreal, nonsensical or transcendental nature in their overall theme.


}}
}}
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*'''[[Effect::Auditory enhancement]]'''
*'''[[Effect::Auditory enhancement]]'''
*'''[[Effect::Auditory distortion]]'''
*'''[[Effect::Auditory distortion]]'''
*'''[[Effect::Auditory hallucinations]]'''
*'''[[Effect::Auditory hallucination]]'''


}}
}}
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{{#ask: [[Category:25C-NBOH]][[Category:Experience]]|format=ul|Columns=1}}
{{#ask: [[Category:25C-NBOH]][[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_25INBOMe.shtml Erowid Experience Vaults: 25C-NBOH]
 
*[https://www.erowid.org/experiences/subs/exp_25CNBOH.shtml Erowid Experience Vaults: 25C-NBOH]


==Toxicity and harm potential==
==Toxicity and harm potential==
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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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===Dangerous interactions===
===Dangerous interactions===
{{DangerousInteractions/Intro}}
{{DangerousInteractions/Intro}}
{{DangerousInteractions/Psychedelics}}


*'''[[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}}
==Legal status==
*'''[[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}}
{{legalStub}}
*'''[https://en.wikipedia.org/wiki/Lithium_(medication) 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}}


==Legality==
*'''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>
{{legalStub}}
*'''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>
*'''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>
*'''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>
*'''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==
*[[Responsible use]]
*[[Responsible use]]
*[[Research chemical]]
*[[Research chemical]]
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==External links==
==External links==
*[https://en.wikipedia.org/wiki/25C-NBOH 25C-NBOH (Wikipedia)]
*[https://en.wikipedia.org/wiki/25C-NBOH 25C-NBOH (Wikipedia)]
*[https://isomerdesign.com/PiHKAL/explore.php?id=1252 25C-NBOH (Isomer Design)]
*[https://isomerdesign.com/PiHKAL/explore.php?id=1252 25C-NBOH (Isomer Design)]
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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:Psychedelic]]
{{#set:Featured=true
{{#set:Featured=true
}}
}}
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