25C-NBOH: Difference between revisions

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==Chemistry==

25C-NBOH or 2C-C-NBOH, is a serotonergic N-benzyl derivative of the substituted phenethylamine psychedelic known as [[2C-C]]. 25C-NBOH is a substituted phenethylamine with methoxy groups CH3O- attached to carbons R2 and R5 as well as an bromine atom attached to carbon R4. It differs from [[2C-B]] structurally through a substitution on the amine (NH2) with a 2-hydroxybenzyl (BOH) group. 25C-NBOH shares this 2-hydroxybenzyl substitution with other chemicals of the NBOH family. This NBOH addition is comprised of a hydroxy ether OH- bound to a benzene ring at R2.

25C-NBOH or 2C-C-NBOH, is a serotonergic N-benzyl derivative of the substituted phenethylamine psychedelic known as [[2C-C]]. 25C-NBOH is a substituted phenethylamine with methoxy groups CH3O- attached to carbons R2 and R5 as well as an bromine atom attached to carbon R4. It differs from [[2C-C]] structurally through a substitution on the amine (NH2) with a 2-hydroxybenzyl (BOH) group. 25C-NBOH shares this 2-hydroxybenzyl substitution with other chemicals of the NBOH family. This NBOH addition is comprised of a hydroxy ether OH- bound to a benzene ring at R2.

==Pharmacology==

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25C-NBOH has efficacy at the [[serotonin#The 5-HT system|5-HT2A 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-HT2A receptor with a pEC50 value of 9.~~87 nM~~<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>It ~~has~~ a ~~pKi of 0.061 nM~~ at ~~the human 5HT~~2A ~~receptor~~, ~~similar to the better-known compound 25B-NBOMe~~.<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)~~: 243–9. PMC 3963123. PMID 24397362~~. https://doi.org/10.1021/cn400216u</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-HT2A receptor with a pEC50 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>

It acts as a potent [[serotonin]] [[receptor]] [[agonist]] with similar affinity to the better-known compound [[25C-NBOMe]] at 5-HT2A and 5-HT2C 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>

However, the role of these interactions and how they result in the [[psychedelic]] experience continues to remain elusive.

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{{further|Research chemicals#Toxicity and harm potential|Responsible use #Hallucinogens}}

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 ~~25B~~-NBOMe and other members of 25x-NBOMe series. The [[LD50|LD50]] 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|LD50]] 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>

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 ==Chemistry==
-C-NBOH or 2C-C-NBOH, is a serotonergic N-benzyl derivative of the substituted phenethylamine psychedelic known as [[2C-C]]. 25C-NBOH is a substituted phenethylamine with methoxy groups CH<sub>3</sub>O- attached to carbons R<sub>2</sub> and R<sub>5</sub> as well as an bromine atom attached to carbon R<sub>4</sub>. It differs from [[2C-B]] structurally through a substitution on the amine (NH<sub>2</sub>) with a 2-hydroxybenzyl (BOH) group. 25C-NBOH shares this 2-hydroxybenzyl substitution with other chemicals of the NBOH family. This NBOH addition is comprised of a hydroxy ether OH- bound to a benzene ring at R<sub>2</sub>.
+C-NBOH or 2C-C-NBOH, is a serotonergic N-benzyl derivative of the substituted phenethylamine psychedelic known as [[2C-C]]. 25C-NBOH is a substituted phenethylamine with methoxy groups CH<sub>3</sub>O- attached to carbons R<sub>2</sub> and R<sub>5</sub> as well as an bromine atom attached to carbon R<sub>4</sub>. It differs from [[2C-C]] structurally through a substitution on the amine (NH<sub>2</sub>) with a 2-hydroxybenzyl (BOH) group. 25C-NBOH shares this 2-hydroxybenzyl substitution with other chemicals of the NBOH family. This NBOH addition is comprised of a hydroxy ether OH- bound to a benzene ring at R<sub>2</sub>.
 ==Pharmacology==
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 C-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 9.87 nM<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>It has a pKi of 0.061 nM at the human 5HT<sub>2A</sub> receptor, similar to the better-known compound 25B-NBOMe.<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): 243–9. PMC 3963123. PMID 24397362. https://doi.org/10.1021/cn400216u</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>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>
+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>
 However, the role of these interactions and how they result in the [[psychedelic]] experience continues to remain elusive.
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 {{toxicity}}
 {{further|Research chemicals#Toxicity and harm potential|Responsible use #Hallucinogens}}
-C-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 25B-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]].
+C-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]].
 C-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>