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25B-NBOMe: Difference between revisions
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{{Headerpanel|{{Warning/25B-NBOMe}}}} | {{Headerpanel|{{Warning/25B-NBOMe}}}} | ||
{{SummarySheet}} | {{SummarySheet}} | ||
{{SubstanceBox/25B-NBOMe}} | {{SubstanceBox/25B-NBOMe}} | ||
'''25B-NBOMe''' (also known as '''Cimbi-36''', '''NBOMe-2C-B''' and '''2C-B-NBOMe''') is novel [[Psychoactive class::psychedelic]] substance of the [[chemical class::phenethylamine]] class. It is a member of the 25x-NBOMe series, a recently discovered group of potent psychedelic compounds derived from the [[2C-x]] family. The name 25B-NBOMe, which is short-hand for 2C-B-NBOMe, indicates it is a derivative of the phenethylamine psychedelic 2C-B. | |||
25B-NBOMe was discovered in 2004 by Ralf Heim at the Free University of Berlin.<ref name="Heim2004">{{cite journal | vauthors=((Heim, R.)) | title=Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2 -Methoxybenzyl-Partialstruktur: Entwicklung eines neuen Struktur-Wirkungskonzepts | date= 2004 | language=german | url=https://refubium.fu-berlin.de/handle/fub188/11995 | doi=10.17169/refubium-16193}}</ref> It acts as a potent partial agonist for the 5-HT<sub>2A</sub> receptor.<ref name="25BSAR">{{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> It has been used in clinical trials with an evaluation dose for safety consideration to humans of only 1 microgram. Such a dose was determined to be only 1/300th the dose expected to be hallucinogenic to humans and that recreational use would greatly exceed doses determined to be safe to humans.<ref name="25BSAR" /> This substance had no history of human use before being sold online as a [[designer drug]] in 2010.{{citation needed}} | |||
[[Subjective effects]] include [[stimulation]], [[geometry|open and closed-eye visuals]], [[time distortion]], [[euphoria]], and [[ego loss]]. Anecdotal reports suggest 25B-NBOMe to be an active [[hallucinogen]] at a dose of as little as 250–500 µg, making it a similar potency to other phenethylamine derived [[hallucinogens]] such as [[Bromo-DragonFLY]].<ref>{{Citation | title=Erowid Bromo-Dragonfly Vault : Dosage | url=https://erowid.org/chemicals/bromo_dragonfly/bromo_dragonfly_dose.shtml}}</ref> It is worth noting that compounds of the [[25x-NBOMe|NBOMe]] class are not [[oral|orally]] active and should therefore be taken [[sublingual|sublingually]] by placing them into one's mouth and allowing it to absorb over a period of 15-30 minutes. | |||
Extremely little is known about the pharmacological properties, metabolism, and toxicity of 25B-NBOMe in humans. Numerous members of the [[25x-NBOMe]] series have been associated with hospitalizations and deaths. Along with its highly sensitive dose-response and unpredictable effects, many reports also suggest that this substance may be overly difficult to use safely. Therefore it is highly advised to use [[harm reduction practices]] if using this substance. | |||
==Chemistry== | ==Chemistry== | ||
[[File:25bnbome_and_2cb.png|250px|thumb|right|A comparison of 25B-NBOMe and 2C-B.]] | [[File:25bnbome_and_2cb.png|250px|thumb|right|A comparison of 25B-NBOMe and 2C-B.]] | ||
25B-NBOMe or 2C-B-NBOMe is a serotonergic N-benzyl derivative of the substituted phenethylamine psychedelic known as [[2C-B]]. 25B-NBOMe 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 a bromine atom attached to carbon R<sub>4</sub>. It differs from [[2C-B]] structurally through a substitution on the amine (NH2) with a 2-methoxybenzyl (BOMe) group. 25B-NBOMe shares this 2-methoxybenzyl substitution with other chemicals of the NBOMe family. This NBOMe addition contains a methoxy ether CH<sub>3</sub>O- bound to a benzene ring at R<sub>2</sub>. | 25B-NBOMe or 2C-B-NBOMe is a serotonergic N-benzyl derivative of the substituted phenethylamine psychedelic known as [[2C-B]]. 25B-NBOMe 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 a bromine atom attached to carbon R<sub>4</sub>. It differs from [[2C-B]] structurally through a substitution on the amine (NH2) with a 2-methoxybenzyl (BOMe) group. 25B-NBOMe shares this 2-methoxybenzyl substitution with other chemicals of the NBOMe family. This NBOMe addition contains a methoxy ether CH<sub>3</sub>O- bound to a benzene ring at R<sub>2</sub>. | ||
The compound has a density of 1.3 (±0.1) g/cm^3. | |||
==Pharmacology== | ==Pharmacology== | ||
{{Further|Serotonergic psychedelic}} | {{Further|Serotonergic psychedelic}} | ||
25B-NBOMe has efficacy at the [[serotonin#The 5-HT system|5-HT<sub>2A</sub> receptor]] where it acts as a potent [[Agonist#Agonists|partial agonist]].<ref | 25B-NBOMe has efficacy at the [[serotonin#The 5-HT system|5-HT<sub>2A</sub> receptor]] where it acts as a potent [[Agonist#Agonists|partial agonist]].<ref name="Heim2004"/><ref>{{cite journal | vauthors=((Silva, Maria Elena)) | title=Theoretical study of the interaction of agonists with the 5-HT2A receptor | date= 2009 | url=https://epub.uni-regensburg.de/id/eprint/12119 | doi=10.5283/EPUB.12119}}</ref><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><ref name="25BSAR"/> However, the role of these interactions and how they result in the [[psychedelic]] experience continues to remain elusive. | ||
==Subjective effects== | ==Subjective effects== | ||
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{{effects/base | {{effects/base | ||
|{{effects/physical| | |{{effects/physical| | ||
*'''[[Effect::Stimulation]]''' - In terms of its effects on the physical energy levels of the user, 25B-NBOMe is usually considered to be energetic and stimulating, but it can be considered less stimulating when compared to [[25I-NBOMe]]. For most people, this substance induces a unique type of physical stimulation which can be described as feeling extremely energetic but in a way which does not force the person to move unless they genuinely choose to do so. For others, however, the stimulation can be quite uncontrollable, occasionally resulting in bodily shakes and a grinding of the teeth comparable to that of [[MDMA]] and traditional stimulants such as [[amphetamine]], but this is manifested much less consistently when compared to that of [[25I-NBOMe]] | |||
*'''[[Effect::Mouth numbing]]''' - Assuming the substance has been taken sublingually, the very first physical effect which a person will notice immediately after [[Routes_of_administration#Sublingual|sublingual]] absorption is a strong, unpleasant metallic chemical taste. This is accompanied by a very obvious feeling of general numbness of the tongue and mouth which can stay for up to an hour after the blotter paper has been consumed. This is a key difference when it comes to determining whether one's blotter paper contains [[LSD]] or one of the NBOMe series. | *'''[[Effect::Mouth numbing]]''' - Assuming the substance has been taken sublingually, the very first physical effect which a person will notice immediately after [[Routes_of_administration#Sublingual|sublingual]] absorption is a strong, unpleasant metallic chemical taste. This is accompanied by a very obvious feeling of general numbness of the tongue and mouth which can stay for up to an hour after the blotter paper has been consumed. This is a key difference when it comes to determining whether one's blotter paper contains [[LSD]] or one of the NBOMe series. | ||
*'''[[Effect::Spontaneous physical sensations]]''' - The "body high" itself can be described as a generally mild, all-encompassing, soft but euphoric tingling sensation. This tingling sensation is also accompanied by spontaneous rushes of euphoria that become longer and more drawn out proportional to the dosage consumed. | *'''[[Effect::Spontaneous physical sensations]]''' - The "body high" itself can be described as a generally mild, all-encompassing, soft but euphoric tingling sensation. This tingling sensation is also accompanied by spontaneous rushes of euphoria that become longer and more drawn out proportional to the dosage consumed. | ||
*'''[[Effect::Perception of bodily lightness]]''' - In terms of the body’s perceived weight, this substance consistently leaves people feeling extremely light, often to the point of total weightlessness. | *'''[[Effect::Perception of bodily lightness]]''' - In terms of the body’s perceived weight, this substance consistently leaves people feeling extremely light, often to the point of total weightlessness. | ||
*'''[[Effect::Nausea]]''' - As the user begins to come up, nausea is not uncommon and can sometimes result in initial vomiting, but passes once this has either happened or the trip begins to fully set in. In comparison to other psychedelics such as [[psilocin]], [[LSD]], [[2C-E]] and [[2C-I]], this could actually be very considered very mild in its intensity. | |||
*'''[[Effect::Nausea]]''' - As the | |||
*'''[[Effect::Vasoconstriction]]''' | *'''[[Effect::Vasoconstriction]]''' | ||
*'''[[Effect::Increased heart rate]]''' | *'''[[Effect::Increased heart rate]]''' | ||
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The visual geometry that is present throughout this trip is often described as similar in appearance to that of [[LSD]]. They can be comprehensively described as algorithmic in geometric style, intricate in complexity, fine and zoomed out in detail, fast and smooth in motion, structured in shape, colourful in scheme, glossy in colour, sharp around the edges and mostly rounded across their corners. In comparison to other more commonly used psychedelics they can be described as significantly more intricate than the visual geometry found within [[2C-I]] and most of the [[2C-x]] family in general as well as completely on par with [[LSD]], [[psilocin]] and [[DMT]] at appropriately high dosages. | The visual geometry that is present throughout this trip is often described as similar in appearance to that of [[LSD]]. They can be comprehensively described as algorithmic in geometric style, intricate in complexity, fine and zoomed out in detail, fast and smooth in motion, structured in shape, colourful in scheme, glossy in colour, sharp around the edges and mostly rounded across their corners. In comparison to other more commonly used psychedelics they can be described as significantly more intricate than the visual geometry found within [[2C-I]] and most of the [[2C-x]] family in general as well as completely on par with [[LSD]], [[psilocin]] and [[DMT]] at appropriately high dosages. | ||
In terms of their behaviour, 25B-NBOMe’s geometry leads onto [[Effect::8A Geometry|Level 8A]] visual geometry with [[8B Geometry|Level 8B]] remaining so far unconfirmed within this substance. They also seem to consistently build up in visual intensity when the | In terms of their behaviour, 25B-NBOMe’s geometry leads onto [[Effect::8A Geometry|Level 8A]] visual geometry with [[8B Geometry|Level 8B]] remaining so far unconfirmed within this substance. They also seem to consistently build up in visual intensity when the user stares at a central point. This eventually envelops the visual field and creates the sensation that the user has broken through into a continuously shifting geometric landscape or structure with a vast sense of immersive physical size attributed to it. | ||
====Hallucinatory states==== | ====Hallucinatory states==== | ||
*'''[[Effect::Transformations]]''' | *'''[[Effect::Transformations]]''' | ||
*'''[[Effect::Internal | *'''[[Effect::Internal hallucination]]''' - (''[[effect::autonomous entities]]''; ''[[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 internal in their manifestation, 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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===Experience reports=== | ===Experience reports=== | ||
There are currently no anecdotal reports which describe the effects of this compound within our [[experience index]]. Additional experience reports can be found here: | There are currently no anecdotal reports which describe the effects of this compound within our [[experience index]]. Additional experience reports can be found here: | ||
* [https://www.erowid.org/experiences/subs/exp_25BNBOMe.shtml Erowid Experience Vaults: 25B-NBOMe] | |||
*[https://www.erowid.org/experiences/subs/exp_25BNBOMe.shtml Erowid Experience Vaults: 25B-NBOMe] | |||
==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}} | ||
25B-NBOMe is a relatively new substance, and little is known about its pharmacological risks or its interaction with other substances. The lethal dosage has not yet been determined. One case has been reported on where 25B-NBOMe was identified as the cause of death for a 17-year-old boy.<ref>Designer Drug Identified As Cause Of Plano Teen’s Death | | 25B-NBOMe is a relatively new substance, and little is known about its pharmacological risks or its interaction with other substances. The lethal dosage has not yet been determined. One case has been reported on where 25B-NBOMe was identified as the cause of death for a 17-year-old boy.<ref>{{Citation | title=Designer Drug Identified As Cause Of Plano Teen’s Death | url=https://www.cbsnews.com/dfw/news/designer-drug-identified-as-cause-of-plano-teens-death/}}</ref> | ||
It is advised that due to 25B-NBOMe's extreme potency it should not be insufflated as this method of administration is [[Toxicity::potentially fatal at heavy dosages]].<ref> | It is advised that due to 25B-NBOMe's extreme potency it should not be insufflated as this method of administration is [[Toxicity::potentially fatal at heavy dosages]].<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> | ||
25B-NBOMe has been used in clinical trials with an evaluation dose for safety consideration to humans of only 1 microgram; Such a dose is 300× lower than the dose expected to be hallucinogenic to humans and it is expected that recreational use would greatly exceed doses determined to be safe to humans.<ref>Preclinical Safety Assessment of the 5-HT2A | 25B-NBOMe has been used in clinical trials with an evaluation dose for safety consideration to humans of only 1 microgram; Such a dose is 300× lower than the dose expected to be hallucinogenic to humans and it is expected that recreational use would greatly exceed doses determined to be safe to humans.<ref>Preclinical Safety Assessment of the 5-HT2A | ||
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===Tolerance and addiction potential=== | ===Tolerance and addiction potential=== | ||
25B-NBOMe is [[Addiction potential::not habit-forming]] and the desire to use it can actually decrease with use. It is most often self-regulating. | 25B-NBOMe 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 25B-NBOMe is built [[Time to full tolerance::almost immediately after ingestion]]. After that, it takes about [[Time to half tolerance::1 week]] for the tolerance to be reduced to half and [[Time to zero tolerance::2 weeks]] to be back at baseline (in the absence of further consumption). 25B-NBOMe presents cross-tolerance with [[Cross-tolerance::all [[psychedelic]]s]], meaning that after the consumption of 25B-NBOMe all psychedelics will have a reduced effect. | |||
===Overdose=== | |||
{{NBOMeOD}} | |||
===Dangerous interactions=== | ===Dangerous interactions=== | ||
{{DangerousInteractions}} | {{DangerousInteractions/Intro}} | ||
{{DangerousInteractions/NBOMe}} | |||
==Legal status== | |||
*''' | *'''Austria''': Since June 26, 2019, 25B-NBOMe is illegal to possess, produce and sell under the SMG. (Suchtmittelgesetz Österreich)<ref>https://www.ris.bka.gv.at/Dokumente/BgblAuth/BGBLA_2019_II_167/BGBLA_2019_II_167.pdfsig</ref> | ||
*''' | *'''Brazil''': Possession, production and sale is illegal as it is listed on Portaria SVS/MS nº 344.<ref>http://portal.anvisa.gov.br/documents/10181/3115436/%281%29RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7</ref> | ||
*''' | *'''Canada''': 25B-NBOMe would be considered Schedule III as it is a derivative of 2,5-dimethoxyphenethylamine.<ref>{{Citation | vauthors=((Branch, L. S.)) | year=2022 | title=Consolidated federal laws of Canada, Controlled Drugs and Substances Act | url=https://laws-lois.justice.gc.ca/eng/acts/C-38.8/page-12.html}}</ref> | ||
*'''China''': As of October 2015, 25B-NBOMe is a controlled substance in China.<ref>关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | http://www.sfda.gov.cn/WS01/CL0056/130753.html</ref> | |||
*'''Germany''': 25B-NBOMe is controlled under Anlage I BtMG (Narcotics Act, Schedule I) as of December 13, 2014.<ref>{{cite web|url=https://www.bgbl.de/xaver/bgbl/start.xav?startbk=Bundesanzeiger_BGBl&jumpTo=bgbl114s1999.pdf#__bgbl__%2F%2F*%5B%40attr_id%3D%27bgbl114s1999.pdf%27%5D__1576023093735|title=Achtundzwanzigste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften|publisher=Bundesanzeiger Verlag|access-date=December 11, 2019|language=de}}</ref><ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/anlage_i.html|title=Anlage I BtMG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 11, 2019|language=de}}</ref> It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.<ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/__29.html|title=§ 29 BtMG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 11, 2019|language=de}}</ref> | |||
*'''Italy''': 25B-NBOMe is a Schedule 1 controlled substance in Italy.<ref>Tabella 1 Stupefacenti dello Stato Italiano |http://www.salute.gov.it/imgs/C_17_pagineAree_3729_listaFile_itemName_0_file.pdf</ref> | |||
*'''Japan''': 25B-NBOMe is a narcotic drug in Japan effective November 1st, 2015.<ref>[https://www.mhlw.go.jp/stf/houdou/0000098723.html "新たに４物質を麻薬に指定し、規制の強化を図ります"] (in Japanese). 厚生労働省 [Ministry of Health, Labour and Welfare (MHLW)]. Retrieved May 2, 2022.</ref> | |||
*'''Latvia''': 25B-NBOMe is a Schedule I controlled substance.<ref>{{Citation | title=Zaudējis spēku - Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem | url=https://likumi.lv/doc.php?id=121086}}</ref> | |||
*'''New Zealand''': 25B-NBOMe is a Schedule 2 controlled substance in New Zealand.<ref>{{Citation | title=Misuse of Drugs Act 1975 No 116 (as at 07 December 2021), Public Act – New Zealand Legislation | url=https://www.legislation.govt.nz/act/public/1975/0116/latest/whole.html}}</ref> | |||
*'''Sweden''': 25B-NBOMe is classed as Schedule I.<ref>{{Citation | title=Läkemedelsverkets författningssamling | url= http://www.lakemedelsverket.se/upload/lvfs/LVFS_2013-15.pdf}}</ref> | |||
*'''Switzerland''': 25B-NBOMe is a controlled substance specifically named under Verzeichnis D.<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:''' 25B-NBOMe is a classed as drug and is illegal to possess, produce, supply, or import.<ref name="Bakanlar Kurulu Kararı - Karar Sayısı : 2013/5742">{{Citation | title=Başbakanlık Mevzuatı Geliştirme ve Yayın Genel Müdürlüğü | url=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> | |||
*'''United Kingdom''': 25B-NBOMe 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> | |||
*'''United States''': On Nov 15, 2013, the DEA added 25B-NBOMe to Schedule I using their emergency scheduling powers, making it "temporarily" in Schedule I for 2 years.<ref>http://www.justice.gov/dea/divisions/hq/2013/hq111513.shtml</ref> | |||
== | ==See also== | ||
*[[Responsible use]] | *[[Responsible use]] | ||
*[[Research chemical]] | *[[Research chemical]] | ||
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==External links== | ==External links== | ||
*[https://en.wikipedia.org/wiki/25B-NBOMe 25B-NBOMe (Wikipedia)] | *[https://en.wikipedia.org/wiki/25B-NBOMe 25B-NBOMe (Wikipedia)] | ||
*[https://isomerdesign.com/PiHKAL/explore.php?id=5526 25B-NBOMe (Isomer Design)] | *[https://isomerdesign.com/PiHKAL/explore.php?id=5526 25B-NBOMe (Isomer Design)] | ||
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==References== | ==References== | ||
<references /> | <references /> | ||
[[Category:Psychoactive substance]] | [[Category:Psychoactive substance]] | ||
[[Category:Psychedelic]] | |||
[[Category:25x-NBOMe]] | |||
[[Category:Research chemical]] | [[Category:Research chemical]] | ||
{{#set:Featured=true | {{#set:Featured=true | ||
|RN=CH₂-C₆H₄-OCH₃ | |RN=CH₂-C₆H₄-OCH₃ | ||