25I-NBOMe: Difference between revisions

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'''25I-NBOMe''' ('''2C-I-NBOMe''') is a derivative of the [[Chemical class::Phenethylamine|substituted phenethylamine]] [[Psychoactive class::psychedelic]] [[2C-I]], discovered in 2003 by Ralf Heim at the Free University of Berlin,<ref name="Ralf Heim PhD. (2010-02-28)">Ralf Heim PhD. (2010-02-28) "Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts." | http://www.diss.fu-berlin.de/diss/receive/FUDISS_thesis_000000001221 (in German). diss.fu-berlin.de. Retrieved 2013-05-10.</ref> and subsequently investigated by a team at Purdue University led by [[David E. Nichols|David Nichols]].<ref name="Michael Robert Braden PhD. (2007)">Michael Robert Braden PhD. (2007). "Towards a biophysical understanding of hallucinogen action." | http://proquest.umi.com/pqdlink?Ver=1&Exp=01-23-2014&FMT=7&DID=1417800971&RQT=309&attempt=1&cfc=1 Purdue University. Retrieved 2012-08-08.</ref>

It is worth noting that compounds of the [[25x-NBOMe|NBOMe]] class are not [[oral]]ly active and should therefore be taken [[sublingual]]ly by simply placing the substance into one's mouth and allowing it to ~~slowly~~ absorb over a period of 30 minutes.

It is worth noting that compounds of the [[25x-NBOMe|NBOMe]] class are not [[oral]]ly active and should, therefore, be taken [[sublingual]]ly by simply placing the substance into one's mouth and allowing it to absorb over a period of 30 minutes slowly.

25I-NBOMe can also be vaporized and inhaled; this may cause significantly quicker effects and shorter duration as is expected from that route of administration. However, this route of administration is not recommended, unless using precise liquid measurement, due to the difficulties of measuring and handling substances active in the microgram range.

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In comparison to [[2C-I]], the addition of an NBOMe group to the structure results in a sixteen-fold increase in potency, allowing even the most extreme of dosages to fit in liquid form onto tabs and blotter paper, which people often mistake for [[LSD]]. 25i-NBOMe has a distinctly bitter and metallic taste that [[LSD]] does not have, which can be useful in determining what substance is really on the blotter.

This chemical had no history of human use ~~prior to~~ being sold online as a [[designer drug]] in 2010.

This chemical had no history of human use before being sold online as a [[designer drug]] in 2010.

==Chemistry==

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25I-NBOMe has efficacy at the [[serotonin#The 5-HT system|5-HT2A receptor]] where it acts as a potent [[Agonist#Agonists|partial agonist]]. However, the role of these interactions and how they result in the [[psychedelic]] experience continues to remain elusive.

This compound is pharmacologically unique when compared to other psychedelics through its action on [[serotonin]] receptors. It is one of the only [[Agonist#Agonists|full agonists]] for the human [[Serotonin#The 5-HT system|5-HT2A receptor]] receptor in existence.<ref name="pmid21174090">Ettrup, A. E. A. ; Hansen, M.; Santini, M. A.; Paine, J.; Gillings, N.; Palner, M.; Lehel, S.; Herth, M. M.; Madsen, J. (2010). "Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT2A agonist PET tracers". European Journal of Nuclear Medicine and Molecular Imaging 38 (4): 681–693. (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/21174090</ref> In comparison, classical psychedelics such as [[LSD]], [[DMT]] and [[psilocin]] can only be considered [[Agonist#Agonists|partial agonists]].

This compound is pharmacologically unique when compared to other psychedelics through its action on [[serotonin]] receptors. It is one of the only [[Agonist#Agonists|full agonists]] for the human [[Serotonin#The 5-HT system|5-HT2A receptor]] receptor in existence.<ref name="pmid21174090">Ettrup, A. E. A.; Hansen, M.; Santini, M. A.; Paine, J.; Gillings, N.; Palner, M.; Lehel, S.; Herth, M. M.; Madsen, J. (2010). "Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT2A agonist PET tracers". European Journal of Nuclear Medicine and Molecular Imaging 38 (4): 681–693. (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/21174090</ref> In comparison, classical psychedelics such as [[LSD]], [[DMT]] and [[psilocin]] can only be considered [[Agonist#Agonists|partial agonists]].

The [[Ki values]] of the following targets were greater than 500 Ki: [[5-HT1A]], [[D3]], [[H2]], [[5-HT1D]], [[α1A adrenergic]], [[δ opioid]], [[serotonin uptake transporter]], [[5-HT5A]], [[5-HT1B]], [[D2]], [[5-HT7]], [[D1]], [[5-HT3]], [[5-HT1E]], [[D5]], [[muscarinic M1-M5]], [[H3]], and the [[dopamine uptake transporter]].<ref name="high specific">High specific activity tritium-labeled N-(2-methoxybenzyl)-2,5-dimethoxy-4-iodophenethylamine (INBMeO): a high-affinity 5-HT2A receptor-selective agonist radioligand (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/18468904</ref>

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The effects listed below are based upon the [[subjective effects index]] and personal experiences of [[PsychonautWiki]] [[Special:TopUsers|contributors]]. The listed effects will rarely (if ever) occur all at once, but heavier dosages will increase the chances and are more likely to induce a full range of effects.

===Physical effects===

*'''[[Effect::Sublingual numbing]]''' - Assuming the substance has been taken [[sublingual]]ly, the very first physical effect which a person will notice immediately after 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 the key difference when it comes to determining whether your blotter paper contains [[LSD]] or one of the [[NBOMe]] series.

*'''[[Effect::Sublingual numbing]]''' - Assuming the substance has been taken [[sublingual]]ly, the very first physical effect which a person will notice immediately after sublingual absorption is a strong, unpleasant metallic chemical taste. This is accompanied by a very distinct 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 the key difference when it comes to determining whether your blotter paper contains [[LSD]] or one of the [[NBOMe]] series.

*'''[[Effect::Spontaneous tactile 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 [[Physical euphoria|euphoria]] that become longer and more drawn out proportional to the dosage consumed.

*'''[[Effect::Spontaneous tactile sensations]]''' - The "body high" itself can be described as a mild, all-encompassing, soft but euphoric tingling sensation. This tingling sensation is also accompanied by spontaneous rushes of [[Physical euphoria|euphoria]] that become longer and more drawn out proportional to the dosage consumed.

*'''[[Effect::Perception of decreased weight]]''' - In terms of the body’s perceived weight, this substance consistently leaves people feeling extremely light, often to the point of total weightlessness.

*'''[[Effect::Stimulation]]''' - In terms of its effects on the physical energy levels of the tripper 25I-NBOMe is usually considered to be very energetic and stimulating. 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 tripper 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]].

*'''[[Effect::Stimulation]]''' - In terms of its effects on the physical energy levels of the tripper 25I-NBOMe is usually considered to be very energetic and stimulating. 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 tripper to move unless they genuinely choose to do so. For others, however, the stimulation can be quite uncontrollably, occasionally resulting in bodily shakes and a grinding of the teeth comparable to that of [[MDMA]] and traditional stimulants such as [[amphetamine]].

*'''[[Effect::Nausea]]''' - As the ~~tripper~~ 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 considered very mild in its intensity.

*'''[[Effect::Nausea]]''' - As the user begins to come up, nausea is not uncommon and can sometimes result in initial vomiting, although nausea usually disappears when the user has vomited or the trip fully set in. In comparison to other psychedelics such as [[psilocin]], [[LSD]], [[2C-E]] and [[2C-I]], this could actually be considered very mild in its intensity.

*'''[[Effect::Vasoconstriction]]'''

*'''[[Effect::Increased heart rate]]'''

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====[[Effect::Geometry]]====

The visual geometry that is present throughout this trip is often said to be 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 equally angular as well as 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 said to be 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, colorful in scheme, glossy in color, sharp around the edges and equally angular as well as 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~~, 25I-NBOMe’s geometry leads onto [[Effect::8A Geometry|Level 8A]] visual geometry with [[Level 8B]] remaining so far unconfirmed within this substance. They also seem to consistently build up in visual intensity when the tripper stares at a central point. This eventually envelops the visual field and creates the sensation that the tripper has broken through into a continuously shifting geometric landscape or structure with a vast sense of immersive physical size attributed to it.

Regarding their behavior, 25I-NBOMe’s geometry leads onto [[Effect::8A Geometry|Level 8A]] visual geometry with [[Level 8B]] remaining so far unconfirmed within this substance. They also seem to consistently build up in visual intensity when the tripper stares at a central point. This eventually envelops the visual field and creates the sensation that the tripper has broken through into a continuously shifting geometric landscape or structure with a vast sense of immersive physical size attributed to it.

====Hallucinatory states====

25I-NBOMe is capable of producing a full range of hallucinatory states within the level 1 - 3 range extremely consistently. However, level 4 hallucinatory breakthroughs are reported but very ~~uncommon~~ and inconsistent in comparison to other more commonly used psychedelics such as [[psilocin]], [[2C-E]] and [[DMT]].

25I-NBOMe is capable of producing a full range of hallucinatory states within the level 1 - 3 range extremely consistently. However, level 4 hallucinatory breakthroughs are reported but very different and inconsistent in comparison to other more commonly used psychedelics such as [[psilocin]], [[2C-E]] and [[DMT]].

These effects include:

@@ Line 8: / Line 8: @@
 '''25I-NBOMe''' ('''2C-I-NBOMe''') is a derivative of the [[Chemical class::Phenethylamine|substituted phenethylamine]] [[Psychoactive class::psychedelic]] [[2C-I]], discovered in 2003 by Ralf Heim at the Free University of Berlin,<ref name="Ralf Heim PhD. (2010-02-28)">Ralf Heim PhD. (2010-02-28) "Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts." | http://www.diss.fu-berlin.de/diss/receive/FUDISS_thesis_000000001221 (in German). diss.fu-berlin.de. Retrieved 2013-05-10.</ref> and subsequently investigated by a team at Purdue University led by [[David E. Nichols|David Nichols]].<ref name="Michael Robert Braden PhD. (2007)">Michael Robert Braden PhD. (2007). "Towards a biophysical understanding of hallucinogen action." | http://proquest.umi.com/pqdlink?Ver=1&Exp=01-23-2014&FMT=7&DID=1417800971&RQT=309&attempt=1&cfc=1 Purdue University. Retrieved 2012-08-08.</ref>
-It is worth noting that compounds of the [[25x-NBOMe|NBOMe]] class are not [[oral]]ly active and should therefore be taken [[sublingual]]ly by simply placing the substance into one's mouth and allowing it to slowly absorb over a period of 30 minutes.
+It is worth noting that compounds of the [[25x-NBOMe|NBOMe]] class are not [[oral]]ly active and should, therefore, be taken [[sublingual]]ly by simply placing the substance into one's mouth and allowing it to absorb over a period of 30 minutes slowly.
 I-NBOMe can also be vaporized and inhaled; this may cause significantly quicker effects and shorter duration as is expected from that route of administration. However, this route of administration is not recommended, unless using precise liquid measurement, due to the difficulties of measuring and handling substances active in the microgram range.
@@ Line 14: / Line 14: @@
 In comparison to [[2C-I]], the addition of an NBOMe group to the structure results in a sixteen-fold increase in potency, allowing even the most extreme of dosages to fit in liquid form onto tabs and blotter paper, which people often mistake for [[LSD]]. 25i-NBOMe has a distinctly bitter and metallic taste that [[LSD]] does not have, which can be useful in determining what substance is really on the blotter.
-This chemical had no history of human use prior to being sold online as a [[designer drug]] in 2010.
+This chemical had no history of human use before being sold online as a [[designer drug]] in 2010.
 ==Chemistry==
@@ Line 23: / Line 23: @@
 I-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]]. However, the role of these interactions and how they result in the [[psychedelic]] experience continues to remain elusive.
-This compound is pharmacologically unique when compared to other psychedelics through its action on [[serotonin]] receptors. It is one of the only [[Agonist#Agonists|full agonists]] for the human [[Serotonin#The 5-HT system|5-HT<sub>2A</sub> receptor]] receptor in existence.<ref name="pmid21174090">Ettrup, A. E. A. ; Hansen, M.; Santini, M. A.; Paine, J.; Gillings, N.; Palner, M.; Lehel, S.; Herth, M. M.; Madsen, J. (2010). "Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT2A agonist PET tracers". European Journal of Nuclear Medicine and Molecular Imaging 38 (4): 681–693. (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/21174090</ref> In comparison, classical psychedelics such as [[LSD]], [[DMT]] and [[psilocin]] can only be considered [[Agonist#Agonists|partial agonists]].
+This compound is pharmacologically unique when compared to other psychedelics through its action on [[serotonin]] receptors. It is one of the only [[Agonist#Agonists|full agonists]] for the human [[Serotonin#The 5-HT system|5-HT<sub>2A</sub> receptor]] receptor in existence.<ref name="pmid21174090">Ettrup, A. E. A.; Hansen, M.; Santini, M. A.; Paine, J.; Gillings, N.; Palner, M.; Lehel, S.; Herth, M. M.; Madsen, J. (2010). "Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT2A agonist PET tracers". European Journal of Nuclear Medicine and Molecular Imaging 38 (4): 681–693. (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/21174090</ref> In comparison, classical psychedelics such as [[LSD]], [[DMT]] and [[psilocin]] can only be considered [[Agonist#Agonists|partial agonists]].
 The [[Ki values]] of the following targets were greater than 500 Ki: [[5-HT1A]], [[D3]], [[H2]], [[5-HT1D]], [[α1A adrenergic]], [[δ opioid]], [[serotonin uptake transporter]], [[5-HT5A]], [[5-HT1B]], [[D2]], [[5-HT7]], [[D1]], [[5-HT3]], [[5-HT1E]], [[D5]], [[muscarinic M1-M5]], [[H3]], and the [[dopamine uptake transporter]].<ref name="high specific">High specific activity tritium-labeled N-(2-methoxybenzyl)-2,5-dimethoxy-4-iodophenethylamine (INBMeO): a high-affinity 5-HT2A receptor-selective agonist radioligand (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/18468904</ref>
@@ Line 56: / Line 56: @@
 The effects listed below are based upon the [[subjective effects index]] and personal experiences of [[PsychonautWiki]] [[Special:TopUsers|contributors]]. The listed effects will rarely (if ever) occur all at once, but heavier dosages will increase the chances and are more likely to induce a full range of effects.
 ===Physical effects===
-*'''[[Effect::Sublingual numbing]]''' - Assuming the substance has been taken [[sublingual]]ly, the very first physical effect which a person will notice immediately after 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 the key difference when it comes to determining whether your blotter paper contains [[LSD]] or one of the [[NBOMe]] series.
+*'''[[Effect::Sublingual numbing]]''' - Assuming the substance has been taken [[sublingual]]ly, the very first physical effect which a person will notice immediately after sublingual absorption is a strong, unpleasant metallic chemical taste. This is accompanied by a very distinct 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 the key difference when it comes to determining whether your blotter paper contains [[LSD]] or one of the [[NBOMe]] series.
-*'''[[Effect::Spontaneous tactile 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 [[Physical euphoria|euphoria]] that become longer and more drawn out proportional to the dosage consumed.
+*'''[[Effect::Spontaneous tactile sensations]]''' - The "body high" itself can be described as a mild, all-encompassing, soft but euphoric tingling sensation. This tingling sensation is also accompanied by spontaneous rushes of [[Physical euphoria|euphoria]] that become longer and more drawn out proportional to the dosage consumed.
 *'''[[Effect::Perception of decreased weight]]''' - In terms of the body’s perceived weight, this substance consistently leaves people feeling extremely light, often to the point of total weightlessness.
-*'''[[Effect::Stimulation]]''' - In terms of its effects on the physical energy levels of the tripper 25I-NBOMe is usually considered to be very energetic and stimulating. 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 tripper 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]].
+*'''[[Effect::Stimulation]]''' - In terms of its effects on the physical energy levels of the tripper 25I-NBOMe is usually considered to be very energetic and stimulating. 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 tripper to move unless they genuinely choose to do so. For others, however, the stimulation can be quite uncontrollably, occasionally resulting in bodily shakes and a grinding of the teeth comparable to that of [[MDMA]] and traditional stimulants such as [[amphetamine]].
-*'''[[Effect::Nausea]]''' - As the tripper 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 considered very mild in its intensity.
+*'''[[Effect::Nausea]]''' - As the user begins to come up, nausea is not uncommon and can sometimes result in initial vomiting, although nausea usually disappears when the user has vomited or the trip fully set in. In comparison to other psychedelics such as [[psilocin]], [[LSD]], [[2C-E]] and [[2C-I]], this could actually be considered very mild in its intensity.
 *'''[[Effect::Vasoconstriction]]'''
 *'''[[Effect::Increased heart rate]]'''
@@ Line 107: / Line 107: @@
 ====[[Effect::Geometry]]====
-The visual geometry that is present throughout this trip is often said to be 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 equally angular as well as 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 said to be 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, colorful in scheme, glossy in color, sharp around the edges and equally angular as well as 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, 25I-NBOMe’s geometry leads onto [[Effect::8A Geometry|Level 8A]] visual geometry with [[Level 8B]] remaining so far unconfirmed within this substance. They also seem to consistently build up in visual intensity when the tripper stares at a central point. This eventually envelops the visual field and creates the sensation that the tripper has broken through into a continuously shifting geometric landscape or structure with a vast sense of immersive physical size attributed to it.
+Regarding their behavior, 25I-NBOMe’s geometry leads onto [[Effect::8A Geometry|Level 8A]] visual geometry with [[Level 8B]] remaining so far unconfirmed within this substance. They also seem to consistently build up in visual intensity when the tripper stares at a central point. This eventually envelops the visual field and creates the sensation that the tripper has broken through into a continuously shifting geometric landscape or structure with a vast sense of immersive physical size attributed to it.
 ====Hallucinatory states====
-I-NBOMe is capable of producing a full range of hallucinatory states within the level 1 - 3 range extremely consistently. However, level 4 hallucinatory breakthroughs are reported but very uncommon and inconsistent in comparison to other more commonly used psychedelics such as [[psilocin]], [[2C-E]] and [[DMT]].
+I-NBOMe is capable of producing a full range of hallucinatory states within the level 1 - 3 range extremely consistently. However, level 4 hallucinatory breakthroughs are reported but very different and inconsistent in comparison to other more commonly used psychedelics such as [[psilocin]], [[2C-E]] and [[DMT]].
 These effects include: