NBx

File:NBx.svg

The general structure for a N-benzylphenethylamine compound

N-benzylphenethylamine or NBx is the general form of s series of phenethylamines which have an N-benzyl substitution.

The most recognized members include the sub-series 25x-NBOMe and 25x-NBOH series of psychedelics. They have often been misrepresented as LSD, which has lead to numerous accidental overdoses, difficult experiences as well as health problems and fatalities.

It is strongly recommended that one should inform themselves first and most importantly with these. Both of them (25x-NBOx) are the only compounds which are largely distributed as well are associated with major risks, dangers and fatalities, which are not found for many of the other NBx compounds listed here.

Chemistry

In a comparison of NBx and phenethylamine chemicals, each NBx molecule is a N-benzyl derivative of the corresponding phenethylamine molecule. This change in structure generally results a minor or major increase in potency.

The term NBx denotes the addition from a phenethylamine backbone through a substitution at the amine (NH2) with a benzyl (Bx) group.

There are many possible N-benzylphenethylamine compounds which can be further devided into several sub-classes. It should be noted that most of these sub-categories have different nomenclature for their naming rules.

• x-NB*
  • 25x-NB* - 25x-NBx compounds are derived from the 2C-x series, where the constituents of 25x refer to the two methoxy substitutions on the 2 and 5 position on the benzene ring on the phenethylamine and x denotes the substitution of the corresponding 2C-x.
  • x1x2-NB* - If the N-Benzyl derivative is not derived from 2C-x, DOx or other compounds with official names that have a x-NB* name, but also substituted with only methoxy groups on the phenyl ring of the phenethylamine (at positions 2, 3, 5 and/or 6, with the exception of the 4 position, then an universal nomenclature can be applied where x1 refers to one or more of the position number of methoxy groups attached while x2 still denotes the corresponding substitution at position 4 with official denotation letters or that of a corresponding, officially named phenethylamine compound. (e.g. ???????)
  • x-NB* - the x can also denote the official name of a phenethylamine compound. They should be regarded as obsolete if other notations can be used instead. (e.g. 2C-I-NBOMe = 25i-NBOMe, DOB-NBOMe, Mescaline-NBOMe, 2C-B-FLY-NBOMe).

• *-NB - nbenzyl

• *-NBx* - The x of the NBxOMe represents the position/-s of the substitutions on the benzene ring of the N-benzyl substiitution that follows (*). If a single group is substituted at the 2 position, then the 2 is not denoted (eg. 25i-NBOMe = 25i-NB2OMe)
  • *-NBxO* - oxy
    • *-NBxOMe - methoxy
    • *-NBxOH - hydroxy
  • *-NBxF - fluorine
  • *-NBxMD - methlenedioxy, if MD on 2 and 3 position it is not noted at x

• Rarely, substances with official names that do not correlate one one of the two *-NBx or x-NB* sub-denotations

• Official names which are not correlated to an NBx notation (e.g. MDBZ, Clobenzorex, C30-NBOMe)

WILL REVISIT THIS

List of N-benzylphenethylamine compounds

Compound	R4	Structure
25B-NBOMe	Br
25C-NBOMe	Cl
25D-NBOMe	CH3
25I-NBOMe	I
25N-NBOMe	NO2
25iP-NBOMe	CH(CH3)2

Toxicity and harm potential

This toxicity and harm potential section is a stub. As a result, it may contain incomplete or even dangerously wrong information! You can help by expanding upon or correcting it. Note: Always conduct independent research and use harm reduction practices if using this substance.

Tolerance and addiction potential

Members of the psychedelic-acting sub-series of N-benzylphenethylamines are not habit-forming and the desire to use them can actually decrease with use. They are thought to be most often self-regulating.

Some N-benzylphenethylderivatives have primarily stimulating effects which can carry risk of being habit-forming, although most of these compounds are not very active compared to traditional stimulants which have a decreased risk of being addicting.

This can also be applied to tolerance to the effects:

Tolerance to most if not all members of the psychedelic derivatives are built almost immediately after ingestion. After that, it takes about 1 week for the tolerance to be reduced to half and 2 weeks to be back to baseline (in the absence of further consumption). Members of the 25x-NBOMe series present cross-tolerance with [[Cross-tolerance::all psychedelics]], meaning that after the consumption of any member of the 25x-NBOMe series all psychedelics will have a reduced effect.

Tolerance of most members of the stimulating derivatives are built after consecutive dosing for several days. After that, it takes about 1 week for the tolerance to be reduced to half and 2 weeks to be back to baseline (in the absence of further consumption). Members of the stimulating derivatived present cross-tolerance with [[Cross-tolerance::all stimulants]], meaning that after the consumption of any member of these derivatives, stimulants will have a reduced effect.

Overdose

Overdoses are serious regarding most importantly the 25x-NBOMe series an to a lesser extent the 25x-NBOH series. Due to the very high potency and seemingly unpredictable effects the margin between a normal and an overdose of NBOMe compounds is extremely small when compared to many other substances. The exact toxic dose is unclear since it seems to depend a lot on personal physiology, rather than predominantly dose. However, various anecdotal reports suggest that dangerous side effects begin to appear when exceeding 1000 μg and it possibly becoming lethal for the more sensitive people at roughly 2000 μg. Reports of other people surviving much higher doses, sometimes even without any major side effects have been documented as well.

There is also the uncertainty of dosage on blotter paper since it is rather difficult to lay such an exact dosage. Insufflating, vaporizing or drinking tinctures of this substance is highly discouraged because of this and has been tied to many documented deaths. One study found that 25I‐NBOMe and 25C‐NBOMe blotter papers contained 'hotspots' with higher quantities of the drug, implying an inherent risk of overdosing.

The overdose effects of NBOMes are typically a dangerously high heart rate, blood pressure, hyperthermia and significant vasoconstriction also accompanied by confusion, delusions, panic attacks, aggressive behavior, numbness or pain, amnesia and often seizures. The risks in an overdose include anything from organ failure to cardiac arrest and death. There are also multiple reports of people lethally injuring themselves or falling to death. Benzodiazepines or antipsychotics can help with the psychological effects during an overdose although medical attention should always be called in even a possible overdose of 25I-NBOMe.

Dangerous interactions

Warning: Many psychoactive substances that are reasonably safe to use on their own can suddenly become dangerous and even life-threatening when combined with certain other substances. The following list provides some known dangerous interactions (although it is not guaranteed to include all of them).

Always conduct independent research (e.g. Google, DuckDuckGo, PubMed) to ensure that a combination of two or more substances is safe to consume. Some of the listed interactions have been sourced from TripSit. Due to the highly unpredictable nature of the NBOMe series, it is generally advised to avoid mixing them with other psychoactive substances.

• 2C-T-X - The 2C-T-X phenethylamines can be unpredictable in their interactions and the NBOMes are known to be unpredictable even alone. As a result, this combination should be avoided.
• 5-MeO-xxt - The 5-MeO tryptamines can be unpredictable in their interactions and the NBOMes are known to be unpredictable even alone. As a result, this combination should be avoided.
• Amphetamines - Amphetamines and NBOMes both provide considerable stimulation. When combined they can result in tachycardia, hypertension, vasoconstriction and, in extreme cases, heart failure. The anxiogenic and focusing effects of stimulants are also not good in combination with psychedelics as they can lead to unpleasant thought loops. NBOMes are known to cause seizures and stimulants can increase this risk.
• aMT
• Caffeine - Caffeine can bring out the natural stimulation from psychedelic drugs to make it uncomfortable. High doses can cause anxiety which is hard to handle while tripping.
• Cannabis - Cannabis has an unexpectedly strong and unpredictable synergy with the effects of psychedelics. Caution is advised with this combination as it can significantly increase the risk of adverse psychological reactions like anxiety, paranoia, panic attacks, and psychosis. Users are advised to start off with only a fraction of their normal cannabis dose and take long breaks between hits to avoid over intake.
• Cocaine - Cocaine and NBOMes both provide considerable stimulation. When combined they can result in severe vasoconstriction, tachycardia, hypertension, and in extreme cases heart failure.
• DOx
• DXM
• Lithium - Lithium is commonly prescribed in the treatment of [https://en.wikipedia.org/wiki/Bipolar_disorder bipolar disorder. There is a large body of anecdotal evidence that suggests taking it with psychedelics significantly increases the risk of psychosis and seizures. As a result, this combination is strictly discouraged.
• MAOIs - MAO-B inhibitors can increase the potency and duration of phenethylamines unpredictably.
• MDMA
• MXE - As an NMDA antagonist, MXE potentiates NBOMes which can be unpleasantly intense.
• Tramadol - Tramadol is well known to lower seizure threshold and NBOMes have also shown a tendency to cause severe seizures

Serotonin syndrome risk

Combinations with the following substances can cause dangerously high serotonin levels. Serotonin syndrome requires immediate medical attention and can be fatal if left untreated.

• MAOIs - Such as banisteriopsis caapi, syrian rue, phenelzine, selegiline, and moclobemide.
• Serotonin releasers - Such as MDMA, 4-FA, methamphetamine, methylone and αMT.
• SSRIs - Such as citalopram and sertraline
• [[Wikipedia:SNRIs|DangerousInteraction::SNRIs]] - Such as tramadol and venlafaxine
• 5-HTP

Legal status

This legality section is a stub. As such, it may contain incomplete or wrong information. You can help by expanding it.

• Austria: The 25x-NBOMe family is illegal to possess, produce and sell under the NPSG (Neue-Psychoaktive-Substanzen-Gesetz Österreich).
• United States: In the US, some of the 25x-NBOMe chemicals are listed as Schedule I substances and others may be considered analogues under the Federal Analogue Act.
• United Kingdom: The majority of synthesised 25x-NBOMe substances are Class A drugs in the United Kingdom as a result of the N-benzylphenethylamine catch-all clause. Any compounds not covered by the clause are illegal to produce, supply, or import under the Psychoactive Substance Act, which came into effect on May 26th, 2016.

See also

• Responsible use
• Psychedelics
• Phenethylamines
• 25x-NBOMe
• 25x-NBOH
• 2C-x
• DOx

External links

• 25-NB (Wikipedia)

Literature

• 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
• Heim, Ralf (2004). "Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur". Freie Universität Berlin. Retrieved 27 June 2015.
• 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 Freely accessible. PMID 24397362. https://doi.org/10.1021/cn400216u
• Ettrup, 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. PMID 21174090. https://doi.org/10.1007/s00259-010-1686-8