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General structure of 25-NB derivatives, where R is usually 2,5-dimethoxy-4-(alkyl or halogen), R1 is usually H but rarely methyl, and Cyc is usually 2-substituted phenyl but can be other heterocycles.

The 25-NB (25x-NBx) series, sometimes alternatively referred to as the NBOMe compounds, is a family of serotonergic psychedelics. [1] They are substituted phenethylamines and were derived from the 2C family. [1] They act as selective agonists of the serotonin 5-HT2A receptor. [2] [3] [4] [5] [6] [7] [8] The 25-NB family is unique relative to other classes of psychedelics in that they are, generally speaking, extremely potent and relatively selective for the 5-HT2A receptor. [1] Use of NBOMe series drugs has caused many deaths and hospitalisations since the drugs popularisation in the 2010s. This is primarily due to their high potency, unpredictable pharmacokinetics, and sellers passing off the compounds in the series as LSD. [9]

Toxicity and harm potential

NBOMe compounds are often associated with life-threatening toxicity and death. [10] [11] Studies on NBOMe family of compounds demonstrated that the substance exhibit neurotoxic and cardiotoxic activity. [12] Reports of autonomic dysfunction remains prevalent with NBOMe compounds, with most individuals experiencing sympathomimetic toxicity such as vasoconstriction, hypertension and tachycardia in addition to hallucinations. [13] [14] [15] [16] [17] Other symptoms of toxidrome of include agitation or aggression, seizure, hyperthermia, diaphoresis, hypertonia, rhabdomyolysis, and death. [13] [17] [11] Researchers report that NBOMe intoxication frequently display signs of serotonin syndrome. [18] The likelihood of seizure is higher in NBOMes compared to other psychedelics. [12]

NBOMe and NBOHs are regularly sold as LSD in blotter papers, [11] [19] which have a bitter taste and different safety profiles. [13] [10] Despite high potency, recreational doses of LSD have only produced low incidents of acute toxicity. [10] Fatalities involved in NBOMe intoxication suggest that a significant number of individuals ingested the substance which they believed was LSD, [15] and researchers report that "users familiar with LSD may have a false sense of security when ingesting NBOMe inadvertently". [13] While most fatalities are due to the physical effects of the drug, there have also been reports of death due to self-harm and suicide under the influence of the substance. [20] [21] [13]

Given limited documentation of NBOMe consumption, the long-term effects of the substance remain unknown. [13] NBOMe compounds are not active orally, [a] and are usually taken sublingually. [1]: 3  When NBOMes are administered sublingually, numbness of the tongue and mouth followed by a metallic chemical taste was observed, and researchers describe this physical side effect as one of the main discriminants between NBOMe compounds and LSD. [23] [24] [25]

Neurotoxic and cardiotoxic actions

Many of the NBOMe compounds have high potency agonist activity at additional 5-HT receptors and prolonged activation of 5-HT2B can cause cardiac valvulopathy in high doses and chronic use. [11] [16] 5-HT2B receptors have been strongly implicated in causing drug-induced valvular heart disease. [26] [27] [28] The high affinity of NBOMe compounds for adrenergic α1 receptor has been reported to contribute to the stimulant-type cardiovascular effects. [16]

In vitro studies, 25C-NBOMe has been shown to exhibit cytotoxicity on neuronal cell lines SH-SY5Y, PC12, and SN471, and the compound was more potent than methamphetamine at reducing the visibility of the respective cells; the neurotoxicity of the compound involves activation of MAPK/ERK cascade and inhibition of Akt/PKB signaling pathway. [12] 25C-NBOMe, including the other derivative 25D-NBOMe, reduced the visibility of cardiomyocytes H9c2 cells, and both substances downregulated expression level of p21 (CDC24/RAC)-activated kinase 1 (PAK1), an enzyme with documented cardiac protective effects. [12]

Preliminary studies on 25C-NBOMe have shown that the substance is toxic to development, heart health, and brain health in zebrafish, rats, and Artemia salina, a common organism for studying potential drug effects on humans, but more research is needed on the topic, the dosages, and if the toxicology results apply to humans. Researchers of the study also recommended further investigation of the drug's potential in damaging pregnant women and their fetus due to the substance's damaging effects to development. [29] [30]

Emergency treatment

At present, there are no specific antidotes for NBOMes, and all acute intoxication is managed by symptomatic treatments, such as administration of benzodiazepines, antipsychotic drugs, and antiarrhythmic agents, such as beta blockers; some emergency interventions are intended to specifically treat rhabdomyolysis, which may lead to critical complications such as metabolic acidosis and acute kidney injury. [12]

Chemical structure

The 25-NB compounds are mostly N-benzylphenethylamines, [1] [31] though in some cases the phenyl ring of the N-benzyl group is replaced by other heterocycles such as thiophene, pyridine, furan, tetrahydrofuran, benzodioxole or naphthalene, among others. [32] [33]

Generally speaking, they have methoxy groups at the 2 and 5 positions of the phenyl ring, a substitution such as a halogen or alkyl group at the 4 position of the phenyl ring, and a methoxy or other substitution (e.g., hydroxyl, fluoro) at the 2 position of the N- benzyl ring. [1] More rarely, other substitution patterns may be present [34] [35] (see e.g. NBOMe-mescaline, 25G-NBOMe, 2CBFly-NBOMe, 25C-NB3OMe). They differ from the 2C series by the presence of the N-benzyl moiety. [1]

Rarely an alpha-methyl group is present making them N-benzyl amphetamines rather than N-benzyl phenethylamines, but this greatly reduces potency and activity. However in some cases where a side chain methyl group is cyclised back to the ring (e.g. in 2CBCB-NBOMe) or links the two alpha positions (e.g. in DMBMPP), this can improve selectivity for the 5-HT2A receptor subtype. [36]

List of 25-NB derivatives

25I-NBOMe, the most well-known 25-NB derivative

This list includes notable compounds representative of most of the structural variations that have been explored in this series, but is by no means exhaustive. Many derivatives invented for scientific study into the structure-activity relationships of 5-HT2 receptor agonists have never appeared as designer drugs, while conversely some derivatives that have appeared as designer drugs are structurally novel and of unknown pharmacological activity (e.g. C30-NBOMe, 5-APB-NBOMe).

Chemical structure Common name Chemical name CAS number R R1 Cyc
25B-NB N-benzyl-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 155639-26-2 2,5-dimethoxy-4-bromo H phenyl
25C-NB N-benzyl-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane 1391487-65-2 2,5-dimethoxy-4-chloro H phenyl
25I-NB N-benzyl-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 919797-18-5 2,5-dimethoxy-4-iodo H phenyl
25I-NMeTh N-[(thiophen-2-yl)methyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 1391499-03-8 2,5-dimethoxy-4-iodo H thiophen-2-yl
25B-NMePyr N-[(pyridin-2-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1391499-21-0 2,5-dimethoxy-4-bromo H pyridin-2-yl
25I-NMeFur N-[(furan-2-yl)methyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 1391498-93-3 2,5-dimethoxy-4-iodo H furan-2-yl
25I-NMeTHF N-[(tetrahydrofuran-2-yl)methyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 2,5-dimethoxy-4-iodo H tetrahydrofuran-2-yl
25B-NBF N-(2-fluorobenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1539266-17-5 2,5-dimethoxy-4-bromo H 2-fluorophenyl
25B-NBOH N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1335331-46-8 2,5-dimethoxy-4-bromo H 2-hydroxyphenyl
25B-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1026511-90-9 2,5-dimethoxy-4-bromo H 2-methoxyphenyl
25B-NB23DM N-(2,3-dimethoxybenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1391493-68-7 2,5-dimethoxy-4-bromo H 2,3-dimethoxyphenyl
25B-NB25DM N-(2,5-dimethoxybenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 2,5-dimethoxy-4-bromo H 2,5-dimethoxyphenyl
25B-NMe7BF N-[(benzofuran-7-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1391492-46-8 2,5-dimethoxy-4-bromo H benzofuran-7-yl
25B-NMe7DHBF N-[(2,3-dihydrobenzofuran-7-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1391492-40-2 2,5-dimethoxy-4-bromo H 2,3-dihydrobenzofuran-7-yl
25B-NMe7BT N-[(benzothiophen-7-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1391492-59-3 2,5-dimethoxy-4-bromo H benzothiophen-7-yl
25B-NMe7Box N-[(benzoxazol-7-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1391498-73-9 2,5-dimethoxy-4-bromo H benzoxazol-7-yl
25B-NMe7Ind N-[(indol-7-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1391498-28-4 2,5-dimethoxy-4-bromo H indol-7-yl
25B-NMe7Indz N-[(indazol-7-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1391498-43-3 2,5-dimethoxy-4-bromo H indazol-7-yl
25B-NMe7Bim N-[(benzimidazol-7-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1391498-62-6 2,5-dimethoxy-4-bromo H benzimidazol-7-yl
FECIMBI-36 N-[(2-fluoroethoxy)benzyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 2,5-dimethoxy-4-bromo H 2-(2-fluoroethoxy)phenyl
DOB-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminopropane 2,5-dimethoxy-4-bromo methyl 2-methoxyphenyl
25C-NB3OMe N-(3-methoxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane 1566571-34-3 2,5-dimethoxy-4-chloro H 3-methoxyphenyl
25C-NB4OMe N-(4-methoxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane 1566571-35-4 2,5-dimethoxy-4-chloro H 4-methoxyphenyl
C30-NBOMe N-(3,4,5-trimethoxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane 1445574-98-0 2,5-dimethoxy-4-chloro H 3,4,5-trimethoxyphenyl
25C-NBF N-(2-fluorobenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane 1539266-21-1 2,5-dimethoxy-4-chloro H 2-fluorophenyl
25C-NBCl N-(2-chlorobenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane 2,5-dimethoxy-4-chloro H 2-chlorophenyl
25C-NBOH N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane 1391488-16-6 2,5-dimethoxy-4-chloro H 2-hydroxyphenyl
25C-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane 1227608-02-7 2,5-dimethoxy-4-chloro H 2-methoxyphenyl
25C-NBOEt N-(2-ethoxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane 2,5-dimethoxy-4-chloro H 2-ethoxyphenyl
25C-NBOiPr N-(2-isopropoxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane 2,5-dimethoxy-4-chloro H 2-isopropoxyphenyl
25F-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-fluorophenyl)-2-aminoethane 1373917-84-0 2,5-dimethoxy-4-fluoro H 2-methoxyphenyl
25CN-NBOH N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-cyanophenyl)-2-aminoethane 1539266-32-4 2,5-dimethoxy-4-cyano H 2-hydroxyphenyl
25CN-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-cyanophenyl)-2-aminoethane 1354632-16-8 2,5-dimethoxy-4-cyano H 2-methoxyphenyl
25D-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-methylphenyl)-2-aminoethane 1354632-02-2 2,5-dimethoxy-4-methyl H 2-methoxyphenyl
25D-NBOH N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-methylphenyl)-2-aminoethane 1391488-44-0 2,5-dimethoxy-4-methyl H 2-hydroxyphenyl
25E-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-ethylphenyl)-2-aminoethane 1354632-14-6 2,5-dimethoxy-4-ethyl H 2-methoxyphenyl
25E-NBOH N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-ethylphenyl)-2-aminoethane 1391489-79-4 2,5-dimethoxy-4-ethyl H 2-hydroxyphenyl
25G-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-3,4-dimethylphenyl)-2-aminoethane 1354632-65-7 2,5-dimethoxy-3,4-dimethyl H 2-methoxyphenyl
25H-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxyphenyl)-2-aminoethane 1566571-52-5 2,5-dimethoxy H 2-methoxyphenyl
25I-NB34MD N-(3,4-methylenedioxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 1391497-81-6 2,5-dimethoxy-4-iodo H 3,4-methylenedioxyphenyl
25I-NB3OMe N-(3-methoxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 1566571-40-1 2,5-dimethoxy-4-iodo H 3-methoxyphenyl
25I-NB4OMe N-(4-methoxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 1566571-41-2 2,5-dimethoxy-4-iodo H 4-methoxyphenyl
25I-NBF N-(2-fluorobenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 919797-21-0 2,5-dimethoxy-4-iodo H 2-fluorophenyl
25I-NBBr N-(2-bromobenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 1648649-98-2 2,5-dimethoxy-4-iodo H 2-bromophenyl
25I-NBTFM N-[2-(trifluoromethyl)benzyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 2,5-dimethoxy-4-iodo H 2-(trifluoromethyl)phenyl
25I-NBMD N-(2,3-methylenedioxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 919797-25-4 2,5-dimethoxy-4-iodo H 2,3-methylenedioxyphenyl
25B-NBMD N-(2,3-methylenedioxybenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1354632-19-1 2,5-dimethoxy-4-bromo H 2,3-methylenedioxyphenyl
25C-NBMD N-(2,3-methylenedioxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane 1373879-26-5 2,5-dimethoxy-4-chloro H 2,3-methylenedioxyphenyl
25D-NBMD N-(2,3-methylenedioxybenzyl)-1-(2,5-dimethoxy-4-methylphenyl)-2-aminoethane 1391488-97-3 2,5-dimethoxy-4-methyl H 2,3-methylenedioxyphenyl
25I-NBOH N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 919797-20-9 2,5-dimethoxy-4-iodo H 2-hydroxyphenyl
25I-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 919797-19-6 2,5-dimethoxy-4-iodo H 2-methoxyphenyl
DOI-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane 2,5-dimethoxy-4-iodo methyl 2-methoxyphenyl
25I-NBMeOH N-[2-(hydroxymethyl)benzyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 1391494-71-5 2,5-dimethoxy-4-iodo H 2-(hydroxymethyl)phenyl
25I-NBAm N-[2-(carbamoyl)benzyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 1391494-85-1 2,5-dimethoxy-4-iodo H 2-(carbamoyl)phenyl
25I-NMe7DHBF N-[(2,3-dihydrobenzofuran-7-yl)methyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 2,5-dimethoxy-4-iodo H 2,3-dihydrobenzofuran-7-yl
25I-N2Nap1OH N-[(1-hydroxynaphthalen-2-yl)methyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 2,5-dimethoxy-4-iodo H 1-hydroxynaphthalen-2-yl
25I-N3MT2M N-[(3-methoxythiophen-2-yl)methyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 1354632-66-8 2,5-dimethoxy-4-iodo H 3-methoxythiophen-2-yl
25I-N4MT3M N-[(4-methoxythiophen-3-yl)methyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 1354632-73-7 2,5-dimethoxy-4-iodo H 4-methoxythiophen-3-yl
25iP-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-isopropylphenyl)-2-aminoethane 1391487-83-4 2,5-dimethoxy-4-isopropyl H 2-methoxyphenyl
25N-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminoethane 1354632-03-3 2,5-dimethoxy-4-nitro H 2-methoxyphenyl
25N-NBOEt [37] N-(2-ethoxybenzyl)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminoethane 2,5-dimethoxy-4-nitro H 2-ethoxyphenyl
25N-NB-2-OH-3-Me N-(2-hydroxy-3-methylbenzyl)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminoethane 2,5-dimethoxy-4-nitro H 2-hydroxy-3-methylphenyl
25N-NBOCF2H N-(2-difluoromethoxybenzyl)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminoethane 2,5-dimethoxy-4-nitro H 2-difluoromethoxyphenyl
25N-NBPh [38] N-[(2-phenyl)benzyl]-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminoethane 2,5-dimethoxy-4-nitro H o-biphenyl
25N-N1-Nap N-[(naphthalen-1-yl)methyl]-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminoethane 2,5-dimethoxy-4-nitro H 1-naphthyl
25P-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-propylphenyl)-2-aminoethane 1391489-07-8 2,5-dimethoxy-4-propyl H 2-methoxyphenyl
25P-NBOH N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-propylphenyl)-2-aminoethane 1391490-34-8 2,5-dimethoxy-4-propyl H 2-hydroxyphenyl
25TFM-NBOMe N-(2-methoxybenzyl)-1-[2,5-dimethoxy-4-(trifluoromethyl)phenyl]-2-aminoethane 1027161-33-6 2,5-dimethoxy-4-(trifluoromethyl) H 2-methoxyphenyl
25O-NBcP N-(2-cyclopropylbenzyl)-1-(2,4,5-trimethoxyphenyl)-2-aminoethane 2,4,5-trimethoxy H 2-cyclopropylphenyl
25T-NBOMe N-(2-methoxybenzyl)-1-[2,5-dimethoxy-4-(methylthio)phenyl]-2-aminoethane 1539266-47-1 2,5-dimethoxy-4-(methylthio) H 2-methoxyphenyl
25T2-NBOMe N-(2-methoxybenzyl)-1-[2,5-dimethoxy-4-(ethylthio)phenyl]-2-aminoethane 1539266-51-7 2,5-dimethoxy-4-(ethylthio) H 2-methoxyphenyl
25T4-NBOMe N-(2-methoxybenzyl)-1-[2,5-dimethoxy-4-(isopropylthio)phenyl]-2-aminoethane 1354632-17-9 2,5-dimethoxy-4-(isopropylthio) H 2-methoxyphenyl
25T7-NBOMe N-(2-methoxybenzyl)-1-[2,5-dimethoxy-4-(propylthio)phenyl]-2-aminoethane 1539266-55-1 2,5-dimethoxy-4-(propylthio) H 2-methoxyphenyl
25T7-NBOH N-(2-hydroxybenzyl)-1-[2,5-dimethoxy-4-(propylthio)phenyl]-2-aminoethane 1354632-41-9 2,5-dimethoxy-4-(propylthio) H 2-hydroxyphenyl
25AM-NBOMe [39] N-(2-methoxybenzyl)-1-[2,5-dimethoxy-4-pentylphenyl]-2-aminoethane 2,5-dimethoxy-4-(n-pentyl) H 2-methoxyphenyl
NBOMe-mescaline N-(2-methoxybenzyl)-1-(3,4,5-trimethoxyphenyl)-2-aminoethane 1354632-01-1 3,4,5-trimethoxy H 2-methoxyphenyl
NBOMe-escaline N-(2-methoxybenzyl)-1-(3,5-dimethoxy-4-ethoxyphenyl)-2-aminoethane 3,5-dimethoxy-4-ethoxy H 2-methoxyphenyl
NBOMe-thiobuscaline N-(2-methoxybenzyl)-1-(3,5-dimethoxy-4-butylthiophenyl)-2-aminoethane 3,5-dimethoxy-4-(n-butylthio) H 2-methoxyphenyl
MDPEA-NBOMe N-(2-methoxybenzyl)-1-(3,4-methylenedioxyphenyl)-2-aminoethane 3,4-methylenedioxy H 2-methoxyphenyl
2C2-NBOMe N-(2-methoxybenzyl)-1-(2-methoxy-4,5-methylenedioxyphenyl)-2-aminoethane 2-methoxy-4,5-methylenedioxy H 2-methoxyphenyl
MDBZ N-benzyl-1-(3,4-methylenedioxyphenyl)-2-aminopropane 65033-29-6 3,4-methylenedioxy methyl phenyl
Clobenzorex N-(2-chlorobenzyl)-1-phenyl-2-aminopropane 13364-32-4 H methyl 2-chlorophenyl
4-EA-NBOMe N-(2-methoxybenzyl)-1-(4-ethylphenyl)-2-aminopropane 4-ethyl methyl 2-methoxyphenyl
5-APB-NBOMe N-(2-methoxybenzyl)-1-(benzofuran-5-yl)-2-aminopropane benzofuran-5-yl instead of phenyl methyl 2-methoxyphenyl

Similar compounds with related structures are also known including;

Chemical structure Common name Chemical name CAS number
25B-N1POMe N-[1-(2-methoxyphenyl)ethyl]-2,5-dimethoxy-4-bromophenethylamine 1335331-49-1 (R)
1335331-51-5 (S)
2C-B-AN [40] [41] 2-phenyl-2-[2-(2,5-dimethoxy-4-bromophenyl)ethylamino]acetonitrile
25B-N(BOMe)2 2-(4-Bromo-2,5-dimethoxyphenyl)-N,N-bis(2-methoxybenzyl)ethan-1-amine
2CBCB-NBOMe N-[(3-bromo-2,5-dimethoxy-bicyclo[4,2,0]octa-1,3,5-trien-7-yl)methyl]-1-(2-methoxyphenyl)methanamine 1354634-09-5
2CBFly-NBOMe N-(2-methoxybenzyl)-1-(8-bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran-4-yl)-2-aminoethane 1335331-42-4
2C-B-DRAGONFLY-NBOH N-(2-hydroxybenzyl)-1-(8-bromobenzo[1,2-b:4,5-b']difuran-4-yl)-2-aminoethane 1335331-45-7
2C-B-FLY-NB2EtO5Cl [42] N-(2-ethoxy-5-chlorobenzyl)-1-(8-bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran-4-yl)-2-aminoethane
DMBMPP (S,S)-2-(2,5-dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine 1391499-52-7
25B-NAcPip 2-{[2-(4-bromo-2,5-dimethoxyphenyl)ethyl]amino}-1-(piperidin-1-yl)ethanone
ZDCM-04 1,3-dimethyl-7-{2-[1-(2,5-dimethoxy-4-chlorophenyl)propan-2-ylamino]ethyl}purine-2,6-dione
RH-34 3-[2-(2-methoxybenzylamino)ethyl]-1H-quinazoline-2,4-dione 1028307-48-3
5-MeO-T-NBOMe [43] N-(2-methoxybenzyl)-5-methoxytryptamine 1335331-37-7
5MT-NB3OMe N-(3-methoxybenzyl)-5-methoxytryptamine 1648553-42-7

Legality

United Kingdom

A large number of substances in the 25-NB class are Class A drugs in the United Kingdom as a result of the N-benzylphenethylamine catch-all clause in the Misuse of Drugs Act 1971 [44] or are otherwise covered by the Psychoactive Substances Act 2016. [45]

See also

Notes

  1. ^ The potency of N-benzylphenethylamines via buccal, sublingual, or nasal absorption is 50-100 greater (by weight) than oral route compared to the parent 2C-x compounds. [22] Researchers hypothesize the low oral metabolic stability of N-benzylphenethylamines is likely causing the low bioavailability on the oral route, although the metabolic profile of this compounds remains unpredictable; therefore researchers state that the fatalities linked to these substances may partly be explained by differences in the metabolism between individuals. [22]

External links

References

  1. ^ a b c d e f g Adam H (18 January 2017). "Pharmacology and Toxicology of N-Benzylphenethylamine ("NBOMe") Hallucinogens". Neuropharmacology of New Psychoactive Substances. Current Topics in Behavioral Neurosciences. Vol. 32. Springer. pp. 283–311. doi: 10.1007/7854_2016_64. ISBN  978-3-319-52444-3. PMID  28097528.
  2. ^ Pertz HH, Rheineck A, Elz S (1999-01-01). "N-Benzylated derivatives of the hallucinogenic drugs mescaline and escaline as partial agonists at rat vascular 5-HT2A receptors". Naunyn-Schmiedeberg's Archives of Pharmacology. 359: R29. Archived from the original on September 25, 2015.
  3. ^ Heim R (February 28, 2010). Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts (Thesis) (in German). Berlin: Freie Univ. Retrieved 2013-05-10.
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Retrieved from " https://en.wikipedia.org/?title=25-NB&oldid=1197396738"
From Wikipedia, the free encyclopedia
General structure of 25-NB derivatives, where R is usually 2,5-dimethoxy-4-(alkyl or halogen), R1 is usually H but rarely methyl, and Cyc is usually 2-substituted phenyl but can be other heterocycles.

The 25-NB (25x-NBx) series, sometimes alternatively referred to as the NBOMe compounds, is a family of serotonergic psychedelics. [1] They are substituted phenethylamines and were derived from the 2C family. [1] They act as selective agonists of the serotonin 5-HT2A receptor. [2] [3] [4] [5] [6] [7] [8] The 25-NB family is unique relative to other classes of psychedelics in that they are, generally speaking, extremely potent and relatively selective for the 5-HT2A receptor. [1] Use of NBOMe series drugs has caused many deaths and hospitalisations since the drugs popularisation in the 2010s. This is primarily due to their high potency, unpredictable pharmacokinetics, and sellers passing off the compounds in the series as LSD. [9]

Toxicity and harm potential

NBOMe compounds are often associated with life-threatening toxicity and death. [10] [11] Studies on NBOMe family of compounds demonstrated that the substance exhibit neurotoxic and cardiotoxic activity. [12] Reports of autonomic dysfunction remains prevalent with NBOMe compounds, with most individuals experiencing sympathomimetic toxicity such as vasoconstriction, hypertension and tachycardia in addition to hallucinations. [13] [14] [15] [16] [17] Other symptoms of toxidrome of include agitation or aggression, seizure, hyperthermia, diaphoresis, hypertonia, rhabdomyolysis, and death. [13] [17] [11] Researchers report that NBOMe intoxication frequently display signs of serotonin syndrome. [18] The likelihood of seizure is higher in NBOMes compared to other psychedelics. [12]

NBOMe and NBOHs are regularly sold as LSD in blotter papers, [11] [19] which have a bitter taste and different safety profiles. [13] [10] Despite high potency, recreational doses of LSD have only produced low incidents of acute toxicity. [10] Fatalities involved in NBOMe intoxication suggest that a significant number of individuals ingested the substance which they believed was LSD, [15] and researchers report that "users familiar with LSD may have a false sense of security when ingesting NBOMe inadvertently". [13] While most fatalities are due to the physical effects of the drug, there have also been reports of death due to self-harm and suicide under the influence of the substance. [20] [21] [13]

Given limited documentation of NBOMe consumption, the long-term effects of the substance remain unknown. [13] NBOMe compounds are not active orally, [a] and are usually taken sublingually. [1]: 3  When NBOMes are administered sublingually, numbness of the tongue and mouth followed by a metallic chemical taste was observed, and researchers describe this physical side effect as one of the main discriminants between NBOMe compounds and LSD. [23] [24] [25]

Neurotoxic and cardiotoxic actions

Many of the NBOMe compounds have high potency agonist activity at additional 5-HT receptors and prolonged activation of 5-HT2B can cause cardiac valvulopathy in high doses and chronic use. [11] [16] 5-HT2B receptors have been strongly implicated in causing drug-induced valvular heart disease. [26] [27] [28] The high affinity of NBOMe compounds for adrenergic α1 receptor has been reported to contribute to the stimulant-type cardiovascular effects. [16]

In vitro studies, 25C-NBOMe has been shown to exhibit cytotoxicity on neuronal cell lines SH-SY5Y, PC12, and SN471, and the compound was more potent than methamphetamine at reducing the visibility of the respective cells; the neurotoxicity of the compound involves activation of MAPK/ERK cascade and inhibition of Akt/PKB signaling pathway. [12] 25C-NBOMe, including the other derivative 25D-NBOMe, reduced the visibility of cardiomyocytes H9c2 cells, and both substances downregulated expression level of p21 (CDC24/RAC)-activated kinase 1 (PAK1), an enzyme with documented cardiac protective effects. [12]

Preliminary studies on 25C-NBOMe have shown that the substance is toxic to development, heart health, and brain health in zebrafish, rats, and Artemia salina, a common organism for studying potential drug effects on humans, but more research is needed on the topic, the dosages, and if the toxicology results apply to humans. Researchers of the study also recommended further investigation of the drug's potential in damaging pregnant women and their fetus due to the substance's damaging effects to development. [29] [30]

Emergency treatment

At present, there are no specific antidotes for NBOMes, and all acute intoxication is managed by symptomatic treatments, such as administration of benzodiazepines, antipsychotic drugs, and antiarrhythmic agents, such as beta blockers; some emergency interventions are intended to specifically treat rhabdomyolysis, which may lead to critical complications such as metabolic acidosis and acute kidney injury. [12]

Chemical structure

The 25-NB compounds are mostly N-benzylphenethylamines, [1] [31] though in some cases the phenyl ring of the N-benzyl group is replaced by other heterocycles such as thiophene, pyridine, furan, tetrahydrofuran, benzodioxole or naphthalene, among others. [32] [33]

Generally speaking, they have methoxy groups at the 2 and 5 positions of the phenyl ring, a substitution such as a halogen or alkyl group at the 4 position of the phenyl ring, and a methoxy or other substitution (e.g., hydroxyl, fluoro) at the 2 position of the N- benzyl ring. [1] More rarely, other substitution patterns may be present [34] [35] (see e.g. NBOMe-mescaline, 25G-NBOMe, 2CBFly-NBOMe, 25C-NB3OMe). They differ from the 2C series by the presence of the N-benzyl moiety. [1]

Rarely an alpha-methyl group is present making them N-benzyl amphetamines rather than N-benzyl phenethylamines, but this greatly reduces potency and activity. However in some cases where a side chain methyl group is cyclised back to the ring (e.g. in 2CBCB-NBOMe) or links the two alpha positions (e.g. in DMBMPP), this can improve selectivity for the 5-HT2A receptor subtype. [36]

List of 25-NB derivatives

25I-NBOMe, the most well-known 25-NB derivative

This list includes notable compounds representative of most of the structural variations that have been explored in this series, but is by no means exhaustive. Many derivatives invented for scientific study into the structure-activity relationships of 5-HT2 receptor agonists have never appeared as designer drugs, while conversely some derivatives that have appeared as designer drugs are structurally novel and of unknown pharmacological activity (e.g. C30-NBOMe, 5-APB-NBOMe).

Chemical structure Common name Chemical name CAS number R R1 Cyc
25B-NB N-benzyl-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 155639-26-2 2,5-dimethoxy-4-bromo H phenyl
25C-NB N-benzyl-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane 1391487-65-2 2,5-dimethoxy-4-chloro H phenyl
25I-NB N-benzyl-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 919797-18-5 2,5-dimethoxy-4-iodo H phenyl
25I-NMeTh N-[(thiophen-2-yl)methyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 1391499-03-8 2,5-dimethoxy-4-iodo H thiophen-2-yl
25B-NMePyr N-[(pyridin-2-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1391499-21-0 2,5-dimethoxy-4-bromo H pyridin-2-yl
25I-NMeFur N-[(furan-2-yl)methyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 1391498-93-3 2,5-dimethoxy-4-iodo H furan-2-yl
25I-NMeTHF N-[(tetrahydrofuran-2-yl)methyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 2,5-dimethoxy-4-iodo H tetrahydrofuran-2-yl
25B-NBF N-(2-fluorobenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1539266-17-5 2,5-dimethoxy-4-bromo H 2-fluorophenyl
25B-NBOH N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1335331-46-8 2,5-dimethoxy-4-bromo H 2-hydroxyphenyl
25B-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1026511-90-9 2,5-dimethoxy-4-bromo H 2-methoxyphenyl
25B-NB23DM N-(2,3-dimethoxybenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1391493-68-7 2,5-dimethoxy-4-bromo H 2,3-dimethoxyphenyl
25B-NB25DM N-(2,5-dimethoxybenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 2,5-dimethoxy-4-bromo H 2,5-dimethoxyphenyl
25B-NMe7BF N-[(benzofuran-7-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1391492-46-8 2,5-dimethoxy-4-bromo H benzofuran-7-yl
25B-NMe7DHBF N-[(2,3-dihydrobenzofuran-7-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1391492-40-2 2,5-dimethoxy-4-bromo H 2,3-dihydrobenzofuran-7-yl
25B-NMe7BT N-[(benzothiophen-7-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1391492-59-3 2,5-dimethoxy-4-bromo H benzothiophen-7-yl
25B-NMe7Box N-[(benzoxazol-7-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1391498-73-9 2,5-dimethoxy-4-bromo H benzoxazol-7-yl
25B-NMe7Ind N-[(indol-7-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1391498-28-4 2,5-dimethoxy-4-bromo H indol-7-yl
25B-NMe7Indz N-[(indazol-7-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1391498-43-3 2,5-dimethoxy-4-bromo H indazol-7-yl
25B-NMe7Bim N-[(benzimidazol-7-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1391498-62-6 2,5-dimethoxy-4-bromo H benzimidazol-7-yl
FECIMBI-36 N-[(2-fluoroethoxy)benzyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 2,5-dimethoxy-4-bromo H 2-(2-fluoroethoxy)phenyl
DOB-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminopropane 2,5-dimethoxy-4-bromo methyl 2-methoxyphenyl
25C-NB3OMe N-(3-methoxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane 1566571-34-3 2,5-dimethoxy-4-chloro H 3-methoxyphenyl
25C-NB4OMe N-(4-methoxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane 1566571-35-4 2,5-dimethoxy-4-chloro H 4-methoxyphenyl
C30-NBOMe N-(3,4,5-trimethoxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane 1445574-98-0 2,5-dimethoxy-4-chloro H 3,4,5-trimethoxyphenyl
25C-NBF N-(2-fluorobenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane 1539266-21-1 2,5-dimethoxy-4-chloro H 2-fluorophenyl
25C-NBCl N-(2-chlorobenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane 2,5-dimethoxy-4-chloro H 2-chlorophenyl
25C-NBOH N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane 1391488-16-6 2,5-dimethoxy-4-chloro H 2-hydroxyphenyl
25C-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane 1227608-02-7 2,5-dimethoxy-4-chloro H 2-methoxyphenyl
25C-NBOEt N-(2-ethoxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane 2,5-dimethoxy-4-chloro H 2-ethoxyphenyl
25C-NBOiPr N-(2-isopropoxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane 2,5-dimethoxy-4-chloro H 2-isopropoxyphenyl
25F-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-fluorophenyl)-2-aminoethane 1373917-84-0 2,5-dimethoxy-4-fluoro H 2-methoxyphenyl
25CN-NBOH N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-cyanophenyl)-2-aminoethane 1539266-32-4 2,5-dimethoxy-4-cyano H 2-hydroxyphenyl
25CN-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-cyanophenyl)-2-aminoethane 1354632-16-8 2,5-dimethoxy-4-cyano H 2-methoxyphenyl
25D-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-methylphenyl)-2-aminoethane 1354632-02-2 2,5-dimethoxy-4-methyl H 2-methoxyphenyl
25D-NBOH N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-methylphenyl)-2-aminoethane 1391488-44-0 2,5-dimethoxy-4-methyl H 2-hydroxyphenyl
25E-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-ethylphenyl)-2-aminoethane 1354632-14-6 2,5-dimethoxy-4-ethyl H 2-methoxyphenyl
25E-NBOH N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-ethylphenyl)-2-aminoethane 1391489-79-4 2,5-dimethoxy-4-ethyl H 2-hydroxyphenyl
25G-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-3,4-dimethylphenyl)-2-aminoethane 1354632-65-7 2,5-dimethoxy-3,4-dimethyl H 2-methoxyphenyl
25H-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxyphenyl)-2-aminoethane 1566571-52-5 2,5-dimethoxy H 2-methoxyphenyl
25I-NB34MD N-(3,4-methylenedioxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 1391497-81-6 2,5-dimethoxy-4-iodo H 3,4-methylenedioxyphenyl
25I-NB3OMe N-(3-methoxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 1566571-40-1 2,5-dimethoxy-4-iodo H 3-methoxyphenyl
25I-NB4OMe N-(4-methoxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 1566571-41-2 2,5-dimethoxy-4-iodo H 4-methoxyphenyl
25I-NBF N-(2-fluorobenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 919797-21-0 2,5-dimethoxy-4-iodo H 2-fluorophenyl
25I-NBBr N-(2-bromobenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 1648649-98-2 2,5-dimethoxy-4-iodo H 2-bromophenyl
25I-NBTFM N-[2-(trifluoromethyl)benzyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 2,5-dimethoxy-4-iodo H 2-(trifluoromethyl)phenyl
25I-NBMD N-(2,3-methylenedioxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 919797-25-4 2,5-dimethoxy-4-iodo H 2,3-methylenedioxyphenyl
25B-NBMD N-(2,3-methylenedioxybenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1354632-19-1 2,5-dimethoxy-4-bromo H 2,3-methylenedioxyphenyl
25C-NBMD N-(2,3-methylenedioxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane 1373879-26-5 2,5-dimethoxy-4-chloro H 2,3-methylenedioxyphenyl
25D-NBMD N-(2,3-methylenedioxybenzyl)-1-(2,5-dimethoxy-4-methylphenyl)-2-aminoethane 1391488-97-3 2,5-dimethoxy-4-methyl H 2,3-methylenedioxyphenyl
25I-NBOH N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 919797-20-9 2,5-dimethoxy-4-iodo H 2-hydroxyphenyl
25I-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 919797-19-6 2,5-dimethoxy-4-iodo H 2-methoxyphenyl
DOI-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane 2,5-dimethoxy-4-iodo methyl 2-methoxyphenyl
25I-NBMeOH N-[2-(hydroxymethyl)benzyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 1391494-71-5 2,5-dimethoxy-4-iodo H 2-(hydroxymethyl)phenyl
25I-NBAm N-[2-(carbamoyl)benzyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 1391494-85-1 2,5-dimethoxy-4-iodo H 2-(carbamoyl)phenyl
25I-NMe7DHBF N-[(2,3-dihydrobenzofuran-7-yl)methyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 2,5-dimethoxy-4-iodo H 2,3-dihydrobenzofuran-7-yl
25I-N2Nap1OH N-[(1-hydroxynaphthalen-2-yl)methyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 2,5-dimethoxy-4-iodo H 1-hydroxynaphthalen-2-yl
25I-N3MT2M N-[(3-methoxythiophen-2-yl)methyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 1354632-66-8 2,5-dimethoxy-4-iodo H 3-methoxythiophen-2-yl
25I-N4MT3M N-[(4-methoxythiophen-3-yl)methyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 1354632-73-7 2,5-dimethoxy-4-iodo H 4-methoxythiophen-3-yl
25iP-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-isopropylphenyl)-2-aminoethane 1391487-83-4 2,5-dimethoxy-4-isopropyl H 2-methoxyphenyl
25N-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminoethane 1354632-03-3 2,5-dimethoxy-4-nitro H 2-methoxyphenyl
25N-NBOEt [37] N-(2-ethoxybenzyl)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminoethane 2,5-dimethoxy-4-nitro H 2-ethoxyphenyl
25N-NB-2-OH-3-Me N-(2-hydroxy-3-methylbenzyl)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminoethane 2,5-dimethoxy-4-nitro H 2-hydroxy-3-methylphenyl
25N-NBOCF2H N-(2-difluoromethoxybenzyl)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminoethane 2,5-dimethoxy-4-nitro H 2-difluoromethoxyphenyl
25N-NBPh [38] N-[(2-phenyl)benzyl]-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminoethane 2,5-dimethoxy-4-nitro H o-biphenyl
25N-N1-Nap N-[(naphthalen-1-yl)methyl]-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminoethane 2,5-dimethoxy-4-nitro H 1-naphthyl
25P-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-propylphenyl)-2-aminoethane 1391489-07-8 2,5-dimethoxy-4-propyl H 2-methoxyphenyl
25P-NBOH N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-propylphenyl)-2-aminoethane 1391490-34-8 2,5-dimethoxy-4-propyl H 2-hydroxyphenyl
25TFM-NBOMe N-(2-methoxybenzyl)-1-[2,5-dimethoxy-4-(trifluoromethyl)phenyl]-2-aminoethane 1027161-33-6 2,5-dimethoxy-4-(trifluoromethyl) H 2-methoxyphenyl
25O-NBcP N-(2-cyclopropylbenzyl)-1-(2,4,5-trimethoxyphenyl)-2-aminoethane 2,4,5-trimethoxy H 2-cyclopropylphenyl
25T-NBOMe N-(2-methoxybenzyl)-1-[2,5-dimethoxy-4-(methylthio)phenyl]-2-aminoethane 1539266-47-1 2,5-dimethoxy-4-(methylthio) H 2-methoxyphenyl
25T2-NBOMe N-(2-methoxybenzyl)-1-[2,5-dimethoxy-4-(ethylthio)phenyl]-2-aminoethane 1539266-51-7 2,5-dimethoxy-4-(ethylthio) H 2-methoxyphenyl
25T4-NBOMe N-(2-methoxybenzyl)-1-[2,5-dimethoxy-4-(isopropylthio)phenyl]-2-aminoethane 1354632-17-9 2,5-dimethoxy-4-(isopropylthio) H 2-methoxyphenyl
25T7-NBOMe N-(2-methoxybenzyl)-1-[2,5-dimethoxy-4-(propylthio)phenyl]-2-aminoethane 1539266-55-1 2,5-dimethoxy-4-(propylthio) H 2-methoxyphenyl
25T7-NBOH N-(2-hydroxybenzyl)-1-[2,5-dimethoxy-4-(propylthio)phenyl]-2-aminoethane 1354632-41-9 2,5-dimethoxy-4-(propylthio) H 2-hydroxyphenyl
25AM-NBOMe [39] N-(2-methoxybenzyl)-1-[2,5-dimethoxy-4-pentylphenyl]-2-aminoethane 2,5-dimethoxy-4-(n-pentyl) H 2-methoxyphenyl
NBOMe-mescaline N-(2-methoxybenzyl)-1-(3,4,5-trimethoxyphenyl)-2-aminoethane 1354632-01-1 3,4,5-trimethoxy H 2-methoxyphenyl
NBOMe-escaline N-(2-methoxybenzyl)-1-(3,5-dimethoxy-4-ethoxyphenyl)-2-aminoethane 3,5-dimethoxy-4-ethoxy H 2-methoxyphenyl
NBOMe-thiobuscaline N-(2-methoxybenzyl)-1-(3,5-dimethoxy-4-butylthiophenyl)-2-aminoethane 3,5-dimethoxy-4-(n-butylthio) H 2-methoxyphenyl
MDPEA-NBOMe N-(2-methoxybenzyl)-1-(3,4-methylenedioxyphenyl)-2-aminoethane 3,4-methylenedioxy H 2-methoxyphenyl
2C2-NBOMe N-(2-methoxybenzyl)-1-(2-methoxy-4,5-methylenedioxyphenyl)-2-aminoethane 2-methoxy-4,5-methylenedioxy H 2-methoxyphenyl
MDBZ N-benzyl-1-(3,4-methylenedioxyphenyl)-2-aminopropane 65033-29-6 3,4-methylenedioxy methyl phenyl
Clobenzorex N-(2-chlorobenzyl)-1-phenyl-2-aminopropane 13364-32-4 H methyl 2-chlorophenyl
4-EA-NBOMe N-(2-methoxybenzyl)-1-(4-ethylphenyl)-2-aminopropane 4-ethyl methyl 2-methoxyphenyl
5-APB-NBOMe N-(2-methoxybenzyl)-1-(benzofuran-5-yl)-2-aminopropane benzofuran-5-yl instead of phenyl methyl 2-methoxyphenyl

Similar compounds with related structures are also known including;

Chemical structure Common name Chemical name CAS number
25B-N1POMe N-[1-(2-methoxyphenyl)ethyl]-2,5-dimethoxy-4-bromophenethylamine 1335331-49-1 (R)
1335331-51-5 (S)
2C-B-AN [40] [41] 2-phenyl-2-[2-(2,5-dimethoxy-4-bromophenyl)ethylamino]acetonitrile
25B-N(BOMe)2 2-(4-Bromo-2,5-dimethoxyphenyl)-N,N-bis(2-methoxybenzyl)ethan-1-amine
2CBCB-NBOMe N-[(3-bromo-2,5-dimethoxy-bicyclo[4,2,0]octa-1,3,5-trien-7-yl)methyl]-1-(2-methoxyphenyl)methanamine 1354634-09-5
2CBFly-NBOMe N-(2-methoxybenzyl)-1-(8-bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran-4-yl)-2-aminoethane 1335331-42-4
2C-B-DRAGONFLY-NBOH N-(2-hydroxybenzyl)-1-(8-bromobenzo[1,2-b:4,5-b']difuran-4-yl)-2-aminoethane 1335331-45-7
2C-B-FLY-NB2EtO5Cl [42] N-(2-ethoxy-5-chlorobenzyl)-1-(8-bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran-4-yl)-2-aminoethane
DMBMPP (S,S)-2-(2,5-dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine 1391499-52-7
25B-NAcPip 2-{[2-(4-bromo-2,5-dimethoxyphenyl)ethyl]amino}-1-(piperidin-1-yl)ethanone
ZDCM-04 1,3-dimethyl-7-{2-[1-(2,5-dimethoxy-4-chlorophenyl)propan-2-ylamino]ethyl}purine-2,6-dione
RH-34 3-[2-(2-methoxybenzylamino)ethyl]-1H-quinazoline-2,4-dione 1028307-48-3
5-MeO-T-NBOMe [43] N-(2-methoxybenzyl)-5-methoxytryptamine 1335331-37-7
5MT-NB3OMe N-(3-methoxybenzyl)-5-methoxytryptamine 1648553-42-7

Legality

United Kingdom

A large number of substances in the 25-NB class are Class A drugs in the United Kingdom as a result of the N-benzylphenethylamine catch-all clause in the Misuse of Drugs Act 1971 [44] or are otherwise covered by the Psychoactive Substances Act 2016. [45]

See also

Notes

  1. ^ The potency of N-benzylphenethylamines via buccal, sublingual, or nasal absorption is 50-100 greater (by weight) than oral route compared to the parent 2C-x compounds. [22] Researchers hypothesize the low oral metabolic stability of N-benzylphenethylamines is likely causing the low bioavailability on the oral route, although the metabolic profile of this compounds remains unpredictable; therefore researchers state that the fatalities linked to these substances may partly be explained by differences in the metabolism between individuals. [22]

External links

References

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  43. ^ Nichols DE, Sassano MF, Halberstadt AL, Klein LM, Brandt SD, Elliott SP, Fiedler WJ (July 2015). "N-Benzyl-5-methoxytryptamines as Potent Serotonin 5-HT2 Receptor Family Agonists and Comparison with a Series of Phenethylamine Analogues". ACS Chemical Neuroscience. 6 (7): 1165–1175. doi: 10.1021/cn500292d. PMC  4505863. PMID  25547199.
  44. ^ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". www.legislation.gov.uk.
  45. ^ "Psychoactive Substances Act 2016". www.legislation.gov.uk.
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