25-NB

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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. 25-NB-structure-general.png
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]

Contents

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, [lower-alpha 1] 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 2C-I-NBOMe-skeletal.svg
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 structureCommon nameChemical nameCAS numberRR1Cyc
25B-NB structure.png 25B-NB N-benzyl-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane155639-26-22,5-dimethoxy-4-bromoHphenyl
25C-NB structure.png 25C-NBN-benzyl-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane1391487-65-22,5-dimethoxy-4-chloroHphenyl
25I-NB structure.png 25I-NBN-benzyl-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane919797-18-52,5-dimethoxy-4-iodoHphenyl
25I-NMeTh structure.png 25I-NMeThN-[(thiophen-2-yl)methyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane1391499-03-82,5-dimethoxy-4-iodoHthiophen-2-yl
25B-NMePyr structure.png 25B-NMePyrN-[(pyridin-2-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane1391499-21-02,5-dimethoxy-4-bromoHpyridin-2-yl
25I-NMeFur structure.png 25I-NMeFurN-[(furan-2-yl)methyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane1391498-93-32,5-dimethoxy-4-iodoHfuran-2-yl
25I-NMeTHF structure.png 25I-NMeTHFN-[(tetrahydrofuran-2-yl)methyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane2,5-dimethoxy-4-iodoHtetrahydrofuran-2-yl
25B-NBF.svg 25B-NBF N-(2-fluorobenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane1539266-17-52,5-dimethoxy-4-bromoH2-fluorophenyl
25B-NBOH structure.png 25B-NBOH N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane1335331-46-82,5-dimethoxy-4-bromoH2-hydroxyphenyl
2C-B-NBOMe-skeletal.svg 25B-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane1026511-90-92,5-dimethoxy-4-bromoH2-methoxyphenyl
25B-NB23DM structure.png 25B-NB23DMN-(2,3-dimethoxybenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane1391493-68-72,5-dimethoxy-4-bromoH2,3-dimethoxyphenyl
25B-NB25DM structure.png 25B-NB25DMN-(2,5-dimethoxybenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane2,5-dimethoxy-4-bromoH2,5-dimethoxyphenyl
25B-NMe7BF structure.png 25B-NMe7BFN-[(benzofuran-7-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane1391492-46-82,5-dimethoxy-4-bromoHbenzofuran-7-yl
25B-NMe7DHBF structure.png 25B-NMe7DHBFN-[(2,3-dihydrobenzofuran-7-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane1391492-40-22,5-dimethoxy-4-bromoH2,3-dihydrobenzofuran-7-yl
25B-NMe7BT structure.png 25B-NMe7BTN-[(benzothiophen-7-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane1391492-59-32,5-dimethoxy-4-bromoHbenzothiophen-7-yl
25B-NMe7Box structure.png 25B-NMe7BoxN-[(benzoxazol-7-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane1391498-73-92,5-dimethoxy-4-bromoHbenzoxazol-7-yl
25B-NMe7Ind structure.png 25B-NMe7IndN-[(indol-7-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane1391498-28-42,5-dimethoxy-4-bromoHindol-7-yl
25B-NMe7Indz structure.png 25B-NMe7IndzN-[(indazol-7-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane1391498-43-32,5-dimethoxy-4-bromoHindazol-7-yl
25B-NMe7Bim structure.png 25B-NMe7BimN-[(benzimidazol-7-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane1391498-62-62,5-dimethoxy-4-bromoHbenzimidazol-7-yl
FECIMBI-36 structure.png FECIMBI-36N-[(2-fluoroethoxy)benzyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane2,5-dimethoxy-4-bromoH2-(2-fluoroethoxy)phenyl
DOB-NBOMe structure.png DOB-NBOMeN-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminopropane2,5-dimethoxy-4-bromomethyl2-methoxyphenyl
25C-NB3OMe.svg 25C-NB3OMe N-(3-methoxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane1566571-34-32,5-dimethoxy-4-chloroH3-methoxyphenyl
25C-NB4OMe.svg 25C-NB4OMe N-(4-methoxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane1566571-35-42,5-dimethoxy-4-chloroH4-methoxyphenyl
C30-NBOMe structure.png C30-NBOMeN-(3,4,5-trimethoxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane1445574-98-02,5-dimethoxy-4-chloroH3,4,5-trimethoxyphenyl
25C-NBF.svg 25C-NBF N-(2-fluorobenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane1539266-21-12,5-dimethoxy-4-chloroH2-fluorophenyl
25C-NBCl structure.png 25C-NBClN-(2-chlorobenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane2,5-dimethoxy-4-chloroH2-chlorophenyl
NBOH-2CC structure.png 25C-NBOH N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane1391488-16-62,5-dimethoxy-4-chloroH2-hydroxyphenyl
2C-C-NBOMe-skeletal.svg 25C-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane1227608-02-72,5-dimethoxy-4-chloroH2-methoxyphenyl
25C-NBOEt structure.png 25C-NBOEtN-(2-ethoxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane2,5-dimethoxy-4-chloroH2-ethoxyphenyl
25C-NBOiPr structure.png 25C-NBOiPrN-(2-isopropoxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane2,5-dimethoxy-4-chloroH2-isopropoxyphenyl
25F-NBOMe structure.png 25F-NBOMeN-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-fluorophenyl)-2-aminoethane1373917-84-02,5-dimethoxy-4-fluoroH2-methoxyphenyl
NBOH-2CCN structure.png 25CN-NBOH N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-cyanophenyl)-2-aminoethane1539266-32-42,5-dimethoxy-4-cyanoH2-hydroxyphenyl
25CN-NBOMe.svg 25CN-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-cyanophenyl)-2-aminoethane1354632-16-82,5-dimethoxy-4-cyanoH2-methoxyphenyl
25D-NBOMe2DACS.svg 25D-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-methylphenyl)-2-aminoethane1354632-02-22,5-dimethoxy-4-methylH2-methoxyphenyl
25D-NBOH structure.png 25D-NBOHN-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-methylphenyl)-2-aminoethane1391488-44-02,5-dimethoxy-4-methylH2-hydroxyphenyl
2C-E-NBOMe 2DACS.svg 25E-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-ethylphenyl)-2-aminoethane1354632-14-62,5-dimethoxy-4-ethylH2-methoxyphenyl
25E-NBOH structure.png 25E-NBOH N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-ethylphenyl)-2-aminoethane1391489-79-42,5-dimethoxy-4-ethylH2-hydroxyphenyl
25G-NBOMe.svg 25G-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-3,4-dimethylphenyl)-2-aminoethane1354632-65-72,5-dimethoxy-3,4-dimethylH2-methoxyphenyl
25H-NBOMe.svg 25H-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxyphenyl)-2-aminoethane1566571-52-52,5-dimethoxyH2-methoxyphenyl
25I-NB34MD.svg 25I-NB34MD N-(3,4-methylenedioxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane1391497-81-62,5-dimethoxy-4-iodoH3,4-methylenedioxyphenyl
25I-NB3OMe.svg 25I-NB3OMe N-(3-methoxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane1566571-40-12,5-dimethoxy-4-iodoH3-methoxyphenyl
25I-NB4OMe.svg 25I-NB4OMe N-(4-methoxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane1566571-41-22,5-dimethoxy-4-iodoH4-methoxyphenyl
25i-NBF.svg 25I-NBF N-(2-fluorobenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane919797-21-02,5-dimethoxy-4-iodoH2-fluorophenyl
25I-NBBr structure.png 25I-NBBrN-(2-bromobenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane1648649-98-22,5-dimethoxy-4-iodoH2-bromophenyl
25I-NBTFM structure.png 25I-NBTFMN-[2-(trifluoromethyl)benzyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane2,5-dimethoxy-4-iodoH2-(trifluoromethyl)phenyl
25I-NBMD.svg 25I-NBMD N-(2,3-methylenedioxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane919797-25-42,5-dimethoxy-4-iodoH2,3-methylenedioxyphenyl
25B-NBMD structure.png 25B-NBMDN-(2,3-methylenedioxybenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane1354632-19-12,5-dimethoxy-4-bromoH2,3-methylenedioxyphenyl
25C-NBMD structure.png 25C-NBMDN-(2,3-methylenedioxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane1373879-26-52,5-dimethoxy-4-chloroH2,3-methylenedioxyphenyl
25D-NBMD structure.png 25D-NBMDN-(2,3-methylenedioxybenzyl)-1-(2,5-dimethoxy-4-methylphenyl)-2-aminoethane1391488-97-32,5-dimethoxy-4-methylH2,3-methylenedioxyphenyl
2C-I-NBOH-skeletal.svg 25I-NBOH N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane919797-20-92,5-dimethoxy-4-iodoH2-hydroxyphenyl
2C-I-NBOMe-skeletal.svg 25I-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane919797-19-62,5-dimethoxy-4-iodoH2-methoxyphenyl
DOI-NBOMe structure.png DOI-NBOMeN-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane2,5-dimethoxy-4-iodomethyl2-methoxyphenyl
25I-NBMeOH structure.png 25I-NBMeOHN-[2-(hydroxymethyl)benzyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane1391494-71-52,5-dimethoxy-4-iodoH2-(hydroxymethyl)phenyl
25I-NBAm structure.png 25I-NBAmN-[2-(carbamoyl)benzyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane1391494-85-12,5-dimethoxy-4-iodoH2-(carbamoyl)phenyl
25I-NMe7DHBF structure.png 25I-NMe7DHBFN-[(2,3-dihydrobenzofuran-7-yl)methyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane2,5-dimethoxy-4-iodoH2,3-dihydrobenzofuran-7-yl
25I-N2Nap1OH structure.png 25I-N2Nap1OHN-[(1-hydroxynaphthalen-2-yl)methyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane2,5-dimethoxy-4-iodoH1-hydroxynaphthalen-2-yl
25I-N3MT2M structure.png 25I-N3MT2MN-[(3-methoxythiophen-2-yl)methyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane1354632-66-82,5-dimethoxy-4-iodoH3-methoxythiophen-2-yl
25I-N4MT3M structure.png 25I-N4MT3MN-[(4-methoxythiophen-3-yl)methyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane1354632-73-72,5-dimethoxy-4-iodoH4-methoxythiophen-3-yl
25iP-NBOMe.svg 25iP-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-isopropylphenyl)-2-aminoethane1391487-83-42,5-dimethoxy-4-isopropylH2-methoxyphenyl
25N-NBOMe structure 300px.png 25N-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminoethane1354632-03-32,5-dimethoxy-4-nitroH2-methoxyphenyl
25N-NBOEt structure.png 25N-NBOEt [37] N-(2-ethoxybenzyl)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminoethane2,5-dimethoxy-4-nitroH2-ethoxyphenyl
25N-NB-2-OH-3-Me structure.png 25N-NB-2-OH-3-MeN-(2-hydroxy-3-methylbenzyl)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminoethane2,5-dimethoxy-4-nitroH2-hydroxy-3-methylphenyl
25N-NBOCF2H structure.png 25N-NBOCF2HN-(2-difluoromethoxybenzyl)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminoethane2,5-dimethoxy-4-nitroH2-difluoromethoxyphenyl
25N-NBPh structure.png 25N-NBPh [38] N-[(2-phenyl)benzyl]-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminoethane2,5-dimethoxy-4-nitroHo-biphenyl
25N-N1-Nap structure.png 25N-N1-Nap N-[(naphthalen-1-yl)methyl]-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminoethane2,5-dimethoxy-4-nitroH1-naphthyl
25P-NBOMe2DACS.svg 25P-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-propylphenyl)-2-aminoethane1391489-07-82,5-dimethoxy-4-propylH2-methoxyphenyl
25P-NBOH structure.png 25P-NBOHN-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-propylphenyl)-2-aminoethane1391490-34-82,5-dimethoxy-4-propylH2-hydroxyphenyl
2C-TFM-NBOMe.svg 25TFM-NBOMe N-(2-methoxybenzyl)-1-[2,5-dimethoxy-4-(trifluoromethyl)phenyl]-2-aminoethane1027161-33-62,5-dimethoxy-4-(trifluoromethyl)H2-methoxyphenyl
25O-NBcPr structure.png 25O-NBcP N-(2-cyclopropylbenzyl)-1-(2,4,5-trimethoxyphenyl)-2-aminoethane2,4,5-trimethoxyH2-cyclopropylphenyl
25T-NBOMe structure.png 25T-NBOMeN-(2-methoxybenzyl)-1-[2,5-dimethoxy-4-(methylthio)phenyl]-2-aminoethane1539266-47-12,5-dimethoxy-4-(methylthio)H2-methoxyphenyl
25T2-NBOMe structure.png 25T2-NBOMeN-(2-methoxybenzyl)-1-[2,5-dimethoxy-4-(ethylthio)phenyl]-2-aminoethane1539266-51-72,5-dimethoxy-4-(ethylthio)H2-methoxyphenyl
25T4-NBOMe structure.png 25T4-NBOMeN-(2-methoxybenzyl)-1-[2,5-dimethoxy-4-(isopropylthio)phenyl]-2-aminoethane1354632-17-92,5-dimethoxy-4-(isopropylthio)H2-methoxyphenyl
25T7-NBOMe structure.png 25T7-NBOMe N-(2-methoxybenzyl)-1-[2,5-dimethoxy-4-(propylthio)phenyl]-2-aminoethane1539266-55-12,5-dimethoxy-4-(propylthio)H2-methoxyphenyl
25T7-NBOH structure.png 25T7-NBOHN-(2-hydroxybenzyl)-1-[2,5-dimethoxy-4-(propylthio)phenyl]-2-aminoethane1354632-41-92,5-dimethoxy-4-(propylthio)H2-hydroxyphenyl
NBOMe-2C-AM structure.png 25AM-NBOMe [39] N-(2-methoxybenzyl)-1-[2,5-dimethoxy-4-pentylphenyl]-2-aminoethane2,5-dimethoxy-4-(n-pentyl)H2-methoxyphenyl
NBOMe-mescaline-molecule.png NBOMe-mescaline N-(2-methoxybenzyl)-1-(3,4,5-trimethoxyphenyl)-2-aminoethane1354632-01-13,4,5-trimethoxyH2-methoxyphenyl
Escaline-NBOMe structure.png NBOMe-escalineN-(2-methoxybenzyl)-1-(3,5-dimethoxy-4-ethoxyphenyl)-2-aminoethane3,5-dimethoxy-4-ethoxyH2-methoxyphenyl
NBOMe-thiobuscaline structure.png NBOMe-thiobuscalineN-(2-methoxybenzyl)-1-(3,5-dimethoxy-4-butylthiophenyl)-2-aminoethane3,5-dimethoxy-4-(n-butylthio)H2-methoxyphenyl
MDPEA-NBOMe structure.png MDPEA-NBOMeN-(2-methoxybenzyl)-1-(3,4-methylenedioxyphenyl)-2-aminoethane3,4-methylenedioxyH2-methoxyphenyl
2C2-NBOMe structure.png 2C2-NBOMe N-(2-methoxybenzyl)-1-(2-methoxy-4,5-methylenedioxyphenyl)-2-aminoethane2-methoxy-4,5-methylenedioxyH2-methoxyphenyl
MDBZ.svg MDBZ N-benzyl-1-(3,4-methylenedioxyphenyl)-2-aminopropane65033-29-63,4-methylenedioxymethylphenyl
Clobenzorex structure.svg Clobenzorex N-(2-chlorobenzyl)-1-phenyl-2-aminopropane13364-32-4Hmethyl2-chlorophenyl
4EA-NBOMe structure.png 4-EA-NBOMe N-(2-methoxybenzyl)-1-(4-ethylphenyl)-2-aminopropane4-ethylmethyl2-methoxyphenyl
5APB-NBOMe structure.png 5-APB-NBOMeN-(2-methoxybenzyl)-1-(benzofuran-5-yl)-2-aminopropanebenzofuran-5-yl instead of phenylmethyl2-methoxyphenyl

Similar compounds with related structures are also known including;

Chemical structureCommon nameChemical nameCAS number
25B-N1POMe structure.png 25B-N1POMeN-[1-(2-methoxyphenyl)ethyl]-2,5-dimethoxy-4-bromophenethylamine1335331-49-1 (R)
1335331-51-5 (S)
2CB-AN structure.png 2C-B-AN [40] [41] 2-phenyl-2-[2-(2,5-dimethoxy-4-bromophenyl)ethylamino]acetonitrile
25B-N(BOMe)2 structure.png 25B-N(BOMe)22-(4-Bromo-2,5-dimethoxyphenyl)-N,N-bis(2-methoxybenzyl)ethan-1-amine
2CBCB-NBOMe-skeletal.svg 2CBCB-NBOMe N-[(3-bromo-2,5-dimethoxy-bicyclo[4,2,0]octa-1,3,5-trien-7-yl)methyl]-1-(2-methoxyphenyl)methanamine1354634-09-5
2CBFly-NBOMe.svg 2CBFly-NBOMe N-(2-methoxybenzyl)-1-(8-bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran-4-yl)-2-aminoethane1335331-42-4
2CB-DRAGONFLY-NBOH structure.png 2C-B-DRAGONFLY-NBOHN-(2-hydroxybenzyl)-1-(8-bromobenzo[1,2-b:4,5-b']difuran-4-yl)-2-aminoethane1335331-45-7
2CBFLY-NB2EtO5Cl structure.png 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
SS9b structure.png DMBMPP (S,S)-2-(2,5-dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine1391499-52-7
25B-NAcPip structure.png 25B-NAcPip2-{[2-(4-bromo-2,5-dimethoxyphenyl)ethyl]amino}-1-(piperidin-1-yl)ethanone
ZDCM-04 structure.png ZDCM-04 1,3-dimethyl-7-{2-[1-(2,5-dimethoxy-4-chlorophenyl)propan-2-ylamino]ethyl}purine-2,6-dione
RH-34 structure.png RH-34 3-[2-(2-methoxybenzylamino)ethyl]-1H-quinazoline-2,4-dione1028307-48-3
5MT-NBOMe structure.png 5-MeO-T-NBOMe [43] N-(2-methoxybenzyl)-5-methoxytryptamine1335331-37-7
5MT-NB3OMe structure.png 5MT-NB3OMeN-(3-methoxybenzyl)-5-methoxytryptamine1648553-42-7

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]

Related Research Articles

<span class="mw-page-title-main">Serotonin receptor agonist</span> Neurotransmission-modulating substance

A serotonin receptor agonist is an agonist of one or more serotonin receptors. They activate serotonin receptors in a manner similar to that of serotonin, a neurotransmitter and hormone and the endogenous ligand of the serotonin receptors.

<span class="mw-page-title-main">25I-NBOH</span> Chemical compound

25I-NBOH is a derivative of the phenethylamine-derived hallucinogen 2C-I that was discovered in 2006 by a team at Purdue University.

<span class="mw-page-title-main">25I-NBOMe</span> Synthetic hallucinogen

25I-NBOMe is a novel synthetic psychoactive substance with strong hallucinogenic properties, synthesized in 2003 for research purposes. Since 2010, it has circulated in the recreational drug scene, often misrepresented as LSD. The recreational usage of 25I is associated with severe intoxication and deaths in humans.

<span class="mw-page-title-main">25B-NBOMe</span> Chemical compound

25B-NBOMe is a derivative of the phenethylamine psychedelic 2C-B, discovered in 2004 by Ralf Heim at the Free University of Berlin. It acts as a potent full agonist for the 5HT2A receptor. Anecdotal reports from users 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. Duration of effects lasts about 12–16 hours, although the parent compound is rapidly cleared from the blood when used in the radiolabeled form in tracer doses. Recently, Custodio et al (2019) evaluated the potential involvement of dysregulated dopaminergic system, neuroadaptation, and brain wave changes which may contribute to the rewarding and reinforcing properties of 25B-NBOMe in rodents.

<span class="mw-page-title-main">25I-NBF</span> Chemical compound

25I-NBF is a derivative of the phenethylamine hallucinogen 2C-I, which acts as a highly potent partial agonist for the human 5-HT2A receptor, with bias towards the β-arrestin 2 coupled signalling pathway. It has been studied in its 11C radiolabelled form as a potential ligand for mapping the distribution of 5-HT2A receptors in the brain, using positron emission tomography (PET).

<span class="mw-page-title-main">25TFM-NBOMe</span> Chemical compound

25TFM-NBOMe is a derivative of the phenethylamine hallucinogen 2C-TFM, discovered in 2004 by Ralf Heim at the Free University of Berlin. It acts as a potent partial agonist for the 5-HT2A receptor, though its relative potency is disputed, with some studies finding it to be of lower potency than 25I-NBOMe, while others show it to be of similar or higher potency, possibly because of differences in the assay used. 2C-TFM-NB2OMe can be taken to produce psychedelic effects similar to 2C-I-NB2OMe and 2C-D-NB2OMe.

<span class="mw-page-title-main">25C-NBOMe</span> Psychedelic drug

25C-NBOMe is a psychedelic drug and derivative of the psychedelic phenethylamine 2C-C. 25C-NBOMe appeared on online vendor sites in 2010 but was not reported in the literature until 2011. It acts as a potent agonist of the 5-HT2A receptor, and has been studied in its 11C radiolabelled form as a potential ligand for mapping the distribution of 5-HT2A receptors in the brain, using positron emission tomography (PET). Multiple deaths have occurred from usage of 25C-NBOMe due to the ease of accidental overdose. The long-term toxic effects of the drug have not been researched.

<span class="mw-page-title-main">25D-NBOMe</span> Chemical compound

25D-NBOMe is a derivative of the phenethylamine derived hallucinogen 2C-D. It acts in a similar manner to related compounds such as 25I-NBOMe, which is a potent agonist at the 5-HT2A receptor. 25D-NBOMe has been sold as a street drug since 2010 and produces similar effects in humans to related compounds such as 25I-NBOMe and 25C-NBOMe. It was banned as a Temporary Class Drug in the UK on 10 June 2013 after concerns about its recreational use.

<span class="mw-page-title-main">25C-NBOH</span> Chemical compound

25-C-NBOH is a derivative of the phenethylamine derived hallucinogen 2C-C which has been sold as a designer drug. It has similar serotonin receptor affinity to the better-known compound 25C-NBOMe.

<span class="mw-page-title-main">25CN-NBOMe</span> Chemical compound

25CN-NBOMe is a derivative of the phenethylamine 2C-CN. It acts in a similar manner to related compounds such as 25I-NBOMe, which are potent agonists at the 5HT2A receptor.

<span class="mw-page-title-main">25N-NBOMe</span> Chemical compound

25N-NBOMe is a derivative of the hallucinogen 2C-N. The pharmacological properties of 25N-NBOMe have not been described in the scientific literature, but it is believed to act in a similar manner to related compounds such as 25I-NBOMe and 25C-NBOMe, which are potent agonists at the 5HT2A receptor. 25N-NBOMe has been sold as a street drug and has only been described in the literature in terms of identification by forensic analysis.

<span class="mw-page-title-main">25E-NBOMe</span> Chemical compound

25E-NBOMe is a derivative of the phenethylamine 2C-E. It acts in a similar manner to related compounds such as 25I-NBOMe, which are potent agonists at the 5-HT2A receptor. 25E-NBOMe has been sold as a drug and produces similar effects in humans to related compounds such as 25I-NBOMe and 25C-NBOMe.

<span class="mw-page-title-main">25P-NBOMe</span> Chemical compound

25P-NBOMe is a derivative of the phenethylamine 2C-P. It acts in a similar manner to related compounds such as 25I-NBOMe, which are potent agonists at the 5-HT2A receptor. 25P-NBOMe has been sold as a drug and produces similar effects in humans to related compounds such as 25I-NBOMe and 25C-NBOMe.

<span class="mw-page-title-main">25B-NBOH</span> Chemical compound

25B-NBOH is a derivative of the phenethylamine derived hallucinogen 2C-B which has been sold as a designer drug. It acts as a potent serotonin receptor agonist with similar affinity to the better-known compound 25B-NBOMe at 5-HT2A and 5-HT2C receptors with pKis values of 8.3 and 9.4, respectively.

<span class="mw-page-title-main">25C-NBF</span> Chemical compound

25C-NBF is a derivative of the phenethylamine hallucinogen 2C-C, which acts as a highly potent partial agonist for the human 5-HT2A receptor.

<span class="mw-page-title-main">25G-NBOMe</span> Chemical compound

25G-NBOMe (NBOMe-2C-G) is a derivative of the phenethylamine hallucinogen 2C-G, which acts as a highly potent agonist for the human 5-HT2A receptor.

<span class="mw-page-title-main">25H-NBOMe</span> Chemical compound

25H-NBOMe (NBOMe-2C-H) is a derivative of the phenethylamine hallucinogen 2C-H, which acts as a highly potent full agonist for the human 5-HT2A receptor.

<span class="mw-page-title-main">25iP-NBOMe</span> Chemical compound

25iP-NBOMe is a derivative of the phenethylamine hallucinogen 2C-iP, which acts as a highly potent agonist for the human 5-HT2A receptor.

<span class="mw-page-title-main">25E-NBOH</span> Chemical compound

25E-NBOH is a derivative of the phenethylamine derived hallucinogen 2C-E. It was first developed by Martin Hansen at the University of Copenhagen in 2010 as a brain imaging agent, but has subsequently been sold as a designer drug, first being identified in Brazil in 2018 on seized blotter paper, as well as in Slovenia. It acts as a potent serotonin receptor agonist with similar affinity to better-known compounds such as 25I-NBOMe at 5-HT2A and 5-HT2C receptors.

<span class="mw-page-title-main">N-Benzyl-2C-B</span> Chemical compound

N-Benzyl-2C-B is a recreational designer drug from the 25-NB subgroup of the substituted phenethylamine family, with psychedelic effects. It has a binding affinity (Ki) of 16 nM at the serotonin receptor 5-HT2A and 90 nM at 5-HT2C and reportedly has a potency in between that of 2C-B and NBOMe-2C-B.

References

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  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.
  4. ↑ Silva M (2009). Theoretical study of the interaction of agonists with the 5-HT2A receptor (Ph.D. thesis). Universität Regensburg.
  5. ↑ Hansen M (2011). Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain (Ph.D. thesis). University of Copenhagen.
  6. ↑ Silva ME, Heim R, Strasser A, Elz S, Dove S (January 2011). "Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor". Journal of Computer-Aided Molecular Design. 25 (1): 51–66. Bibcode:2011JCAMD..25...51S. CiteSeerX   10.1.1.688.2670 . doi:10.1007/s10822-010-9400-2. PMID   21088982. S2CID   3103050.
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