Chemistry:25-NB
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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,[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
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 |
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25B-NB | N-benzyl-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane | 155639-26-2 | 2,5-dimethoxy-4-bromo | H | phenyl |
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25C-NB | N-benzyl-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane | 1391487-65-2 | 2,5-dimethoxy-4-chloro | H | phenyl |
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25I-NB | N-benzyl-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane | 919797-18-5 | 2,5-dimethoxy-4-iodo | H | phenyl |
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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 |
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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 |
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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 |
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25I-NMeTHF | N-[(tetrahydrofuran-2-yl)methyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane | 2,5-dimethoxy-4-iodo | H | tetrahydrofuran-2-yl | |
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25B-NBF | N-(2-fluorobenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane | 1539266-17-5 | 2,5-dimethoxy-4-bromo | H | 2-fluorophenyl |
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25B-NBOH | N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane | 1335331-46-8 | 2,5-dimethoxy-4-bromo | H | 2-hydroxyphenyl |
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25B-NBOMe | N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane | 1026511-90-9 | 2,5-dimethoxy-4-bromo | H | 2-methoxyphenyl |
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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 |
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25B-NB25DM | N-(2,5-dimethoxybenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane | 2,5-dimethoxy-4-bromo | H | 2,5-dimethoxyphenyl | |
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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 |
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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 |
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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 |
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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 |
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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 |
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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 |
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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 |
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FECIMBI-36 | N-[(2-fluoroethoxy)benzyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane | 2,5-dimethoxy-4-bromo | H | 2-(2-fluoroethoxy)phenyl | |
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DOB-NBOMe | N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminopropane | 2,5-dimethoxy-4-bromo | methyl | 2-methoxyphenyl | |
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25C-NB3OMe | N-(3-methoxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane | 1566571-34-3 | 2,5-dimethoxy-4-chloro | H | 3-methoxyphenyl |
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25C-NB4OMe | N-(4-methoxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane | 1566571-35-4 | 2,5-dimethoxy-4-chloro | H | 4-methoxyphenyl |
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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 |
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25C-NBF | N-(2-fluorobenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane | 1539266-21-1 | 2,5-dimethoxy-4-chloro | H | 2-fluorophenyl |
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25C-NBCl | N-(2-chlorobenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane | 2,5-dimethoxy-4-chloro | H | 2-chlorophenyl | |
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25C-NBOH | N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane | 1391488-16-6 | 2,5-dimethoxy-4-chloro | H | 2-hydroxyphenyl |
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25C-NBOMe | N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane | 1227608-02-7 | 2,5-dimethoxy-4-chloro | H | 2-methoxyphenyl |
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25C-NBOEt | N-(2-ethoxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane | 2,5-dimethoxy-4-chloro | H | 2-ethoxyphenyl | |
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25C-NBOiPr | N-(2-isopropoxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane | 2,5-dimethoxy-4-chloro | H | 2-isopropoxyphenyl | |
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25F-NBOMe | N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-fluorophenyl)-2-aminoethane | 1373917-84-0 | 2,5-dimethoxy-4-fluoro | H | 2-methoxyphenyl |
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25CN-NBOH | N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-cyanophenyl)-2-aminoethane | 1539266-32-4 | 2,5-dimethoxy-4-cyano | H | 2-hydroxyphenyl |
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25CN-NBOMe | N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-cyanophenyl)-2-aminoethane | 1354632-16-8 | 2,5-dimethoxy-4-cyano | H | 2-methoxyphenyl |
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25D-NBOMe | N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-methylphenyl)-2-aminoethane | 1354632-02-2 | 2,5-dimethoxy-4-methyl | H | 2-methoxyphenyl |
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25D-NBOH | N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-methylphenyl)-2-aminoethane | 1391488-44-0 | 2,5-dimethoxy-4-methyl | H | 2-hydroxyphenyl |
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25E-NBOMe | N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-ethylphenyl)-2-aminoethane | 1354632-14-6 | 2,5-dimethoxy-4-ethyl | H | 2-methoxyphenyl |
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25E-NBOH | N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-ethylphenyl)-2-aminoethane | 1391489-79-4 | 2,5-dimethoxy-4-ethyl | H | 2-hydroxyphenyl |
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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 |
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25H-NBOMe | N-(2-methoxybenzyl)-1-(2,5-dimethoxyphenyl)-2-aminoethane | 1566571-52-5 | 2,5-dimethoxy | H | 2-methoxyphenyl |
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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 |
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25I-NB3OMe | N-(3-methoxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane | 1566571-40-1 | 2,5-dimethoxy-4-iodo | H | 3-methoxyphenyl |
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25I-NB4OMe | N-(4-methoxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane | 1566571-41-2 | 2,5-dimethoxy-4-iodo | H | 4-methoxyphenyl |
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25I-NBF | N-(2-fluorobenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane | 919797-21-0 | 2,5-dimethoxy-4-iodo | H | 2-fluorophenyl |
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25I-NBBr | N-(2-bromobenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane | 1648649-98-2 | 2,5-dimethoxy-4-iodo | H | 2-bromophenyl |
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25I-NBTFM | N-[2-(trifluoromethyl)benzyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane | 2,5-dimethoxy-4-iodo | H | 2-(trifluoromethyl)phenyl | |
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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 |
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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 |
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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 |
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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 |
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25I-NBOH | N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane | 919797-20-9 | 2,5-dimethoxy-4-iodo | H | 2-hydroxyphenyl |
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25I-NBOMe | N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane | 919797-19-6 | 2,5-dimethoxy-4-iodo | H | 2-methoxyphenyl |
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DOI-NBOMe | N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane | 2,5-dimethoxy-4-iodo | methyl | 2-methoxyphenyl | |
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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 |
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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 |
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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 | |
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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 | |
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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 |
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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 |
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25iP-NBOMe | N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-isopropylphenyl)-2-aminoethane | 1391487-83-4 | 2,5-dimethoxy-4-isopropyl | H | 2-methoxyphenyl |
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25N-NBOMe | N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminoethane | 1354632-03-3 | 2,5-dimethoxy-4-nitro | H | 2-methoxyphenyl |
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25N-NBOEt [37] | N-(2-ethoxybenzyl)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminoethane | 2,5-dimethoxy-4-nitro | H | 2-ethoxyphenyl | |
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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 | |
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25N-NBOCF2H | N-(2-difluoromethoxybenzyl)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminoethane | 2,5-dimethoxy-4-nitro | H | 2-difluoromethoxyphenyl | |
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25N-NBPh[38] | N-[(2-phenyl)benzyl]-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminoethane | 2,5-dimethoxy-4-nitro | H | o-biphenyl | |
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25N-N1-Nap | N-[(naphthalen-1-yl)methyl]-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminoethane | 2,5-dimethoxy-4-nitro | H | 1-naphthyl | |
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25P-NBOMe | N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-propylphenyl)-2-aminoethane | 1391489-07-8 | 2,5-dimethoxy-4-propyl | H | 2-methoxyphenyl |
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25P-NBOH | N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-propylphenyl)-2-aminoethane | 1391490-34-8 | 2,5-dimethoxy-4-propyl | H | 2-hydroxyphenyl |
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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 |
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25O-NBcP | N-(2-cyclopropylbenzyl)-1-(2,4,5-trimethoxyphenyl)-2-aminoethane | 2,4,5-trimethoxy | H | 2-cyclopropylphenyl | |
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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 |
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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 |
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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 |
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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 |
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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 |
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25AM-NBOMe [39] | N-(2-methoxybenzyl)-1-[2,5-dimethoxy-4-pentylphenyl]-2-aminoethane | 2,5-dimethoxy-4-(n-pentyl) | H | 2-methoxyphenyl | |
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NBOMe-mescaline | N-(2-methoxybenzyl)-1-(3,4,5-trimethoxyphenyl)-2-aminoethane | 1354632-01-1 | 3,4,5-trimethoxy | H | 2-methoxyphenyl |
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NBOMe-escaline | N-(2-methoxybenzyl)-1-(3,5-dimethoxy-4-ethoxyphenyl)-2-aminoethane | 3,5-dimethoxy-4-ethoxy | H | 2-methoxyphenyl | |
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NBOMe-thiobuscaline | N-(2-methoxybenzyl)-1-(3,5-dimethoxy-4-butylthiophenyl)-2-aminoethane | 3,5-dimethoxy-4-(n-butylthio) | H | 2-methoxyphenyl | |
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MDPEA-NBOMe | N-(2-methoxybenzyl)-1-(3,4-methylenedioxyphenyl)-2-aminoethane | 3,4-methylenedioxy | H | 2-methoxyphenyl | |
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2C2-NBOMe | N-(2-methoxybenzyl)-1-(2-methoxy-4,5-methylenedioxyphenyl)-2-aminoethane | 2-methoxy-4,5-methylenedioxy | H | 2-methoxyphenyl | |
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MDBZ | N-benzyl-1-(3,4-methylenedioxyphenyl)-2-aminopropane | 65033-29-6 | 3,4-methylenedioxy | methyl | phenyl |
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Clobenzorex | N-(2-chlorobenzyl)-1-phenyl-2-aminopropane | 13364-32-4 | H | methyl | 2-chlorophenyl |
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4-EA-NBOMe | N-(2-methoxybenzyl)-1-(4-ethylphenyl)-2-aminopropane | 4-ethyl | methyl | 2-methoxyphenyl | |
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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 |
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25B-N1POMe | N-[1-(2-methoxyphenyl)ethyl]-2,5-dimethoxy-4-bromophenethylamine | 1335331-49-1 (R) 1335331-51-5 (S) |
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2C-B-AN [40][41] | 2-phenyl-2-[2-(2,5-dimethoxy-4-bromophenyl)ethylamino]acetonitrile | |
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25B-N(BOMe)2 | 2-(4-Bromo-2,5-dimethoxyphenyl)-N,N-bis(2-methoxybenzyl)ethan-1-amine | |
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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 |
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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 |
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2C-B-DRAGONFLY-NBOH | N-(2-hydroxybenzyl)-1-(8-bromobenzo[1,2-b:4,5-b']difuran-4-yl)-2-aminoethane | 1335331-45-7 |
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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 | |
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DMBMPP | (S,S)-2-(2,5-dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine | 1391499-52-7 |
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25B-NAcPip | 2-{[2-(4-bromo-2,5-dimethoxyphenyl)ethyl]amino}-1-(piperidin-1-yl)ethanone | |
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ZDCM-04 | 1,3-dimethyl-7-{2-[1-(2,5-dimethoxy-4-chlorophenyl)propan-2-ylamino]ethyl}purine-2,6-dione | |
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RH-34 | 3-[2-(2-methoxybenzylamino)ethyl]-1H-quinazoline-2,4-dione | 1028307-48-3 |
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5-MeO-T-NBOMe[43] | N-(2-methoxybenzyl)-5-methoxytryptamine | 1335331-37-7 |
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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
- ↑ 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
- ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 "Pharmacology and Toxicology of N-Benzylphenethylamine ("NBOMe") Hallucinogens". Neuropharmacology of New Psychoactive Substances. Current Topics in Behavioral Neurosciences. 32. Springer. 18 January 2017. pp. 283–311. doi:10.1007/7854_2016_64. ISBN 978-3-319-52444-3. https://link.springer.com/chapter/10.1007/7854_2016_64.
- ↑ "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. 1999-01-01. http://bitnest.ca/external.php?id=%2502%257F%2505J%2516%251A%2509%2504%2504e%255C%25258%2522UV%2508%2507N%2501Q%2540i%251Ec%250B7kq.
- ↑ Heim R (February 28, 2010). Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts (Thesis) (in Deutsch). Berlin: Freie Univ. Retrieved 2013-05-10.
- ↑ Silva M (2009). Theoretical study of the interaction of agonists with the 5-HT2A receptor (Ph.D. thesis). Universität Regensburg.
- ↑ 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.
- ↑ "Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor". Journal of Computer-Aided Molecular Design 25 (1): 51–66. January 2011. doi:10.1007/s10822-010-9400-2. PMID 21088982. Bibcode: 2011JCAMD..25...51S.
- ↑ "Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs)". Neuropharmacology 99: 546–553. December 2015. doi:10.1016/j.neuropharm.2015.08.034. PMID 26318099. http://edoc.unibas.ch/56163/1/20170921163006_59c3cceeb8e5d.pdf.
- ↑ "Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists". ACS Chemical Neuroscience 5 (3): 243–249. March 2014. doi:10.1021/cn400216u. PMID 24397362.
- ↑ "NBOMe Toxicity and Fatalities: A Review of the Literature". Transformative Medicine 1 (1): 12–18. 2022-03-30. doi:10.54299/tmed/msot8578. ISSN 2831-8978. https://scholarcommons.towerhealth.org/t-med/vol1/iss1/3.
- ↑ 10.0 10.1 10.2 "A cluster of 25B-NBOH poisonings following exposure to powder sold as lysergic acid diethylamide (LSD)". Clinical Toxicology 60 (8): 966–969. 28 March 2022. doi:10.1080/15563650.2022.2053150. PMID 35343858. https://www.tandfonline.com/doi/abs/10.1080/15563650.2022.2053150.
- ↑ 11.0 11.1 11.2 11.3 "Neurochemical pharmacology of psychoactive substituted N-benzylphenethylamines: High potency agonists at 5-HT2A receptors". Biochemical Pharmacology 158: 27–34. December 2018. doi:10.1016/j.bcp.2018.09.024. PMID 30261175.
- ↑ 12.0 12.1 12.2 12.3 12.4 "NBOMes–Highly Potent and Toxic Alternatives of LSD". Frontiers in Neuroscience 14: 78. 26 February 2020. doi:10.3389/fnins.2020.00078. PMID 32174803.
- ↑ 13.0 13.1 13.2 13.3 13.4 13.5 "NBOMe Toxicity and Fatalities: A Review of the Literature". Transformative Medicine 1 (1): 12–18. 30 March 2022. doi:10.54299/tmed/msot8578. ISSN 2831-8978. https://scholarcommons.towerhealth.org/t-med/vol1/iss1/3/.
- ↑ "Effect of -NBOMe Compounds on Sensorimotor, Motor, and Prepulse Inhibition Responses in Mice in Comparison With the 2C Analogs and Lysergic Acid Diethylamide: From Preclinical Evidence to Forensic Implication in Driving Under the Influence of Drugs". Front Psychiatry 13: 875722. 21 April 2022. doi:10.3389/fpsyt.2022.875722. PMID 35530025.
- ↑ 15.0 15.1 "Neurochemical and Behavioral Profiling in Male and Female Rats of the Psychedelic Agent 25I-NBOMe". Frontiers in Pharmacology 10: 1406. 12 December 2019. doi:10.3389/fphar.2019.01406. PMID 31915427.
- ↑ 16.0 16.1 16.2 "Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs)". Neuropharmacology 99: 546–553. December 2015. doi:10.1016/j.neuropharm.2015.08.034. ISSN 1873-7064. PMID 26318099. https://www.sciencedirect.com/science/article/abs/pii/S0028390815300794.
- ↑ 17.0 17.1 "Prevalence of use and acute toxicity associated with the use of NBOMe drugs". Clinical Toxicology 53 (2): 85–92. 6 February 2015. doi:10.3109/15563650.2015.1004179. PMID 25658166. https://www.tandfonline.com/doi/abs/10.3109/15563650.2015.1004179.
- ↑ "Toxic Leukoencephalopathy in a Teenager Caused by the Recreational Ingestion of 25I-NBOMe: A Case Report and Review of Literature". Journal of Medical Cases 8 (6): 174–179. 2017-06-05. doi:10.14740/jmc2811w. ISSN 1923-4163. https://www.journalmc.org/index.php/JMC/article/view/2811.
- ↑ "Analysis of 25I-NBOMe, 25B-NBOMe, 25C-NBOMe and Other Dimethoxyphenyl-N-[(2-Methoxyphenyl) MethylEthanamine Derivatives on Blotter Paper"]. Journal of Analytical Toxicology 39 (8): 617–623. 2015. doi:10.1093/jat/bkv073. PMID 26378135.
- ↑ "Death after 25C-NBOMe and 25H-NBOMe consumption". Forensic Science International 279: e1–e6. October 2017. doi:10.1016/j.forsciint.2017.08.028. PMID 28893436. https://www.sciencedirect.com/science/article/abs/pii/S0379073817303377.
- ↑ "Blunt Craniofacial Trauma as a Manifestation of Excited Delirium Caused by New Psychoactive Substances". Journal of Forensic Sciences 61 (6): 1546–1548. November 2016. doi:10.1111/1556-4029.13212. PMID 27723094. https://onlinelibrary.wiley.com/doi/abs/10.1111/1556-4029.13212.
- ↑ 22.0 22.1 "Correlating the Metabolic Stability of Psychedelic 5-HT2A Agonists with Anecdotal Reports of Human Oral Bioavailability". Neurochemical Research 39 (10): 2018–2023. 14 February 2014. doi:10.1007/s11064-014-1253-y. PMID 24519542. https://link.springer.com/article/10.1007/s11064-014-1253-y.
- ↑ "Analysis of 25 C NBOMe in Seized Blotters by HPTLC and GC–MS". Journal of Chromatographic Science 54 (7): 1153–1158. August 2016. doi:10.1093/chromsci/bmw095. PMID 27406128. PMC 4941995. https://academic.oup.com/chromsci/article/54/7/1153/2754859.
- ↑ "25C-NBOMe: preliminary data on pharmacology, psychoactive effects, and toxicity of a new potent and dangerous hallucinogenic drug". BioMed Research International 2014: 734749. 3 July 2014. doi:10.1155/2014/734749. PMID 25105138.
- ↑ "Pharmacology and toxicology of N-Benzyl-phenylethylamines (25X-NBOMe) hallucinogens". Novel Psychoactive Substances: Classification, Pharmacology and Toxicology (2 ed.). Academic Press. September 2021. pp. 279–300. doi:10.1016/B978-0-12-818788-3.00008-5. ISBN 978-0-12-818788-3. https://www.sciencedirect.com/science/article/abs/pii/B9780128187883000085.
- ↑ "Evidence for possible involvement of 5-HT(2B) receptors in the cardiac valvulopathy associated with fenfluramine and other serotonergic medications". Circulation 102 (23): 2836–41. Dec 2000. doi:10.1161/01.CIR.102.23.2836. PMID 11104741.
- ↑ "Possible role of valvular serotonin 5-HT(2B) receptors in the cardiopathy associated with fenfluramine". Molecular Pharmacology 57 (1): 75–81. Jan 2000. PMID 10617681. https://pubmed.ncbi.nlm.nih.gov/10617681/.
- ↑ "Drugs and valvular heart disease". The New England Journal of Medicine 356 (1): 6–9. Jan 2007. doi:10.1056/NEJMp068265. PMID 17202450. https://www.nejm.org/doi/full/10.1056/NEJMp068265.
- ↑ "25C-NBOMe, a Novel Designer Psychedelic, Induces Neurotoxicity 50 Times More Potent Than Methamphetamine In Vitro". Neurotoxicity Research 35 (4): 993–998. 26 February 2019. doi:10.1007/s12640-019-0012-x. PMID 30806983. https://link.springer.com/article/10.1007/s12640-019-0012-x.
- ↑ "Zebrafish and Artemia salina in vivo evaluation of the recreational 25C-NBOMe drug demonstrates its high toxicity". Toxicology Reports 8: 315–323. 2021. doi:10.1016/j.toxrep.2021.01.010. ISSN 2214-7500. PMID 33598409.
- ↑ "DARK Classics in Chemical Neuroscience: NBOMes". ACS Chemical Neuroscience 11 (23): 3860–3869. December 2020. doi:10.1021/acschemneuro.9b00528. PMID 31657895.
- ↑ Michael Robert Braden (2007). "Towards a biophysical understanding of hallucinogen action". Dissertation: 1–176. https://docs.lib.purdue.edu/dissertations/AAI3287241/.
- ↑ "Structure-activity relationships of serotonin 5-HT2A agonists". Wiley Interdisciplinary Reviews: Membrane Transport and Signaling 1 (5): 559–579. 2012. doi:10.1002/wmts.42.
- ↑ "5-HT2A/5-HT2C Receptor Pharmacology and Intrinsic Clearance of N-Benzylphenethylamines Modified at the Primary Site of Metabolism". ACS Chemical Neuroscience 7 (11): 1614–1619. November 2016. doi:10.1021/acschemneuro.6b00265. PMID 27564969.
- ↑ "In vivo evaluation of [18FFECIMBI-36, an agonist 5-HT2A/2C receptor PET radioligand in nonhuman primate"]. Bioorganic & Medicinal Chemistry Letters 27 (1): 21–23. January 2017. doi:10.1016/j.bmcl.2016.11.043. PMID 27889455.
- ↑ "Extensive rigid analogue design maps the binding conformation of potent N-benzylphenethylamine 5-HT2A serotonin receptor agonist ligands". ACS Chemical Neuroscience 4 (1): 96–109. January 2013. doi:10.1021/cn3000668. PMID 23336049.
- ↑ Wallach J, et al. Selective, Partial and Arrestin-Biased 5-HT2A Agonists with Utility in Various Disorders. Patent WO 2022/241006
- ↑ Wallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, Hennessey JJ, Bock HA, Anderson EI, Sherwood AM, Morris H, de Klein R, Klein AK, Cuccurazzu B, Gamrat J, Fannana T, Zauhar R, Halberstadt AL, McCorvy JD. Identification of 5-HT2A Receptor Signaling Pathways Responsible for Psychedelic Potential. bioRxiv 2023 Jul 31:2023.07.29.551106. doi:10.1101/2023.07.29.551106 PMID 37577474
- ↑ Kruegel AC. Phenalkylamines and Methods of Making and Using the Same. Patent WO 2022/192781
- ↑ Phenethylamine Von der Struktur zur Funktion. Nachtschatten Verlag AG. 2013. p. 843. ISBN 978-3-03788-700-4.
- ↑ "Prodrugs of New Psychoactive Substances (NPS): A New Challenge". Journal of Forensic Sciences 65 (3): 913–920. May 2020. doi:10.1111/1556-4029.14268. PMID 31943218. https://researchonline.ljmu.ac.uk/id/eprint/11926/1/JOFS-19-562.R1_accepted_uncorrected.pdf.
- ↑ "In vitro toxicokinetics and analytical toxicology of three novel NBOMe derivatives: Phase I and II metabolism, plasma protein binding, and detectability in standard urine screening approaches studied by means of hyphenated mass spectrometry". Forensic Toxicology 38: 141–159. 2020. doi:10.1007/s11419-019-00498-7. http://researchonline.ljmu.ac.uk/id/eprint/11258/1/FOTO-D-19-00080.R2_accepted.pdf.
- ↑ "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. July 2015. doi:10.1021/cn500292d. PMID 25547199.
- ↑ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014" (in en). http://www.legislation.gov.uk/uksi/2014/1106/made.
- ↑ "Psychoactive Substances Act 2016" (in en). http://www.legislation.gov.uk/ukpga/2016/2/contents/enacted.
![]() | Original source: https://en.wikipedia.org/wiki/25-NB.
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