The25-NB (25x-NBx) series, orNBOMe series, also known as theN-benzylphenethylamines, is a family ofserotonergicpsychedelics.[1][2] They aresubstituted phenethylamines and were derived from the2C family.[2] The most commonly encountered NBOMe drugs are25I-NBOMe,25B-NBOMe, and25C-NBOMe.[3]
The NBOMe drugs act as selectiveagonists of theserotonin5-HT2 receptors.[4][5][6][7][8][9][10] The 25-NB family is unique relative to other classes of psychedelics in that they are, generally speaking, extremelypotent and quiteselective for the 5-HT2 receptors.[2]
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, unpredictablepharmacokinetics, and sellers passing off the compounds in the series asLSD.[11]
The 25-NB drugs are inactiveorally and instead are typically usedsublingually,buccally, byinsufflation, or sometimes viainhalation.[12][3][13] They are typically employed at doses in the range of 50 to 1,500 μg, variable depending on the specific drug, and havedurations in the range of 3 to 12 hours.[3][13][12][14][15] The table below provides an overview of the major 25-NB drugs and their properties.[3][13][12][14][15]
| Compound | Chemical name | Dose | Duration |
|---|---|---|---|
| 25B-NBOMe | N-(2-Methoxybenzyl)-4-bromo-2,5-dimethoxyphenethylamine | 50–700+ μg | 8–12 hours |
| 25C-NBOMe | N-(2-Methoxybenzyl)-4-chloro-2,5-dimethoxyphenethylamine | 50–1,250+ μg | 3–10 hours |
| 25D-NBOMe | N-(2-Methoxybenzyl)-4-methyl-2,5-dimethoxyphenethylamine | 300–1,200+ μg | Unknown |
| 25E-NBOMe | N-(2-Methoxybenzyl)-4-ethyl-2,5-dimethoxyphenethylamine | 50–800 μg | 5–10 hours |
| 25H-NBOMe | N-(2-Methoxybenzyl)-2,5-dimethoxyphenethylamine | Unknown | Unknown |
| 25I-NBOMe | N-(2-Methoxybenzyl)-4-iodo-2,5-dimethoxyphenethylamine | 50–1,200 μg | 4–10 hours |
| 25N-NBOMe | N-(2-Methoxybenzyl)-4-nitro-2,5-dimethoxyphenethylamine | 100–1,300+ μg | 5–10 hours |
| 25P-NBOMe | N-(2-Methoxybenzyl)-4-propyl-2,5-dimethoxyphenethylamine | 100–1,500 μg | Unknown |
| 25T2-NBOMe | N-(2-Methoxybenzyl)-4-ethylthio-2,5-dimethoxyphenethylamine | 100–1,000 μg | Unknown |
| 25T4-NBOMe | N-(2-Methoxybenzyl)-4-isopropylthio-2,5-dimethoxyphenethylamine | 150–1,200 μg | Unknown |
| 25T7-NBOMe | N-(2-Methoxybenzyl)-4-propylthio-2,5-dimethoxyphenethylamine | Unknown | Unknown |
| Notes: The route of administration issublingual,insufflation, and/orbuccal.[3][13][12] They may also besmoked.[12] NBOMe drugs have very loworalbioavailability.[12]Refs:[3][13][12][16][17][18][14][15][19] | |||
NBOMe compounds are often associated with life-threatening toxicity and death.[20][21] Studies on NBOMe family of compounds demonstrated that the substance exhibit neurotoxic and cardiotoxic activity.[3] Reports ofautonomic dysfunction remains prevalent with NBOMe compounds, with most individuals experiencingsympathomimetic toxicity such asvasoconstriction,hypertension andtachycardia in addition to hallucinations.[22][13][23][24][25] Other symptoms oftoxidrome include agitation oraggression,seizure,hyperthermia,diaphoresis,hypertonia,rhabdomyolysis, and death.[22][25][21] Researchers report that NBOMe intoxication frequently display signs ofserotonin syndrome.[26] The likelihood of seizure is higher in NBOMes compared to other psychedelics.[3]
NBOMe and NBOHs are regularly sold as LSD in blotter papers,[21][27] which have a bitter taste and different safety profiles.[22][20] Despite high potency, recreational doses of LSD have only produced low incidents of acute toxicity.[20] Fatalities involved in NBOMe intoxication suggest that a significant number of individuals ingested the substance which they believed was LSD,[23] and researchers report that "users familiar with LSD may have a false sense of security when ingesting NBOMe inadvertently".[22] While most fatalities are due to the physical effects of the drug, there have also been reports of death due toself-harm and suicide under the influence of the substance.[28][29][22]
Given limited documentation of NBOMe consumption, the long-term effects of the substance remain unknown.[22] NBOMe compounds are not active orally,[a] and are usually taken sublingually.[2]: 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.[31][15][32]
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.[21][24] 5-HT2B receptors have been strongly implicated in causing drug-inducedvalvular heart disease.[33][34][35] The high affinity of NBOMe compounds foradrenergic α1 receptor has been reported to contribute to the stimulant-type cardiovascular effects.[24]
In vitro studies, 25C-NBOMe has been shown to exhibitcytotoxicity on neuronal cell linesSH-SY5Y,PC12, and SN471, and the compound was more potent thanmethamphetamine at reducing the visibility of the respective cells; the neurotoxicity of the compound involves activation ofMAPK/ERK cascade and inhibition ofAkt/PKB signaling pathway.[3] 25C-NBOMe, including the other derivative25D-NBOMe, reduced the visibility ofcardiomyocytes H9c2 cells, and both substances downregulated expression level of p21 (CDC24/RAC)-activated kinase 1 (PAK1), an enzyme with documented cardiac protective effects.[3]
Preliminary studies on 25C-NBOMe have shown that the substance is toxic to development, heart health, and brain health inzebrafish, rats, andArtemia salina, a common organism for studying potential drug effects on humans, but more research is needed on the topic, the doses, 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.[36][37]
At present, there are no specificantidotes for NBOMes, and all acute intoxication is managed bysymptomatic treatments, such as administration ofbenzodiazepines,antipsychotic drugs, andantiarrhythmic agents, such asbeta blockers; some emergency interventions are intended to specifically treatrhabdomyolysis, which may lead to critical complications such asmetabolic acidosis andacute kidney injury.[3]
2C drugs like2C-I aremetabolized by themonoamine oxidase (MAO)enzymes, including bothMAO-A andMAO-B.[38][39] As a result, 2C drugs may be potentiated bymonoamine oxidase inhibitors (MAOIs), such asphenelzine,tranylcypromine,moclobemide, andselegiline.[38][39][40] This has the potential to lead tooverdose and serioustoxicity.[38][39][40] In contrast to 2C drugs, 25I-NBOMe has been found not to be metabolized by MAO-A or MAO-B and instead only bycytochrome P450 enzymes.[41] Other 25-NB drugs besides 25I-NBOMe were not assessed.[41]
The NBOMe drugs are highlypotent andselectiveagonists of theserotonin5-HT2 receptors, including of the5-HT2A,5-HT2B, and5-HT2C receptors.[1][3][42][43][44] However, they are much less potent andefficacious at the serotonin 5-HT2B receptor compared to the serotonin 5-HT2A and 5-HT2C receptors.[3][44] The drugs are highly selective for the serotonin 5-HT2 receptors over otherserotonin receptors and over a variety of otherbiological targets.[1][3][42][43] They are likewise inactive asmonoamine reuptake inhibitors andreleasing agents.[42] Many of the NBOMe drugs arepartial agonists of the rat and mousetrace amine-associated receptor 1 (TAAR1), but they are inactive as agonists of the human TAAR1.[45]
In accordance with their psychedelic effects, NBOMe drugs induce thehead-twitch response, a behavioral proxy of psychedelic effects, in rodents.[46] They have also been found to producehyperlocomotion at low doses andhypolocomotion at high doses in rodents.[46]
Unlike most other serotonergic psychedelics, the NBOMe drugs25B-NBOMe and25N-NBOMe have been found to producereinforcing effects in rodents, and hence may havemisuse potential.[3][47][48] Relatedly, 25B-NBOMe robustly increaseddopamine levels in thenucleus accumbens similarly tomethamphetamine.[3][47] The reinforcing effects of 25B-NBOMe were not blocked by serotonin 5-HT2A receptor antagonism, and it is unclear how they are produced.[3][47] However, some NBOMe drugs, such as 25N-NBOMe, have been found to increasephosphorylation of thedopamine transporter (DAT) in thestriatum similarly to methamphetamine in rodents.[49][48] DAT phosphorylation is associated withdopaminereverse transport andefflux, which in turn increasesextracellular dopamine levels.[49][48]
Similarly to other psychedelics likeDOI and2C-T-7,tolerance has been found to gradually develop to the head-twitch response induced by 25I-NBOMe with chronic administration in rodents.[46][50]
No human clinical data exist on the pharmacology of NBOMe derivatives as of 2020.[51]
The 25-NB compounds are mostlyN-benzylphenethylamines,[2][1] though in some cases the phenyl ring of the N-benzyl group is replaced by other heterocycles such asthiophene,pyridine,furan,tetrahydrofuran,benzodioxole ornaphthalene, among others.[52][53]
Generally speaking, they havemethoxy groups at the 2 and 5 positions of thephenyl ring, asubstitution such as ahalogen oralkyl group at the 4 position of the phenyl ring, and a methoxy or other substitution (e.g.,hydroxyl,fluoro) at the 2 position of theN-benzyl ring.[2] More rarely, other substitution patterns may be present[54][55] (see e.g.NBOMe-mescaline,2,4,6-TMPEA-NBOMe,25G-NBOMe,2CBFly-NBOMe,25C-NB3OMe). They differ from the 2C series by the presence of theN-benzylmoiety.[2]
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. in2CBCB-NBOMe) or links the two alpha positions (e.g. inDMBMPP), this can improve selectivity for the 5-HT2A receptor subtype.[56]
2C-B, the first major2C drug and ananalogue ofmescaline, was first described byAlexander Shulgin in the 1970s.[1]Richard Glennon and colleaguessynthesized and described25B-NB (N-benzyl-2C-B) along with a variety of other 25-NBderivatives in 1994.[57][1][58] It was observed at the time that 25B-NB had slightly higheraffinity for the serotonin 5-HT2A receptor than 2C-B and that other 25-NB derivatives with substituents on thebenzyl ring showed very high affinity for the receptor, though functional data were not reported.[57][58]
N-Benzyl derivatives of theketanserin-relatedquinazolinedioneEZS-8, such asRH-34, were first described by Heinz Pertz, Sigurd Elz, and Ralf Heim by 1996 or 1998.[59][60][61]NBOMe-mescaline andNBOMe-escaline were first described by Pertz and colleagues by 1999,[62][63] while25B-NBOMe was first described by Heim and colleagues in 1999.[64][65]25I-NBOMe and other 25-NB compounds such as25TFM-NBOMe and2CBFly-NBOMe were described by Heim and colleagues by 2000.[66][67][68][69] 25I-NBOMe and other 25-NB drugs were subsequently further described by Heim in his dissertation in 2003.[69]25C-NBOMe was not described in the literature until 2010.[70][71] The discovery of the 25-NB compounds by Heim and colleagues has been described byDavid E. Nichols as structurally remarkable, sinceN-alkylation of psychedelic phenethylamines, for instanceBeatrice (N-methyl-DOM), has otherwise invariably abolished the hallucinogenic effects of this class of compounds.[64]
The NBOMe drugs, primarily 25I-NBOMe, were encountered as novelrecreational drugs by 2010, and by 2012 had eclipsed other psychedelics likeLSD andpsilocybin-containing mushrooms in popularity, at least for a time.[1][72][73][74] Various NBOMes, such as 25I-NBOMe, becameSchedule Icontrolled substances in theUnited States in 2013.[1]
The 2C-NBOMe family arecontrolled substances inCanada.[75]
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 theMisuse of Drugs Act 1971[76] or are otherwise covered by thePsychoactive Substances Act 2016.[77]
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 asdesigner 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).
| Structure | Name | Chemical name | CAS # | 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 |
 | DOM-NBOMe | N-(2-methoxybenzyl)-4-methyl-2,5-dimethoxy-2-aminopropane | 2836395-73-2 | 2,5-dimethoxy-4-methyl | methyl | 2-methoxyphenyl |
 | 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[78] | 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[79] | 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-NBOMe | N-(2-methoxybenzyl)-1-[2,5-dimethoxy-4-methoxyphenyl]-2-aminoethane | ? | 2,5-dimethoxy-4-methoxy | H | 2-methoxyphenyl |
 | 25O-NBcP | N-(2-cyclopropylbenzyl)-1-(2,4,5-trimethoxyphenyl)-2-aminoethane | 2,4,5-trimethoxy | H | 2-cyclopropylphenyl | |
 | RS130-180 | N-(2-propargyloxy)-2,5-dimethoxy-4-(dimethylamino)phenethylamine | 4-(N,N-dimethylamino) | H | 2-(prop-2-yn-1-yloxy)phenyl | |
 | 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 |
 | 25T-TFM-NCPM[80] | N-cyclopropylmethyl-1-[2,5-dimethoxy-4-(trifluoromethylthio)phenyl]-2-aminoethane | 2,5-dimethoxy-4-(trifluoromethylthio) | H | cyclopropylmethyl | |
 | 25AM-NBOMe[81] | 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 | |
 | 2,4,6-TMPEA-NBOMe | N-(2-methoxybenzyl)-1-(2,4,6-trimethoxyphenyl)-2-aminoethane | 2,4,6-trimethoxy | H | 2-methoxyphenyl | |
 | MDPEA-NBOMe | N-(2-methoxybenzyl)-1-(3,4-methylenedioxyphenyl)-2-aminoethane | 3,4-methylenedioxy | H | 2-methoxyphenyl | |
 | Lophophine-NBOMe (MMDPEA-NBOMe) | N-(2-methoxybenzyl)-1-(3-methoxy-4,5-methylenedioxyphenyl)-2-aminoethane | 3-methoxy-4,5-methylenedioxy | H | 2-methoxyphenyl | |
 | 2C2-NBOMe (MMDPEA-2-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 | |
 | PEA-NBOMe | N-(2-methoxybenzyl)phenethylamine | 3241-03-0 | H | H | 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:
| Structure | Name | Chemical name | CAS # |
|---|---|---|---|
 | 5-DM-25B-NBOMe | 2-bromo-4-methoxy-5-(2-{[(2-methoxyphenyl)methyl]amino}ethyl)phenol | ? |
 | 25B-N1POMe | N-[1-(2-methoxyphenyl)ethyl]-2,5-dimethoxy-4-bromophenethylamine | 1335331-49-1 (R) 1335331-51-5 (S) |
 | TGF-8027 | N-[1-(2-hydroxyphenyl)ethyl]-2,5-dimethoxy-4-cyanophenethylamine | ? |
 | 2C-B-AN[82][83] | 2-phenyl-2-[2-(2,5-dimethoxy-4-bromophenyl)ethylamino]acetonitrile | |
2_structure.png) | 25B-N(BOMe)2[84] | 2-(4-Bromo-2,5-dimethoxyphenyl)-N,N-bis(2-methoxybenzyl)ethan-1-amine | |
 | 25CN-N3DHBF[85] | 4-(2-[(2,3-dihydro-1-benzofuran-3-yl)amino]ethyl)-2,5-dimethoxybenzonitrile | |
 | 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[86] | 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 (juncosamine) | (S,S)-2-(2,5-dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine | 1391499-52-7 |
 | 2CLisaB | 2-[2-(4-bromo-2,5-dimethoxyphenyl)ethyl]-1,2,3,4-tetrahydroisoquinoline | |
 | 2C-B-3PIP-NBOMe | 3-(4-bromo-2,5-dimethoxyphenyl)-1-[(2-methoxyphenyl)methyl]piperidine | |
 | 2C-B-3PIP-POMe | 5-(4-bromo-2,5-dimethoxyphenyl)-2-(2-methoxyphenyl)piperidine | |
 | 2CBecca | 4-(4-bromo-2,5-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinoline | |
 | 2CJP | 4-(4-bromo-2,5-dimethoxyphenyl)-2,3,4,5-tetrahydro-1H-2-benzazepine | |
 | 25D-NM-NDEAOP | 3-[2-(2,5-dimethoxy-4-methylphenyl)ethyl-methylamino]-N,N-diethylpropanamide | |
 | 25B-NAcPip | 2-{[2-(4-bromo-2,5-dimethoxyphenyl)ethyl]amino}-1-(piperidin-1-yl)ethanone | |
 | ZDCM-04 (DOC-fenethylline) | 1,3-dimethyl-7-{2-[1-(2,5-dimethoxy-4-chlorophenyl)propan-2-ylamino]ethyl}purine-2,6-dione | |
 | RH-34 (EZS-8-NBOMe) | 3-[2-(2-methoxybenzylamino)ethyl]-1H-quinazoline-2,4-dione | 1028307-48-3 |
 | N-Benzyltryptamine (NBnT) | N-benzyltryptamine | 15741-79-4 |
 | 4-HO-NBnT | 4-Hydroxy-N-benzyltryptamine | |
 | 5-MeO-NBnT | 5-Methoxy-N-benzyltryptamine | 25100-31-6 |
 | 5-MeO-T-NBOMe[87] | N-(2-methoxybenzyl)-5-methoxytryptamine | 1335331-37-7 |
 | 5MT-NB3OMe | N-(3-methoxybenzyl)-5-methoxytryptamine | 1648553-42-7 |
 | NEtPhOH-THPI | 3-(1-(2-hydroxyphenylethyl)-1,2,3,6-tetrahydropyridin-5-yl)-1H-indole | |
 | NBOMe-LAD (LSD-NBOMe) | N,N-diethyl-6-[(2-methoxyphenyl)methyl]-9,10-didehydroergoline-8β-carboxamide | ? |
 | PHENETH-LAD | N,N-Diethyl-6-(2-phenylethyl)-9,10-didehydroergoline-8β-carboxamide | ? |
Recently, a new class of psychedelic compounds named NBOMe (or 25X-NBOMe) has appeared on the illegal drug market. NBOMes are analogs of the 2C family of phenethylamine drugs, originally synthesized by Alexander Shulgin, that contain a N-(2-methoxy)benzyl substituent. The most frequently reported drugs from this group are 25I-NBOMe, 25B-NBOMe, and 25C-NBOMe. NBOMe compounds are ultrapotent and highly efficacious agonists of serotonin 5-HT2A and 5-HT2C receptors (Ki values in low nanomolar range) with more than 1000-fold selectivity for 5-HT2A compared with 5-HT1A. They display higher affinity for 5-HT2A receptors than their 2C counterparts and have markedly lower affinity, potency, and efficacy at the 5-HT2B receptor compared to 5-HT2A or 5-HT2C.
Table 4 Human potency data for selected hallucinogens. [...]
25N-NBOMe and other 2C drug derivatives similarly increased p-DAT levels in the NAc and striatum of mice (Seo et al. 2019). [...] increased p-DAT levels lead to an increase in dopamine release, which contribute to elevated dopamine levels.
No human pharmacological data exist [for NBOMe compounds], although metabolism has been investigated in vitro.
The aim of the study was to characterize the partial agonism of congeners of well-established 5-HT2A receptor ligands, identified in a series of ergot alkaloids (so-called ergoline reverse esters with lysergol and dihydrolysergol-I as alcoholic component), indolyltetrahydropyridines (RU 24969 and two derivatives), and quinazolinediones (derivatives of ketanserin), at 5-HT2A receptors in rat tail artery. [...] Quinazolinediones (derivatives of ketanserin) showed weak agonist activity (pKp = 3.83 - 4.66, α = 0.17 - 0,46) and antagonized contractile responses to 5-HT with calculated pKp values of 3.52 - 5.12.
Although the most active tryptamine hallucinogens are N,N-dialkylated, the phenethylamines generally cannot tolerate even a single N-substitution. Even small groups such as methyl or ethyl (see Table 2) abolish their hallucinogenic activity. It was quite remarkable, therefore, when Heim and coworkers reported that N-benzyl groups afforded compounds with remarkable affinity and potency (Heim et al. 1999; Elz et al. 2002; Heim 2003). An oxygen atom at the ortho position of the N-benzyl group enhanced activity further (Braden et al. 2006).
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