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| Formula | C20H27NO3 |
| Molar mass | 329.440 g·mol−1 |
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25G-NBOMe (NBOMe-2C-G) is a derivative of thephenethylaminehallucinogen2C-G, which acts as a highlypotentagonist for thehuman5-HT2Areceptor.[1]
NBOMe compounds are often associated with life-threatening toxicity and death.[2][3] Studies on NBOMe family of compounds demonstrated that the substance exhibit neurotoxic and cardiotoxic activity.[4] Reports ofautonomic dysfunction remains prevalent with NBOMe compounds, with most individuals experiencingsympathomimetic toxicity such asvasoconstriction,hypertension andtachycardia in addition to hallucinations.[5][6][7][8][9] Other symptoms oftoxidrome include agitation oraggression,seizure,hyperthermia,diaphoresis,hypertonia,rhabdomyolysis, and death.[5][9][3] Researchers report that NBOMe intoxication frequently display signs ofserotonin syndrome.[10] The likelihood of seizure is higher in NBOMes compared to other psychedelics.[4]
NBOMe and NBOHs are regularly sold as LSD in blotter papers,[3][11] which have a bitter taste and different safety profiles.[5][2] Despite high potency, recreational doses of LSD have only produced low incidents of acute toxicity.[2] Fatalities involved in NBOMe intoxication suggest that a significant number of individuals ingested the substance which they believed was LSD,[7] and researchers report that "users familiar with LSD may have a false sense of security when ingesting NBOMe inadvertently".[5] 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.[12][13][5]
Given limited documentation of NBOMe consumption, the long-term effects of the substance remain unknown.[5] NBOMe compounds are not active orally,[a] and are usually taken sublingually.[15]: 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.[16][17][18]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.[3][8] 5-HT2B receptors have been strongly implicated in causing drug-inducedvalvular heart disease.[19][20][21] The high affinity of NBOMe compounds foradrenergic α1 receptor has been reported to contribute to the stimulant-type cardiovascular effects.[8]
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.[4] 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.[4]
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 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.[22][23]The Riksdag added 25G-NBOMe toNarcotic Drugs Punishments Act underswedish schedule I ("substances, plant materials and fungi which normally do not have medical use") as of January 16, 2015, published byMedical Products Agency (MPA) in regulationLVFS 2014:11 listed as25G-NBOMe, and2-(2,5-dimetoxi-3,4-dimetylfenyl)-N-(2-metoxibensyl)etanamin.[24]
This substance is aClass A drug in the United Kingdom as a result of theN-benzylphenethylamine catch-all clause in theMisuse of Drugs Act 1971.[25]
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.
