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25H-NBOMe

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25H-NBOMe
Clinical data
Other names2C-H-NBOMe; NBOMe-2C-H; DMPEA-NBOMe; N-(2-Methoxybenzyl)-2,5-dimethoxyphenethylamine; 2,5-Dimethoxy-N-(2-methoxybenzyl)phenethylamine
Drug classSerotonin 5-HT receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
Legal status
Identifiers
  • 2-(2,5-Dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC18H23NO3
Molar mass301.386 g·mol−1
3D model (JSmol)
  • COC1=CC(=C(C=C1)OC)CCNCC2=CC=CC=C2OC
  • InChI=1S/C18H23NO3/c1-20-16-8-9-18(22-3)14(12-16)10-11-19-13-15-6-4-5-7-17(15)21-2/h4-9,12,19H,10-11,13H2,1-3H3
  • Key:RMLXCDMTGWSEOU-UHFFFAOYSA-N

25H-NBOMe, also known as 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.[2]

Use and effects

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The active dose range of 25H-NBOMe in humans has not been reported and hence is unknown.[3] This is in notable contrast to many other NBOMe drugs.[3]

Toxicity and harm potential

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This section is an excerpt from 25-NB § Toxicity and harm potential.[edit]

NBOMe compounds are often associated with life-threatening toxicity and death.[4][5] Studies on NBOMe family of compounds demonstrated that the substance exhibit neurotoxic and cardiotoxic activity.[6] 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.[7][8][9][10][11] Other symptoms of toxidrome include agitation or aggression, seizure, hyperthermia, diaphoresis, hypertonia, rhabdomyolysis, and death.[7][11][5] Researchers report that NBOMe intoxication frequently display signs of serotonin syndrome.[12] The likelihood of seizure is higher in NBOMes compared to other psychedelics.[6]

NBOMe and NBOHs are regularly sold as LSD in blotter papers,[5][13] which have a bitter taste and different safety profiles.[7][4] Despite high potency, recreational doses of LSD have only produced low incidents of acute toxicity.[4] Fatalities involved in NBOMe intoxication suggest that a significant number of individuals ingested the substance which they believed was LSD,[9] and researchers report that "users familiar with LSD may have a false sense of security when ingesting NBOMe inadvertently".[7] 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.[14][15][7]

Given limited documentation of NBOMe consumption, the long-term effects of the substance remain unknown.[7] NBOMe compounds are not active orally,[a] and are usually taken sublingually.[17]: 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.[18][19][20]

Neurotoxic and cardiotoxic actions

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This section is an excerpt from 25-NB § Neurotoxic and cardiotoxic actions.[edit]

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.[5][10] 5-HT2B receptors have been strongly implicated in causing drug-induced valvular heart disease.[21][22][23] The high affinity of NBOMe compounds for adrenergic α1 receptor has been reported to contribute to the stimulant-type cardiovascular effects.[10]

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.[6] 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.[6]

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.[24][25]

Emergency treatment

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This section is an excerpt from 25-NB § Emergency treatment.[edit]
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.[6]

Interactions

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See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

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Pharmacodynamics

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25H-NBOMe activities
Target Affinity (Ki, nM)
5-HT1A 4,520–6,973 (Ki)
28,400 (EC50Tooltip half-maximal effective concentration)
52% (EmaxTooltip maximal efficacy)
5-HT1B ND
5-HT1D ND
5-HT1E ND
5-HT1F ND
5-HT2A 2.83–49.4 (Ki)
11.0–490 (EC50)
38–144% (Emax)
5-HT2B 62.9 (Ki)
340–463 (EC50)
11–38% (Emax)
5-HT2C 16.4–130 (Ki)
13.8 (EC50)
96% (Emax)
5-HT3 ND
5-HT4 ND
5-HT5A ND
5-HT6 ND
5-HT7 ND
α1A 550
α1B, α1D ND
α2A 530
α2B, α2C ND
β1–β3 ND
D1 14,000
D2 7,700
D3 20,000
D4, D5 ND
H1 4,100
H2–H4 ND
M1–M5 ND
I1 ND
σ1, σ2 ND
MOR ND
DOR ND
KOR ND
TAAR1Tooltip Trace amine-associated receptor 1 >20,000 (Ki) (mouse)
1,400–1,500 (Ki) (rat)
6,100 (EC50) (mouse)
3,000 (EC50) (rat)
>10,000 (EC50) (human)
53% (Emax) (mouse)
37% (Emax) (rat)
SERTTooltip Serotonin transporter 2,220–2,300 (Ki)
2,080–12,000 (IC50Tooltip half-maximal inhibitory concentration)
IA (EC50)
NETTooltip Norepinephrine transporter 5,500–16,300 (Ki)
3,650–10,000 (IC50)
IA (EC50)
DATTooltip Dopamine transporter 35,000–81,400 (Ki)
120,000 (IC50)
IA (EC50)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [26][27][28][29][30][31]
[32][33][34][35][36][37]

25H-NBOMe acts as an agonist of the serotonin 5-HT2 receptors.[38][28]

Its affinity for the serotonin 5-HT2A receptor (Ki = 2.83 nM) was 133-fold higher than that of 2C-H and 24-fold higher than that of 25H-NB (N-benzyl-2C-H), whereas it was 4-fold lower than that of 2C-I and 64-fold lower than that of 25I-NBOMe.[28] In terms of activational potency at the receptor, the drug's potency (EC50Tooltip half-maximal effective concentration = 15.3 nM) was 67-fold higher than that of 2C-H, whereas it was 6-fold lower than that of 2C-I and 35-fold lower than that of 25I-NBOMe.[28] Hence, unlike other NBOMe drugs, 25H-NBOMe appears to have affinity and activational potency at the serotonin 5-HT2A receptor more in line with the 2C psychedelics like 2C-I and much lower than NBOMe drugs like 25I-NBOMe.[28]

25H-NBOMe produces hyperlocomotion, a stimulant-like effect, and the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[32][38][39] Its potency in inducing the head-twitch response was variably lower than that of other NBOMe drugs like 25I-NBOMe and 25B-NBOMe.[38][32] Conversely, its potency in inducing hyperlocomotion was about the same as that of 25I-NBOMe and 25C-NBOMe.[38] The drug has also been found to produce antidepressant-like effects in rodents.[39] 25H-NBOMe has shown reinforcing effects in rodents.[38][40] This included conditioned place preference (CPP) and self-administration.[38][40]

History

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25H-NBOMe was first described in the scientific literature by Ralf Heim at the Free University of Berlin by 2003.[27]

Society and culture

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Sweden

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The Riksdag added 25H-NBOMe to Narcotic Drugs Punishments Act under swedish schedule I ("substances, plant materials and fungi which normally do not have medical use") as of August 1, 2013, published by Medical Products Agency (MPA) in regulation LVFS 2013:15 listed as 25H-NBOMe, and 2-(2,5-dimetoxifenyl)-N-(2-metoxibensyl)etanamin.[41]

United Kingdom

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This substance is a Class A drug in the United Kingdom as a result of the N-benzylphenethylamine catch-all clause in the Misuse of Drugs Act 1971.[42]

See also

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Notes

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  1. ^ The potency of N-benzylphenethylamines via buccal, sublingual, or nasal absorption is 50- to 100-fold greater (by weight) than oral route compared to the parent 2C-x compounds.[16] 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.[16]

References

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  1. ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  2. ^ Amy E, Katherine W, John R, Sonyoung K, Robert J, Aaron J (December 2018). "Neurochemical pharmacology of psychoactive substituted N-benzylphenethylamines: High potency agonists at 5-HT2A receptors". Biochemical Pharmacology. 158: 27–34. doi:10.1016/j.bcp.2018.09.024. PMC 6298744. PMID 30261175.
  3. ^ a b Luethi D, Liechti ME (October 2018). "Monoamine Transporter and Receptor Interaction Profiles in Vitro Predict Reported Human Doses of Novel Psychoactive Stimulants and Psychedelics". Int J Neuropsychopharmacol. 21 (10): 926–931. doi:10.1093/ijnp/pyy047. PMC 6165951. PMID 29850881. Supplementary Table S2. Dose estimates and data sources for psychedelics.
  4. ^ a b c Sean I, Joe R, Jennifer S, and Shaun G (28 March 2022). "A cluster of 25B-NBOH poisonings following exposure to powder sold as lysergic acid diethylamide (LSD)". Clinical Toxicology. 60 (8): 966–969. doi:10.1080/15563650.2022.2053150. PMID 35343858. S2CID 247764056.
  5. ^ a b c d Amy E, Katherine W, John R, Sonyoung K, Robert J, Aaron J (December 2018). "Neurochemical pharmacology of psychoactive substituted N-benzylphenethylamines: High potency agonists at 5-HT2A receptors". Biochemical Pharmacology. 158: 27–34. doi:10.1016/j.bcp.2018.09.024. PMC 6298744. PMID 30261175.
  6. ^ a b c d e Jolanta Z, Monika K, and Piotr A (26 February 2020). "NBOMes–Highly Potent and Toxic Alternatives of LSD". Frontiers in Neuroscience. 14: 78. doi:10.3389/fnins.2020.00078. PMC 7054380. PMID 32174803. 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.
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  19. ^ Francesco SB, Ornella C, Gabriella A, Giuseppe V, Rita S, Flaminia BP, Eduardo C, Pierluigi S, Giovanni M, Guiseppe B, Fabrizio S (3 July 2014). "25C-NBOMe: preliminary data on pharmacology, psychoactive effects, and toxicity of a new potent and dangerous hallucinogenic drug". BioMed Research International. 2014: 734749. doi:10.1155/2014/734749. PMC 4106087. PMID 25105138.
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