25H-NBOMe

Last updated

25H-NBOMe
25H-NBOMe.svg
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 class Serotonin 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
Formula C18H23NO3
Molar mass 301.386 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]

Contents

Use and effects

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

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

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

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

Pharmacology

Pharmacodynamics

25H-NBOMe activities
Target Affinity (Ki, nM)
5-HT1A 4,520–6,973 (Ki)
28,400 (EC50 Tooltip half-maximal effective concentration)
52% (Emax Tooltip 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
TAAR1 Tooltip 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)
SERT Tooltip Serotonin transporter2,220–2,300 (Ki)
2,080–12,000 (IC50 Tooltip half-maximal inhibitory concentration)
IA (EC50)
NET Tooltip Norepinephrine transporter5,500–16,300 (Ki)
3,650–10,000 (IC50)
IA (EC50)
DAT Tooltip Dopamine transporter35,000–81,400 (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 (EC50 Tooltip 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

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

Society and culture

Sweden

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

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

Notes

  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

  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. 1 2 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. 1 2 3 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. 1 2 3 4 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. 1 2 3 4 5 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.
  7. 1 2 3 4 5 6 Lipow M, Kaleem SZ, Espiridion E (30 March 2022). "NBOMe Toxicity and Fatalities: A Review of the Literature". Transformative Medicine. 1 (1): 12–18. doi: 10.54299/tmed/msot8578 . ISSN   2831-8978. S2CID   247888583.
  8. ↑ Tirri M, Bilel S, Arfè R, Corli G, Marchetti B, Bernardi T, Boccuto F, Serpelloni G, Botrè F, De-Giorgio F, Golembiowska K, Marti M (2022). "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. doi: 10.3389/fpsyt.2022.875722 . PMC   9069068 . PMID   35530025.
  9. 1 2 Cristina M, Matteo M, Nicholas P, Maria C, Micaela T, Raffaella A, Maria L (12 December 2019). "Neurochemical and Behavioral Profiling in Male and Female Rats of the Psychedelic Agent 25I-NBOMe". Frontiers in Pharmacology. 10 1406. doi: 10.3389/fphar.2019.01406 . PMC   6921684 . PMID   31915427.
  10. 1 2 3 Anna R, Dino L, Julia R, Daniele B, Marius H, Matthias L (December 2015). "Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs)" . Neuropharmacology. 99: 546–553. doi:10.1016/j.neuropharm.2015.08.034. ISSN   1873-7064. PMID   26318099. S2CID   10382311.
  11. 1 2 David W, Roumen S, Andrew C, Paul D (6 February 2015). "Prevalence of use and acute toxicity associated with the use of NBOMe drugs" . Clinical Toxicology. 53 (2): 85–92. doi:10.3109/15563650.2015.1004179. PMID   25658166. S2CID   25752763.
  12. ↑ Humston C, Miketic R, Moon K, Ma P, Tobias J (2017-06-05). "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. doi: 10.14740/jmc2811w . ISSN   1923-4163.
  13. ↑ Justin P, Stephen R, Kylin A, Alphonse P, Michelle P (2015). "Analysis of 25I-NBOMe, 25B-NBOMe, 25C-NBOMe and Other Dimethoxyphenyl-N-[(2-Methoxyphenyl) Methyl]Ethanamine Derivatives on Blotter Paper". Journal of Analytical Toxicology. 39 (8): 617–623. doi:10.1093/jat/bkv073. PMC   4570937 . PMID   26378135.
  14. ↑ Morini L, Bernini M, Vezzoli S, Restori M, Moretti M, Crenna S, Papa P, Locatelli C, Osculati AM, Vignali C, Groppi A (October 2017). "Death after 25C-NBOMe and 25H-NBOMe consumption" . Forensic Science International. 279: e1 –e6. doi:10.1016/j.forsciint.2017.08.028. PMID   28893436.
  15. ↑ Byard RW, Cox M, Stockham P (November 2016). "Blunt Craniofacial Trauma as a Manifestation of Excited Delirium Caused by New Psychoactive Substances" . Journal of Forensic Sciences. 61 (6): 1546–1548. doi:10.1111/1556-4029.13212. PMID   27723094. S2CID   4734566.
  16. 1 2 Sabastian LP, Christoffer B, Martin H, Martin AC, Jan K, Jesper LK (14 February 2014). "Correlating the Metabolic Stability of Psychedelic 5-HT2A Agonists with Anecdotal Reports of Human Oral Bioavailability" . Neurochemical Research. 39 (10): 2018–2023. doi:10.1007/s11064-014-1253-y. PMID   24519542. S2CID   254857910.
  17. ↑ Adam H (18 January 2017). "Pharmacology and Toxicology of N-Benzylphenethylamine ("NBOMe") Hallucinogens". Neuropharmacology of New Psychoactive Substances. Current Topics in Behavioral Neurosciences. Vol. 32. Springer. pp. 283–311. doi:10.1007/7854_2016_64. ISBN   978-3-319-52444-3. PMID   28097528.
  18. ↑ Boris D, Cristian C, Marcelo K, Edwar F, Bruce KC (August 2016). "Analysis of 25 C NBOMe in Seized Blotters by HPTLC and GC–MS". Journal of Chromatographic Science. 54 (7): 1153–1158. doi:10.1093/chromsci/bmw095. PMC   4941995 . PMID   27406128.
  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.{{cite journal}}: CS1 maint: article number as page number (link)
  20. ↑ Adam JP, Simon HT, Simon LH (September 2021). "Pharmacology and toxicology of N-Benzyl-phenylethylamines (25X-NBOMe) hallucinogens". Novel Psychoactive Substances: Classification, Pharmacology and Toxicology (2 ed.). Academic Press. pp. 279–300. doi:10.1016/B978-0-12-818788-3.00008-5. ISBN   978-0-12-818788-3. S2CID   240583877.
  21. ↑ Rothman RB, Baumann MH, Savage JE, Rauser L, McBride A, Hufeisen SJ, Roth BL (Dec 2000). "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. doi: 10.1161/01.CIR.102.23.2836 . PMID   11104741.
  22. ↑ Fitzgerald LW, Burn TC, Brown BS, Patterson JP, Corjay MH, Valentine PA, Sun JH, Link JR, Abbaszade I, Hollis JM, Largent BL, Hartig PR, Hollis GF, Meunier PC, Robichaud AJ, Robertson DW (Jan 2000). "Possible role of valvular serotonin 5-HT(2B) receptors in the cardiopathy associated with fenfluramine". Molecular Pharmacology. 57 (1): 75–81. doi:10.1016/S0026-895X(24)26444-0. PMID   10617681.
  23. ↑ Roth BL (Jan 2007). "Drugs and valvular heart disease" . The New England Journal of Medicine. 356 (1): 6–9. doi:10.1056/NEJMp068265. PMID   17202450.
  24. ↑ Xu P, Qiu Q, Li H, Yan S, Yang M, Naman CB, Wang Y, Zhou W, Shen H, Cui W (26 February 2019). "25C-NBOMe, a Novel Designer Psychedelic, Induces Neurotoxicity 50 Times More Potent Than Methamphetamine In Vitro" . Neurotoxicity Research. 35 (4): 993–998. doi:10.1007/s12640-019-0012-x. PMID   30806983. S2CID   255763701.
  25. ↑ Álvarez-Alarcón N, Osorio-Méndez JJ, Ayala-Fajardo A, Garzón-Méndez WF, Garavito-Aguilar ZV (2021). "Zebrafish and Artemia salina in vivo evaluation of the recreational 25C-NBOMe drug demonstrates its high toxicity". Toxicology Reports. 8: 315–323. Bibcode:2021ToxR....8..315A. doi:10.1016/j.toxrep.2021.01.010. ISSN   2214-7500. PMC   7868744 . PMID   33598409.
  26. ↑ "Kᵢ Database". PDSP. 20 June 2025. Retrieved 20 June 2025.
  27. 1 2 Heim R (2004). Development of a new structure-activity conceptSynthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2 -Methoxybenzyl-Partialstruktur: Entwicklung eines neuen Struktur-Wirkungskonzepts (PDF). Universitätsbibliothek (Thesis). Freie Universität Berlin. doi:10.17169/refubium-16193 . Retrieved 20 June 2025.
  28. 1 2 3 4 5 Braden MR, Parrish JC, Naylor JC, Nichols DE (December 2006). "Molecular interaction of serotonin 5-HT2A receptor residues Phe339(6.51) and Phe340(6.52) with superpotent N-benzyl phenethylamine agonists". Mol Pharmacol. 70 (6): 1956–1964. doi:10.1124/mol.106.028720. PMID   17000863.
  29. ↑ Braden MR (2007). Towards a biophysical understanding of hallucinogen action (Ph.D. thesis). Purdue University. ProQuest   304838368.
  30. ↑ Silva M (2009). Theoretical study of the interaction of agonists with the 5-HT2A receptor (PhD.). Universität Regensburg. Table 5.1: Agonistic potency (pEC50) and intrinsic activity (Emax) of 5-HT2AR partial agonistic arylethylamines (indole, methoxybenzene and quinazolinedione derivatives) used in the study. [...] [Compound] 229 [...]
  31. ↑ 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". J Comput Aided Mol Des. 25 (1): 51–66. Bibcode:2011JCAMD..25...51S. doi:10.1007/s10822-010-9400-2. PMID   21088982.
  32. 1 2 3 Burgos-Villaseca J, Klagges-Troncoso J, Decker A, Navarro H, Brea J, Sáez-Briones P, Tirapegui C, Cassels BK (2014). Caracterización Farmacológica In Vitro e In Vivo del Agonista Serotoninérgico 5-HT2 Superpotente 25B-NBOMe: Modulación de Sus Efectos Inducida por Bromación Aromática. XXXVI Congreso Anual de la Sociedad de Farmacología de Chile (in Spanish). doi:10.13140/2.1.4332.8322 . Retrieved 20 June 2025.
  33. ↑ Rickli A, Luethi D, Reinisch J, Buchy D, Hoener MC, Liechti ME (December 2015). "Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs)" (PDF). Neuropharmacology. 99: 546–553. doi:10.1016/j.neuropharm.2015.08.034. PMID   26318099.
  34. ↑ Eshleman AJ, Wolfrum KM, Reed JF, Kim SO, Johnson RA, Janowsky A (December 2018). "Neurochemical pharmacology of psychoactive substituted N-benzylphenethylamines: High potency agonists at 5-HT2A receptors". Biochem Pharmacol. 158: 27–34. doi:10.1016/j.bcp.2018.09.024. PMC   6298744 . PMID   30261175.
  35. ↑ Pottie E, Cannaert A, Stove CP (October 2020). "In vitro structure-activity relationship determination of 30 psychedelic new psychoactive substances by means of β-arrestin 2 recruitment to the serotonin 2A receptor". Arch Toxicol. 94 (10): 3449–3460. Bibcode:2020ArTox..94.3449P. doi:10.1007/s00204-020-02836-w. PMID   32627074.
  36. ↑ Pottie E, Kupriyanova OV, Brandt AL, Laprairie RB, Shevyrin VA, Stove CP (April 2021). "Serotonin 2A Receptor (5-HT2AR) Activation by 25H-NBOMe Positional Isomers: In Vitro Functional Evaluation and Molecular Docking". ACS Pharmacol Transl Sci. 4 (2): 479–487. doi:10.1021/acsptsci.0c00189. PMC   8033611 . PMID   33860178.
  37. ↑ Simmler LD, Buchy D, Chaboz S, Hoener MC, Liechti ME (April 2016). "In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1" (PDF). J Pharmacol Exp Ther. 357 (1): 134–144. doi:10.1124/jpet.115.229765. PMID   26791601. Archived from the original (PDF) on 2025-05-09.
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  39. 1 2 Ferri BG, de Novais CO, Bonani RS, de Barros WA, de Fátima Â, Vilela FC, Giusti-Paiva A (September 2023). "Psychoactive substances 25H-NBOMe and 25H-NBOH induce antidepressant-like behavior in male rats". Eur J Pharmacol. 955 175926. doi: 10.1016/j.ejphar.2023.175926 . PMID   37479015.
  40. 1 2 Jo C, Joo H, Youn DH, Kim JM, Hong YK, Lim NY, Kim KS, Park SJ, Choi SO (November 2022). "Rewarding and Reinforcing Effects of 25H-NBOMe in Rodents". Brain Sci. 12 (11): 1490. doi: 10.3390/brainsci12111490 . PMC   9688077 . PMID   36358416.
  41. ↑ "Läkemedelsverkets föreskrifter - LVFS och HSLF-FS;Läkemedelsverket/Swedish Medical Products Agency" (PDF). Archived (PDF) from the original on 2013-09-28.
  42. ↑ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Statutory Instruments 2014 No. 1106. www.legislation.gov.uk.
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