25B-NBOMe

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25B-NBOMe, also known as NBOMe-2C-B and Cimbi-36, is a psychedelic drug of the 25-NB (NBOMe) family derived from 2C-B. It acts as a potent full agonist for the 5HT2A receptor.[1][2][3] Duration of effects lasts about 3 to 10Script error: No such module "String".hours,[4] although the parent compound is rapidly cleared from the blood when used in the radiolabeled form in tracer doses.[5] Recently, Custodio et al. (2019) evaluated the potential involvement of dysregulated dopaminergic system, neuroadaptation, and brain wave changes which may contribute to the rewarding and reinforcing properties of 25B-NBOMe in rodents.[6]

The carbon-11 labeled version of this compound ([11C]Cimbi-36) was synthesized and validated as a radioactive tracer for positron emission tomography (PET) in Copenhagen.[7][8][9] As a 5-HT2A receptor agonist PET radioligand, [11C]Cimbi-36 was hypothesized to provide a more functional marker of these receptors. Also, [11C]Cimbi-36 is investigated as a potential marker of serotonin release and thus could serve as an indicator of serotonin levels in vivo. [11C]Cimbi-36 is now undergoing clinical trials as a PET-ligand in humans.[10][11][12]

25B-NBOMe was first described in the scientific literature by Ralf Heim and colleagues at the Free University of Berlin by 1999.[13]

Use and effects

The dose range of 25B-NBOMe has been given as 0.05 to 0.7Script error: No such module "String".mg sublingually, with a typical dose estimate of 0.4Script error: No such module "String".mg.[14]

Toxicity and harm potential

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Neurotoxic and cardiotoxic actions

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Emergency treatment

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Interactions

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Pharmacology

Pharmacodynamics

25B-NBOMe activities
Target Affinity (Ki, nM)
5-HT1A 1,255–3,600
5-HT1B >10,000
5-HT1D 1,472
5-HT1E >10,000
5-HT1F ND
5-HT2A 0.19–0.8 (Ki)
0.12–40 (EC50Tooltip half-maximal effective concentration)
28–167% (EmaxTooltip maximal efficacy)
5-HT2B 0.5 (Ki)
7.3–10 (EC50)
19–79% (Emax)
5-HT2C 1.7–6.2 (Ki)
0.90–12 (EC50)
93–110% (Emax)
5-HT3 >10,000
5-HT4 ND
5-HT5A 4,087
5-HT6 48
5-HT7 4,720
α1A 430–1,256
α1B 6,180
α1D 2,253
α2A 430–3,551
α2B 1,264
α2C 646
β1 6,719
β2 >10,000
β3 ND
D1 9,300–>10,000
D2 840–>10,000
D3 718–2,700
D4 2,253
D5 >10,000
H1 80
H2 ND
H3 >10,000
H4 ND
M1–M4 >10,000
M5 5,241
I1 ND
σ1 310
σ2 64
MOR >10,000
DOR ND
KOR 642
TAAR1Tooltip Trace amine-associated receptor 1 4,500 (Ki) (mouse)
280 (Ki) (rat)
6,100 (EC50) (mouse)
1,200 (EC50) (rat)
>10,000 (EC50) (human)
47% (Emax) (mouse)
37% (Emax) (rat)
SERTTooltip Serotonin transporter 388–840 (Ki)
4,900–7,100 (IC50Tooltip half-maximal inhibitory concentration)
ND (EC50)
NETTooltip Norepinephrine transporter 1,100–1,718 (Ki)
6,700–11,000 (IC50)
ND (EC50)
DATTooltip Dopamine transporter 7,200–>10,000 (Ki)
99,000–117,000 (IC50)
ND (EC50)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [15][16][17][18][8][19][20][21]
[22][23][24][25][26][27][28]

25B-NBOMe is a selective serotonin 5-HT2 receptor agonist.[16] It showed roughly the same affinity for the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors in one study (Ki = 0.5–1.7Script error: No such module "String".nM).[16] However, in another study, it showed 12- to 20-fold selectivity for the serotonin 5-HT2A receptor (Ki = 0.5Script error: No such module "String".nM) over the serotonin 5-HT2B and 5-HT2C receptors (Ki = 10 and 6.2Script error: No such module "String".nM, respectively).[29] The drug is highly selective for the serotonin 5-HT2 receptors over a variety of other serotonin receptors, as well as over various other monoamine receptors and over the monoamine transporters (>200-fold selectivity).[16][29] However, 25B-NBOMe is a low-potency partial agonist of the rat and mouse trace amine-associated receptor 1 (TAAR1) but is inactive at the human TAAR1.[28]

25B-NBOMe has been found to increase levels of glutamate, serotonin, dopamine, and acetylcholine in the frontal cortex, striatum, and nucleus accumbens in rats.[30] Other serotonergic psychedelics like LSD and DOI have also been found to increase glutamate levels in the frontal cortex in rodents, and this effect can be blocked by the serotonin 5-HT2A receptor antagonist volinanserin (MDL-100,907).[30] 25B-NBOMe shows an inverted U-shaped dose–response curve in terms of neurotransmitter elevations in multiple brain areas.[30] This may be due to an inhibitory effect of serotonin 5-HT2C receptors at higher doses.[30] 25B-NBOMe produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents, and this effect shows an inverted U-shaped dose–response curve similarly to its influences on neurotransmitter levels.[30] The head twitches and hallucinogenic effects of 25B-NBOMe may be due to increased cortical glutamate release secondary to serotonin 5-HT2A receptor activation.[30] The effects of 25B-NBOMe on levels of other neurotransmitters, such as accumbal dopamine concentrations, may also be mediated by activation of serotonin 5-HT2A receptors and glutamate elevation.[30] It has been suggested that the serotonin elevations with 25B-NBOMe may be involved in its production of serotonin syndrome in humans.[29]

Unlike many other serotonergic psychedelics, 25B-NBOMe has been found to produce reinforcing effects in rodents, including conditioned place preference (CPP) and self-administration, and hence may have misuse potential.[31][32][29] Accordingly, 25B-NBOMe robustly increased dopamine levels in the nucleus accumbens in rodents similarly to but a lesser extent than methamphetamine, and its reinforcing effects could be blocked by the dopamine receptor antagonists SCH-23390 and haloperidol.[31][32][29] Serotonin 5-HT2A receptor activation is known to increase dopamine release in the mesolimbic pathway.[32] However, the reinforcing effects of 25B-NBOMe were not blocked by the selective serotonin 5-HT2A receptor antagonist ketanserin.[31][32] Similarly to 25B-NBOMe, 25N-NBOMe has also shown reinforcing effects in rodents.[33] More research is needed to elucidate how 25B-NBOMe and other NBOMe drugs produce reinforcing effects in animals.[32]

25B-NBOMe has been found to decrease locomotor activity in rodents.[34][30]

Chemistry

Analogues and derivatives

Template:2C-B analogues and derivatives

Another analogue of 25B-NBOMe is DOB-NBOMe.

History

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25B-NBOMe was first described in the scientific literature, in the form of conference abstracts, by Ralf Heim and colleagues at the Free University of Berlin by 1999.[13]

Society and culture

Legal status

Canada

As of October 31, 2016; 25B-NBOMe is a controlled substance (Schedule III) in Canada.[35]

China

As of October 2015 25B-NBOMe is a controlled substance in China.[36]

Czech Republic

25B-NBOMe is banned in the Czech Republic.[37]

Finland

Scheduled in the "government decree on substances, preparations and plants considered to be narcotic drugs".[38]

Russia

Banned as a narcotic drug since May 5, 2015.[39]

Sweden

In Sweden, the Riksdag added 25B-NBOMe to schedule I ("substances, plant materials and fungi which normally do not have medical use") as narcotics in Sweden as of August 1, 2013, published by the Medical Products Agency in their regulation LVFS 2013:15 listed as 25B-NBOMe 2-(4-bromo-2,5-dimetoxifenyl)-N-(2-metoxibensyl)etanamin.[40]

United Kingdom

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United States

In November 2013, the U.S. Drug Enforcement Administration placed 25B-NBOMe (along with 25I-NBOMe and 25C-NBOMe) in Schedule I of the Controlled Substances Act, making it illegal to manufacture, buy, possess, process, or distribute.[41]

Notes

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References

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  7. ↑ Script error: No such module "citation/CS1".
  8. ↑ a b Script error: No such module "Citation/CS1".
  9. ↑ Script error: No such module "Citation/CS1".
  10. ↑ Script error: No such module "citation/CS1".
  11. ↑ Script error: No such module "citation/CS1".
  12. ↑ Script error: No such module "Citation/CS1".
  13. ↑ a b Heim, R., Pertz, H. H., & Elz, S. (1999). Preparation and in vitro pharmacology of novel secondary amine-type 5-HT2A receptor agonists: from submillimolar to subnanomolar activity. Arch. Pharm. Pharm. Med. Chem, 332, 34. https://bitnest.netfirms.com/external/Arch.Pharm.Pharm.Med.Chem/331.S1.34
  14. ↑ Script error: No such module "Citation/CS1".
  15. ↑ Script error: No such module "citation/CS1".
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  17. ↑ Script error: No such module "Citation/CS1".
  18. ↑ Script error: No such module "Citation/CS1".
  19. ↑ Script error: No such module "Citation/CS1".
  20. ↑ Hansen, M. (2010). Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain: PhD Thesis. Faculty of Pharmaceutical Sciences, University of Copenhagen. https://bitnest.netfirms.com/external/Theses/Hansen2011
  21. ↑ Script error: No such module "Citation/CS1".
  22. ↑ Script error: No such module "Citation/CS1".
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  27. ↑ Script error: No such module "Citation/CS1".
  28. ↑ a b Script error: No such module "Citation/CS1".
  29. ↑ a b c d e Script error: No such module "Citation/CS1".
  30. ↑ a b c d e f g h Script error: No such module "Citation/CS1".
  31. ↑ a b c Script error: No such module "Citation/CS1".
  32. ↑ a b c d e Script error: No such module "Citation/CS1".
  33. ↑ Script error: No such module "Citation/CS1".
  34. ↑ Script error: No such module "Citation/CS1".
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  36. ↑ Script error: No such module "citation/CS1".
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  38. ↑ Script error: No such module "citation/CS1".
  39. ↑ Script error: No such module "citation/CS1".
  40. ↑ Script error: No such module "citation/CS1".
  41. ↑ Script error: No such module "citation/CS1".

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External links

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