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25C-NBOMe

25C-NBOMe
Clinical data
Other namesNBOMe-2C-C; 2C-C-NBOMe; Cimbi-82; N-(2-Methoxybenzyl)-4-chloro-2,5-dimethoxyphenethylamine
Routes of
administration		Sublingual, others
Drug classSerotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
Legal status
Identifiers
  • 2-(4-chloro-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H22ClNO3
Molar mass335.83 g·mol−1
3D model (JSmol)
  • COc2ccccc2CNCCc(cc1OC)c(OC)cc1Cl
  • InChI=1S/C18H22ClNO3/c1-21-16-7-5-4-6-14(16)12-20-9-8-13-10-18(23-3)15(19)11-17(13)22-2/h4-7,10-11,20H,8-9,12H2,1-3H3 checkY
  • Key:FJFPOGCVVLUYAQ-UHFFFAOYSA-N checkY
  (verify)

25C-NBOMe, also known as NBOMe-2C-C, 2C-C-NBOMe, or Cimbi-82, is a psychedelic drug and derivative of the psychedelic phenethylamine 2C-C.[3] It acts as a potent agonist of the 5-HT2A receptor,[4] and has been studied in its 11C radiolabelled form as a potential ligand for mapping the distribution of 5-HT2A receptors in the brain, using positron emission tomography (PET).[5][6] Multiple deaths have occurred from usage of 25C-NBOMe due to the ease of accidental overdose. The long-term toxic effects of the drug have not been researched. 25C-NBOMe was first described in the scientific literature by 2010.[7][5]

Use and effects

Blotter paper containing 25C-NBOMe

25C-NBOMe is extremely potent and the effects of the drug increase greatly within a small window of dosage adjustment. Overdose may occur at as little as double an average dose. With inaccurate dosing of street blotter paper, when mistaken for LSD, or when taken as a powder or liquid, this has resulted in multiple accidental deaths.[8]

One study has shown that 25C-NBOMe blotters have 'hotspots' of the drug and the dosage is not evenly applied over the surface of the paper, which could lead to overdose.[9] Sublingually, the threshold for the onset of hallucinogenic effects reportedly is about 100–250 μg, with mild effects at 250–450, strong effects at 450–800, and very strong effects over 800 μg.[10]

NBOMe-substituted compounds have a diminished absorption rate passing through mucous membranes, but generally remain inactive when taken orally. Buccal, sublingual or insufflated routes of administration are all viable options. Absorption rate buccally and sublingually can be increased when complexed with HPBCD complexing sugar, however the most efficient is nasal administration, which shortens the duration while increasing intensity, but has been attributed to several overdoses and deaths.[11]

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.[12][13] Studies on NBOMe family of compounds demonstrated that the substance exhibit neurotoxic and cardiotoxic activity.[14] 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.[15][16][17][18][19] Other symptoms of toxidrome include agitation or aggression, seizure, hyperthermia, diaphoresis, hypertonia, rhabdomyolysis, and death.[15][19][13] Researchers report that NBOMe intoxication frequently display signs of serotonin syndrome.[20] The likelihood of seizure is higher in NBOMes compared to other psychedelics.[14]

NBOMe and NBOHs are regularly sold as LSD in blotter papers,[13][21] which have a bitter taste and different safety profiles.[15][12] Despite high potency, recreational doses of LSD have only produced low incidents of acute toxicity.[12] Fatalities involved in NBOMe intoxication suggest that a significant number of individuals ingested the substance which they believed was LSD,[17] and researchers report that "users familiar with LSD may have a false sense of security when ingesting NBOMe inadvertently".[15] 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.[22][23][15]

Given limited documentation of NBOMe consumption, the long-term effects of the substance remain unknown.[15] NBOMe compounds are not active orally,[a] and are usually taken sublingually.[25]: 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.[26][27][28]

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.[13][18] 5-HT2B receptors have been strongly implicated in causing drug-induced valvular heart disease.[29][30][31] The high affinity of NBOMe compounds for adrenergic α1 receptor has been reported to contribute to the stimulant-type cardiovascular effects.[18]

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.[14] 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.[14]

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.[32][33]

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.[14]

Interactions

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

Pharmacology

Pharmacodynamics

25C-NBOMe activities
Target Affinity (Ki, nM)
5-HT1A 2,353–5,000
5-HT1B 2,372
5-HT1D 1,024
5-HT1E 5,776
5-HT1F ND
5-HT2A 0.7–1.6 (Ki)
1.46–150 (EC50Tooltip half-maximal effective concentration)
82–167% (EmaxTooltip maximal efficacy)
5-HT2B 1.1 (Ki)
100 (EC50)
16% (Emax)
5-HT2C 5.2–5.4 (Ki)
3.24 (EC50)
103% (Emax)
5-HT3 >10,000
5-HT4 ND
5-HT5A 4,796
5-HT6 36.2
5-HT7 1,729
α1A 810–2,319
α1B >10,000
α1D >10,000
α2A 560–3,175
α2B 224
α2C 185
β1–β3 ND
D1 12,000
D2 1,600–7,508
D3 878–3,500
D4 >10,000
D5 >10,000
H1 90
H2–H4 ND
M1–M3 >10,000
M4 5,410
M5 >10,000
I1 ND
σ1 441
σ2 41
MOR ND (Ki)
10,000–>122,000 (EC50)
<5–82% (Emax)
DOR ND
KOR ND
TAAR1Tooltip Trace amine-associated receptor 1 15,000 (Ki) (mouse)
520 (Ki) (rat)
6,700 (EC50) (mouse)
1,600 (EC50) (rat)
>10,000 (EC50) (human)
48% (Emax) (mouse)
29% (Emax) (rat)
SERTTooltip Serotonin transporter 1,500–>10,000 (Ki)
7,300 (IC50Tooltip half-maximal inhibitory concentration)
ND (EC50)
NETTooltip Norepinephrine transporter 1,600–>10,000 (Ki)
5,900 (IC50)
ND (EC50)
DATTooltip Dopamine transporter 14,000 (Ki)
70,000 (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: [34][5][35][36][37][38][39][40]

25C-NBOMe acts as a serotonin 5-HT2 receptor agonist, including of the serotonin 5-HT2A receptor.

Chemistry

25C-NBOMe is derived from the psychedelic phenethylamine 2C-C by substitution on the amine with a 2-methoxybenzyl group. 25C-NBOMe is a clumpy white powder with a notably bitter and metallic taste.[41]

Analogues and derivatives

Analogues and derivatives of 2C-C:

25C-NB*:

N-(2C)-fentanyl:

History

See also: 25-NB § History

25C-NBOMe was first described in the scientific literature by Anders Ettrup and colleagues by 2010.[7][5]

Society and culture

Recreational use

25C-NBOMe has been found on blotter mimics sold as LSD.[41]

Canada

As of October 31, 2016; 25C-NBOMe is a controlled substance (Schedule III) in Canada.[43]

China

As of October 2015, 25C-NBOMe is a controlled substance in China.[44]

Czech Republic

25C-NBOMe is banned in the Czech Republic.[45]

Israel

The NBOMe series of psychoactives became controlled in Israel in May, 2013.[46][47]

New Zealand

25C-NBOMe was sold as a designer drug in New Zealand in early 2012, but was withdrawn from sale after a statement by Associate Health Minister Peter Dunne that 25C-NBOMe would be considered to be substantially similar in chemical structure to the illegal hallucinogen DOB, and was therefore a Class C controlled drug analogue.[48]

Russia

Russia became the first country to regulate the NBOME class. The entire NBOMe series of psychoactives became controlled in the Russian Federation starting October, 2011.[46][49]

Sweden

Sveriges riksdag added 25C-NBOMe to schedule I ("substances, plant materials and fungi which normally do not have medical use") as narcotics in Sweden as of Aug 1, 2013, published by Medical Products Agency in their regulation LVFS 2013:15 listed as 25C-NBOMe 2-(4-kloro-2,5-dimetoxifenyl)-N-(2-metoxibensyl)etanamin.[50]

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.[51]

United States

Several NBOMe series compounds will be temporarily scheduled in the United States for 2 years. The temporary scheduling applies to 25C-NBOMe, 25B-NBOMe, and 25I-NBOMe.[52] In November 2015, the temporary scheduling was extended for another year.[53]

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.[24] 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.[24]

References

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  53. ^ Drug Enforcement Administration (November 2015). "Schedules of Controlled Substances: Extension of Temporary Placement of Three Synthetic Phenethylamines in Schedule I. Final order". Federal Register. 80 (219): 70657–70659. PMID 26567439.


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Prefix: a b c d e f g h i j k l m n o p q r s t u v w x y z 0 1 2 3 4 5 6 7 8 9

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