NBOMe-mescaline, also known as mescaline-NBOMe, M-NBOMe, or N-(2-methoxybenzyl)-3,4,5-trimethoxyphenethylamine, is a serotonin receptor agonist and putative psychedelic drug of the phenethylamine, scaline, and N-benzylphenethylamine (NBOMe) families. It is the N-(2-methoxybenzyl) derivative of mescaline.

Use and effects The active dose range of NBOMe-mescaline in humans has not been clearly reported and hence is unknown. This is in notable contrast to many other NBOMe drugs.

However, Daniel Trachsel has reported that NBOMe-mescaline at an oral dose of 50mg three times separated by 1.5hours each (150mg total over about 4.5hours) produced hallucinogenic effects and was somewhat more potent than mescaline, but only lasted 5 or 6hours with the employed dosing scheme. It was estimated that the duration if a single dose were to be taken would probably be about 2 to 3hours. NBOMe drugs are known to have very poor oral bioavailability, so NBOMe-mescaline could be much more potent by parenteral routes such as sublingual or intranasal administration.

In terms of its effects, NBOMe-mescaline was described as somehow shifting the axis of the field of vision. Its effects, or rather after-effects, were described as unpleasant.

Interactions

Pharmacology Pharmacodynamics + Target Affinity (Ki, nM) 5-HT1A 21,000 5-HT1B 5-HT1D 5-HT1E 5-HT1F 5-HT2A 140 (Ki)3,000 ()33% () 5-HT2B (Ki)>20,000 () () 5-HT2C 640 (Ki) () () 5-HT3 5-HT4 5-HT5A 5-HT6 5-HT7 α1A 3,000 α1B, α1D α2A 810 α2B, α2C β1–β3 D1 >14,000 D2 9,600 D3 >17,000 D4, D5 H1 14,000 H2–H4 M1–M5 I1 σ1, σ2 >20,000 (Ki) (mouse)13,000 (Ki) (rat)>30,000 () (mouse)>30,000 () (rat)>10,000 () (human) () (mouse) () (rat) 24,000 (Ki)85,000 () () 46,000 (Ki)89,000 () () >30,000 (Ki)449,000 () () Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs:

NBOMe-mescaline is a partial agonist of serotonin receptors, with a 5-HT2A pKi originally reported as 7.3 (i.e. Ki of approximately 50nM), though more modern techniques assayed it as 140nM at 5-HT2A and 640nM at 5-HT2C, making it one of the least potent compounds among the N-benzylphenethylamines. Nonetheless, it is 68-fold more potent than mescaline as a serotonin 5-HT2A receptor agonist in vitro. However, in another study, it was only about 3.3-fold more potent as a serotonin 5-HT2A receptor agonist compared to mescaline in vitro. The interactions of NBOMe-mescaline with various receptors and transporters have been characterized and described.

Chemistry Solubility of the hydrochloride salt: ~5 mg/ml in Phosphate Buffered Saline (PBS) @ pH 7.2; ~10 mg/ml in ethanol & DMF; ~20 mg/ml in DMSO.Cayman Chemical's Mescaline NBOMe HCl MSDS

Synthesis NBOMe-mescaline can be synthesized from mescaline and 2-methoxybenzaldehyde, via reductive alkylation. That can be done stepwise by first making the imine and then reducing the formed imine with sodium borohydride, or by direct reaction with sodium triacetoxyborohydride. An alternative production method which removes the need to obtain the illegal compound mescaline as an isolated precursor can be achieved via a one-pot reaction utilizing 3,4,5-trimethoxyphenylacetonitrile with Lithium Aluminium Hydride as a reducing agent.

History NBOMe-mescaline and NBOMe-escaline were first reported in 1999 resulting from research performed at Free University of Berlin concerning their activity as partial agonists at rat vascular 5-HT2A receptors. NBOMe-mescaline was first reported in September 2008 to have been self administered by humans as a psychedelic drug at some unspecified point prior.25B-NB (n-Benzyl-2C-B) @ BlueLight.org It first became available as a commodity in the research chemical market in May 2010 several months after a few 25x-NBOMes became available.

Society and culture Legal status International NBOMe-mescaline is not listed in the schedules set out by the United Nations' Single Convention on Narcotic Drugs from 1961 nor their Convention on Psychotropic Substances from 1971, so the signatory countries to these international drug control treaties are not required by said treaties to control NBOMe-mescaline.

Canada NBOMe-mescaline is not a controlled substance in Canada as of 2025.

United Kingdom

United States NBOMe-mescaline is not listed in the list of scheduled controlled substances in the USA. It is therefore not scheduled at the federal level in the United States, but it is possible that NBOMe-mescaline could legally be considered an analog of mescaline, and therefore sales or possession could potentially be prosecuted under the Federal Analogue Act.Erowid Analog Law Vault : Federal Controlled Substance Analogue Act Summary

See also Scaline N-Benzylphenethylamine NBOMe-escaline Mescaline-FLY 2,4,6-TMPEA-NBOMe DOM-NBOMe 5-APB-NBOMe 2C2-NBOMe

References

External links NBOMe-mescaline - Isomer Design The Big & Dandy NBOMe-Mescaline Thread - Bluelight Mescaline-NBOMe (also 345-NBOMe) - Erowid Experience Vaults