NBOMe-mescaline or mescaline-NBOMe is a synthetic

substituted phenethylamine Substituted phenethylamines (or simply phenethylamines) are a chemical class of organic compounds that are based upon the phenethylamine structure; the class is composed of all the derivative compounds of phenethylamine which can be formed by ...

. It is a partial agonist of serotonin receptors with a 5-HT_2A pKi originally reported as 7.3 (i.e. Ki of approximately 50nM), though more modern techniques assayed it as 140nM at 5-HT_2A and 640nM at 5-HT_2C, making it one of the least potent compounds among the N-benzyl phenethylamines.

History

NBOMe-mescaline and NBOMe-escaline were first reported in 1999 resulting from research performed at

Free University of Berlin The Free University of Berlin (, often abbreviated as FU Berlin or simply FU) is a public research university in Berlin, Germany. It is consistently ranked among Germany's best universities, with particular strengths in political science and t ...

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
/ref> It first became available as a commodity in the research chemical market in May 2010 several months after a few 25x- NBOMes became available.

Properties and chemistry

Solubility of the hydrochloride salt: ~5 mg/ml in Phosphate Buffered Saline (PBS) @ pH 7.2; ~10 mg/ml in

ethanol Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an alcohol with the chemical formula . Its formula can be also written as or (an ethyl group linked to a ...

& DMF; ~20 mg/ml in

DMSO Dimethyl sulfoxide (DMSO) is an organosulfur compound with the formula ( CH3)2. This colorless liquid is the sulfoxide most widely used commercially. It is an important polar aprotic solvent that dissolves both polar and nonpolar compounds ...

.Cayman Chemical's Mescaline NBOMe HCl MSDS
/ref>

Synthesis

NBOMe-mescaline can be synthesized from mescaline and 2-methoxybenzaldehyde, via reductive

alkylation Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecti ...

. That can be done stepwise by first making the

imine In organic chemistry, an imine ( or ) is a functional group or organic compound containing a carbon–nitrogen double bond (). The nitrogen atom can be attached to a hydrogen or an organic group (R). The carbon atom has two additional single bon ...

and then reducing the formed imine with

sodium borohydride Sodium borohydride, also known as sodium tetrahydridoborate and sodium tetrahydroborate, is an inorganic compound with the formula Na BH4. This white solid, usually encountered as an aqueous basic solution, is a reducing agent that finds applica ...

, or by direct reaction with

sodium triacetoxyborohydride Sodium triacetoxyborohydride, also known as sodium triacetoxyhydroborate, commonly abbreviated STAB, is a chemical compound with the formula Na(CH3COO)3BH. Like other borohydrides, it is used as a reducing agent in organic synthesis. This colourle ...

. 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 In chemistry a one-pot synthesis is a strategy to improve the efficiency of a chemical reaction whereby a reactant is subjected to successive chemical reactions in just one reactor. This is much desired by chemists because avoiding a lengthy sepa ...

utilizing 3,4,5-trimethoxy phenylacetonitrile with Lithium Aluminium Hydride as a reducing agent.

Psychedelic dosage in humans

There have been very few reports of human use of NBOMe-mescaline. Psychedelic visual, auditory and mental effects start around 50 mg intranasally.The Big & Dandy NBOMe-Mescaline Thread @ BlueLight.org
/ref>

Legal status

NBOMe-mescaline is not listed in the schedules set out by the

United Nations The United Nations (UN) is an intergovernmental organization whose stated purposes are to maintain international peace and security, develop friendly relations among nations, achieve international cooperation, and be a centre for harmoniz ...

Single Convention on Narcotic Drugs The Single Convention on Narcotic Drugs, 1961 (Single Convention, 1961 Convention, or C61) is an international treaty that controls activities (cultivation, production, supply, trade, transport) of specific narcotic drugs and lays down a syste ...

from 1961 nor their Convention on Psychotropic Substances from 1971,UN International Drug Control Conventions
/ref> so the signatory countries to these international drug control treaties are not required by said treaties to control NBOMe-mescaline.

United States

NBOMe-mescaline is not listed in the list of scheduled controlled substances in the USA.§1308.11 Schedule I.
/ref> It is therefore not scheduled at the federal level in the

United States The United States of America (U.S.A. or USA), commonly known as the United States (U.S. or US) or America, is a country primarily located in North America. It consists of 50 states, a federal district, five major unincorporated territori ...

, but it is possible that NBOMe-mescaline could legally be considered an

analog Analog or analogue may refer to: Computing and electronics * Analog signal, in which information is encoded in a continuous variable ** Analog device, an apparatus that operates on analog signals *** Analog electronics, circuits which use analog ...

of mescaline, and therefore sales or possession could potentially be prosecuted under the

Federal Analogue Act The Federal Analogue Act, , is a section of the United States Controlled Substances Act passed in 1986 which allows any chemical "substantially similar" to a controlled substance listed in Schedule I or II to be treated as if it were listed in ...

.Erowid Analog Law Vault : Federal Controlled Substance Analogue Act Summary
/ref>

United Kingdom

References

External links

NBOMe-mescaline @ IsomerDesign

The Big & Dandy NBOMe-Mescaline Thread @ BlueLight.org

Erowid Experience Vaults: Mescaline-NBOMe (also 345-NBOMe)
{{Phenethylamines 25-NB (psychedelics) Entheogens Psychedelic phenethylamines Serotonin receptor agonists