NBOMe-mescaline, also known as mescaline-NBOMe, M-NBOMe, or ''N''-(2-methoxybenzyl)-3,4,5-trimethoxyphenethylamine, is a

serotonin receptor agonist A serotonin receptor agonist is an agonist of one or more serotonin receptors. They activate serotonin receptors in a manner similar to that of serotonin (5-hydroxytryptamine; 5-HT), a neurotransmitter and hormone and the endogenous ligand of t ...

and putative

psychedelic drug Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary mental states (known as psychedelic experiences or "trips") and a perceived "expansion of consciousness". Also referred to as classic halluc ...

of the

phenethylamine Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace ami ...

, scaline, and ''N''-benzylphenethylamine (NBOMe) families. It is the ''N''-(2-methoxybenzyl)

derivative In mathematics, the derivative is a fundamental tool that quantifies the sensitivity to change of a function's output with respect to its input. The derivative of a function of a single variable at a chosen input value, when it exists, is t ...

mescaline Mescaline, also known as mescalin or mezcalin, and in chemical terms 3,4,5-trimethoxyphenethylamine, is a natural product, naturally occurring psychedelic drug, psychedelic alkaloid, protoalkaloid of the substituted phenethylamine class, found ...

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 Daniel Trachsel is a Swiss people, Swiss chemist who studies psychedelic drug, psychedelics and entactogens. He has developed and published on a large number of novel psychedelic and entactogen chemical compound, compounds, including their psycho ...

has reported that NBOMe-mescaline at an

oral The word oral may refer to: Relating to the mouth * Relating to the mouth, the first portion of the alimentary canal that primarily receives food and liquid **Oral administration of medicines ** Oral examination (also known as an oral exam or ora ...

dose of 50mg three times separated by 1.5hours each (150mg total over about 4.5hours) produced

hallucinogen Hallucinogens, also known as psychedelics, entheogens, or historically as psychotomimetics, are a large and diverse class of psychoactive drugs that can produce altered states of consciousness characterized by major alterations in thought, mo ...

ic 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 In pharmacology, bioavailability is a subcategory of absorption and is the fraction (%) of an administered drug that reaches the systemic circulation. By definition, when a medication is administered intravenously, its bioavailability is 100%. H ...

, so NBOMe-mescaline could be much more potent by

parenteral In pharmacology and toxicology, a route of administration is the way by which a drug, fluid, poison, or other substance is taken into the body. Routes of administration are generally classified by the location at which the substance is applied. ...

route Route or routes may refer to: * Air route, route structure or airway * GPS route, a series of one or more GPS waypoints * Route (gridiron football), a path run by a wide receiver * Route (command), a program used to configure the routing table * ...

s such as

sublingual Sublingual (List of abbreviations used in medical prescriptions, abbreviated SL), from the Latin for "under the tongue", refers to the pharmacological route of administration by which substances diffuse into the blood through Tissue (biology), t ...

intranasal administration Nasal administration, popularly known as snorting, is a route of administration in which drugs are insufflation (medicine), insufflated through the nose. It can be a form of either topical administration or systemic administration, as the drugs t ...

. 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

NBOMe-mescaline is a

partial agonist In pharmacology, partial agonists are drugs that bind to and activate a given Receptor (biochemistry), receptor, but have only partial Intrinsic activity, efficacy at the receptor relative to a full agonist. They may also be considered Ligand (bio ...

serotonin receptor 5-HT receptors, 5-hydroxytryptamine receptors, or serotonin receptors, are a group of G protein-coupled receptor and ligand-gated ion channels found in multiple tissues including the central and peripheral nervous systems. They mediate both ex ...

s, with a 5-HT_2A pK_i originally reported as 7.3 (i.e. K_i 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''-benzylphenethylamines. Nonetheless, it is 68-fold more potent than mescaline as a serotonin 5-HT_2A receptor agonist ''

in vitro ''In vitro'' (meaning ''in glass'', or ''in the glass'') Research, studies are performed with Cell (biology), cells or biological molecules outside their normal biological context. Colloquially called "test-tube experiments", these studies in ...

''. However, in another study, it was only about 3.3-fold more potent as a serotonin 5-HT_2A receptor agonist compared to mescaline ''in vitro''. The interactions of NBOMe-mescaline with various

receptor Receptor may refer to: * Sensory receptor, in physiology, any neurite structure that, on receiving environmental stimuli, produces an informative nerve impulse *Receptor (biochemistry), in biochemistry, a protein molecule that receives and respond ...

s and transporters have been characterized and described.

Chemistry

Solubility of the

hydrochloride salt In chemistry, a hydrochloride is an acid salt resulting, or regarded as resulting, from the reaction of hydrochloric acid with an organic base (e.g. an amine). An alternative name is chlorhydrate, which comes from French. An archaic alternative ...

: ~5 mg/ml in Phosphate Buffered Saline (PBS) @ pH 7.2; ~10 mg/ml in

ethanol Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...

& DMF; ~20 mg/ml in

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

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

Synthesis

NBOMe-mescaline can be synthesized from

and 2-methoxybenzaldehyde, via reductive

alkylation Alkylation is a chemical reaction that entails transfer of an alkyl group. 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 effecting al ...

. 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 (sometimes written as ). It is a white crystalline solid, usually encountered as an aqueous basic solution. Sodi ...

, or by direct reaction with

sodium triacetoxyborohydride Sodium triacetoxyborohydride, also known as sodium triacetoxyhydroborate, commonly abbreviated STAB, is a chemical compound with the formula . Like other borohydrides, it is used as a reducing agent in organic synthesis. This colourless salt is pr ...

. 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 in which a reactant is subjected to successive chemical reactions in just one reactor. This is much desired by chemists because avoiding a lengthy ...

utilizing 3,4,5-trimethoxy phenylacetonitrile with

Lithium Aluminium Hydride Lithium aluminium hydride, commonly abbreviated to LAH, is an inorganic compound with the chemical formula or . It is a white solid, discovered by Finholt, Bond and Schlesinger in 1947. This compound is used as a reducing agent in organic synthe ...

as a reducing agent.

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 university, public research university in Berlin, Germany. It was founded in West Berlin in 1948 with American support during the early Cold War period a ...

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

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-

NBOMe The 25-NB (25''x''-NB''x'') series, or NBOMe series, also known as the ''N''-benzylphenethylamines, is a family of serotonergic psychedelics. They are substituted phenethylamines and were derived from the 2C (psychedelics), 2C family. The most c ...

s became available.

Society and culture

Legal status

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

United Nations The United Nations (UN) is the Earth, global intergovernmental organization established by the signing of the Charter of the United Nations, UN Charter on 26 June 1945 with the stated purpose of maintaining international peace and internationa ...

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) involving specific narcotic drugs and lays down a ...

from 1961 nor their

Convention on Psychotropic Substances The Convention on Psychotropic Substances of 1971 is a United Nations treaty designed to control psychoactive drugs such as amphetamine-type stimulants, barbiturates, benzodiazepines, and psychedelics signed in Vienna, Austria on 21 February ...

from 1971, so the signatory countries to these international drug control treaties are not required by said treaties to control NBOMe-mescaline.

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 The United States of America (USA), also known as the United States (U.S.) or America, is a country primarily located in North America. It is a federal republic of 50 U.S. state, states and a federal capital district, Washington, D.C. The 48 ...

, 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 ...

, and therefore sales or

possession Possession may refer to: Law *Dependent territory, an area of land over which another country exercises sovereignty, but which does not have the full right of participation in that country's governance *Drug possession, a crime *Ownership *Pe ...

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 ...

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

References

External links

NBOMe-mescaline - Isomer Design

The Big & Dandy NBOMe-Mescaline Thread - Bluelight

Mescaline-NBOMe (also 345-NBOMe) - Erowid Experience Vaults
{{Phenethylamines 5-HT2A agonists 25-NB (psychedelics) Entheogens Psychedelic phenethylamines Scalines Serotonin receptor agonists