MBDB, also known as ''N''-methyl-1,3-benzodioxolylbutanamine or as 3,4-methylenedioxy-''N''-methyl-α-ethylphenylethylamine, is an

entactogen Entactogens, also known as empathogens or connectogens, are a class of psychoactive drugs that induce the production of experiences of emotional communion, oneness, connectedness, emotional openness—that is, empathy—as particularly observe ...

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 ...

amphetamine Amphetamine (contracted from Alpha and beta carbon, alpha-methylphenethylamine, methylphenethylamine) is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, an ...

, and phenylisobutylamine families related to

MDMA 3,4-Methylenedioxymethamphetamine (MDMA), commonly known as ecstasy (tablet form), and molly (crystal form), is an empathogen–entactogenic drug with stimulant and minor Psychedelic drug, psychedelic properties. In studies, it has been used ...

. It is known by the street names "Eden" and "Methyl-J".

History and effects

MBDB was first synthesized by

pharmacologist Pharmacology is the science of drugs and medications, including a substance's origin, composition, pharmacokinetics, pharmacodynamics, therapeutic use, and toxicology. More specifically, it is the study of the interactions that occur between ...

and

medicinal chemist Medicinal or pharmaceutical chemistry is a scientific discipline at the intersection of chemistry and pharmacy involved with designing and developing pharmaceutical drugs. Medicinal chemistry involves the identification, synthesis and developmen ...

David E. Nichols and later tested by

Alexander Shulgin Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American biochemist, broad researcher of synthetic psychoactive compounds, and author of works regarding these, who independently explored the organic chemistry and ph ...

and described in his book, '' PiHKAL: A Chemical Love Story''. MBDB's dosage, according to ''PiHKAL'', is 180 to 210mg; the proper dosage relative to body mass seems unknown. Its duration is 4 to 6hours, with noticeable after-effects lasting for 1 to 3hours. MBDB was initially developed as a non-

psychedelic 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 halluci ...

entactogen. It has lower effects on the

dopamine Dopamine (DA, a contraction of 3,4-dihydroxyphenethylamine) is a neuromodulatory molecule that plays several important roles in cells. It is an organic chemical of the catecholamine and phenethylamine families. It is an amine synthesized ...

system in comparison to other entactogens such as

. MBDB causes many mild, MDMA-like effects, in particular the lowering of social barriers and inhibitions, pronounced sense of

empathy Empathy is generally described as the ability to take on another person's perspective, to understand, feel, and possibly share and respond to their experience. There are more (sometimes conflicting) definitions of empathy that include but are ...

and

compassion Compassion is a social feeling that motivates people to go out of their way to relieve the physical, mental, or emotional pains of others and themselves. Compassion is sensitivity to the emotional aspects of the suffering of others. When based ...

, and mild

euphoria Euphoria ( ) is the experience (or affect) of pleasure or excitement and intense feelings of well-being and happiness. Certain natural rewards and social activities, such as aerobic exercise, laughter, listening to or making music and da ...

, all of which are present. MBDB tends to produce less euphoria,

psychedelia Psychedelia usually refers to a Aesthetics, style or aesthetic that is resembled in the psychedelic subculture of the 1960s and the psychedelic experience produced by certain psychoactive substances. This includes psychedelic art, psychedelic ...

, and

stimulation Stimulation is the encouragement of development or the cause of activity in general. For example, "The press provides stimulation of political discourse." An interesting or fun activity can be described as "stimulating", regardless of its physic ...

in comparison to MDMA. Clinical studies have found that MBDB produces similar

ic effects to MDMA, but lacks

and

stimulant Stimulants (also known as central nervous system stimulants, or psychostimulants, or colloquially as uppers) are a class of drugs that increase alertness. They are used for various purposes, such as enhancing attention, motivation, cognition, ...

effects. It enhances mood similarly to MDMA, but lacks the pronounced

of MDMA. MBDB produces

prosocial Prosocial behavior is a social behavior that "benefit other people or society as a whole", "such as helping, sharing, donating, co-operating, and volunteering". The person may or may not intend to benefit others; the behavior's prosocial benefi ...

effects similarly to MDMA, although it is said to be moderately less effective.

Chemistry

MBDB is a ring substituted amphetamine and an analogue of

. Like MDMA, it has a methylenedioxy substitution at the 3 and 4 position on the aromatic ring; this is perhaps the most distinctive feature that structurally define analogues of MDMA, in addition to their unique effects, and as a class they are often referred to as "entactogens" to differentiate between typical

amphetamines Substituted amphetamines, or simply amphetamines, are a chemical class, class of compounds based upon the amphetamine structure; it includes all derivative (chemistry), derivative compounds which are formed by replacing, or substitution reacti ...

that (as a general rule) are not ring substituted. MBDB differs from MDMA by having an

ethyl group In organic chemistry, an ethyl group (abbr. Et) is an alkyl substituent with the formula , derived from ethane (). ''Ethyl'' is used in the International Union of Pure and Applied Chemistry The International Union of Pure and Applied ...

instead of a

methyl group In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula (whereas normal methane has the formula ). In formulas, the group is often abbreviated a ...

attached to the

alpha carbon In the nomenclature of organic chemistry, a locant is a term to indicate the position of a functional group or substituent within a molecule. Numeric locants The International Union of Pure and Applied Chemistry (IUPAC) recommends the use of n ...

. Modification at the alpha carbon is uncommon for substituted amphetamines.

Pharmacology

Pharmacodynamics

MBDB acts as a

serotonin–norepinephrine releasing agent A serotonin–norepinephrine releasing agent (SNRA) is a type of drug which induces the release of serotonin and norepinephrine (and epinephrine) in the body and/or brain. Only a few SNRAs are known, examples of which include norfenfluramine ...

(SNRA). Its values for induction of monoamine release are 540nM for

serotonin Serotonin (), also known as 5-hydroxytryptamine (5-HT), is a monoamine neurotransmitter with a wide range of functions in both the central nervous system (CNS) and also peripheral tissues. It is involved in mood, cognition, reward, learning, ...

, 3,300nM for

norepinephrine Norepinephrine (NE), also called noradrenaline (NA) or noradrenalin, is an organic compound, organic chemical in the catecholamine family that functions in the brain and human body, body as a hormone, neurotransmitter and neuromodulator. The ...

(6.1-fold lower than for serotonin), and >100,000 for

(>185-fold lower than for serotonin). However, it may still have slight dopamine-releasing actions. MBDB fully substitutes for

drug discrimination Drug discrimination (DD) is a technique in behavioral neuroscience used to evaluate the discriminative stimulus properties or interoceptive cues of psychoactive drugs. In drug discrimination, a subject is trained on a training drug, and then i ...

tests in rodents. It increases

locomotor activity Locomotor activity is a measure of animal behavior which is employed in scientific research. Hyperlocomotion, also known as locomotor hyperactivity, hyperactivity, or increased locomotor activity, is an effect of certain drugs in animals in whi ...

similarly to but less robustly than

. Likewise, MBDB increases conditioned place preference (CPP) similarly but less efficaciously than MDMA. In contrast to MDMA, which produced

hyperthermia Hyperthermia, also known as overheating, is a condition in which an individual's body temperature is elevated beyond normal due to failed thermoregulation. The person's body produces or absorbs more heat than it dissipates. When extreme te ...

, MBDB instead produced dose- and time-dependent

hypothermia Hypothermia is defined as a body core temperature below in humans. Symptoms depend on the temperature. In mild hypothermia, there is shivering and mental confusion. In moderate hypothermia, shivering stops and confusion increases. In severe ...

. MBDB has similar affinities for the

5-HT_1A and 5-HT_2A receptors as MDMA. However, MBDB did not show the

head-twitch response The head-twitch response (HTR), also sometimes known as wet dog shakes (WDS) in rats, is a rapid side-to-side head movement that occurs in mice and rats in association with serotonin 5-HT2A receptor activation. Serotonergic psychedelics like lys ...

, a behavioral proxy of

effects, at any dose in rodents. In addition, MBDB (as well as MDMA) do not substitute for

lysergic acid diethylamide Lysergic acid diethylamide, commonly known as LSD (from German ; often referred to as acid or lucy), is a Semisynthesis, semisynthetic, Hallucinogen, hallucinogenic compound derived from ergot, known for its powerful psychological effects and ...

(LSD) in

tests. The lack of apparent hallucinogenic effects with MBDB is analogous to the case of

Ariadne In Greek mythology, Ariadne (; ; ) was a Cretan princess, the daughter of King Minos of Crete. There are variations of Ariadne's myth, but she is known for helping Theseus escape from the Minotaur and being abandoned by him on the island of N ...

, the α-ethyl homologue of DOM; (''R'')-Ariadne (BL-3912A) showed no psychedelic effects in humans at doses of up to 270mg orally, whereas DOM is active as a hallucinogen at doses of 5 to 10mg orally. This may be due to lower activational

efficacy Efficacy is the ability to perform a task to a satisfactory or expected degree. The word comes from the same roots as '' effectiveness'', and it has often been used synonymously, although in pharmacology a distinction is now often made betwee ...

at the serotonin 5-HT_2A receptor. MBDB is a

serotonergic neurotoxin A monoamine neurotoxin, or monoaminergic neurotoxin, is a drug that selectively damages or destroys monoaminergic neurons. Monoaminergic neurons are neurons that signal via stimulation by monoamine neurotransmitters including serotonin, dopamine ...

similarly to MDMA. However, MBDB appears to have reduced serotonergic neurotoxicity compared to MDMA at behaviorally equivalent doses. In addition, unlike MDMA, MBDB does not produce

dopaminergic neurotoxicity A monoamine neurotoxin, or monoaminergic neurotoxin, is a drug that selectively damages or destroys monoaminergic neurons. Monoaminergic neurons are neurons that signal via stimulation by monoamine neurotransmitters including serotonin, dopamine ...

in mice. MBDB and its individual

enantiomer In chemistry, an enantiomer (Help:IPA/English, /ɪˈnænti.əmər, ɛ-, -oʊ-/ Help:Pronunciation respelling key, ''ih-NAN-tee-ə-mər''), also known as an optical isomer, antipode, or optical antipode, is one of a pair of molecular entities whi ...

s, (''S'')-MBDB and (''R'')-MBDB, show similar behavioral effects in animals.

Pharmacokinetics

The

metabolism Metabolism (, from ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cellular processes; the co ...

of MBDB has been described in the

scientific literature Scientific literature encompasses a vast body of academic papers that spans various disciplines within the natural and social sciences. It primarily consists of academic papers that present original empirical research and theoretical ...

Legal status

Unlike MDMA, MBDB is not internationally scheduled under the United Nations

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 ...

. The thirty-second meeting of the WHO Expert Committee on Drug Dependence (September 2000) evaluated MBDB and recommended against scheduling. From the WHO Expert Committee assessment of MBDB: :''Although MBDB is both structurally and pharmacologically similar to MDMA, the limited available data indicate that its stimulant and euphoriant effects are less pronounced than those of MDMA. There have been no reports of adverse or toxic effects of MBDB in humans. Law enforcement data on illicit trafficking of MBDB in Europe suggest that its availability and abuse may now be declining after reaching a peak during the latter half of the 1990s. For these reasons, the Committee did not consider the abuse liability of MBDB would constitute a significant risk to public health, thereby warranting its placement under international control. Scheduling of MBDB was therefore not recommended.''

Australia

MBDB is considered a Schedule 9 Prohibited substance in Australia under the Poisons Standard (October 2015). A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.

Finland

Scheduled in the "government decree on psychoactive substances banned from the consumer market".

Russia

MBDB is included into Schedule 1 of the Controlled Substances Act.

Sweden

''Sveriges riksdags'' health ministry ' classified MBDB as "health hazard" under the act ' (translated ''Act on the Prohibition of Certain Goods Dangerous to Health'') as of Feb 25, 1999, in their regulation SFS 1999:58 listed as "2-metylamino-1-(3,4-metylendioxifenyl)-butan (MBDB)", making it illegal to sell or possess.

Research

MBDB is being assessed by PharmAla Biotech for potential medical use as a

pharmaceutical drug Medication (also called medicament, medicine, pharmaceutical drug, medicinal product, medicinal drug or simply drug) is a drug used to diagnose, cure, treat, or prevent disease. Drug therapy ( pharmacotherapy) is an important part of the ...

, for instance to treat

autism Autism, also known as autism spectrum disorder (ASD), is a neurodevelopmental disorder characterized by differences or difficulties in social communication and interaction, a preference for predictability and routine, sensory processing d ...

References

External links

PiHKAL entry

METHYL-J (MBDB) entry in PiHKAL • info

Erowid MBDB vault
{{Phenethylamines Designer drugs Entactogens Experimental drugs Experimental entactogens Methylenedioxyphenethylamines Monoaminergic neurotoxins Phenylisobutylamines Serotonin-norepinephrine releasing agents