1,3-Benzodioxolyl-''N''-methylbutanamine (''N''-methyl-1,3-benzodioxolylbutanamine, MBDB, 3,4-methylenedioxy-''N''-methyl-α-ethylphenylethylamine) is an entactogen 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 amin ...

chemical class Chemical classification systems attempt to classify elements or compounds according to certain chemical functional or structural properties. Whereas the structural properties are largely intrinsic, functional properties and the derived classificat ...

. It is known by the street names Eden and Methyl-J. MBDB is a ring substituted amphetamine and an analogue of

MDMA 3,4-Methylenedioxymethamphetamine (MDMA), commonly seen in Tablet (pharmacy), tablet form (ecstasy) and crystal form (molly or mandy), is a potent empathogen–entactogen with stimulant properties primarily used for Recreational dru ...

. Like MDMA, it has a methylene dioxy 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 psychostimulant amphetamines 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's nomenclature of organic chemistry for a saturated ...

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 . In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in many ...

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 us ...

; all other parts are identical. Modification at the alpha carbon is uncommon for substituted amphetamines. It has IC₅₀ values of 784 nM against 5-HT, 7825 nM against

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

, and 1233 nM against

norepinephrine Norepinephrine (NE), also called noradrenaline (NA) or noradrenalin, is an organic chemical in the catecholamine family that functions in the brain and body as both a hormone and neurotransmitter. The name "noradrenaline" (from Latin '' ad'', ...

. Its metabolism has been described in scientific literature. MBDB was first synthesized by

pharmacologist Pharmacology is a branch of medicine, biology and pharmaceutical sciences concerned with drug or medication action, where a drug may be defined as any artificial, natural, or endogenous (from within the body) molecule which exerts a biochemica ...

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 David Earl Nichols (born December 23, 1944, Covington, Kentucky) is an Americans, American pharmacologist and medicinal chemist. Previously the Robert C. and Charlotte P. Anderson Distinguished Chair in Pharmacology at Purdue University, Nichol ...

and later tested by

Alexander Shulgin Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American medicinal chemist, biochemist, organic chemist, pharmacologist, psychopharmacologist, and author. He is credited with introducing 3,4-methylenedioxymethamph ...

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

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 the capacity to understand or feel what another person is experiencing from within their frame of reference, that is, the capacity to place oneself in another's position. Definitions of empathy encompass a broad range of social, co ...

and

compassion Compassion motivates people to go out of their way to relieve the physical, mental or emotional pains of others and themselves. Compassion is often regarded as being sensitive to the emotional aspects of the suffering of others. When based on n ...

, mood lift, 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, and stimulation in comparison to MDMA.

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, amphetamine-type stimulants, barbiturates, benzodiazepines, and Psychedelic drug, psychede ...

. 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.

Russia

MBDB is included into Schedule 1 of the Controlled Substances Act

Sweden

Riksdag, ''Sveriges riksdags'' health ministry ''Statens folkhälsoinstitut'' classified MBDB as "health hazard" under the act ''Lagen om förbud mot vissa hälsofarliga varor'' (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.

References

External links