1,3-Benzodioxolylbutanamine (also known as 3,4-methylenedioxybutanphenamine, MDB, BDB, J, and 3,4-methylenedioxy-α-ethylphenethylamine) is an entactogenic drug 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 the α-

ethyl Ethyl may refer to: Arts and entertainment * Cold Ethyl, a Swedish rock band *Ethyl Sinclair, a character in the ''Dinosaurs'' television show Science and technology * Ethyl group, an organic chemistry moiety * Ethyl alcohol (or ethanol) * E ...

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 MDPEA and

MDA MDA, mda, or ''variation'', may refer to: Places * Moldova, a country in Europe with the ISO 3166-1 country code MDA Politics * Meghalaya Democratic Alliance (2018), ruling coalition government in the Indian State of Meghalaya led by National Pe ...

and the

methylenedioxy Methylenedioxy is the term used in the field of chemistry, particularly in organic chemistry, for a functional group with the structural formula R-O-CH2-O-R' which is connected to the rest of a molecule by two chemical bonds. The methylenedioxy gr ...

analogue of α-ethylphenethylamine. BDB was first synthesized 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 ...

. In his book '' PiHKAL'', the dosage range is listed as 150–230 mg and the duration is listed as 4–8 hours. BDB produces entactogenic,

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 effects. Although pleasant and euphoric, BDB is also fairly sedating and some users feel that the lack of stimulant effect makes it less enjoyable than other similar drugs. Additional side effects associated with BDB include

nystagmus Nystagmus is a condition of involuntary (or voluntary, in some cases) eye movement. Infants can be born with it but more commonly acquire it in infancy or later in life. In many cases it may result in reduced or limited vision. Due to the invol ...

and

dizziness Dizziness is an imprecise term that can refer to a sense of disorientation in space, vertigo, or lightheadedness. It can also refer to disequilibrium or a non-specific feeling, such as giddiness or foolishness. Dizziness is a common medical c ...

. Very little data exists about the pharmacological properties, metabolism, and toxicity of BDB. Animal studies and anecdotal reports show that BDB is a slightly more potent

serotonin Serotonin () or 5-hydroxytryptamine (5-HT) is a monoamine neurotransmitter. Its biological function is complex and multifaceted, modulating mood, cognition, reward, learning, memory, and numerous physiological processes such as vomiting and vas ...

releasing agent A monoamine releasing agent (MRA), or simply monoamine releaser, is a drug that induces the synapse, release of a monoamine neurotransmitter from the synapse, presynaptic neuron into the synapse, leading to an increase in the extracellular conc ...

than its

methylated In the chemical sciences, methylation denotes the addition of a methyl group on a substrate, or the substitution of an atom (or group) by a methyl group. Methylation is a form of alkylation, with a methyl group replacing a hydrogen atom. These t ...

sister

compound Compound may refer to: Architecture and built environments * Compound (enclosure), a cluster of buildings having a shared purpose, usually inside a fence or wall ** Compound (fortification), a version of the above fortified with defensive struct ...

methylbenzodioxylbutanamine 1,3-Benzodioxolyl-''N''-methylbutanamine (''N''-methyl-1,3-benzodioxolylbutanamine, MBDB, 3,4-methylenedioxy-''N''-methyl-α-ethylphenylethylamine) is an entactogen of the phenethylamine chemical class. It is known by the street names Eden and ...

(MBDB; "Eden", "Methyl-J"). However, it is more commonly known as a

metabolite In biochemistry, a metabolite is an intermediate or end product of metabolism. The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, c ...

of the ''N''-

alkyl In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term ''alkyl'' is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of . A cycloalkyl is derived from a cycloalk ...

ated analogues MBDB and

ethylbenzodioxylbutanamine Ethylbenzodioxolylbutanamine (EBDB; Ethyl-J) is a lesser-known entactogen, stimulant, and psychedelic. It is the ''N''-ethyl analogue of benzodioxylbutanamine (BDB; "J"), and also the α-ethyl analogue of methylenedioxyethylamphetamine (MDEA ...

(EBDB; "Ethyl-J") which have appeared in

methylenedioxymethamphetamine 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 ...

(MDMA; "Ecstasy", "Adam", "Empathy", "Molly", "E", "X", "XTC") tablets. Although BDB itself has not been reported as being sold as "Ecstasy", urine analysis of "Ecstasy" users suggest that this drug may have appeared as a street drug, although it is unclear whether the positive urine test for BDB resulted from consumption of BDB itself or merely as a metabolite of MBDB.

Legal status

1,3-Benzodioxolylbutanamine is illegal in Germany (

Anlage I Anlage may refer to: * Allele, a specific version of a gene, as used by Gregor Mendel * Anlage Süd, a headquarters facility of the German Third Reich in Strzyżów, Poland * Primordium, the initial clustering of embryonic cells from which a body ...

)

References

{{DEFAULTSORT:Benzodioxolylbutanamine, 1,3- Psychedelic phenethylamines Benzodioxoles Serotonin-norepinephrine-dopamine releasing agents Entactogens and empathogens

Legal status

See also

References