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J (psychedelic)
Encyclopedia
Benzodioxolylbutanamine (BDB; J; 3,4-methylenedioxy
-α
-ethyl
phenethylamine
) is an entactogen, psychedelic
, and stimulant
of the phenethylamine
chemical class. It is the α
-ethyl
analogue of methylenedioxyphenethylamine
(MDPEA) and methylenedioxyamphetamine (MDA; Tenamfetamine; "Hug Drug", "Love Drug").
BDB was first synthesized by Alexander Shulgin
. In his book PiHKAL (Phenethylamines i Have Known And Loved)
, the dosage range is listed as 150–230 mg, and the duration is listed as 4–8 hours. BDB produces entactogenic, MDMA-like effects. While 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 and dizziness
. 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
releasing agent
than its methylated sister compound
methylbenzodioxylbutanamine (MBDB; "Eden", "Methyl-J"). However, it is more commonly known as a metabolite
of the N-alkylated analogues MBDB and ethylbenzodioxylbutanamine (EBDB; "Ethyl-J") which have appeared in so-called methylenedioxymethamphetamine
(MDMA; "Ecstasy", "Adam", "Empathy", "Molly", "E", "X", "XTC") tablets. While 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.
Methylenedioxy
Methylenedioxy in the field of chemistry, particularly in organic chemistry, is the name 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 group consists of two oxygen atoms connected to a methylene...
-α
Alpha carbon
The alpha carbon in organic chemistry refers to the first carbon that attaches to a functional group . By extension, the second carbon is the beta carbon, and so on....
-ethyl
Ethyl group
In chemistry, an ethyl group is an alkyl substituent derived from ethane . It has the formula -C2H5 and is very often abbreviated -Et.Ethylation is the formation of a compound by introduction of the ethyl functional group, C2H5....
phenethylamine
Phenethylamine
Phenylethylamine or phenethylamine is a natural monoamine alkaloid, trace amine, and also the name of a class of chemicals with many members well known for psychoactive drug and stimulant effects. Studies suggest that phenylethylamine functions as a neuromodulator or neurotransmitter in the...
) is an entactogen, psychedelic
Psychedelic drug
A psychedelic substance is a psychoactive drug whose primary action is to alter cognition and perception. Psychedelics are part of a wider class of psychoactive drugs known as hallucinogens, a class that also includes related substances such as dissociatives and deliriants...
, and stimulant
Stimulant
Stimulants are psychoactive drugs which induce temporary improvements in either mental or physical function or both. Examples of these kinds of effects may include enhanced alertness, wakefulness, and locomotion, among others...
of the phenethylamine
Phenethylamine
Phenylethylamine or phenethylamine is a natural monoamine alkaloid, trace amine, and also the name of a class of chemicals with many members well known for psychoactive drug and stimulant effects. Studies suggest that phenylethylamine functions as a neuromodulator or neurotransmitter in the...
chemical class. It is the α
Alpha carbon
The alpha carbon in organic chemistry refers to the first carbon that attaches to a functional group . By extension, the second carbon is the beta carbon, and so on....
-ethyl
Ethyl group
In chemistry, an ethyl group is an alkyl substituent derived from ethane . It has the formula -C2H5 and is very often abbreviated -Et.Ethylation is the formation of a compound by introduction of the ethyl functional group, C2H5....
analogue of methylenedioxyphenethylamine
Methylenedioxyphenethylamine
3,4-Methylenedioxyphenethylamine , also known as homopiperonylamine, is a substituted phenethylamine formed by adding a methylenedioxy group to phenethylamine...
(MDPEA) and methylenedioxyamphetamine (MDA; Tenamfetamine; "Hug Drug", "Love Drug").
BDB was first synthesized by Alexander Shulgin
Alexander Shulgin
Alexander "Sasha" Theodore Shulgin is an American pharmacologist, chemist, artist, and drug developer.Shulgin is credited with the popularization of MDMA, commonly known as ecstasy, in the late 1970s and early 1980s, especially for psychopharmaceutical use and the treatment of depression and...
. In his book PiHKAL (Phenethylamines i Have Known And Loved)
PiHKAL
PiHKAL: A Chemical Love Story is a book by Dr. Alexander Shulgin and Ann Shulgin which was published in 1991. The subject of the work is psychoactive phenethylamine chemical derivatives, notably those that act as psychedelics and/or empathogen-entactogens...
, the dosage range is listed as 150–230 mg, and the duration is listed as 4–8 hours. BDB produces entactogenic, MDMA-like effects. While 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 and dizziness
Dizziness
Dizziness refers to an impairment in spatial perception and stability. The term is somewhat imprecise. It can be used to mean vertigo, presyncope, disequilibrium, or a non-specific feeling such as giddiness or foolishness....
. 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
Potency (pharmacology)
In the field of pharmacology, potency is a measure of drug activity expressed in terms of the amount required to produce an effect of given intensity. A highly potent drug evokes a larger response at low concentrations, while a drug of lower potency evokes a small response at low concentrations...
serotonin
Serotonin
Serotonin or 5-hydroxytryptamine is a monoamine neurotransmitter. Biochemically derived from tryptophan, serotonin is primarily found in the gastrointestinal tract, platelets, and in the central nervous system of animals including humans...
releasing agent
Releasing agent
A releasing agent , or simply releaser, is a drug that induces the release of a neurotransmitter from the presynaptic neuron into the synapse, leading to an increase in the extracellular concentrations of the neurotransmitter. Many drugs use neurotransmitter release to exert their psychological and...
than its methylated sister compound
Chemical compound
A chemical compound is a pure chemical substance consisting of two or more different chemical elements that can be separated into simpler substances by chemical reactions. Chemical compounds have a unique and defined chemical structure; they consist of a fixed ratio of atoms that are held together...
methylbenzodioxylbutanamine (MBDB; "Eden", "Methyl-J"). However, it is more commonly known as a metabolite
Metabolite
Metabolites are the intermediates and products of metabolism. The term metabolite is usually restricted to small molecules. A primary metabolite is directly involved in normal growth, development, and reproduction. Alcohol is an example of a primary metabolite produced in large-scale by industrial...
of the N-alkylated analogues MBDB and ethylbenzodioxylbutanamine (EBDB; "Ethyl-J") which have appeared in so-called methylenedioxymethamphetamine
Methylenedioxymethamphetamine
MDMA is an entactogenic drug of the phenethylamine and amphetamine class of drugs. In popular culture, MDMA has become widely known as "ecstasy" , usually referring to its street pill form, although this term may also include the presence of possible adulterants...
(MDMA; "Ecstasy", "Adam", "Empathy", "Molly", "E", "X", "XTC") tablets. While 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.
See also
- α-Ethylphenethylamine
- 1-(4-Methylphenyl)-2-aminobutane
- Ethylbenzodioxolylbutanamine (EBDB; Ethyl-J)
- Methylbenzodioxolylbutanamine (MBDB; Methyl-J; "Eden")