6-APDB
Encyclopedia
6--2,3-dihydrobenzofuran (6-APDB, 4-Desoxy-MDA, EMA-3) is a stimulant
and entactogen drug
of the phenethylamine
and amphetamine
classes. It is an analogue of MDA
where the heterocyclic 4-position oxygen
from the 3,4-methylenedioxy
ring
has been replaced with a methylene
group
. 5-APDB (3-Desoxy-MDA) is an analogue of 6-APDB where the 3-position oxygen has been replaced with a methylene instead. 6-APDB, along with 5-APDB, was first synthesized
by David E. Nichols
in the early 1990s while investigating non-neurotoxic MDMA analogues.
In animal studies, 6-APDB fully substitutes for MBDB and MMAI
but not for amphetamine
or LSD
. In vitro
, 6-APDB has been shown to inhibit
the reuptake
of serotonin
, dopamine
, and norepinephrine
with IC50
values of 322 nM, 1,997 nM, and 980 nM, respectively. These values are very similar to those of MDA, but with those for the catecholamine
s slightly lower in comparison, perhaps more similarly to MDMA. In contrast, 5-APDB is highly selective for serotonin. Though 6-APDB does not substitute for amphetamine in rats at the doses used in referenced study, based on its in vitro profile it can be suggested that it may have amphetamine-like effects at higher doses.
The unsaturated benzofuran derivative 6-APB
, or 6-(2-aminopropyl)benzofuran is also known, but the difference in pharmacological effects between 6-APB and 6-APDB is unclear.
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...
and entactogen drug
Drug
A drug, broadly speaking, is any substance that, when absorbed into the body of a living organism, alters normal bodily function. There is no single, precise definition, as there are different meanings in drug control law, government regulations, medicine, and colloquial usage.In pharmacology, a...
of the phenethylamine
Substituted phenethylamine
The substituted phenethylamines are chemical compounds with the 2-phenethylamine chemical structure modified at the phenyl ring, sidechain, and/or amino group. Some of them are psychoactive drugs, including stimulants, psychedelics, opioids, and entactogens, which exert their effects primarily...
and amphetamine
Substituted amphetamine
Substituted amphetamines are a chemical class of stimulants, entactogens, hallucinogens, and other drugs. They feature a phenethylamine core with a methyl group attached to the alpha carbon resulting in amphetamine, along with additional substitutions...
classes. It is an analogue of MDA
3,4-Methylenedioxyamphetamine
3,4-Methylenedioxyamphetamine , also known as tenamfetamine , is a psychedelic and entactogenic drug of the phenethylamine and amphetamine chemical classes...
where the heterocyclic 4-position oxygen
Oxygen
Oxygen is the element with atomic number 8 and represented by the symbol O. Its name derives from the Greek roots ὀξύς and -γενής , because at the time of naming, it was mistakenly thought that all acids required oxygen in their composition...
from the 3,4-methylenedioxy
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...
ring
Functional group
In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. The same functional group will undergo the same or similar chemical reaction regardless of the size of the molecule it is a part of...
has been replaced with a methylene
Methylene
Methylene is a chemical species in which a carbon atom is bonded to two hydrogen atoms. Three different possibilities present themselves:* the -CH2- substituent group: e.g., dichloromethane ....
group
Functional group
In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. The same functional group will undergo the same or similar chemical reaction regardless of the size of the molecule it is a part of...
. 5-APDB (3-Desoxy-MDA) is an analogue of 6-APDB where the 3-position oxygen has been replaced with a methylene instead. 6-APDB, along with 5-APDB, was first synthesized
Organic synthesis
Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic molecules can often contain a higher level of complexity compared to purely inorganic compounds, so the synthesis of organic compounds has...
by David E. Nichols
David E. Nichols
David E. Nichols is an American pharmacologist and medicinal chemist.Presently the Robert C. and Charlotte P. Anderson Distinguished Chair in Pharmacology at Purdue University, Nichols has worked in the field of psychoactive drugs since 1969...
in the early 1990s while investigating non-neurotoxic MDMA analogues.
In animal studies, 6-APDB fully substitutes for MBDB and MMAI
5-Methoxy-6-methyl-2-aminoindane
5-Methoxy-6-methyl-2-aminoindane , is a drug developed in the 1990s by a team led by David E. Nichols at Purdue University. It acts as a non-neurotoxic and highly selective serotonin releasing agent and produces entactogen effects in humans...
but not for amphetamine
Amphetamine
Amphetamine or amfetamine is a psychostimulant drug of the phenethylamine class which produces increased wakefulness and focus in association with decreased fatigue and appetite.Brand names of medications that contain, or metabolize into, amphetamine include Adderall, Dexedrine, Dextrostat,...
or LSD
LSD
Lysergic acid diethylamide, abbreviated LSD or LSD-25, also known as lysergide and colloquially as acid, is a semisynthetic psychedelic drug of the ergoline family, well known for its psychological effects which can include altered thinking processes, closed and open eye visuals, synaesthesia, an...
. In vitro
In vitro
In vitro refers to studies in experimental biology that are conducted using components of an organism that have been isolated from their usual biological context in order to permit a more detailed or more convenient analysis than can be done with whole organisms. Colloquially, these experiments...
, 6-APDB has been shown to inhibit
Reuptake inhibitor
A reuptake inhibitor , also known as a transporter blocker, is a drug that inhibits the plasmalemmal transporter-mediated reuptake of a neurotransmitter from the synapse into the pre-synaptic neuron, leading to an increase in the extracellular concentrations of the neurotransmitter and therefore an...
the reuptake
Reuptake
Reuptake, or re-uptake, is the reabsorption of a neurotransmitter by a neurotransmitter transporter of a pre-synaptic neuron after it has performed its function of transmitting a neural impulse....
of 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...
, dopamine
Dopamine
Dopamine is a catecholamine neurotransmitter present in a wide variety of animals, including both vertebrates and invertebrates. In the brain, this substituted phenethylamine functions as a neurotransmitter, activating the five known types of dopamine receptors—D1, D2, D3, D4, and D5—and their...
, and norepinephrine
Norepinephrine
Norepinephrine is the US name for noradrenaline , a catecholamine with multiple roles including as a hormone and a neurotransmitter...
with IC50
IC50
The half maximal inhibitory concentration is a measure of the effectiveness of a compound in inhibiting biological or biochemical function. This quantitative measure indicates how much of a particular drug or other substance is needed to inhibit a given biological process by half...
values of 322 nM, 1,997 nM, and 980 nM, respectively. These values are very similar to those of MDA, but with those for the catecholamine
Catecholamine
Catecholamines are molecules that have a catechol nucleus consisting of benzene with two hydroxyl side groups and a side-chain amine. They include dopamine, as well as the "fight-or-flight" hormones adrenaline and noradrenaline released by the adrenal medulla of the adrenal glands in response to...
s slightly lower in comparison, perhaps more similarly to MDMA. In contrast, 5-APDB is highly selective for serotonin. Though 6-APDB does not substitute for amphetamine in rats at the doses used in referenced study, based on its in vitro profile it can be suggested that it may have amphetamine-like effects at higher doses.
The unsaturated benzofuran derivative 6-APB
6-APB
6-benzofuran or 1-benzofuran-6-ylpropan-2-amine is thought to be a stimulant and entactogen drug although to date, no authoritative source can say even whether or not it is psychoactive. Chemically, it is of the phenethylamine and substituted amphetamine classes...
, or 6-(2-aminopropyl)benzofuran is also known, but the difference in pharmacological effects between 6-APB and 6-APDB is unclear.
See also
- 5-APB5-APB5-benzofuran or 1-benzofuran-5-ylpropan-2-amine is a drug claimed to act as an agonist of the 5-HT2C receptor, which has been sold as a designer drug...
- 6-APB6-APB6-benzofuran or 1-benzofuran-6-ylpropan-2-amine is thought to be a stimulant and entactogen drug although to date, no authoritative source can say even whether or not it is psychoactive. Chemically, it is of the phenethylamine and substituted amphetamine classes...
- 5-APDB
- 5-(2-Aminopropyl)indole5-(2-Aminopropyl)indole5-indole is an indole derivative which is mentioned in TIHKAL as a fairly potent and long-lasting stimulant drug. It is related to several well known drugs, and can be viewed both as a structural isomer of α-MT , and as a ring-substituted derivative of amphetamine...
- EthylenedioxymethamphetamineEDMA3,4-Ethylenedioxy-N-methylamphetamine is an entactogen drug of the amphetamine class. It is an analogue of MDMA where the methylenedioxy ring has been replaced by an ethylenedioxy ring. EDMA was first synthesized by Alexander Shulgin. In his book PiHKAL, the dosage is listed as 150–250 mg,...
- IndanylaminopropaneIndanylaminopropaneIndanylaminopropane , sometimes incorrectly referred to as indanylamphetamine, is an entactogen and psychedelic drug of the phenethylamine and amphetamine classes...
- Naphthylaminopropane
- TetralinylaminopropaneTetralinylaminopropaneTetralinylaminopropane is an entactogen drug of the amphetamine class which acts as a selective serotonin releasing agent . It has IC50 values of 121 nM, 6,436 nM, and 3,371 nM for inhibiting the reuptake of serotonin, dopamine, and norepinephrine, respectively...