-2,3-dihydrobenzofuran.gif)
5-(2-Aminopropyl)-2,3-dihydrobenzofuran
Encyclopedia
5--2,3-dihydrobenzofuran (5-APDB, 3-Desoxy-MDA, EMA-4) is a putative entactogen drug
of the phenethylamine
and amphetamine
classes. It is an analogue of the MDA where the heterocyclic 3-position oxygen from the 3,4-methylenedioxy
ring
has been replaced by a methylene
group
. 6-APDB is an anlogue of 5-APDB where the 4-position oxygen has been replaced by a methylene instead. 5-APDB was developed by a team led by David E. Nichols
at Purdue University
as part of their research into non-neurotoxic analogues of MDMA.
In animal studies, 5-APDB's effects generalize most closely to non-stimulant
MDMA analogues such as MBDB
and MMAI, while producing no substitution for LSD
or amphetamine
. In vitro
studies show that 5-APDB acts as a highly selective
serotonin releasing agent
(SSRA), with IC50
values of 130 nM, 7,089 nM, and 3,238 nM for inhibiting
the reuptake
of serotonin
, dopamine
, and norepinephrine
, respectively. In contrast, 6-APDB is more balanced on the three monoamine
neurotransmitter
s and acts more similarly to MDA and MDMA. Anecdotal reports from human users suggest that 5-APDB produces mild empathy
but with relatively little euphoria
and is accompanied by sedation
.
Methoxy-substituted analogues of 5-APDB and 6-APDB have also been made and substituted for DOM
in animal tests, although they were around 10x less potent than DOM.
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 the MDA where the heterocyclic 3-position oxygen 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 by 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...
. 6-APDB is an anlogue of 5-APDB where the 4-position oxygen has been replaced by a methylene instead. 5-APDB was developed by a team led 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...
at Purdue University
Purdue University
Purdue University, located in West Lafayette, Indiana, U.S., is the flagship university of the six-campus Purdue University system. Purdue was founded on May 6, 1869, as a land-grant university when the Indiana General Assembly, taking advantage of the Morrill Act, accepted a donation of land and...
as part of their research into non-neurotoxic analogues of MDMA.
In animal studies, 5-APDB's effects generalize most closely to non-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...
MDMA analogues such as MBDB
MBDB
Methylbenzodioxolylbutanamine is an entactogen of the phenethylamine chemical class. MBDB is a closely related chemical analogue of MDMA, with the only difference between the two molecules being an ethyl group instead of a methyl group attached to the alpha carbon.MBDB was first synthesized by...
and MMAI, while producing no substitution for 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...
or 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,...
. 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...
studies show that 5-APDB acts as a highly selective
Binding selectivity
Binding selectivity refers to the differing affinities with which different ligands bind to a substrate forming a complex. A selectivity coefficient is the equilibrium constant for the reaction of displacement by one ligand of another ligand in a complex with the substrate...
serotonin releasing agent
Serotonin releasing agent
A serotonin releasing agent is a type of drug which induces the release of serotonin from the pre-synaptic neuron into the synapse...
(SSRA), 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 130 nM, 7,089 nM, and 3,238 nM for inhibiting
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...
, respectively. In contrast, 6-APDB is more balanced on the three monoamine
Monoamine neurotransmitter
thumb|right|350px| A phylogenetic tree showing how a number of monoamine receptors are related to each other.Monoamine neurotransmitters are neurotransmitters and neuromodulators that contain one amino group that is connected to an aromatic ring by a two-carbon chain...
neurotransmitter
Neurotransmitter
Neurotransmitters are endogenous chemicals that transmit signals from a neuron to a target cell across a synapse. Neurotransmitters are packaged into synaptic vesicles clustered beneath the membrane on the presynaptic side of a synapse, and are released into the synaptic cleft, where they bind to...
s and acts more similarly to MDA and MDMA. Anecdotal reports from human users suggest that 5-APDB produces mild empathy
Empathy
Empathy is the capacity to recognize and, to some extent, share feelings that are being experienced by another sapient or semi-sapient being. Someone may need to have a certain amount of empathy before they are able to feel compassion. The English word was coined in 1909 by E.B...
but with relatively little euphoria
Euphoria
Euphoria is an emotional and mental state defined as a sense of great elation and well being.Euphoria may also refer to:* Euphoria , a genus of scarab beetles* Euphoria, a genus name previously used for the longan and other trees...
and is accompanied by sedation
Sedation
Sedation is the reduction of irritability or agitation by administration of sedative drugs, generally to facilitate a medical procedure or diagnostic procedure...
.
Methoxy-substituted analogues of 5-APDB and 6-APDB have also been made and substituted for DOM
2,5-Dimethoxy-4-methylamphetamine
2,5-Dimethoxy-4-methylamphetamine is a psychedelic and a substituted amphetamine...
in animal tests, although they were around 10x less potent than DOM.
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...
- 6-APDB6-APDB6--2,3-dihydrobenzofuran 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-(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...