5-(2-Aminopropyl)-2,3-dihydrobenzofuran (5-APDB, 3-Desoxy-MDA, EMA-4) is a putative entactogen

drug A drug is any chemical substance that causes a change in an organism's physiology or psychology when consumed. Drugs are typically distinguished from food and substances that provide nutritional support. Consumption of drugs can be via insuffla ...

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 ...

and

amphetamine Amphetamine (contracted from alpha- methylphenethylamine) is a strong central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity. It is also commonly used ...

classes. It is an analogue of MDA where the heterocyclic 3-position oxygen from the 3,4- methylenedioxy ring has been replaced by a methylene bridge. 6-APDB is an analogue of 5-APDB where the 4-position oxygen has been replaced by a methylene bridge instead. 5-APDB was developed by a team led by

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 ...

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 Stimulants (also often referred to as psychostimulants or colloquially as uppers) is an overarching term that covers many drugs including those that increase activity of the central nervous system and the body, drugs that are pleasurable and inv ...

MDMA analogues such as MBDB and

MMAI 5-Methoxy-6-methyl-2-aminoindane (MMAI) 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 (SSRA) and produces entactogen effects in ...

, while producing no substitution for LSD or

. '' 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 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 ...

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 norepinephrine, respectively. In contrast, 6-APDB is more balanced on the three monoamine

neurotransmitter A neurotransmitter is a signaling molecule secreted by a neuron to affect another cell across a synapse. The cell receiving the signal, any main body part or target cell, may be another neuron, but could also be a gland or muscle cell. Neuro ...

s and acts more similarly to MDA and MDMA. Methoxy-substituted analogues of 5-APDB and 6-APDB have also been made and substituted for

DOM Dom or DOM may refer to: People and fictional characters * Dom (given name), including fictional characters * Dom (surname) * Dom La Nena (born 1989), stage name of Brazilian-born cellist, singer and songwriter Dominique Pinto * Dom people, an et ...

in animal tests, although they were around one tenth as potent as DOM.

Legal status

China

As of October 2015 5-APDB is a controlled substance in China.

UK

On June 10, 2013 5-APDB and a number of analogues were classified as Temporary Class Drugs in the UK following an ACMD recommendation. This means that sale and import of the named substances are criminal offences and are treated as for class B drugs.

References

{{DEFAULTSORT:Aminopropyl)-2,3-dihydrobenzofuran, 5-(2- Designer drugs 5-Benzofuranethanamines Substituted amphetamines Serotonin releasing agents Entactogens and empathogens