5-APDB
Chemical compound
From Wikipedia, the free encyclopedia
5-APDB, also known as 5-(2-aminopropyl)-2,3-dihydrobenzofuran or as 3-desoxy-MDA, is an entactogen of the phenethylamine, amphetamine, and dihydrobenzofuran families.[2] It is an analogue of MDA where the heterocyclic 3-position oxygen from the 3,4-methylenedioxy ring has been replaced by a methylene bridge.[2] 6-APDB is an analogue of 5-APDB where the 4-position oxygen has been replaced by a methylene bridge instead.[2] 5-APDB was developed by a team led by David E. Nichols at Purdue University as part of their research into non-neurotoxic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 and first described in 1993.[3][4][5][6][7][2]
- None
 | |
| Clinical data | |
|---|---|
| Other names | 5-(2-Aminopropyl)-2,3-dihydrobenzofuran; 3-Desoxy-MDA; EMA-4; BF5AP |
| Routes of administration | Oral |
| Drug class | Entactogen; Serotonin releasing agent; Serotonin receptor modulator |
| ATC code |
|
| Legal status | |
| Legal status |
|
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| UNII | |
| CompTox Dashboard (EPA) | |
| Chemical and physical data | |
| Formula | C11H15NO |
| Molar mass | 177.247 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
  (what is this?) (verify) | |
Interactions
Pharmacology
Pharmacodynamics
In animal drug discrimination 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.[2] 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.[2] It also has activities at serotonin receptors.[6]
Chemistry
5-APDB, also known as 5-(2-aminopropyl)benzofuran, is a phenethylamine, amphetamine, and benzofuran and an analogue of 3,4-methylenedioxyamphetamine (MDA).
Synthesis
The chemical synthesis of 5-APDB has been described.[2]
Analogues
In contrast to 5-APDB, 6-APDB is more balanced on the three monoamine neurotransmitters and acts more similarly to MDA and MDMA.[2]
Methoxy-substituted analogues of 5-APDB and 6-APDB have also been made and substituted for DOM in animal tests, although they were around one tenth as potent as DOM.[8][9]
History
5-APDB, along with 6-APDB, was described by David E. Nichols and colleagues at Purdue University as an MDMA analogue in 1993.[3][4][5][6][7][2] Subsequently, the non-dihydrogenated benzofurans 5-APB and 6-APB emerged as novel designer drugs in 2010.[5][4][6] Prior to this, 5-APB and 6-APB had been patented and first described by Eli Lilly and Company as serotonin 5-HT2C receptor agonists for potential medical applications in 2000.[3][4][5] 5-APB and 6-APB are often confused with 5-APDB and 6-APDB.[4]
Society and culture
Legal status
Canada
5-APDB is a Schedule I controlled substance in Canada due phenethylamine blanket-ban language.[10]
China
As of October 2015 5-APDB is a controlled substance in China.[11]
United Kingdom
On June 10, 2013, 5-APDB and a number of analogues were classified as Temporary Class Drugs in the UK following an ACMD recommendation.[12] This means that sale and import of the named substances are criminal offences and are treated as for class B drugs.[13]
United States
5-APDB is not an explicitly controlled substance in the United States.[14] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.