5-APDB

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families.^[2] It is an analogue of MDA where the heterocyclic 3-position oxygen from the 3,4-methylenedioxy ring has been replaced by a methylene bridge.^[2] 6-APDB is an analogue of 5-APDB where the 4-position oxygen has been replaced by a methylene bridge instead.^[2] 5-APDB was developed by a team led by David E. Nichols at Purdue University as part of their research into non-neurotoxic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]}

5-APDB

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	None
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics)[1] CA: Schedule I DE: NpSG (Industrial and scientific use only) UK: Class B
Identifiers
IUPAC name 1-(2,3-Dihydro-1-benzofuran-5-yl)propan-2-amine
CAS Number	152624-03-8 N
PubChem CID	192601
ChemSpider	167143 N
UNII	UI10BAJ8SH
CompTox Dashboard (EPA)	DTXSID70934560
Chemical and physical data
Formula	C11H15NO
Molar mass	177.247 g·mol−1
3D model (JSmol)	Interactive image
SMILES Cl.CC(N)Cc1cc2CCOc2cc1
InChI InChI=1S/C11H15NO.ClH/c1-8(12)6-9-2-3-11-10(7-9)4-5-13-11;/h2-3,7-8H,4-6,12H2,1H3;1H Y Key:BZKLFXQUBIRXAK-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Interactions

See also: MDMA § Interactions, Trip killer § Antidotes of other hallucinogens, and MDMA/citalopram

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-HT_2C 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

China

As of October 2015 5-APDB is a controlled substance in China.^[10]

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.^[11] This means that sale and import of the named substances are criminal offences and are treated as for class B drugs.^[12]

See also

• Substituted benzofuran