5-APDB

5-APDB

Systematic (IUPAC) name
1-(2,3-dihydro-1-benzofuran-5-yl)propan-2-amine
Clinical data
Pregnancy cat.	?
Legal status	Uncontrolled (but may be covered under the Federal Analogue Act in the United States and under similar bills in other countries)
Routes	Oral
Identifiers
CAS number	152623-94-4 N
ATC code	None
PubChem	CID 192601
ChemSpider	21073073 Y
Chemical data
Formula	C11H15NO
Mol. mass	177.242 g/mol
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
N (what is this?)  (verify)

5-(2-Aminopropyl)-2,3-dihydrobenzofuran (5-APDB, 3-Desoxy-MDA, EMA-4) is a putative entactogen drug of the phenethylamine and amphetamine classes.^[1] It is an analogue of MDA where the heterocyclic 3-position oxygen from the 3,4-methylenedioxy ring has been replaced by a methylene bridge.^[1] 6-APDB is an analogue of 5-APDB where the 4-position oxygen has been replaced by a methylene bridge instead.^[1] 5-APDB was developed by a team led by David E. Nichols at Purdue University as part of their research into non-neurotoxic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.^[1]

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.^[1] 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.^[1] In contrast, 6-APDB is more balanced on the three monoamine neurotransmitters and acts more similarly to MDA and MDMA.^[1] Anecdotal reports from human users suggest that 5-APDB produces mild empathy but with relatively little euphoria and is accompanied by sedation.^{[citation needed]}

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.^[2][3]

On June 10th 2013 5-APDB and a number of analogues were classified as Temporary Class Drugs in the UK following an ACMD recommendation.^[4] This means that sale and import of the named substances are criminal offences and are treated as for class B drugs.^[5] 5-apdb has been used to stop bad comedown effects, panic attacks and withdrawals from methamphetamine, ice, a-pvp and mdpv producing a calmative sedative effect. Future use in treating patient with amphetamine problems in hospital emergency situations looks promising. Caution: when this compound (5-apdb) is mixed with hallucinogenic chemicals bad reactions including overdose may occur even at low doses.

See also

• 5-APB
• 6-APB
• 6-APDB
• 5-(2-Aminopropyl)indole
• Ethylenedioxymethamphetamine
• Indanylaminopropane
• Naphthylaminopropane
• Tetralinylaminopropane

References