5-APDB

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5-APDB
File:3-desoxy-MDA.svg
Clinical data
Other names5-(2-Aminopropyl)-2,3-dihydrobenzofuran; 3-Desoxy-MDA; EMA-4; BF5AP
Routes of
administration		Oral
Drug classEntactogen; Serotonin releasing agent; Serotonin receptor modulator
ATC code
  • None
Legal status
Legal status
Identifiers
  • 1-(2,3-Dihydro-1-benzofuran-5-yl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
E number{{#property:P628}}
CompTox Dashboard (EPA)
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Chemical and physical data
FormulaC11H15NO
Molar mass177.247 g·mol−1
3D model (JSmol)
  • Cl.CC(N)Cc1cc2CCOc2cc1
  • 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 checkY
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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families.[2] It is an analogue of MDA where the heterocyclic 3-position oxygen from the 3,4-methylenedioxy ring has been replaced by a methylene bridge.[2] 6-APDB is an analogue of 5-APDB where the 4-position oxygen has been replaced by a methylene bridge instead.[2] 5-APDB was developed by a team led by David E. Nichols at Purdue University as part of their research into non-neurotoxic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]

Interactions

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

Pharmacology

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Pharmacodynamics

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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

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5-APDB, also known as 5-(2-aminopropyl)benzofuran, is a phenethylamine, amphetamine, and benzofuran and an analogue of 3,4-methylenedioxyamphetamine (MDA).

Synthesis

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The chemical synthesis of 5-APDB has been described.[2]

Analogues

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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

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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

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China

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

United Kingdom

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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

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References

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