3-APB

3-APB, also known as 3-(2-aminopropyl)benzofuran or as 1-oxa-α-methyltryptamine (1-oxa-AMT), is a drug of the benzofuran family related to the psychedelic tryptamine α-methyltryptamine (AMT).^[1][2] It is the analogue and bioisostere of AMT in which the nitrogen atom of the indole ring has been replaced with an oxygen atom, resulting in the drug being a benzofuran rather than tryptamine derivative.^[1][2]

Other names3-(2-Aminopropyl)benzofuran; 3-APB; 1-Oxa-α-methyltryptamine; 1-Oxa-AMT

CAS Number

• 105909-13-5

PubChem CID

• 57014554

ChemSpider

• 45884773

Quick facts Clinical data, Other names ...

3-APB

Clinical data
Other names	3-(2-Aminopropyl)benzofuran; 3-APB; 1-Oxa-α-methyltryptamine; 1-Oxa-AMT
Identifiers
IUPAC name 1-(1-benzofuran-3-yl)propan-2-amine
CAS Number	105909-13-5
PubChem CID	57014554
ChemSpider	45884773
CompTox Dashboard (EPA)	DTXSID701303480
Chemical and physical data
Formula	C11H13NO
Molar mass	175.231 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(CC1=COC2=CC=CC=C21)N
InChI InChI=1S/C11H13NO/c1-8(12)6-9-7-13-11-5-3-2-4-10(9)11/h2-5,7-8H,6,12H2,1H3 Key:YOSBGWAOEQRQMP-UHFFFAOYSA-N

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The properties of 3-APB do not yet appear to have been reported.^[1] However, derivatives of 3-APB have been studied and described.^[1][3][4][5] An example is its 5-methoxy analogue mebfap (5-MeO-3-APB; a benzofuran analogue of 5-MeO-AMT), which is known to have high affinity for the serotonin 5-HT₂ receptors.^[1][3][4][5] In addition, 3-APBT, the analogue of 3-APB with a sulfur atom instead of an oxygen atom, is a highly potent serotonin–norepinephrine–dopamine releasing agent (SNDRA) and serotonin receptor agonist, with psychedelic-like but not stimulant-like effects in animals.^[6][1]

Positional isomers of 3-APB such as 5-APB and 6-APB are monoamine releasing agents and entactogens of the amphetamine and benzofuran families.^[7][8][9] Besides 3-APBT, all of the possible positional isomers of the APBTs (i.e., 2-APBT through 7-APBT) are active as potent SNDRAs and at least some also as serotonin 5-HT₂ receptor agonists.^[1][6]