5-APB

Details

Stereochemistry	RACEMIC
Molecular Formula	C11H13NO
Molecular Weight	175.227
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(N)CC1=CC2=C(OC=C2)C=C1

InChI

InChIKey=VKUMKUZDZWHMQU-UHFFFAOYSA-N

InChI=1S/C11H13NO/c1-8(12)6-9-2-3-11-10(7-9)4-5-13-11/h2-5,7-8H,6,12H2,1H3

HIDE SMILES / InChI

Molecular Formula	C11H13NO
Molecular Weight	175.227
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23261499
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/25765500 | https://www.ncbi.nlm.nih.gov/pubmed/25447185

5-(2-Aminopropyl)benzofuran (5-APB) is an empathogenic psychoactive compound of the substituted benzofuran, substituted amphetamine and substituted phenethylamine classes. 5-(2-Aminopropyl)benzofuran is a serotonin–norepinephrine–dopamine reuptake inhibitor and serotonin–norepinephrine–dopamine releasing agent. The toxicity and long-term health effects of recreational 5-APB use do not seem to have been studied in any scientific context and the exact toxic dosage is unknown/ 5-(2-Aminopropyl)benzofuran 's high affinity for the 5-HT2b receptor makes it likely that 5-APB would be cardiotoxic with long-term use, as seen in other 5-HT2B agonists such as fenfluramine and MDMA.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Dopamine transporter 180 Target ID: CHEMBL238 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23261499	Inhibitor 8297	6.3 null [pKi]
Serotonin transporter 178 Target ID: CHEMBL228 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23261499	Inhibitor 8297	5.78 null [pKi]
Norepinephrine transporter 191 Target ID: CHEMBL222 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23261499	Inhibitor 8297	6.33 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
5-(2-Aminopropyl)benzofuran and phenazepam demonstrate the possibility of dependence by increasing dopamine levels in the brain.	2016 Oct	27502147

Patents

Sample Use Guides

In Vivo Use Guide

400mg leads to fatal intoxication in human

Route of Administration: Oral

In Vitro Use Guide

Inhibition of the human NET, DAT and SERT was assessed in HEK 293 cells that were stably transfected with the transporters. Cells were suspended in uptake buffer. We incubated the cells for 10 min with different concentrations of the test compounds (5-(2-Aminopropyl)benzofuran) and then added the corresponding [3H] monoamine (5 nM final concentration) at room temperature. After 10 min, we stopped uptake by separating the cells from the buffer using centrifugation through silicone oil. The centrifugation tubes were frozen in liquid nitrogen and cut to separate the cell pellet from the silicone oil and assay buffer layers. The cell pellet was then lysed. Scintillation fluid was added, and radioactivity was counted on a β-counter.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 19:49:42 UTC 2023` Edited by `admin` on `Sat Dec 16 19:49:42 UTC 2023`
Record UNII	2M3825704H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

5-APB

Common Name

English

.ALPHA.-METHYL-5-BENZOFURANETHANAMINE

Systematic Name

English

1-(BENZOFURAN-5-YL)PROPAN-2-AMINE

Systematic Name

English

5-(2-AMINOPROPYL)BENZOFURAN

Systematic Name

English

5-BENZOFURANETHANAMINE, .ALPHA.-METHYL-

Systematic Name

English

Classification Tree Code System Code

WIKIPEDIA

Designer-drugs-5-APB