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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 of 5-APB

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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
6.3 null [pKi]
5.78 null [pKi]
6.33 null [pKi]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

400mg leads to fatal intoxication in human
Route of Administration: Oral
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 GMT 2023
Edited
by admin
on Sat Dec 16 19:49:42 GMT 2023
Record UNII
2M3825704H
Record Status Validated (UNII)
Record Version
  • Download
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
Created by admin on Sat Dec 16 19:49:43 GMT 2023 , Edited by admin on Sat Dec 16 19:49:43 GMT 2023
Code System Code Type Description
FDA UNII
2M3825704H
Created by admin on Sat Dec 16 19:49:43 GMT 2023 , Edited by admin on Sat Dec 16 19:49:43 GMT 2023
PRIMARY
EPA CompTox
DTXSID10101010
Created by admin on Sat Dec 16 19:49:43 GMT 2023 , Edited by admin on Sat Dec 16 19:49:43 GMT 2023
PRIMARY
CAS
286834-81-9
Created by admin on Sat Dec 16 19:49:43 GMT 2023 , Edited by admin on Sat Dec 16 19:49:43 GMT 2023
PRIMARY
PUBCHEM
9837232
Created by admin on Sat Dec 16 19:49:43 GMT 2023 , Edited by admin on Sat Dec 16 19:49:43 GMT 2023
PRIMARY
WIKIPEDIA
5-APB
Created by admin on Sat Dec 16 19:49:43 GMT 2023 , Edited by admin on Sat Dec 16 19:49:43 GMT 2023
PRIMARY
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SALT/SOLVATE -> PARENT
OFF-TARGET->AGONIST
Indeed all drugs and drug metabolites that induce heart valvular disease in humans activate 5-HT2B receptors in vivo and in vitro and this activity is thought to be important for the development of fibrotic lesions upon chronic human administration.
Ki
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ACTIVE MOIETY