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| Other names | 3-(2-Aminopropyl)benzofuran; 3-APB; 1-Oxa-α-methyltryptamine; 1-Oxa-AMT |
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| Formula | C11H13NO |
| Molar mass | 175.231 g·mol−1 |
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3-APB, also known as3-(2-aminopropyl)benzofuran or as1-oxa-α-methyltryptamine (1-oxa-AMT), is adrug of thebenzofuran family related to thepsychedelictryptamineα-methyltryptamine (AMT).[1][2] It is theanalogue andbioisostere of AMT in which thenitrogenatom of theindolering has been replaced with anoxygen atom, resulting in the drug being a benzofuran rather than tryptaminederivative.[1][2]
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 analoguemebfap (5-MeO-3-APB; a benzofuran analogue of5-MeO-AMT), which is known to have highaffinity for theserotonin5-HT2 receptors.[1][3][4][5] In addition,3-APBT, the analogue of 3-APB with asulfuratom instead of anoxygen atom, is a highlypotentserotonin–norepinephrine–dopamine releasing agent (SNDRA) andserotonin receptor agonist, withpsychedelic-like but notstimulant-like effects in animals.[6][1]
Positional isomers of 3-APB such as5-APB and6-APB aremonoamine releasing agents andentactogens of theamphetamine and benzofuran families.[7][8][9] Besides 3-APBT, all of the possible positional isomers of theAPBTs (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]
The 5-HT2A receptor is the primary target for LSD, psilocybin, and other hallucinogenic drugs in the brain [76, 77]. Other hallucinogenic drugs acting strongly at 5-HT2A include 3-API [78, 79], while, by contrast, 5-API displays a much lower potency and efficacy [18]. Hence, the interaction of APIs with the 5-HT2A receptor is dependent on the position of the alkylamine side chain on the indole ring. Although relevant data have not been reported for 3-APB, the 5-methoxy-substituted derivative 5-methoxy-3-(2-aminopropyl)benzofuran has high affinity for 5-HT2A sites [80]. In line with the activity of 5-API, both 5-APB and 6-APB have been shown to be active at 5-HT2A with relatively low potency and efficacy [20]. Given those previous findings, it is notable that 3-APBT, 5-APBT, and 6-APBT are highly efficacious 5-HT2A agonists. Hence, compared to APIs and APBs, the ability of APBTs to activate the 5-HT2A receptor does not depend on side chain position.
