mebfap

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| image = Mebfap structure.png

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| class = Serotonin receptor modulator

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| CAS_number = 140853-59-4

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| PubChem = 3025750

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| ChemSpiderID = 2291437

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| ChEMBL = 304628

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| synonyms = MEBFAP; 1-(5-Methoxybenzofuran-3-yl)-2-aminopropane; 5-Methoxy-3-(2-aminopropyl)benzofuran; 5-MeO-3-APB; 3-(2-Aminopropyl)-5-methoxybenzofuran

| IUPAC_name = 1-(5-methoxy-1-benzofuran-3-yl)propan-2-amine

| C=12 | H=15 | N=1 | O=2

| SMILES = CC(CC1=COC2=C1C=C(C=C2)OC)N

| StdInChI = 1S/C12H15NO2/c1-8(13)5-9-7-15-12-4-3-10(14-2)6-11(9)12/h3-4,6-8H,5,13H2,1-2H3

| StdInChIKey = PMAFEFSQHHKAKM-UHFFFAOYSA-N

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Mebfap, also known as 1-(5-methoxybenzofuran-3-yl)-2-aminopropane, is a serotonin receptor modulator of the benzofuran family.{{cite book | vauthors = Nichols DE | title = Chemistry and Structure-Activity Relationships of Psychedelics | series = Current Topics in Behavioral Neurosciences| volume = 36 | issue = | pages = 1–43 | date = 2018 | pmid = 28401524 | doi = 10.1007/7854_2017_475 | isbn = 978-3-662-55878-2 | quote = Replacing the indole nitrogen of the tryptamines with an oxygen atom affords a benzo[b]furan, another potential bioisostere of tryptamines. Compounds 13 and 14 both had about one-sixth the affinity of their indole congeners, using displacement of [125I]DOI from rat frontal cortical homogenate (Tomaszewski et al. 1992). McKenna et al. (1990) reported a similar finding, assessing ability of N-methyl-N-isopropyltryptamine to displace [125I]-R-DOI from rat cortical homogenate, compared with its benzo[b]furan isostere. The tryptamine IC50 of 38 nM was about 13-fold lower than the benzofuran, which had an IC50 of 500 nM. }}{{cite journal | vauthors=Nichols DE | title=Structure–activity relationships of serotonin 5-HT2A agonists | journal=Wiley Interdisciplinary Reviews: Membrane Transport and Signaling | volume=1 | issue=5 | date=2012 | issn=2190-460X | doi=10.1002/wmts.42 | doi-access=free | pages=559–579 | access-date=7 February 2025 | url=https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=e28e0e22c3145af5a787c34fbedbaa8f81e1ed6b | quote=Other potential bioisosteres of tryptamines would include replacing the indole N with an oxygen atom to give benzo[b]furans (Figure 7). The dimethylamino compound 10 and the racemic α-methyl congener 11 both had about one-sixth the affinity of their indole congeners, measured using displacement of [125I]DOI from rat frontal cortical homogenate.10 This result parallels the findingsby McKenna et al.,4 who compared N-methyl-Nisopropyltryptamine with its benzofuran isostere in its ability to displace [125I]-R-DOI from rat cortical homogenate. In that report, the tryptamine had an IC50 of 38 nM whereas the benzofuran IC50 was 500 nM, 13-fold lower affinity. [...] FIGURE 7 | Benzofuran bioisosteres of tryptamines.}}{{cite journal | vauthors = Tomaszewski Z, Johnson MP, Huang X, Nichols DE | title = Benzofuran bioisosteres of hallucinogenic tryptamines | journal = Journal of Medicinal Chemistry | volume = 35 | issue = 11 | pages = 2061–2064 | date = May 1992 | pmid = 1534585 | doi = 10.1021/jm00089a017 }} It is an analogue of 5-MeO-AMT in which the indole ring has been replaced with a benzofuran ring. Put another way, it is the analogue of 5-MeO-AMT in which the nitrogen atom in its indole ring has been replaced with a carbon atom to make a benzofuran ring. The drug is a ligand of serotonin receptors similarly to 5-MeO-AMT, but shows about one-sixth the affinity of 5-MeO-AMT. Mebfap was first described in the scientific literature by 1992.