Mebfap

Mebfap
Clinical data
Other names	MEBFAP; 1-(5-Methoxybenzofuran-3-yl)-2-aminopropane; 5-Methoxy-3-(2-aminopropyl)benzofuran; 5-MeO-3-APB; 3-(2-Aminopropyl)-5-methoxybenzofuran
Drug class	Serotonin receptor modulator
Identifiers
	IUPAC name 1-(5-methoxy-1-benzofuran-3-yl)propan-2-amine;
CAS Number	140853-59-4;
PubChem CID	3025750;
ChemSpider	2291437;
ChEMBL	ChEMBL304628;
Chemical and physical data
Formula	C12H15NO2
Molar mass	205.257 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(CC1=COC2=C1C=C(C=C2)OC)N;
	InChI InChI=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; Key:PMAFEFSQHHKAKM-UHFFFAOYSA-N;

Mebfap, also known as 1-(5-methoxybenzofuran-3-yl)-2-aminopropane, is a serotonin receptor modulator of the benzofuran family.^[1]^[2]^[3] It is an analogue of 5-MeO-AMT in which the indole ring has been replaced with a benzofuran ring.^[1]^[2]^[3] 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.^[1]^[2]^[3] The drug is a ligand of serotonin receptors similarly to 5-MeO-AMT, but shows about one-sixth the affinity of 5-MeO-AMT.^[1]^[2]^[3] Mebfap was first described in the scientific literature by 1992.^[3]

^ ^a ^b ^c ^d Nichols DE (2018). Chemistry and Structure-Activity Relationships of Psychedelics. Current Topics in Behavioral Neurosciences. Vol. 36. pp. 1–43. doi:10.1007/7854_2017_475. ISBN 978-3-662-55878-2. PMID 28401524. 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.
^ ^a ^b ^c ^d Nichols DE (2012). "Structure–activity relationships of serotonin 5-HT2A agonists". Wiley Interdisciplinary Reviews: Membrane Transport and Signaling. 1 (5): 559–579. doi:10.1002/wmts.42. ISSN 2190-460X. Retrieved 7 February 2025. 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.
^ ^a ^b ^c ^d ^e Tomaszewski Z, Johnson MP, Huang X, Nichols DE (May 1992). "Benzofuran bioisosteres of hallucinogenic tryptamines". Journal of Medicinal Chemistry. 35 (11): 2061–2064. doi:10.1021/jm00089a017. PMID 1534585.

[Nichols2018-1] Nichols DE (2018). Chemistry and Structure-Activity Relationships of Psychedelics. Current Topics in Behavioral Neurosciences. Vol. 36. pp. 1–43. doi:10.1007/7854_2017_475. ISBN 978-3-662-55878-2. PMID 28401524. 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.

[Nichols2012-2] Nichols DE (2012). "Structure–activity relationships of serotonin 5-HT2A agonists". Wiley Interdisciplinary Reviews: Membrane Transport and Signaling. 1 (5): 559–579. doi:10.1002/wmts.42. ISSN 2190-460X. Retrieved 7 February 2025. 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.

[TomaszewskiJohnsonHuang1992-3] Tomaszewski Z, Johnson MP, Huang X, Nichols DE (May 1992). "Benzofuran bioisosteres of hallucinogenic tryptamines". Journal of Medicinal Chemistry. 35 (11): 2061–2064. doi:10.1021/jm00089a017. PMID 1534585.

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