2C2-NBOMe

2C2-NBOMe
Identifiers
	IUPAC name N-(2-methoxybenzyl)-1-(2-methoxy-4,5-methylenedioxyphenyl)-2-aminoethane;
Chemical and physical data
Formula	C18H21NO4
Molar mass	315.369 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COc1ccccc1CNCCc1cc2OCOc2cc1OC;
	InChI InChI=1S/C18H21NO4/c1-20-15-6-4-3-5-14(15)11-19-8-7-13-9-17-18(23-12-22-17)10-16(13)21-2/h3-6,9-10,19H,7-8,11-12H2,1-2H3; Key:XPZZCRFMAACBFQ-UHFFFAOYSA-N;

2C2-NBOMe (NBOMe-MMDPEA-2) is a phenethylamine derivative from the 25-NB class. It acts as a potent agonist at the 5-HT_2A receptor with weaker activity at 5-HT_2B and 5-HT_2C, and produces a head-twitch response in animal studies which often correlates with potential for psychedelic effects in humans. It is related in structure to psychedelic amphetamine derivatives such as MMDA-2 and is the first phenethylamine derivative with a methylenedioxy substitution on the phenyl ring but no alkyl substitution on the alpha carbon, that has been shown to produce psychedelic-appropriate responding in animals.^[1]^[2]

References

^ WO 2022241006, Wallach J, McCorvy J, Halberstadt A, "Selective, Partial and Arrestin-Biased 5-HT2A Agonists with Utility in Various Disorders.", published 17 November 2022, assigned to Saint Joseph's University, The Medical College Of Wisconsin, Inc., The Regents Of The University Of California
^ Wallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, et al. (July 2023). "Identification of 5-HT_2A Receptor Signaling Pathways Responsible for Psychedelic Potential". bioRxiv. doi:10.1101/2023.07.29.551106. PMC 10418054. PMID 37577474.

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[1] WO 2022241006, Wallach J, McCorvy J, Halberstadt A, "Selective, Partial and Arrestin-Biased 5-HT2A Agonists with Utility in Various Disorders.", published 17 November 2022, assigned to Saint Joseph's University, The Medical College Of Wisconsin, Inc., The Regents Of The University Of California

[pmid37577474-2] Wallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, et al. (July 2023). "Identification of 5-HT_2A Receptor Signaling Pathways Responsible for Psychedelic Potential". bioRxiv. doi:10.1101/2023.07.29.551106. PMC 10418054. PMID 37577474.

[1]

[2]

Identifiers

IUPAC name N-(2-methoxybenzyl)-1-(2-methoxy-4,5-methylenedioxyphenyl)-2-aminoethane
Chemical and physical data
Formula	C₁₈H₂₁NO₄
Molar mass	315.369 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES COc1ccccc1CNCCc1cc2OCOc2cc1OC
InChI InChI=1S/C18H21NO4/c1-20-15-6-4-3-5-14(15)11-19-8-7-13-9-17-18(23-12-22-17)10-16(13)21-2/h3-6,9-10,19H,7-8,11-12H2,1-2H3 Key:XPZZCRFMAACBFQ-UHFFFAOYSA-N

2C2-NBOMe

See also

References