N-Acetylmescaline

N-Acetylmescaline
Names
	Preferred IUPAC name N-[2-(3,4,5-Trimethoxyphenyl)ethyl]acetamide
Identifiers
CAS Number	4593-89-9;
3D model (JSmol)	Interactive image;
ChemSpider	90893;
PubChem CID	100597;
CompTox Dashboard (EPA)	DTXSID10196660 ;
	InChI InChI=1S/C13H19NO4/c1-9(15)14-6-5-10-7-11(16-2)13(18-4)12(8-10)17-3/h7-8H,5-6H2,1-4H3,(H,14,15) Key: SNMFNOQKGANWHD-UHFFFAOYSA-N; InChI=1/C13H19NO4/c1-9(15)14-6-5-10-7-11(16-2)13(18-4)12(8-10)17-3/h7-8H,5-6H2,1-4H3,(H,14,15) Key: SNMFNOQKGANWHD-UHFFFAOYAH;
	SMILES O=C(NCCc1cc(OC)c(OC)c(OC)c1)C;
Properties
Chemical formula	C13H19NO4
Molar mass	253.298 g·mol−1
Melting point	93 to 94 °C (199 to 201 °F; 366 to 367 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

N-Acetylmescaline is a mescaline derivative found in trace quantities in peyote (Lophophora williamsii).^[1] It is a metabolite of mescaline in humans, but it has little pharmacological effects of its own.^[2] At doses of up to 750 mg, only mild drowsiness was observed.^[2]^[3] Hence, N-acetylmescaline appears to be inactive as a hallucinogen.^[3]

N-Acetylmescaline has microtubule assembly inhibitory activity.^[4]

References

^ ^a ^b John Buckingham (ed.). Dictionary of Natural Products. Vol. 6. p. 3842.
^ ^a ^b Maxwell Gordon (ed.). Psychopharmacological Agents. Vol. 4. p. 94.
^ ^a ^b Mangner TJ (1978). Potential Psychotomimetic Antagonists. N,n -diethyl-1-methyl-3-aryl-1, 2, 5, 6-tetrahydropyridine-5-carboxamides (Ph.D. thesis). University of Michigan. doi:10.7302/11268. Archived from the original on 30 March 2025. Two N-substituted mescaline analogs isolated from L. williamsii are N-methylmescaline (62a) and N-acetylmescaline (62b).95 N-Methylmescaline shows no central effects at a dose which would represent many times the level that would be encountered in a normal dose of peyote.67 N-Acetylmescaline, which has been identified as a metabolite of mescaline in man, is centrally inactive to 750 mg.96
^ Dumortier, C; Potenziano, JL; Bane, S; Engelborghs, Y (1997). "The mechanism of tubulin-colchicine recognition--a kinetic study of the binding of a bicyclic colchicine analogue with a minor modification of the a ring". European Journal of Biochemistry. 249 (1): 265–9. doi:10.1111/j.1432-1033.1997.t01-1-00265.x. PMID 9363778.

[Buckingham-1] John Buckingham (ed.). Dictionary of Natural Products. Vol. 6. p. 3842.

[Gordon-2] Maxwell Gordon (ed.). Psychopharmacological Agents. Vol. 4. p. 94.

[Mangner1978-3] Mangner TJ (1978). Potential Psychotomimetic Antagonists. N,n -diethyl-1-methyl-3-aryl-1, 2, 5, 6-tetrahydropyridine-5-carboxamides (Ph.D. thesis). University of Michigan. doi:10.7302/11268. Archived from the original on 30 March 2025. Two N-substituted mescaline analogs isolated from L. williamsii are N-methylmescaline (62a) and N-acetylmescaline (62b).95 N-Methylmescaline shows no central effects at a dose which would represent many times the level that would be encountered in a normal dose of peyote.67 N-Acetylmescaline, which has been identified as a metabolite of mescaline in man, is centrally inactive to 750 mg.96

[4] Dumortier, C; Potenziano, JL; Bane, S; Engelborghs, Y (1997). "The mechanism of tubulin-colchicine recognition--a kinetic study of the binding of a bicyclic colchicine analogue with a minor modification of the a ring". European Journal of Biochemistry. 249 (1): 265–9. doi:10.1111/j.1432-1033.1997.t01-1-00265.x. PMID 9363778.

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