N-Acetylmescaline

N-Acetylmescaline
Identifiers
	IUPAC name N-[2-(3,4,5-trimethoxyphenyl)ethyl]acetamide;
CAS Number	4593-89-9;
PubChem CID	100597;
ChemSpider	90893;
CompTox Dashboard (EPA)	DTXSID10196660 ;
Chemical and physical data
Formula	C13H19NO4
Molar mass	253.298 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	93 to 94 °C (199 to 201 °F)
	SMILES O=C(NCCc1cc(OC)c(OC)c(OC)c1)C;
	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;

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 activity 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 Buckingham J, Macdonald F, eds. (1996). Dictionary of Natural Products. Vol. 6. Chapman & Hall. p. 3842. ISBN 978-0-412-54110-0.
^ ^a ^b Shulgin AT (1976). "Psychotomimetic Agents". In Gordon M (ed.). Psychopharmacological Agents. Vol. 4. Academic Press. p. 94. ISBN 978-0-323-15963-0.
^ ^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 (October 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): 265–269. doi:10.1111/j.1432-1033.1997.t01-1-00265.x. PMID 9363778.

External links

N-Acetylmescaline - Isomer Design

[Buckingham-1] Buckingham J, Macdonald F, eds. (1996). Dictionary of Natural Products. Vol. 6. Chapman & Hall. p. 3842. ISBN 978-0-412-54110-0.

[Gordon-2] Shulgin AT (1976). "Psychotomimetic Agents". In Gordon M (ed.). Psychopharmacological Agents. Vol. 4. Academic Press. p. 94. ISBN 978-0-323-15963-0.

[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 (October 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): 265–269. doi:10.1111/j.1432-1033.1997.t01-1-00265.x. PMID 9363778.

[1]

[2]

[3]

[4]

See also

References

External links