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N-Acetylmescaline

From Wikipedia, the free encyclopedia
N-Acetylmescaline
Names
Preferred IUPAC name
N-[2-(3,4,5-Trimethoxyphenyl)ethyl]acetamide
Identifiers
3D model (JSmol)
ChemSpider
  • 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
  • O=C(NCCc1cc(OC)c(OC)c(OC)c1)C
Properties
C13H19NO4
Molar mass 253.298 g·mol−1
Melting point 93 to 94 °C (199 to 201 °F; 366 to 367 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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]

N-Acetylmescaline has microtubule assembly inhibitory activity.[3]

References

[edit]
  1. ^ a b John Buckingham (ed.). Dictionary of Natural Products. Vol. 6. p. 3842.
  2. ^ a b Maxwell Gordon (ed.). Psychopharmacological Agents. Vol. 4. p. 94.
  3. ^ 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.