Anhalidine

Last updated
Anhalidine
Anhalidine.svg
Names
Preferred IUPAC name
6,7-Dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-8-ol
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C12H17NO3/c1-13-5-4-8-6-10(15-2)12(16-3)11(14)9(8)7-13/h6,14H,4-5,7H2,1-3H3
    Key: DTXOXOHMRGAFDX-UHFFFAOYSA-N
  • InChI=1/C12H17NO3/c1-13-5-4-8-6-10(15-2)12(16-3)11(14)9(8)7-13/h6,14H,4-5,7H2,1-3H3
    Key: DTXOXOHMRGAFDX-UHFFFAOYAS
  • OC1=C(C(OC)=CC2=C1CN(C)CC2)OC
Properties
C12H17NO3
Molar mass 223.272 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Anhalidine is a naturally occurring tetrahydroisoquinoline based alkaloid which can be isolated from Lophophora williamsii ; [1] it has also been detected other cactii [2] and several species of Acacia . [3] [4] It is part of a family of compounds that are structurally related to mescaline. Anhalidine has been found to act as a potent inverse agonist of the serotonin 5-HT7 receptor. [5]

Contents

See also

References

  1. ↑ Lundström, Jan; Agurell, Stig (1967). "Thin-layer chromatography of the peyote alkaloids". Journal of Chromatography A. 30 (1): 271–272. doi:10.1016/S0021-9673(00)84157-6. ISSN   0021-9673. PMID   4293618.
  2. ↑ Roush, Robin A.; Cooks, R. Graham.; Sweetana, Stephanie A.; McLaughlin, Jerry L. (1985). "Search for new alkaloids in Pachycereus weberi by tandem mass spectrometry". Analytical Chemistry. 57 (1): 109–114. doi:10.1021/ac00279a030. ISSN   0003-2700. PMID   3985330.
  3. ↑ Clement, Beverly A.; Goff, Christina M.; Forbes, T. David A. (1997). "Toxic amines and alkaloids from Acacia berlandieri". Phytochemistry. 46 (2): 249–254. Bibcode:1997PChem..46..249C. doi:10.1016/S0031-9422(97)00240-9. ISSN   0031-9422.
  4. ↑ Clement, Beverly A; Goff, Christina M; Forbes, T.David A (1998). "Toxic amines and alkaloids from Acacia rigidula". Phytochemistry. 49 (5): 1377–1380. Bibcode:1998PChem..49.1377C. doi:10.1016/S0031-9422(97)01022-4. ISSN   0031-9422.
  5. ↑ Chan CB, Pottie E, Simon IA, Rossebø AG, Herth MM, Harpsøe K, Kristensen JL, Stove CP, Poulie CB (February 2025). "Synthesis, Pharmacological Characterization, and Binding Mode Analysis of 8-Hydroxy-Tetrahydroisoquinolines as 5-HT7 Receptor Inverse Agonists". ACS Chem Neurosci. 16 (3): 439–451. doi:10.1021/acschemneuro.4c00667. PMID   39836645.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.