Jump to content

Anhalidine

From Wikipedia, the free encyclopedia

Anhalidine
Clinical data
Other namesN-Methylanhalamine; 8-Hydroxy-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline; 8-Hydroxy-6,7-dimethoxy-2-methyl-THIQ
Drug classSerotonin 5-HT7 receptor inverse agonist
ATC code
  • None
Identifiers
  • 6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-8-ol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H17NO3
Molar mass223.272 g·mol−1
3D model (JSmol)
  • OC1=C(C(OC)=CC2=C1CN(C)CC2)OC
  • 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

Anhalidine is a naturally occurring tetrahydroisoquinoline alkaloid found in Lophophora williamsii (peyote);[1] it has also been detected in 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]

See also

[edit]

References

[edit]
  1. ↑ Lundström J, Agurell S (September 1967). "Thin-layer chromatography of the peyote alkaloids". Journal of Chromatography A. 30 (1): 271–272. doi:10.1016/S0021-9673(00)84157-6. PMID 4293618.
  2. ↑ Roush RA, Cooks RG, Sweetana SA, McLaughlin JL (January 1985). "Search for new alkaloids in Pachycereus weberi by tandem mass spectrometry". Analytical Chemistry. 57 (1): 109–114. doi:10.1021/ac00279a030. PMID 3985330.
  3. ↑ Clement BA, Goff CM, Forbes TD (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 BA, Goff CM, Forbes TD (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, et al. (February 2025). "Synthesis, Pharmacological Characterization, and Binding Mode Analysis of 8-Hydroxy-Tetrahydroisoquinolines as 5-HT7 Receptor Inverse Agonists". ACS Chemical Neuroscience. 16 (3): 439–451. doi:10.1021/acschemneuro.4c00667. hdl:1854/LU-01JQ6WFR8R7G85440FRY2248HG. PMID 39836645.
[edit]
Retrieved from "https://en.wikipedia.org/w/index.php?title=Anhalidine&oldid=1361488957"