Anhalamine

Last updated
Anhalamine
Anhalamine.svg
Names
Preferred IUPAC name
6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinolin-8-ol
Identifiers
3D model (JSmol)
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C11H15NO3/c1-14-9-5-7-3-4-12-6-8(7)10(13)11(9)15-2/h5,12-13H,3-4,6H2,1-2H3
    Key: DVQVXTPSJBCBJI-UHFFFAOYSA-N
  • InChI=1/C11H15NO3/c1-14-9-5-7-3-4-12-6-8(7)10(13)11(9)15-2/h5,12-13H,3-4,6H2,1-2H3
    Key: DVQVXTPSJBCBJI-UHFFFAOYAR
  • COC1=C(C(=C2CNCCC2=C1)O)OC
Properties
C11H15NO3
Molar mass 209.245 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Anhalamine is a naturally occurring tetrahydroisoquinoline alkaloid which can be isolated from Lophophora williamsii . [1] It is structurally related to mescaline. [2] It has been found to act as a potent inverse agonist of the serotonin 5-HT7 receptor. [3]

See also

References

  1. ↑ Lundström, J; Agurell, S (August 1968). "Biosynthesis of mescaline and anhalamine in peyote. IIa". Tetrahedron Letters. 9 (42): 4437–40. doi:10.1016/s0040-4039(01)99153-1. PMID   5672059.
  2. ↑ Ghansah, E.; Kopsombut, P.; Maleque, M.A.; Brossi, A. (February 1993). "Effects of mescaline and some of its analogs on cholinergic neuromuscular transmission". Neuropharmacology. 32 (2): 169–174. doi:10.1016/0028-3908(93)90097-M. PMID   8383816. S2CID   42388554.
  3. ↑ 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.


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