Article · Wikipedia archive · Last revised Jun 6, 2026

Anhalamine

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

Last revised
Jun 6, 2026
Read time
≈ 1 min
Length
211 w
Citations
3
Source
Wikipedia ↗
Anhalamine
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Names
Preferred IUPAC name
6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinolin-8-ol
Identifiers
3D model (JSmol)
ChemSpider
KEGG
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

See also

References

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. hdl:1854/LU-01JQ6WFR8R7G85440FRY2248HG. PMID 39836645.