Anhalamine

Anhalamine
Clinical data
Other names	8-Hydroxy-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline; 8-Hydroxy-6,7-dimethoxy-THIQ
Drug class	Serotonin 5-HT7 receptor inverse agonist
ATC code	None;
Identifiers
	IUPAC name 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-8-ol;
CAS Number	643-60-7 ;
PubChem CID	69510;
ChemSpider	62716;
UNII	J4WH1Y00ON;
KEGG	C12231 ;
CompTox Dashboard (EPA)	DTXSID80214527 ;
Chemical and physical data
Formula	C11H15NO3
Molar mass	209.245 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC1=C(C(=C2CNCCC2=C1)O)OC;
	InChI 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;

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]

References

↑ Lundström J, Agurell S (August 1968). "Biosynthesis of mescaline and anhalamine in peyote. IIa". Tetrahedron Letters. 9 (42): 4437–4440. doi:10.1016/s0040-4039(01)99153-1. PMID 5672059.
↑ Ghansah E, Kopsombut P, Malleque MA, 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.
↑ 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.