:Anhalamine

{{Chembox

| ImageFile = Anhalamine.svg

| ImageSize = 200px

| PIN = 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinolin-8-ol

| OtherNames =

|Section1={{Chembox Identifiers

| CASNo = 643-60-7

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = J4WH1Y00ON

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C12231

| PubChem = 69510

| ChemSpiderID = 62716

| SMILES = COC1=C(C(=C2CNCCC2=C1)O)OC

| 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

| InChIKey = DVQVXTPSJBCBJI-UHFFFAOYAR

| StdInChI = 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

| StdInChIKey = DVQVXTPSJBCBJI-UHFFFAOYSA-N

}}

|Section2={{Chembox Properties

| Formula =

|C=11 |H=15 |N=1 |O=3

| MolarMass =

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| Density =

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|Section3={{Chembox Hazards

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Anhalamine is a naturally occurring tetrahydroisoquinoline alkaloid which can be isolated from Lophophora williamsii.{{cite journal|last1=Lundström|first1=J|last2=Agurell|first2=S|title=Biosynthesis of mescaline and anhalamine in peyote. IIa.|journal=Tetrahedron Letters|date=August 1968|volume=9|issue=42|pages=4437–40|pmid=5672059|doi=10.1016/s0040-4039(01)99153-1}} It is structurally related to mescaline.{{cite journal|last1=Ghansah|first1=E.|last2=Kopsombut|first2=P.|last3=Maleque|first3=M.A.|last4=Brossi|first4=A.|title=Effects of mescaline and some of its analogs on cholinergic neuromuscular transmission|journal=Neuropharmacology|date=February 1993|volume=32|issue=2|pages=169–174|doi=10.1016/0028-3908(93)90097-M|pmid=8383816 |s2cid=42388554 }} It has been found to act as a potent inverse agonist of the serotonin 5-HT₇ receptor.{{cite journal | vauthors = Chan CB, Pottie E, Simon IA, Rossebø AG, Herth MM, Harpsøe K, Kristensen JL, Stove CP, Poulie CB | title = Synthesis, Pharmacological Characterization, and Binding Mode Analysis of 8-Hydroxy-Tetrahydroisoquinolines as 5-HT7 Receptor Inverse Agonists | journal = ACS Chem Neurosci | volume = 16 | issue = 3 | pages = 439–451 | date = February 2025 | pmid = 39836645 | doi = 10.1021/acschemneuro.4c00667 | url = }}