:Anhalonidine

{{Chembox

| ImageFile = Anhalonidine.svg

| ImageSize = 200px

| ImageAlt =

| IUPACName = (1S)-1,2,3,4-Tetrahydro-6,7-dimethoxy-1-methyl-8-isoquinolinol

| OtherNames = N-Desmethylpellotine

|Section1={{Chembox Identifiers

| CASNo = 17627-77-9

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

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

| UNII = 23XP4B16AN

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

| KEGG = C16704

| PubChem = 87201

| ChemSpiderID = 78662

| SMILES = C[C@H]1c2c(cc(c(c2O)OC)OC)CCN1

| InChI = 1/C12H17NO3/c1-7-10-8(4-5-13-7)6-9(15-2)12(16-3)11(10)14/h6-7,13-14H,4-5H2,1-3H3/t7-/m0/s1

| InChIKey = PRNZAMQMBOFSJY-ZETCQYMHBW

| StdInChI = 1S/C12H17NO3/c1-7-10-8(4-5-13-7)6-9(15-2)12(16-3)11(10)14/h6-7,13-14H,4-5H2,1-3H3/t7-/m0/s1

| StdInChIKey = PRNZAMQMBOFSJY-ZETCQYMHSA-N}}

|Section2={{Chembox Properties

| Formula =

| C=12 | H=17 |N=1 |O=3

| MolarMass =

| Appearance =

| Density =

| MeltingPtC = 160

| MeltingPt_ref ={{cite journal|last1=Späth|first1=Ernst|title=Über die Anhaloniumalkaloide|journal=Monatshefte für Chemie|date=August 1923|volume=43|issue=8|pages=477–484|doi=10.1007/BF01526801|s2cid=197766778 |language=German}}

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|Section3={{Chembox Hazards

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Anhalonidine, also known as N-desmethylpellotine, a naturally occurring tetrahydroisoquinoline alkaloid which can be isolated from certain members of the cactus family, such as Lophophora.{{cite journal|last1=Djerassi|first1=Carl|last2=Smith|first2=C. R.|last3=Marfey|first3=S. P.|last4=McDonald|first4=R. N.|last5=Lemin|first5=A. J.|last6=Figdor|first6=S. K.|last7=Estrada|first7=H.|title=Alkaloid Studies. III.1 Isolation of Pilocereine and Anhalonidine from Four Cactus Species|journal=Journal of the American Chemical Society|date=June 1954|volume=76|issue=12|pages=3215–3217|doi=10.1021/ja01641a034}} It is structurally related to mescaline. Anhalonidine produced no hallucinogenic effects in humans at doses of up to 250{{nbsp}}mg.{{cite journal | vauthors = Shulgin AT | title = Mescaline: the chemistry and pharmacology of its analogs | journal = Lloydia | volume = 36 | issue = 1 | pages = 46–58 | date = March 1973 | pmid = 4576313 | doi = | url = https://bitnest.netfirms.com/external/Lloydia/36.1.46 | quote = Anhalonidine (3) is the homolog of peyotline in which the N-methyl group is absent. In man it appears to act in a manner parallel to peyotline (leading to a heavy-headedness and sedation) but with only about one-fourth the potency. At oral levels of between 100 and 250 mg there was a marked sedation, but no sensory changes whatsoever (5). It is unlikely that this compound contributes to the reported action of panpeyote.}}{{cite thesis | vauthors = Mangner TJ | degree = Ph.D. | publisher = University of Michigan | title=Potential Psychotomimetic Antagonists. N,n -diethyl-1-methyl-3-aryl-1, 2, 5, 6-tetrahydropyridine-5-carboxamides. | date=1978 | doi=10.7302/11268 | url=https://www.proquest.com/openview/f845a6810749d00f70305960adfde737/ | archive-url=https://web.archive.org/web/20250330031605/https://media.proquest.com/media/hms/ORIG/2/9yQxJ?cit%3Aauth=MANGNER%2C+THOMAS+JOSEPH&cit%3Atitle=POTENTIAL+PSYCHOTOMIMETIC+ANTAGONISTS.+N%2CN+...&cit%3Apub=ProQuest+Dissertations+and+Theses&cit%3Avol=&cit%3Aiss=&cit%3Apg=&cit%3Adate=1978&ic=true&cit%3Aprod=ProQuest+Dissertations+%26+Theses+Global&_a=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&_s=QP3F3liRMGFAbHtX3wDWE8eO1gs%3D | archive-date=30 March 2025 | quote=In addition to compounds strictly related to mescaline just described, L. williamsii also contains at least 23 variously substituted tetrahydroisoquinolines,95 of which four have been clinically tested. The two phenolic tetrahydroisoquinolines peyotline (63a) and anhalonidine (63b) were found to produce no sensory distortions, characteristic of the effects of mescaline, at doses of up to 250 mg.98 These compounds appear to induce a calming or sedative effect rather than a psychotomimetic one. Two methylenedioxy tetrahydroisoquinolines, lophophorine (64a) and anhalonine (64b), were also found to lack any psychotomimetic-type effects.98}} However, it has been reported to have a calming or sedative effect instead, with about one-fourth the potency of pellotine and with marked sedation occurring at doses of 100 to 250{{nbsp}}mg. Anhalonidine 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 = }}