anhalonine

{{Chembox

| ImageFile = Anhalonine v2.svg

| ImageSize = 175px

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| IUPACName = 4-methoxy-9-methyl-6,7,8,9-tetrahydro-[1,3]dioxolo[4,5-h]isoquinoline

| OtherNames = 1-Methyl-6-methoxy-7,8-methylenedioxy-1,2,3,4-tetrahydroisoquinoline; 1-Methyl-6-methoxy-7,8-methylenedioxy-THIQ

| Section1 = {{Chembox Identifiers

| CASNo1 = 519-04-0

| index1_label = (S)-

| ChemSpiderID = 454230

| EC_number = 208-260-9

| PubChem = 520752

| StdInChI=1S/C12H15NO3/c1-7-10-8(3-4-13-7)5-9(14-2)11-12(10)16-6-15-11/h5,7,13H,3-4,6H2,1-2H3

| StdInChIKey = YEGBVDVRKMCCON-UHFFFAOYSA-N

| SMILES = CC1C2=C3C(=C(C=C2CCN1)OC)OCO3

| InChI1=1S/C12H15NO3/c1-7-10-8(3-4-13-7)5-9(14-2)11-12(10)16-6-15-11/h5,7,13H,3-4,6H2,1-2H3/t7-/m0/s1

| InChIKey1=YEGBVDVRKMCCON-ZETCQYMHSA-N

| SMILES1 = C[C@H]1C=2C3=C(C(OC)=CC2CCN1)OCO3

}}

| Section2 = {{Chembox Properties

| C=12 | H=15 | N=1 | O=3

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| Section3 = {{Chembox Hazards

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Anhalonine, also known as 1-methyl-6-methoxy-7,8-methylenedioxy-1,2,3,4-tetrahydroisoquinoline, is a tetrahydroisoquinoline alkaloid found in Lophophora williamsii (peyote) and many other cactus species.{{cite book | last=Reti | first=L. | title=The Alkaloids: Chemistry and Physiology | chapter=Chapter 26 Simple Isoquinoline Alkaloids | publisher=Elsevier | volume=4 | date=1954 | isbn=978-0-12-469504-7 | doi=10.1016/s1876-0813(08)60153-0 | url=https://linkinghub.elsevier.com/retrieve/pii/S1876081308601530 | access-date=20 May 2025 | page=7–21}}{{cite journal | last=Cassels | first=Bruce K. | title=Alkaloids of the Cactaceae — The Classics | journal=Natural Product Communications | volume=14 | issue=1 | date=2019 | issn=1934-578X | doi=10.1177/1934578X1901400123 | doi-access=free | page=}}{{cite book | author = Keeper Trout & friends | title = Trout's Notes on The Cactus Alkaloids Nomenclature, Physical properties, Pharmacology & Occurrences (Sacred Cacti Fourth Edition, Part C: Cactus Chemistry: Section 1) | date = 2013 | publisher = Mydriatic Productions/Better Days Publishing | url = https://troutsnotes.com/pdf/C13_CactusAlkaloids.pdf | quote = Pharmacological properties are similar both quantitatively and qualitatively to anhalonidine. Oral dosages of 100 mg. in man [Heffter 1898a] (the only reported human experiment) led to an uneventful tiredness and no noticeable central effects. Shulgin 1973 page 50.}} Peyote contains 3% anhalonine. It is known to be pharmacologically active and is said to be similar in its activity to anhalonidine. Arthur Heffter tried anhalonine via self-experimentation at an oral dose of 100{{nbsp}}mg and found that it was inactive.{{cite journal | last=Gurschler | first=Ivo | title=The fourfold discovery of Mescaline (1896–1919) | journal=Monatshefte für Chemie - Chemical Monthly | volume=150 | issue=5 | date=2019 | issn=0026-9247 | doi=10.1007/s00706-019-02444-0 | doi-access=free | pages=941–947 | url=https://hcommons.org/deposits/download/hc:24666/CONTENT/mccm-d-19-00054-copy.pdf/ | access-date=20 May 2025 | quote=For the sake of completeness, [Arthur Heffter] then went on to test anhalonidine and Lewin’s anhalonine on himself, without any efect. Lophophorine had only mild sedative efects. Thus, there was no doubt that it was “the mescaline which exclusively caused the characteristic symptoms of a mescal[!]-intoxication, and, above all, that it solely induced the yet unprecedented visions” [15].}}{{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 = Anhalonine (5) is the methylenedioxy ether analog of anhalonidine and the N-demethyl homolog of lophophorine. This alkaloid appears to show pharmacological properties similar both quantitatively and qualitatively to its phenolic counterpart anhalonidine. A single reported experiment with 100 mg orally (5) led to an uneventful tiredness without any noticed central effects of a sensory nature.}} Anhalonine was isolated from peyote by Louis Lewin in 1888 and was bioassayed by Heffter with his report published in 1898.