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| Names | |
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| IUPAC name 4-methoxy-9-methyl-6,7,8,9-tetrahydro-[1,3]dioxolo[4,5-h]isoquinoline | |
| Other names 1-Methyl-6-methoxy-7,8-methylenedioxy-1,2,3,4-tetrahydroisoquinoline; 1-Methyl-6-methoxy-7,8-methylenedioxy-THIQ | |
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3D model (JSmol) | |
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| Properties | |
| C12H15NO3 | |
| Molar mass | 221.256 g·mol−1 |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Anhalonine, also known as1-methyl-6-methoxy-7,8-methylenedioxy-1,2,3,4-tetrahydroisoquinoline, is atetrahydroisoquinolinealkaloid found inLophophora williamsii (peyote) and many othercactus species.[1][2][3] Peyote contains 3% anhalonine.[3] It is known to bepharmacologically active and is said to be similar in its activity toanhalonidine.[1][3][4]Arthur Heffter tried anhalonine viaself-experimentation at anoral dose of 100 mg and found that it was inactive.[5][3][4] Anhalonine was isolated from peyote byLouis Lewin in 1888 and wasbioassayed by Heffter with his report published in 1898.[3]
{{cite book}}:ISBN / Date incompatibility (help)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.
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.
For the sake of completeness, [Arthur Heffter] then went on to test anhalonidine and Lewin's anhalonine on himself, without any effect. Lophophorine had only mild sedative effects. 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].
