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Anhalonine
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| 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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| Formula | C12H15NO3 |
| Molar mass | 221.256 g·mol−1 |
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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.[1][2][3] Peyote contains 3% anhalonine.[3] The drug is known to be pharmacologically active and is said to be similar in its activity to anhalonidine.[1][3][4] Arthur Heffter tried anhalonine via self-experimentation at an oral dose of 100 mg and found that it was inactive aside from mild sleepiness.[5][6][3][4] Similarly, Prentiss and Morgan (P&M) tried pure anhalonine at doses of up to 200 mg without any effects.[5][7] Anhalonine was isolated from peyote by Louis Lewin in 1888 and was bioassayed by Heffter with his report published in 1898.[3] P&M's report was published in 1896.[7]
See also
[edit]References
[edit]- ^ a b Reti L (1954). "Chapter 26 Simple Isoquinoline Alkaloids". The Alkaloids: Chemistry and Physiology. Vol. 4. Elsevier. pp. 7–21. doi:10.1016/s1876-0813(08)60153-0. ISBN 978-0-12-469504-7.
{{cite book}}: ISBN / Date incompatibility (help) - ^ Cassels BK (2019). "Alkaloids of the Cactaceae — The Classics". Natural Product Communications. 14 (1) 1934578X1901400123. doi:10.1177/1934578X1901400123. ISSN 1934-578X.
- ^ a b c d e Keeper Trout & friends (2013). Trout's Notes on The Cactus Alkaloids Nomenclature, Physical properties, Pharmacology & Occurrences (Sacred Cacti Fourth Edition, Part C: Cactus Chemistry: Section 1) (PDF). Mydriatic Productions/Better Days Publishing.
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.
- ^ a b Shulgin AT (March 1973). "Mescaline: the chemistry and pharmacology of its analogs". Lloydia. 36 (1): 46–58. PMID 4576313.
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.
- ^ a b Daniel M. Perrine (2001). "Visions of the Night Western Medicine Meets Peyote 1887-1899" (PDF). The Heffter Review of Psychedelic Research. 2: 6–52.
- ^ Gurschler I (2019). "The fourfold discovery of Mescaline (1896–1919)". Monatshefte für Chemie - Chemical Monthly. 150 (5): 941–947. doi:10.1007/s00706-019-02444-0. ISSN 0026-9247.
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].
- ^ a b Prentiss DW, Morgan FP (1896). "Mescal Buttons. Anhalonium lewinii–Hennings. (Lophophora williamsii–lewinii–Coulter)". Transactions of the Association of American Physicians. 11: 289–309.
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