Anhalonine

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Anhalonine
Anhalonine v2.svg
Names
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
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 208-260-9
PubChem CID
  • InChI=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
    Key: YEGBVDVRKMCCON-UHFFFAOYSA-N
  • (S)-:InChI=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
    Key: YEGBVDVRKMCCON-ZETCQYMHSA-N
  • CC1C2=C3C(=C(C=C2CCN1)OC)OCO3
  • (S)-:C[C@H]1C=2C3=C(C(OC)=CC2CCN1)OCO3
Properties
C12H15NO3
Molar mass 221.256 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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] It 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. [5] [3] [4] Anhalonine was isolated from peyote by Louis Lewin in 1888 and was bioassayed by Heffter with his report published in 1898. [3]

Contents

See also

References

  1. 1 2 Reti, L. (1954). "Chapter 26 Simple Isoquinoline Alkaloids". The Alkaloids: Chemistry and Physiology. Vol. 4. Elsevier. p. 7–21. doi:10.1016/s1876-0813(08)60153-0. ISBN   978-0-12-469504-7 . Retrieved 20 May 2025.{{cite book}}: ISBN / Date incompatibility (help)
  2. ↑ Cassels, Bruce K. (2019). "Alkaloids of the Cactaceae — The Classics". Natural Product Communications. 14 (1). doi: 10.1177/1934578X1901400123 . ISSN   1934-578X.
  3. 1 2 3 4 5 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.
  4. 1 2 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.
  5. ↑ Gurschler, Ivo (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 . Retrieved 20 May 2025. 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].



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