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Anhalinine

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Anhalinine
Names
Preferred IUPAC name
6,7,8-Trimethoxy-1,2,3,4-tetrahydroisoquinoline
Other names
O-Methylanhalamine; 6,7,8-Trimethoxy-THIQ
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C12H17NO3/c1-14-10-6-8-4-5-13-7-9(8)11(15-2)12(10)16-3/h6,13H,4-5,7H2,1-3H3
    Key: GOBKARNYNSWQFZ-UHFFFAOYSA-N
  • InChI=1/C12H17NO3/c1-14-10-6-8-4-5-13-7-9(8)11(15-2)12(10)16-3/h6,13H,4-5,7H2,1-3H3
    Key: GOBKARNYNSWQFZ-UHFFFAOYAR
  • COC1=C(C(=C2CNCCC2=C1)OC)OC
Properties
C12H17NO3
Molar mass 223.272 g·mol−1
Melting point 60–61 °C (140–142 °F; 333–334 K)[1]
Boiling point 144–145 °C (291–293 °F; 417–418 K)[1] at 0.1 Torr
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Anhalinine, also known as O-methylanhalamine is a tetrahydroisoquinoline alkaloid found in Lophophora williamsii (peyote) and other cacti.[2][3] It is structurally related to mescaline and is a cyclized phenethylamine analogue of mescaline.[2] Anhalinine is also pharmacologically active, but is only a minor constituent of peyote and is unlikely to contribute to its effects.[4][2][5][6]

Simple isoquinoline alkaloids of mescaline-containing cacti like anhalinine have received relatively little investigation.[2] Arthur Heffter found many of them to produce no effects similar to those of mescaline.[2] However, some of them have been found to produce convulsions in animals at high doses.[2] Anhalinine specifically has been described as having "stimulant" properties due to inhibiting cholinergic neurotransmission.[7][5][8][2] Alexander Shulgin tried anhalinine at small doses of 0.5 to 4.3 mg but experienced no effects.[9]

Anhalinine has been found to act as a low-potency inverse agonist of the serotonin 5-HT7 receptor, with an EC50Tooltip half-maximal effective concentration of 2,722 nM and an EmaxTooltip half-maximal effective concentration of –85%.[10] This was much less potent in terms of this action than certain other tetrahydroisoquinolines like pellotine and anhalidine.[10] Serotonin 5-HT7 receptor inverse agonism might be involved in the sedative and hypnotic effects of certain peyote alkaloids like pellotine and anhalonidine.[11]

Anhalinine was first isolated from peyote by Ernst Späth in 1935.[12][6][13] Shulgin bioassayed it in 1963.[9]

See also

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References

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  1. ^ a b Taylor, E. P. (1952). "236. Synthetic neuromuscular blocking agents. Part III. Miscellaneous quaternary ammonium salts". Journal of the Chemical Society (Resumed): 1309. doi:10.1039/jr9520001309.
  2. ^ a b c d e f g Cassels, Bruce K. (2019). "Alkaloids of the Cactaceae — The Classics". Natural Product Communications. 14 (1). doi:10.1177/1934578X1901400123. ISSN 1934-578X. In contrast to mescaline and hordenine, the simple isoquinoline alkaloids of cacti have attracted little interest. The late 19th century efforts of Heffter and other authors, who generally observed convulsions in different animal species at high doses, were promptly reviewed by Affanasia Mogilewa (1903) who extended her studies to the isolated frog heart [56]. Some of Heffter's self-experiments revealed nothing of interest and, specifically, no effects remotely resembling those of mescaline. [...] A more recent exploration of mescaline and its 1,2,3,4-tetrahydroisoquinoline analog anhalinine at the neuromuscular junction of the frog and nicotinic receptors in rat brain cortex showed that both alkaloids inhibit neuromuscular transmission by blocking acetylcholine release. In the brain they failed to block [125I]α-bungarotoxin binding to nicotinic receptors [59], but this only reflects their low affinity for homomeric α7 and related receptors, and not for the predominant α4β2 subtype.
  3. ^ Lundström, J. (1985). "The Occurrence of Simple Isoquinolines in Plants". The Chemistry and Biology of Isoquinoline Alkaloids. Berlin, Heidelberg: Springer Berlin Heidelberg. p. 47–61. doi:10.1007/978-3-642-70128-3_4. ISBN 978-3-642-70130-6. Retrieved 20 May 2025.
  4. ^ Dinis-Oliveira RJ, Pereira CL, da Silva DD (2019). "Pharmacokinetic and Pharmacodynamic Aspects of Peyote and Mescaline: Clinical and Forensic Repercussions". Curr Mol Pharmacol. 12 (3): 184–194. doi:10.2174/1874467211666181010154139. PMC 6864602. PMID 30318013.
  5. ^ a b Ghansah E, Kopsombut P, Malleque MA, Brossi A (February 1993). "Effects of mescaline and some of its analogs on cholinergic neuromuscular transmission". Neuropharmacology. 32 (2): 169–174. doi:10.1016/0028-3908(93)90097-m. PMID 8383816.
  6. ^ a b Schultes, Richard Evans (1937). "Peyote and Plants Used in the Peyote Ceremony". Botanical Museum Leaflets, Harvard University. 4 (8). Harvard University Herbaria: 129–152. ISSN 0006-8098. JSTOR 41762641. Retrieved 20 May 2025. Anhalinine and Anhalidine have only recently been isolated and in amounts too minute to be of use in physiological tests.
  7. ^ Doesburg-van Kleffens M, Zimmermann-Klemd AM, Gründemann C (December 2023). "An Overview on the Hallucinogenic Peyote and Its Alkaloid Mescaline: The Importance of Context, Ceremony and Culture". Molecules. 28 (24): 7942. doi:10.3390/molecules28247942. PMC 10746114. PMID 38138432.
  8. ^ Vamvakopoulou IA, Narine KA, Campbell I, Dyck JR, Nutt DJ (January 2023). "Mescaline: The forgotten psychedelic". Neuropharmacology. 222: 109294. doi:10.1016/j.neuropharm.2022.109294. PMID 36252614.
  9. ^ a b Alexander Shulgin. Pharmacology Notebook 1. Subacute effects Anhalinine. 1963. https://web.archive.org/web/20250416115643/https://www.erowid.org/library/books_online/shulgin_labbooks/shulgin_labbook1_searchable.pdf#page=81
  10. ^ a b Chan CB, Pottie E, Simon IA, Rossebø AG, Herth MM, Harpsøe K, Kristensen JL, Stove CP, Poulie CB (February 2025). "Synthesis, Pharmacological Characterization, and Binding Mode Analysis of 8-Hydroxy-Tetrahydroisoquinolines as 5-HT7 Receptor Inverse Agonists". ACS Chem Neurosci. 16 (3): 439–451. doi:10.1021/acschemneuro.4c00667. PMID 39836645.
  11. ^ Poulie CB, Chan CB, Parka A, Lettorp M, Vos J, Raaschou A, Pottie E, Bundgaard MS, Sørensen LM, Cecchi CR, Märcher-Rørsted E, Bach A, Herth MM, Decker A, Jensen AA, Elfving B, Kretschmann AC, Stove CP, Kohlmeier KA, Cornett C, Janfelt C, Kornum BR, Kristensen JL (October 2023). "In Vitro and In Vivo Evaluation of Pellotine: A Hypnotic Lophophora Alkaloid". ACS Pharmacol Transl Sci. 6 (10): 1492–1507. doi:10.1021/acsptsci.3c00142. PMC 10580395. PMID 37854625.
  12. ^ 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.
  13. ^ Späth, Ernst; Becke, Friedrich (6 March 1935). "Über ein neues Kakteen‐Alkaloid, das Anhalinin, und zur Konstitution des Anhalonins (XIII. Mitteil. über Kakteen‐Alkaloide)". Berichte der deutschen chemischen Gesellschaft (A and B Series). 68 (3): 501–505. doi:10.1002/cber.19350680324. ISSN 0365-9488. Retrieved 20 May 2025.



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