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Anhalonidine

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Anhalonidine
BERJAYA
BERJAYA
Clinical data
Other namesN-Desmethylpellotine; 8-Hydroxy-6,7-dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline; 8-Hydroxy-6,7-dimethoxy-1-methyl-THIQ
Drug classSerotonin 5-HT7 receptor inverse agonist; Sedative; Hypnotic
ATC code
  • None
Identifiers
  • (1S)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methyl-8-isoquinolinol
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H17NO3
Molar mass223.272 g·mol−1
3D model (JSmol)
Melting point160 °C (320 °F) [1]
  • C[C@H]1c2c(cc(c(c2O)OC)OC)CCN1
  • InChI=1S/C12H17NO3/c1-7-10-8(4-5-13-7)6-9(15-2)12(16-3)11(10)14/h6-7,13-14H,4-5H2,1-3H3/t7-/m0/s1
  • Key:PRNZAMQMBOFSJY-ZETCQYMHSA-N

Anhalonidine, also known as N-desmethylpellotine, a naturally occurring tetrahydroisoquinoline alkaloid which can be isolated from certain members of the cactus family, such as Lophophora, including notably Lophophora williamsii (peyote) (17% of alkaloid content).[2][3][4][5] It is structurally related to mescaline.[4] Anhalonidine produced no hallucinogenic effects in humans at doses of up to 250 mg.[2][4][6] However, it has been reported to have a calming or sedative effect instead, with about one-fourth the potency of pellotine and with sedation or sleepiness occurring at doses of 100 to 250 mg.[2][4][6] Anhalonidine has been found to act as a potent inverse agonist of the serotonin 5-HT7 receptor.[7] Analogues of anhalonidine include anhalamine, anhalidine, anhalinine, gigantine, and pellotine, among others.[8][9][10][2][11]

See also

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References

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  1. ↑ Späth E (August 1923). "Über die Anhaloniumalkaloide". Monatshefte für Chemie (in German). 43 (8): 477–484. doi:10.1007/BF01526801. S2CID 197766778.
  2. 1 2 3 4 Perrine DM (2001). "Visions of the Night Western Medicine Meets Peyote 1887-1899" (PDF). The Heffter Review of Psychedelic Research. 2: 6–52.
  3. ↑ 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). Basel, Switzerland: 7942. doi:10.3390/molecules28247942. PMC 10746114. PMID 38138432.
  4. 1 2 3 4 Shulgin AT (March 1973). "Mescaline: the chemistry and pharmacology of its analogs". Lloydia. 36 (1): 46–58. PMID 4576313. Anhalonidine (3) is the homolog of peyotline in which the N-methyl group is absent. In man it appears to act in a manner parallel to peyotline (leading to a heavy-headedness and sedation) but with only about one-fourth the potency. At oral levels of between 100 and 250 mg there was a marked sedation, but no sensory changes whatsoever (5). It is unlikely that this compound contributes to the reported action of panpeyote.
  5. ↑ Djerassi C, Smith CR, Marfey SP, McDonald RN, Lemin AJ, Figdor SK, et al. (June 1954). "Alkaloid Studies. III.1 Isolation of Pilocereine and Anhalonidine from Four Cactus Species". Journal of the American Chemical Society. 76 (12): 3215–3217. doi:10.1021/ja01641a034.
  6. 1 2 Mangner TJ (1978). Potential Psychotomimetic Antagonists. N,n -diethyl-1-methyl-3-aryl-1, 2, 5, 6-tetrahydropyridine-5-carboxamides (Ph.D. thesis). University of Michigan. doi:10.7302/11268. Archived from the original on 30 March 2025. In addition to compounds strictly related to mescaline just described, L. williamsii also contains at least 23 variously substituted tetrahydroisoquinolines,95 of which four have been clinically tested. The two phenolic tetrahydroisoquinolines peyotline (63a) and anhalonidine (63b) were found to produce no sensory distortions, characteristic of the effects of mescaline, at doses of up to 250 mg.98 These compounds appear to induce a calming or sedative effect rather than a psychotomimetic one. Two methylenedioxy tetrahydroisoquinolines, lophophorine (64a) and anhalonine (64b), were also found to lack any psychotomimetic-type effects.98
  7. ↑ Chan CB, Pottie E, Simon IA, Rossebø AG, Herth MM, Harpsøe K, et al. (February 2025). "Synthesis, Pharmacological Characterization, and Binding Mode Analysis of 8-Hydroxy-Tetrahydroisoquinolines as 5-HT7 Receptor Inverse Agonists". ACS Chemical Neuroscience. 16 (3): 439–451. doi:10.1021/acschemneuro.4c00667. PMID 39836645.
  8. ↑ 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)
  9. ↑ Lundström J (1985). "The Occurrence of Simple Isoquinolines in Plants". The Chemistry and Biology of Isoquinoline Alkaloids. Berlin, Heidelberg: Springer Berlin Heidelberg. pp. 47–61. doi:10.1007/978-3-642-70128-3_4. ISBN 978-3-642-70130-6.
  10. ↑ Cassels BK (2019). "Alkaloids of the Cactaceae — The Classics". Natural Product Communications. 14 (1). doi:10.1177/1934578X1901400123. ISSN 1934-578X.
  11. ↑ Anderson EF (1996). Peyote: The Divine Cactus (2 ed.). University of Arizona Press. ISBN 978-0-8165-1654-4. Archived from the original on 22 September 2022.
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