Anhalonidine

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.^[2]^[3] It is structurally related to mescaline.^[2] Anhalonidine produced no hallucinogenic effects in humans at doses of up to 250 mg.^[2]^[4] However, it has been reported to have a calming or sedative effect instead, with about one-fourth the potency of pellotine and with marked sedation occurring at doses of 100 to 250 mg.^[2]^[4] Anhalonidine has been found to act as a potent inverse agonist of the serotonin 5-HT₇ receptor.^[5]

Quick facts Names, Identifiers ...

Anhalonidine
Names

IUPAC name (1S)-1,2,3,4-Tetrahydro-6,7-dimethoxy-1-methyl-8-isoquinolinol
Other names N-Desmethylpellotine
Identifiers
CAS Number	17627-77-9^Y
3D model (JSmol)	Interactive image
ChemSpider	78662
KEGG	C16704^Y
PubChem CID	87201
UNII	23XP4B16AN^Y
CompTox Dashboard (EPA)	DTXSID60876920
InChI 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 InChI=1/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-ZETCQYMHBW
SMILES C[C@H]1c2c(cc(c(c2O)OC)OC)CCN1
Properties
Chemical formula	C₁₂H₁₇NO₃
Molar mass	223.272 g·mol⁻¹
Melting point	160 °C (320 °F; 433 K)^[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

References

[1]
Späth, Ernst (August 1923). "Über die Anhaloniumalkaloide". Monatshefte für Chemie (in German). 43 (8): 477–484. doi:10.1007/BF01526801. S2CID 197766778.
[2]
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.
[3]
Djerassi, Carl; Smith, C. R.; Marfey, S. P.; McDonald, R. N.; Lemin, A. J.; Figdor, S. K.; Estrada, H. (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.
[4]
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
[5]
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.

See also

References

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