Anhalonidine

Anhalonidine
Names
	IUPAC name (1S)-1,2,3,4-Tetrahydro-6,7-dimethoxy-1-methyl-8-isoquinolinol
Identifiers
CAS Number	17627-77-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	78662;
KEGG	C16704 ;
PubChem CID	87201;
UNII	23XP4B16AN ;
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)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Anhalonidine a naturally occurring alkaloid which can be isolated from certain members of the cactus family, such as Lophophora.^[2] It is structurally related to mescaline. Anhalonidine produced no hallucinogenic effects in humans at doses of up to 250 mg.^[3] However, it has been reported to have a calming or sedative effect instead.^[3]

References

^ Späth, Ernst (August 1923). "Über die Anhaloniumalkaloide". Monatshefte für Chemie (in German). 43 (8): 477–484. doi:10.1007/BF01526801. S2CID 197766778.
^ 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.
^ ^a ^b 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

This article about an alkaloid is a stub. You can help Wikipedia by expanding it.

[1] Späth, Ernst (August 1923). "Über die Anhaloniumalkaloide". Monatshefte für Chemie (in German). 43 (8): 477–484. doi:10.1007/BF01526801. S2CID 197766778.

[2] 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.

[Mangner1978-3] 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

[1]

[2]

[3]

See also

References