Lophophorine

Lophophorine
Names
	IUPAC name 4-Methoxy-8,9-dimethyl-7,9-dihydro-6H-[1,3]dioxolo[4,5-h]isoquinoline
	Other names N-Methylanhalonine
Identifiers
CAS Number	17627-78-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:6536;
ChemSpider	26651;
KEGG	C09573;
PubChem CID	28654;
UNII	UYZ46JKJ8V ;
CompTox Dashboard (EPA)	DTXSID70938780 ;
	InChI InChI=1S/C13H17NO3/c1-8-11-9(4-5-14(8)2)6-10(15-3)12-13(11)17-7-16-12/h6,8H,4-5,7H2,1-3H3 Key: PNFBXEKHLUDPIM-UHFFFAOYSA-N;
	SMILES CC1C2=C3C(=C(C=C2CCN1C)OC)OCO3;
Properties
Chemical formula	C13H17NO3
Molar mass	235.283 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Lophophorine, also known as N-methylanhalonine, is a bio-active alkaloid made by various cacti in the Lophophora family.^[1] It has been found to lack hallucinogenic effects in humans.^[2]

References

^ Bruhn, J. G.; Lindgren, J.-E.; Holmstedt, B.; Adovasio, J. M. (1978). "Peyote alkaloids: identification in a prehistoric specimen of Lophophora from coahuila, Mexico". Science. 199 (4336): 1437–1438. Bibcode:1978Sci...199.1437B. doi:10.1126/science.199.4336.1437. PMID 17796678. S2CID 19355963.
^ 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

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[1] Bruhn, J. G.; Lindgren, J.-E.; Holmstedt, B.; Adovasio, J. M. (1978). "Peyote alkaloids: identification in a prehistoric specimen of Lophophora from coahuila, Mexico". Science. 199 (4336): 1437–1438. Bibcode:1978Sci...199.1437B. doi:10.1126/science.199.4336.1437. PMID 17796678. S2CID 19355963.

[Mangner1978-2] 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

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