WikiMini

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
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
  • 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
  • CC1C2=C3C(=C(C=C2CCN1C)OC)OCO3
Properties
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).

Lophophorine, also known as N-methylanhalonine, is a tetrahydroisoquinoline alkaloid made by various cacti in the Lophophora family.[1] It has been found to lack hallucinogenic effects in humans.[2] Arthur Heffter tried lophophorine at a dose of 20 mg resulted in vasodilation, an immediate headache, and a warm flushed feeling, effects which dissipated within an hour.[3] It has also been said to produce nausea in humans.[3] Lophophorine is described as highly toxic and produces strychnine-like convulsions in animals.[3]

See also

[edit]

References

[edit]
  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.
  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
  3. ^ a b c 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. Oral dosages of 20 mg. in man [Heffter 1898a] led to a distinct vasodilation and immediate accompanying headache and a warm flushed feeling. These responses were lost within the hour.
[edit]
Stub icon

This organic chemistry article is a stub. You can help Wikipedia by expanding it.