Structure via PubChem · Public domain (PubChem)
lophophorine
Sign in to saveAlso known as N-methylanhalonine, (9S)-4-methoxy-8,9-dimethyl-7,9-dihydro-6H-[1,3]dioxolo[4,5-h]isoquinoline
Lophophorine, also known as '''N-methylanhalonine', is a tetrahydroisoquinoline alkaloid made by various cacti in the Lophophora'' family. It has been found to lack hallucinogenic effects in humans. Arthur Heffter tried lophophorine at a dose of 20mg resulted in vasodilation, an immediate headache, and a warm flushed feeling, effects which dissipated within an hour. It has also been said to produce nausea in humans. Lophophorine is described as highly toxic and produces strychnine-like convulsions in animals.
Chemical data
- Formula
- C13H17NO3
- Molecular weight
- 235.28 g/mol
- IUPAC name
- (9S)-4-methoxy-8,9-dimethyl-7,9-dihydro-6H-[1,3]dioxolo[4,5-h]isoquinoline
- SMILES
- C[C@H]1C2=C3C(=C(C=C2CCN1C)OC)OCO3
- InChIKey
- PNFBXEKHLUDPIM-QMMMGPOBSA-N
- XLogP
- 2
- Polar surface area
- 30.9 Ų
- H-bond donors
- 0
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 235.120843404
Show 5 more facts
- found in taxon
- Gymnocalycium stellatum
- canonical SMILES
- O(C=1C=C2C(=C3OCOC13)C(N(C)CC2)C)C
- isomeric SMILES
- C[C@H]1C2=C3C(=C(C=C2CCN1C)OC)OCO3
- chemical formula
- C₁₃H₁₇NO₃
- Commons category
- Lophophorine
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- See also
- References
- External links
Lophophorine, also known as '''N-methylanhalonine', is a tetrahydroisoquinoline alkaloid made by various cacti in the Lophophora family. It has been found to lack hallucinogenic effects in humans. Arthur Heffter tried lophophorine at a dose of 20mg resulted in vasodilation, an immediate headache, and a warm flushed feeling, effects which dissipated within an hour. It has also been said to produce nausea in humans. Lophophorine is described as highly toxic and produces strychnine-like convulsions in animals.
==See also== Substituted tetrahydroisoquinoline Peyophorine (N''-ethylanhalonine) Anhalonine
Excerpted from Wikipedia’s “lophophorine” article, available under the CC BY-SA 4.0 licence.