Lophophine, also known as 3-methoxy-4,5-methylenedioxyphenethylamine (MMDPEA), is a putative psychedelic and

entactogen Entactogens, also known as empathogens or connectogens, are a class of psychoactive drugs that induce the production of experiences of emotional communion, oneness, connectedness, emotional openness—that is, empathy—as particularly observe ...

drug A drug is any chemical substance other than a nutrient or an essential dietary ingredient, which, when administered to a living organism, produces a biological effect. Consumption of drugs can be via insufflation (medicine), inhalation, drug i ...

of the

methylenedioxyphenethylamine 3,4-Methylenedioxyphenethylamine, also known as 3,4-MDPEA, MDPEA, and homopiperonylamine, is a substituted phenethylamine formed by adding a methylenedioxy group to phenethylamine. It is structurally similar to 3,4-Methylenedioxyamphetamine, MD ...

family. It is the α-

demethylated Demethylation is the chemical process resulting in the removal of a methyl group (CH3) from a molecule. A common way of demethylation is the replacement of a methyl group by a hydrogen atom, resulting in a net loss of one carbon and two hydrogen at ...

homologue of MMDA, and is also closely related to

mescaline Mescaline, also known as mescalin or mezcalin, and in chemical terms 3,4,5-trimethoxyphenethylamine, is a natural product, naturally occurring psychedelic drug, psychedelic alkaloid, protoalkaloid of the substituted phenethylamine class, found ...

Alexander Shulgin Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American biochemist, broad researcher of synthetic psychoactive compounds, and author of works regarding these, who independently explored the organic chemistry and ph ...

originally suggested that lophophine may be a natural constituent of

peyote The peyote (; ''Lophophora williamsii'' ) is a small, spineless cactus which contains psychoactive alkaloids, particularly mescaline. is a Spanish word derived from the Nahuatl (), meaning "caterpillar cocoon", from a root , "to glisten". p. ...

(''Lophophora williamsii'') due to it being the only logical chemical intermediate for the

biosynthesis Biosynthesis, i.e., chemical synthesis occurring in biological contexts, is a term most often referring to multi-step, enzyme-Catalysis, catalyzed processes where chemical substances absorbed as nutrients (or previously converted through biosynthe ...

of several tetrahydroisoquinolines known to be present in this cactus species. Subsequently, lophophine was indeed shown to be a minor component of both peyote and San Pedro cactus. Shulgin reports that lophophine is active in the dosage range of 150 to 250mg. He states that at these doses, lophophine has some similarity to mescaline in action, in producing a peaceful elevation of mood,

euphoria Euphoria ( ) is the experience (or affect) of pleasure or excitement and intense feelings of well-being and happiness. Certain natural rewards and social activities, such as aerobic exercise, laughter, listening to or making music and da ...

, and mild enhancement of

visual The visual system is the physiological basis of visual perception (the ability to detect and process light). The system detects, transduces and interprets information concerning light within the visible range to construct an image and buil ...

perception Perception () is the organization, identification, and interpretation of sensory information in order to represent and understand the presented information or environment. All perception involves signals that go through the nervous syste ...

, but without the generation of closed-eye mental imagery. Shulgin also notes that (in contrast to mescaline), lophophine causes no

nausea Nausea is a diffuse sensation of unease and discomfort, sometimes perceived as an urge to vomit. It can be a debilitating symptom if prolonged and has been described as placing discomfort on the chest, abdomen, or back of the throat. Over 30 d ...

. He estimated that it was about twice the potency of mescaline.

References

External links

PiHKAL: #95 Lophophine: 3-Methoxy-4,5-methylenedioxyphenethylamine

Mescaline: The Chemistry and Pharmacology of its Analogues
{{Phenethylamines Methoxyphenethylamines Methylenedioxyphenethylamines Phenol ethers Phenethylamine alkaloids Psychedelic phenethylamines Scalines

See also

References

External links