Lophophine
Encyclopedia
Lophophine, also known as 3-methoxy-4,5-methylenedioxyphenethylamine (MMDPEA; 5-Methoxy-MDPEA), is a psychedelic
and entactogen drug
of the phenethylamine
class. It is the α
-demethylated homologue of MMDA, and is also closely related to mescaline
.
Alexander Shulgin
previously suggested that lophophine may be a natural constituent
of Peyote due to it being the only logical chemical intermediate for the biosynthesis
of several tetrahydroisoquinoline
s known to be present in the species
. Subsequently, it was indeed shown to be a minor component of both Peyote and San Pedro
.
Shulgin reports that lophophine is active
in the dosage
range of 150-250 mg. He states that at these doses, MMDPEA is very similar to mescaline in action, and that a peaceful elevation of mood
, euphoria
, enhancement of visual perception
, and the generation of closed-eye
mental imagery are all present. At dosages above 300 mg, visual distortions that resemble those of standard doses of mescaline are said to begin to appear. Shulgin also notes that in contrast to mescaline, lophophine causes little nausea
or vomiting
.
Psychedelic drug
A psychedelic substance is a psychoactive drug whose primary action is to alter cognition and perception. Psychedelics are part of a wider class of psychoactive drugs known as hallucinogens, a class that also includes related substances such as dissociatives and deliriants...
and entactogen drug
Drug
A drug, broadly speaking, is any substance that, when absorbed into the body of a living organism, alters normal bodily function. There is no single, precise definition, as there are different meanings in drug control law, government regulations, medicine, and colloquial usage.In pharmacology, a...
of the phenethylamine
Substituted phenethylamine
The substituted phenethylamines are chemical compounds with the 2-phenethylamine chemical structure modified at the phenyl ring, sidechain, and/or amino group. Some of them are psychoactive drugs, including stimulants, psychedelics, opioids, and entactogens, which exert their effects primarily...
class. It is the α
Alpha carbon
The alpha carbon in organic chemistry refers to the first carbon that attaches to a functional group . By extension, the second carbon is the beta carbon, and so on....
-demethylated homologue of MMDA, and is also closely related to mescaline
Mescaline
Mescaline or 3,4,5-trimethoxyphenethylamine is a naturally occurring psychedelic alkaloid of the phenethylamine class used mainly as an entheogen....
.
Alexander Shulgin
Alexander Shulgin
Alexander "Sasha" Theodore Shulgin is an American pharmacologist, chemist, artist, and drug developer.Shulgin is credited with the popularization of MDMA, commonly known as ecstasy, in the late 1970s and early 1980s, especially for psychopharmaceutical use and the treatment of depression and...
previously suggested that lophophine may be a natural constituent
Natural resource
Natural resources occur naturally within environments that exist relatively undisturbed by mankind, in a natural form. A natural resource is often characterized by amounts of biodiversity and geodiversity existent in various ecosystems....
of Peyote due to it being the only logical chemical intermediate for the biosynthesis
Biosynthesis
Biosynthesis is an enzyme-catalyzed process in cells of living organisms by which substrates are converted to more complex products. The biosynthesis process often consists of several enzymatic steps in which the product of one step is used as substrate in the following step...
of several tetrahydroisoquinoline
Tetrahydroisoquinoline
Tetrahydroisoquinoline is a secondary amine with the chemical formula C9H11N.-Reactions:Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide....
s known to be present in the species
Species
In biology, a species is one of the basic units of biological classification and a taxonomic rank. A species is often defined as a group of organisms capable of interbreeding and producing fertile offspring. While in many cases this definition is adequate, more precise or differing measures are...
. Subsequently, it was indeed shown to be a minor component of both Peyote and San Pedro
Echinopsis pachanoi
The San Pedro cactus is a fast-growing columnar cactus native to the Andes Mountains of Peru between 2000–3000 m in altitude. It is also found in Argentina, Bolivia, Chile and Ecuador, and it is cultivated in other parts of the world...
.
Shulgin reports that lophophine is active
Activity (chemistry)
In chemical thermodynamics, activity is a measure of the “effective concentration” of a species in a mixture, meaning that the species' chemical potential depends on the activity of a real solution in the same way that it would depend on concentration for an ideal solution.By convention, activity...
in the dosage
Dose (biochemistry)
A dose is a quantity of something that may impact an organism biologically; the greater the quantity, the larger the dose. In nutrition, the term is usually applied to how much of a specific nutrient is in a person's diet or in a particular food, meal, or dietary supplement...
range of 150-250 mg. He states that at these doses, MMDPEA is very similar to mescaline in action, and that a peaceful elevation of mood
Mood (psychology)
A mood is a relatively long lasting emotional state. Moods differ from emotions in that they are less specific, less intense, and less likely to be triggered by a particular stimulus or event....
, euphoria
Euphoria (emotion)
Euphoria is medically recognized as a mental and emotional condition in which a person experiences intense feelings of well-being, elation, happiness, ecstasy, excitement and joy...
, enhancement of visual perception
Perception
Perception is the process of attaining awareness or understanding of the environment by organizing and interpreting sensory information. All perception involves signals in the nervous system, which in turn result from physical stimulation of the sense organs...
, and the generation of closed-eye
CEV
CEV may stand for:*Certified Video Engineer, a professional title regulated by the Society of Broadcast Engineers*Chemins de fer électriques Veveysans, a Swiss railway company*Contemporary English Version, a translation of the Bible into English...
mental imagery are all present. At dosages above 300 mg, visual distortions that resemble those of standard doses of mescaline are said to begin to appear. Shulgin also notes that in contrast to mescaline, lophophine causes little nausea
Nausea
Nausea , is a sensation of unease and discomfort in the upper stomach with an involuntary urge to vomit. It often, but not always, precedes vomiting...
or vomiting
Vomiting
Vomiting is the forceful expulsion of the contents of one's stomach through the mouth and sometimes the nose...
.
See also
- MescalineMescalineMescaline or 3,4,5-trimethoxyphenethylamine is a naturally occurring psychedelic alkaloid of the phenethylamine class used mainly as an entheogen....
- MMDA
- MDPEA