Mescaline, also known as mescalin or mezcalin, and in chemical terms 3,4,5-trimethoxyphenethylamine, is a naturally occurring psychedelic protoalkaloid of the substituted phenethylamine class, known for its hallucinogenic effects comparable to those of LSD and psilocybin. It binds to and activates certain serotonin receptors in the brain, producing hallucinogenic effects.
PiHKAL: A Chemical Love Story is a book by Alexander Shulgin and Ann Shulgin published in 1991. The subject of the work is psychoactive phenethylamine chemical derivatives, notably those that act as psychedelics and/or empathogen-entactogens. The main title, PiHKAL, is an acronym that stands for "Phenethylamines I Have Known and Loved".
2,4,5-Trimethoxyamphetamine (2,4,5-TMA), also known as TMA-2 or as 2,5-dimethoxy-4-methoxyamphetamine (DOMeO), is a psychedelic drug of the phenethylamine and amphetamine families. It is one of the trimethoxyamphetamine (TMA) series of positional isomers. The drug is also notable in being the 4-methoxylated member of the DOx series of drugs.
Trimethoxyamphetamine, also known as 3,4,5-trimethoxyamphetamine (3,4,5-TMA), α-methylmescaline, or mescalamphetamine, is a psychedelic drug of the phenethylamine and amphetamine families. It is one of the trimethoxyamphetamine (TMA) series of positional isomers. The drug is notable in being the amphetamine analogue of mescaline (3,4,5-trimethoxyphenethylamine).
Trimethoxyamphetamines (TMAs) are a family of positionally isomeric psychedelic hallucinogenic drugs. There exist six different TMAs that differ only in the positions of the three methoxy groups: TMA (TMA-1), TMA-2, TMA-3, TMA-4, TMA-5, and TMA-6. The TMAs are substituted amphetamines and are analogues of the phenethylamine cactus alkaloid mescaline and the DOx drugs.
Echinopsis lageniformis, synonyms including Echinopsis scopulicola and Trichocereus bridgesii, is a cactus native to Bolivia. It is known as the Bolivian torch cactus. Among the indigenous populations of Bolivia, it is sometimes called achuma or wachuma, although these names are also applied to related species such as Trichocereus macrogonus which are also used for their psychedelic effects.
2,4,5-Trimethoxyphenethylamine, also known as 2C-O or 2C-OMe, or is a phenethylamine of the 2C family and was first synthesized by Jansen in 1931. It is a positional isomer of the drug mescaline (3,4,5-trimethoxy).
2C (2C-x) is a general name for the family of psychedelic phenethylamines containing methoxy groups on the 2 and 5 positions of a benzene ring. Most of these compounds also carry lipophilic substituents at the 4 position, usually resulting in more potent and more metabolically stable and longer acting compounds.
3,4-Dimethoxyphenethylamine (DMPEA) is a chemical compound of the phenethylamine class. It is an analogue of the major human neurotransmitter dopamine where the 3- and 4-position hydroxy groups have been replaced with methoxy groups. It is also closely related to mescaline which is 3,4,5-trimethoxyphenethylamine and to 3,4-dimethoxyamphetamine (3,4-DMA).
Senegalia berlandieri is a shrub native to the Southwestern United States and northeast Mexico that belongs to the Mimosoid clade of Fabaceae. It grows 1 to 5 metres tall, with blossoms that are spherical and white, occurring from February through April. The berlandieri epithet comes from the name of Jean-Louis Berlandier, a French naturalist who studied wildlife native to Texas and Mexico. S. berlandieri contains a wide variety of alkaloids and has been known to cause toxic reactions in domestic animals such as goats.
Vachellia rigidula, commonly known as blackbrush acacia or chaparro prieto, and also known as Acacia rigidula, is a species of shrub or small tree in the legume family, Fabaceae. Its native range stretches from Texas in the United States south to central Mexico. This perennial is not listed as being threatened. It reaches a height of 5–15 feet (1.5–4.6 m). Blackbrush acacia grows on limestone hillsides and canyons.
Trimethoxyphenethylamines (TMPEA) are a group of positional isomers of the psychedelic cactus alkaloid mescaline. Some of them are described in the book PiHKAL by Alexander Shulgin and Ann Shulgin.
Trichocereus macrogonus, synonym Echinopsis macrogonus, is a species of cactus found in Ecuador, Peru and Bolivia. Two varieties are accepted as of September 2023: var. macrogonus and var. pachanoi. Plants contain varying amounts of the psychoactive alkaloid mescaline. They have been used both ritually and in traditional medicine from pre-Columbian times. Trichocereus macrogonus is one of a number of similar species that may be called San Pedro cactus. Indigenous names include achuma and huachuma, although these too may be applied to similar species.
Trichocereus macrogonus var. pachanoi is a fast-growing columnar cactus found in the Andes at 2,000–3,000 m (6,600–9,800 ft) in altitude. It is one of a number of kinds of cacti known as San Pedro cactus. It is native to Ecuador, Peru and Colombia, but also found in Argentina, Bolivia, Chile and Venezuela and cultivated in other parts of the world. Uses for it include traditional medicine and traditional veterinary medicine, and it is widely grown as an ornamental cactus. It has been used for healing and religious divination in the Andes Mountains region for over 3,000 years.
Substituted phenethylamines are a chemical class of organic compounds that are based upon the phenethylamine structure; the class is composed of all the derivative compounds of phenethylamine which can be formed by replacing, or substituting, one or more hydrogen atoms in the phenethylamine core structure with substituents. Phenylethylamines are also generally found to be central nervous system stimulants with many also being entactogens/empathogens, and hallucinogens.
4-Substituted-2,5-dimethoxyamphetamines (DOx) is a chemical class of substituted amphetamine derivatives featuring methoxy groups at the 2- and 5- positions of the phenyl ring, and a substituent such as alkyl or halogen at the 4- position of the phenyl ring. They are 4-substituted derivatives of 2,5-dimethoxyamphetamine.
Many cacti are known to be psychoactive, containing phenethylamine alkaloids such as mescaline. However, the two main ritualistic (folkloric) genera are Echinopsis, of which the most psychoactive species occur in the San Pedro cactus group, and Lophophora, with peyote being the most psychoactive species. Several other species pertaining to other genera are also psychoactive, though not always used with a ritualistic intent.
Cactus alkaloids are alkaloids that occur in cactus. Structurally, they are tetrahydroisoquinolines and phenylethylamines.
2,3,4,5-Tetramethoxyphenethylamine (TeMPEA) is a drug of the phenethylamine family related to mescaline (3,4,5-trimethoxyphenethylamine) and the 2C drugs. It was reported to be twice as potent as mescaline in producing behavioral changes in animals. However, it does not seem to have been tested in humans. The drug was not described in Alexander Shulgin's PiHKAL, though it was included in the The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. A derivative is 2,3,4,5-tetramethoxyamphetamine (TeMA), which was included in PiHKAL, and was reported to be inactive in humans at the tested doses.
