Mescaline or mescalin (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.
Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary states of consciousness. This causes specific psychological, visual, and auditory changes, and often a substantially altered state of consciousness. Psychedelic states are often compared to meditative, psychodynamic or transcendental types of alterations of mind. The "classical" psychedelics, the psychedelics with the largest scientific and cultural influence, are mescaline, LSD, psilocybin, and DMT.
Alexander Theodore "Sasha" Shulgin was an American medicinal chemist, biochemist, organic chemist, pharmacologist, psychopharmacologist, and author. He is credited with introducing 3,4-methylenedioxymethamphetamine to psychologists in the late 1970s for psychopharmaceutical use and for the discovery, synthesis and personal bioassay of over 230 psychoactive compounds for their psychedelic and entactogenic potential.
PiHKAL: A Chemical Love Story is a book by Dr. 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".
TIHKAL: The Continuation is a 1997 book written by Alexander Shulgin and Ann Shulgin about a family of psychoactive drugs known as tryptamines. A sequel to PIHKAL: A Chemical Love Story, TIHKAL is an acronym that stands for "Tryptamines I Have Known and Loved".
Escaline (3,5-methoxy-4-ethoxyphenethylamine) is a psychedelic drug and entheogen of the phenethylamine class of compounds. Escaline was first synthesized and reported in the scientific literature by Benington, et al., in 1954, but was later re-examined in the laboratory of David E. Nichols, who prepared a series of mescaline analogues that included escaline, proscaline, and isoproscaline. The effects of this and related mescaline analogues in humans were first described by Alexander Shulgin. In his book PiHKAL , Shulgin lists the dosage range as 40 to 60 mg, consumed orally. The duration of action was stated to be 8–12 hours.
Trimethoxyamphetamines (TMAs) are a family of isomeric psychedelic hallucinogenic drugs. There exist six different TMAs that differ only in the position of the three methoxy groups: TMA, TMA-2, TMA-3, TMA-4, TMA-5, and TMA-6. The TMAs are analogs of the phenethylamine cactus alkaloid mescaline. The TMAs are substituted amphetamines, however, their mechanism of action is more complex than that of the unsubstituted compound amphetamine, probably involving agonist activity on serotonin receptors such as the 5HT2A receptor in addition to the generalised dopamine receptor agonism typical of most amphetamines. This action on serotonergic receptors likely underlie the psychedelic effects of these compounds. It is reported that some TMAs elicit a range of emotions ranging from sadness to empathy and euphoria. TMA was first synthesized by Hey, in 1947. Synthesis data as well as human activity data has been published in the book PiHKAL.
Echinopsis lageniformis, the Bolivian torch cactus, is a fast-growing columnar cactus from the high deserts of Bolivia. Among the indigenous populations of Bolivia, it is sometimes called achuma or wachuma, although these names are also applied to related species such as Echinopsis pachanoi which are also used for their psychedelic effects.
Proscaline (4-propoxy-3,5-DMPEA) is a psychedelic and hallucinogenic drug. It has structural properties similar to the drugs mescaline, isoproscaline, and escaline. In PiHKAL, Alexander Shulgin reports that a dose of 30–60 mg produces effects lasting 8–12 hours.
2C-T is a psychedelic and hallucinogenic drug of the 2C family. It is used by some as an entheogen. It has structural and pharmacodynamic properties similar to the drugs mescaline and 2C-T-2.
Lophophine is a putative psychedelic and entactogen drug of the methylenedioxyphenethylamine class. It is the α-demethylated homologue of MMDA, and is also closely related to mescaline.
Isoproscaline or 4-isopropoxy-3,5-dimethoxyphenethylamine is an analog of mescaline. It is closely related to proscaline and was first synthesized by David E. Nichols. It produces hallucinogenic, psychedelic, and entheogenic effects.
TIM, or thioisomescaline, is a series of lesser-known psychedelic drugs similar in structure to mescaline. They were first synthesized by Alexander Shulgin. In his book PiHKAL , none of their durations are known. Very little is known about their dangers or toxicity.
Metaescaline (3,4-dimethoxy-5-ethoxyphenethylamine) is a lesser-known psychedelic drug. It is an analog of mescaline. Metaescaline was first synthesized by Alexander Shulgin. In his book PiHKAL, the dosage range is listed as 200–350 mg, and the duration listed as 8–12 hours. Metaescaline produces mental insights, entactogenic, MDMA-like effects, and TOMSO-like activation. Little data exists about the pharmacological properties, metabolism, and toxicity of metaescaline, though it has been studied to a limited extent in comparison with other related compounds.
Thioproscaline, or 3,5-dimethoxy-4-propylthiophenethylamine, is a lesser-known psychedelic drug. It is the 4-propylthio analog of mescaline. Thioproscaline was first synthesized by Alexander Shulgin. In his book PiHKAL , the dosage range is listed as 20–25 mg, and the duration listed as 10–15 hours. Thioproscaline causes closed-eye visuals, slight open-eye visuals, and a body load. Very little data exists about the pharmacological properties, metabolism, and toxicity of thioproscaline.
The molecular formula C11H17NO3 (molar mass: 211.25 g/mol, exact mass: 211.120843 u) may refer to:
ALPHA (alpha-ethyl-3,4-methylenedioxybenzylamine) is a lesser-known psychedelic drug and a substituted benzylamine. It is also the benzylamine analog of 3,4-methylenedioxyamphetamine (MDA). ALPHA was first synthesized by Alexander Shulgin. In his book PIHKAL on the MDA page, the threshold dosage is listed as 10 mg. At mild threshold dosages there are eyes-closed "dreams" with some body tingling, at higher doses was reported to produce a pleasant, positive feeling. This compound is not anoretic at any dose. It lasts about 3 hours. Very little data exists about the pharmacological properties, metabolism, and toxicity of ALPHA.
Echinopsis pachanoi —known as San Pedro cactus—is a fast-growing columnar cactus native to the Andes Mountains at 2,000–3,000 m (6,600–9,800 ft) in altitude. It is found in Argentina, Bolivia, Colombia, Chile, Ecuador and Peru, and it is 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. It is sometimes confused with its close relative Echinopsis peruviana.
NBOMe-mescaline or mescaline-NBOMe is a synthetic substituted phenethylamine. It is a partial agonist of serotonin receptors with a 5-HT2A pKi originally reported as 7.3, though more modern techniques assayed it as 140nM at 5-HT2A and 640nM at 5-HT2C, making it one of the least potent compounds among the N-benzyl phenethylamines.
2C-Se is a lesser-known psychedelic drug. It was originally named by Alexander Shulgin as described in his book PiHKAL. Shulgin considered 2C-Se to be around three times the potency of mescaline, but was too concerned about toxicity to test it extensively, though he considered it noteworthy as the only psychedelic drug to contain a selenium atom.
