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| Names | |
|---|---|
| Preferred IUPAC name 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinolin-8-ol | |
| Identifiers | |
3D model (JSmol) | |
| ChemSpider | |
| KEGG | |
PubChem CID | |
| UNII | |
CompTox Dashboard (EPA) | |
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| Properties | |
| C11H15NO3 | |
| Molar mass | 209.245 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Anhalamine is a naturally occurring alkaloid which can be isolated from Lophophora williamsii . [1] It is structurally related to mescaline. [2]
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 mental states and an apparent expansion of consciousness. Also referred to as classic hallucinogens or serotonergic hallucinogens, the term psychedelic is sometimes used more broadly to include various types of hallucinogens, such as those which are atypical or adjacent to psychedelia like salvia and MDMA, respectively. This article makes use of the narrower classical definition of psychedelics. Classic psychedelics generally cause specific psychological, visual, and auditory changes, and oftentimes a substantially altered state of consciousness. They have had the largest influence on science and culture, and include mescaline, LSD, psilocybin, and DMT.
Dissociatives, colloquially dissos, are a subclass of hallucinogens which distort perception of sight and sound and produce feelings of detachment – dissociation – from the environment and/or self. Although many kinds of drugs are capable of such action, dissociatives are unique in that they do so in such a way that they produce hallucinogenic effects, which may include dissociation, a general decrease in sensory experience, hallucinations, dream-like states or anesthesia. Despite most dissociatives' main mechanism of action being tied to NMDA receptor antagonism, some of these substances, which are nonselective in action and affect the dopamine and/or opioid systems, may be capable of inducing more direct and repeatable euphoria or symptoms which are more akin to the effects of typical "hard drugs" or common drugs of abuse. This is likely why dissociatives are considered to be addictive with a fair to moderate potential for abuse, unlike psychedelics. Despite some dissociatives, such as phencyclidine (PCP) possessing stimulating properties, most dissociatives seem to have a general depressant effect and can produce sedation, respiratory depression, nausea, disorientation, analgesia, anesthesia, ataxia, cognitive and memory impairment as well as amnesia.
The Heffter Research Institute is a 501(c)(3) nonprofit organization that promotes research with classic hallucinogens and psychedelics, predominantly psilocybin, to contribute to a greater understanding of the mind and to alleviate suffering. Founded in 1993 as a virtual institute, Heffter primarily funds academic and clinical scientists and made more than $3.1 million in grants between 2011 and 2014. Heffter's recent clinical studies have focused on psilocybin-assisted treatment for end-of-life anxiety and depression in cancer patients, as well as alcohol and nicotine addiction.
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.
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.
Macromerine is a phenethylamine derivative. It was first identified from the cactus Coryphantha macromeris. It can also be found in C. runyonii, C. elephantidens, and other related members of the family Cactaceae.
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.
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.
Methallylescaline (4-Methylallyloxy-3,5-dimethoxyphenethylamine) is a lesser-known psychedelic drug. It is the 4-methyl analog of allylescaline. Methallylescaline was first synthesized by Alexander Shulgin. In his book PiHKAL, the dosage range is listed as 40–65 mg and the duration is listed as 12–16 hours. Little data exists about the pharmacological properties, metabolism, and toxicity of methallylescaline, though it is known to be an agonist of 5-HT2A receptors, with effects comparable to that of other mescaline analogs and has been sold as a designer drug.
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.
Hallucinogens are a large and diverse class of psychoactive drugs that can produce altered states of consciousness characterized by major alterations in thought, mood, and perception as well as other changes. Most hallucinogens can be categorized as either being psychedelics, dissociatives, or deliriants.
The peyote is a small, spineless cactus which contains psychoactive alkaloids, particularly mescaline. Peyote is a Spanish word derived from the Nahuatl peyōtl, meaning "caterpillar cocoon", from a root peyōni, "to glisten". Peyote is native to Mexico and southwestern Texas. It is found primarily in the Sierra Madre Occidental, the Chihuahuan Desert and in the states of Nayarit, Coahuila, Nuevo León, Tamaulipas, and San Luis Potosí among scrub. It flowers from March to May, and sometimes as late as September. The flowers are pink, with thigmotactic anthers.
Jimscaline (C-(4,5,6-trimethoxyindan-1-yl)methanamine) is a conformationally-restricted derivative of the cactus-derived hallucinogen mescaline, which was discovered in 2006 by a team at Purdue University led by David E. Nichols. It acts as a potent agonist for the 5-HT2A and 5-HT2C receptors with the more active (R)-enantiomer having a Ki of 69 nM at the human 5-HT2A receptor, and around three times the potency of mescaline in drug-substitution experiments in animals. This discovery that the side chain of the phenethylamine hallucinogens could be constrained to give chiral ligands with increased activity then led to the later development of the super-potent benzocyclobutene derivative TCB-2.
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.
Anhalidine is a naturally occurring tetrahydroisoquinoline based alkaloid which can be isolated from Lophophora williamsii; it has also been detected other cactii and several species of Acacia. It is part of a family of compounds that are structurally related to mescaline.
Anhalinine is a naturally occurring alkaloid which can be isolated from Lophophora williamsii. It is structurally related to mescaline.
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.
Trifluoromescaline (TF-M) is a derivative of the phenethylamine hallucinogen mescaline, which has a trifluoromethoxy group replacing the central methoxy group of mescaline. Synthesis of this compound was first reported by Daniel Trachsel in 2011, alongside many other related compounds. Trifluoromescaline was found to be one of the most potent compounds in the series, with a reported dosage of 15–40 mg, and a slow onset of action and long duration of effects, lasting 14–24 hours or more.
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