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Encyclopedia > Mescaline
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Not to be confused with mesclun.
Mescaline
Systematic (IUPAC) name
3,4,5-trimethoxy-phenethylamine or 2-(3,4,5-trimethoxyphenyl) ethanamine
Identifiers
CAS number 54-04-6
ATC code  ?
PubChem 4076
Chemical data
Formula C11H17NO3 
Mol. mass 211.26 g/mol
SMILES eMolecules & PubChem
Physical data
Melt. point 183–186 °C (361–367 °F) (Sulfate dihydrate)
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

X(AU) X(US) Image File history File links Question_book-new. ... Mesclun is a salad mix of assorted small, young salad leaves. ... Image File history File links Size of this preview: 800 × 534 pixel Image in higher resolution (1124 × 750 pixel, file size: 3 KB, MIME type: image/png) High-resolution black/white PNG made with ChemDraw and IrfanView — see my Wikipedia user talk page for a detailed description. ... Image File history File links Size of this preview: 768 × 599 pixels Full resolution (802 × 626 pixel, file size: 113 KB, MIME type: image/png) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Mescaline User:Sbrools/Gallery ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... PubChem is a database of chemical molecules. ... A chemical formula is an easy way of expressing information about the atoms that constitute a particular chemical compound. ... For other uses, see Carbon (disambiguation). ... This article is about the chemistry of hydrogen. ... General Name, symbol, number nitrogen, N, 7 Chemical series nonmetals Group, period, block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... This article is about the chemical element and its most stable form, or dioxygen. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... The melting point of a solid is the temperature range at which it changes state from solid to liquid. ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... The biological half-life of a substance is the time required for half of that substance to be removed from an organism by either a physical or a chemical process. ... The kidneys are important excretory organs in vertebrates. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ... For other uses, see Australia (disambiguation). ... For other uses of terms redirecting here, see US (disambiguation), USA (disambiguation), and United States (disambiguation) Motto In God We Trust(since 1956) (From Many, One; Latin, traditional) Anthem The Star-Spangled Banner Capital Washington, D.C. Largest city New York City National language English (de facto)1 Demonym American...

Legal status

Prohibited (S9)(AU) Schedule III(CA) Class A(UK) Schedule I(US) The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... The Standard for the Uniform Scheduling of Drugs and Poisons, abbreviated SUSDP, is a document used in the regulation of drugs and poisons in Australia. ... For other uses, see Australia (disambiguation). ... The Controlled Drugs and Substances Act is Canadas federal drug control statute. ... Motto (Latin for From Sea to Sea) Anthem O Canada Royal anthem: God Save the Queen Capital Ottawa Largest city Toronto Official languages English, French Government Parliamentary democracy and federal constitutional monarchy  -  Monarch Queen Elizabeth II  -  Governor General Michaëlle Jean  -  Prime Minister Stephen Harper Establishment  -  Act of Union February... The Misuse of Drugs Act 1971 (c. ... This box:      The Controlled Substances Act (CSA) was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970. ... For other uses of terms redirecting here, see US (disambiguation), USA (disambiguation), and United States (disambiguation) Motto In God We Trust(since 1956) (From Many, One; Latin, traditional) Anthem The Star-Spangled Banner Capital Washington, D.C. Largest city New York City National language English (de facto)1 Demonym American...

Routes Oral, Intravenous

Mescaline or 3,4,5-trimethoxyphenethylamine is a naturally-occurring psychedelic alkaloid of the phenethylamine class. It is mainly used as a recreational drug, an entheogen, and a tool to supplement various types of practices for transcendence, including in meditation, psychonautics, art projects, and illegal psychedelic psychotherapy, whether self administered or not. In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body. ... For psychedelics, see psychedelic drug. ... Chemical structure of ephedrine, a phenethylamine alkaloid An alkaloid is a nitrogen-containing naturally occurring compound, produced by a large variety of organisms, including fungi, plants, animals, and bacteria. ... Phenethylamine, or β-Phenylethylamine, is an alkaloid and monoamine. ... Recreational drug use is the use of psychoactive drugs for recreational rather than medical or spiritual purposes, although the distinction is not always clear. ... This entry covers entheogens as psychoactive substances used in a religious or shamanic context. ... This article is about the instrument. ... In philosophy, transcendental/transcendence, has three different but related primary meanings, all of them derived from the words literal meaning (from Latin), of climbing or going beyond: one that originated in Ancient philosophy, one in Medieval philosophy and one in modern philosophy. ... For other senses of this word, see Meditation (disambiguation). ... For the trance band Psychonaut, see Psychonaut (band). ... This article is about the philosophical concept of Art. ... Psychedelic psychotherapy refers to psychotherapeutic practices involving the use of psychedelic drugs. ...


It occurs naturally in the peyote cactus (Lophophora williamsii), the San Pedro cactus (Echinopsis pachanoi) and the Peruvian Torch cactus (Echinopsis peruviana), and in a number of other members of the Cactaceae. It is also found in small amounts in certain members of the Fabaceae (bean family), including Acacia berlandieri.[1] Mescaline was first isolated and identified in 1897 by the German Arthur Heffter and first synthesized in 1919 by Ernst Späth. Binomial name (Lem. ... Binomial name (Britton and Rose) Friedrich and Rowley Synonyms Trichocereus pachanoi Britton & Rose The San Pedro cactus (Echinopsis pachanoi, syn. ... Binomial name (Britton & Rose) Synonyms Echinopsis peruviana Peruvian Torch cactus (Trichocereus peruvianus) is a fast-growing columnar cactus native to the western slope of the Andes in Peru. ... This article is about the desert plant. ... Subfamilies Faboideae Caesalpinioideae Mimosoideae References GRIN-CA 2002-09-01 The name Fabaceae belongs to either of two families, depending on viewpoint. ... Binomial name Acacia berlandieri Benth. ... Arthur Heffter (June 15, 1859-February 8, 1925) was a German pharmacologist. ... Ernst Späth (14 May 1886 in Bärn– 30 September 1946) in Zurich) was a Austrian chemist. ...

Contents

History and usage

The use of peyote in Native American religious ceremonies has been noted since the earliest European contact, notably by the Huichols in Mexico, but other cacti such as the San Pedro have been used in different regions, from Peru to Ecuador. For other uses, see Native Americans (disambiguation). ... The Huichol are an indigenous ethnic group of Western Central Mexico that live in the Sierra Madre Occidental, in the states of Nayarit and Jalisco. ...


Aldous Huxley experimented with the use of mescaline. So did Aleister Crowley as reported in his diary, as well as the famous sex psychologist Havelock Ellis. Aldous Leonard Huxley (26 July 1894 – 22 November 1963) was an English writer and one of the most prominent members of the famous Huxley family. ... Aleister Crowley, born Edward Alexander Crowley (pronounced ), (12 October 1875 – 1 December 1947), was a British occultist, writer, mountaineer, poet, and yogi. ... Henry Havelock Ellis (February 2, 1859 - July 8, 1939), known as Havelock Ellis, was a British doctor, sexual psychologist and social reformer. ...


In traditional peyote preparations, the top of the cactus is cut from the roots, and dried to make disk-shaped buttons. It is chewed to produce its effect or soaked in water for an intoxicating drink. However, the taste of the cactus is bitter, so users will often grind it into a powder and fill them in capsules to avoid having to taste it. The effective human dosage is 300–500 milligrams of pure mescaline. Hallucinations occur at 300–600mg, which is the equivalent to approximately 20 mescal buttons.


Pharmacokinetics

Although the ED50 is variable with dosage and individual, the LD50 has been measured in various animals and is reported as follows: This article is about the toxicological term. ...

  • 212 mg/kg i.p. (mice)
  • 132 mg/kg i.p. (rats)
  • 328 mg/kg i.p. (guinea pigs)

It is reported that mescaline is 1000-3000 times less potent than LSD, and 30 times less potent than psilocybin[citation needed]. About half the initial dosage is excreted after 6 hours, but some studies suggest that it is not metabolized at all before excretion. Lysergic acid diethylamide, commonly called LSD, LSD-25, or acid. ... Psilocybin (also known as psilocybine) is a psychedelic alkaloid of the tryptamine family, found in psilocybin mushrooms. ...


Tolerance builds with repeated usage, and it is suggested that a cross-tolerance can be developed with LSD and psilocin.[2] It has been suggested that toleration be merged into this article or section. ... Dendritic cells can take up self antigens from other cells and cross-present them to autoreactive T cells. ... Lysergic acid diethylamide, commonly called LSD, LSD-25, or acid. ... Psilocin,(4-HO-DMT) sometimes called psilocine or psilotsin, is a psychedelic (hallucinogenic) mushroom alkaloid. ...


Mescaline appears is not subject to metabolism by CYP2D6[3] and between 20 and 50% of mescaline is excreted in the urine unchanged, and the rest being excreted as the carboxylic acid form of mescaline, a likely result of MAO degredation[4]. Mao could refer to: Mao Zedong, (Mao Tse-Tung in Wade-Giles) leader of the Communist Party of China from 1935 to 1976. ...


Behavioral and non-behavioral effects

Hallucinations produced by mescaline are somewhat different from those of LSD. Hallucinations are consistent with actual experience, but are typically intensifications of the stimulus properties of objects and sounds. Prominence of color is distinctive, appearing brilliant and intense. Unlike LSD, mescaline does not induce distortions of form or kaleidoscopic experiences. However, like LSD, synesthesia can occur.[2] A hallucination is a perception in the absence of a stimulus that the person may or may not believe is real. ... Lysergic acid diethylamide, commonly called LSD, LSD-25, or acid. ... For other uses, see Synesthesia (disambiguation). ...


Mescaline elicits a pattern of sympathetic arousal, with the peripheral nervous system being a major target for this drug.[2] The peripheral nervous system (PNS) can be divided into the somatic nervous system and the autonomic nervous system (ANS). ...


Effects last for up to 12 hours[2].


Mode of action

Mescaline acts similarly to other psychedelic agents [5]. Mescaline binds to, and activates the serotonin 5-HT2A receptor with a high nanomolar affinity [6]. How activating the 5-HT2A receptor leads to hallucinations is still unknown, but it is likely it somehow involves exciting cortical neurons[7]. Look up cortex in Wiktionary, the free dictionary. ... This article is about cells in the nervous system. ...


Legal status

In the US it was made illegal in 1970 by the Comprehensive Drug Abuse Prevention and Control Act.[8] It was prohibited internationally by the 1971 Convention on Psychotropic Substances[9] and is categorized as a Schedule I hallucinogen by the CSA. Mescaline is only legal for certain natives (such as those involved in the Native American Church). Penalties for manufacture or sale can be as high as five years in prison and a fine of $15,000, with a penalty of up to one year and fine of $5000 for possession. In the UK, mescaline is a Class A drug (in powder form, although dried cactus can be bought and sold legally, unlike raw "magic" mushrooms, which are now illegal)[10], and so carries the following penalties. For possession: up to seven years in prison or an unlimited fine or both. For dealing: up to life in prison or an unlimited fine or both. For other uses of terms redirecting here, see US (disambiguation), USA (disambiguation), and United States (disambiguation) Motto In God We Trust(since 1956) (From Many, One; Latin, traditional) Anthem The Star-Spangled Banner Capital Washington, D.C. Largest city New York City National language English (de facto)1 Demonym American... This box:      The Controlled Substances Act (CSA) was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970. ... Year 1971 (MCMLXXI) was a common year starting on Friday (link will display full calendar) of the 1971 Gregorian calendar. ... Convention on Psychotropic Substances Opened for signature February 21, 1971 in Vienna Entered into force August 16, 1976 Conditions for entry into force 40 ratifications Parties 175 The Convention on Psychotropic Substances is a United Nations treaty designed to control psychoactive drugs such as amphetamines, barbiturates, and psychedelics. ... This box:      The Controlled Substances Act (CSA) was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970. ... Native American Church Native American Church, a religious denomination which practices Peyotism or Peyote religion, originated in the U.S. state of Oklahoma, and is the most widespread indigenous religion among Native Americans. ...


Analogs

Phenescaline, an analog of mescaline
Phenescaline, an analog of mescaline

Mescaline has a number of analogs, featuring the methoxy groups altered to include thio groups or to be extended. Examples include, but are not limited to, isomescaline, thiomescaline, escaline, thioescaline, proscaline, isoproscaline, buscaline, thiobuscaline, thioisomescaline, phenescaline, symbescaline, asymbescaline, thioasymbescaline, allylescaline, methallylescaline, metaescaline, and thiometaescaline. Its has an active amphetamine homolog, 3,4,5-trimethoxyamphetamine. Image File history File links Size of this preview: 800 × 353 pixel Image in higher resolution (1040 × 459 pixel, file size: 9 KB, MIME type: image/png) Chemical structure of Phenescaline, drawn in ChemDraw by User:Mark PEA. I, the creator of this work, hereby release it into the public... Image File history File links Size of this preview: 800 × 353 pixel Image in higher resolution (1040 × 459 pixel, file size: 9 KB, MIME type: image/png) Chemical structure of Phenescaline, drawn in ChemDraw by User:Mark PEA. I, the creator of this work, hereby release it into the public... In chemistry, analogs or analogues are compounds in which one or more individual atoms have been replaced, either with a different atom, or with a different functional group. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... For the related sulfur-containing chemical compound, see Thiol. ... Isomescaline, or 2,3,4-trimethoxyphenethylamine, is a lesser-known psychedelic drug. ... TM, or thiomescaline, is a series of lesser-known psychedelic drugs similar in structure to Mescaline. ... Escaline is a psychedelic hallucinogenic drug and entheogen of the phenethylamine class of compounds. ... TE, or thioescaline, is a series of lesser-known psychedelic drugs similar in structure to Escaline. ... Proscaline (or 4-propoxy-3,5-DMPEA) is a psychedelic and hallucinogenic drug, used by some as an entheogen. ... Isoproscaline (or 4-(i)-propyl-3,5-dimethoxyphenethylamine) is an analogue of mescaline. ... Buscaline, or 3,5-dimethoxy-4-butoxyphenethylamine, is a lesser-known psychedelic drug. ... Thiobuscaline, or 3,5-dimethoxy-4-butylthiophenethylamine, is a lesser-known psychedelic drug. ... TIM, or thioisomescaline, is a series of lesser-known psychedelic drugs similar in structure to Mescaline. ... Phenescaline, or 3,5-dimethoxy-4-phenethoxyphenethylamine, is a lesser-known psychedelic drug. ... Symbescaline, or 3,5-diethoxy-4-methoxyphenethylamine, is a lesser-known psychedelic drug. ... Asymbescaline, or 3,4-diethoxy-5-methoxyphenethylamine, is a lesser-known psychedelic drug. ... TASB, or thioasymbescaline, is a series of lesser-known psychedelic drugs similar in structure to Asymbescaline and to Mescaline. ... Allyloxy, or 4-allyloxy-3,5-dimethoxyphenethylamine, is a lesser-known psychedelic drug. ... Methallylescaline, or 4-methallyloxy-3,5-dimethoxyphenethylamine, is a lesser-known psychedelic drug. ... Metaescaline, or 3,4-dimethoxy-5-ethoxyphenethylamine, is a lesser-known psychedelic drug. ... TME, or thiometaescaline, is a series of lesser-known psychedelic drugs similar in structure to Mescaline. ... A homolog in chemistry refers to a chemical compound from a series of compounds that differ only in the number of repeated structural units [1]. A homolog is a special case of an analog. ... TMAs, also known as trimethoxyamphetamines, are a family of isomeric psychedelic hallucinogenic drugs. ...


See also

The Doors of Perception is a 1954 book by Aldous Huxley detailing his experiences when taking mescaline. ... MKULTRA redirects here. ... PiHKAL is a 1991 book by Dr. Alexander Shulgin and Ann Shulgin about psychedelic phenethylamines. ... An assortment of psychoactive drugs A psychoactive drug or psychotropic substance is a chemical substance that acts primarily upon the central nervous system where it alters brain function, resulting in temporary changes in perception, mood, consciousness and behavior. ...

References

Notes

  1. ^ Chemistry of Acacia's from South Texas
  2. ^ a b c d Diaz, Jaime. How Drugs Influence Behavior. Englewood Cliffs: Prentice Hall, 1996
  3. ^ Wu D, Otton SV, Inaba T, Kalow W, Sellers EM (June 1997). "Interactions of amphetamine analogs with human liver CYP2D6". Biochem. Pharmacol. 53 (11): 1605–12. PMID 9264312. 
  4. ^ COCHIN J, WOODS LA, SEEVERS MH (February 1951). "The absorption, distribution and urinary excretion of mescaline in the dog". J. Pharmacol. Exp. Ther. 101 (2): 205–9. PMID 14814616. 
  5. ^ Nichols DE (February 2004). "Hallucinogens". Pharmacol. Ther. 101 (2): 131–81. doi:10.1016/j.pharmthera.2003.11.002. PMID 14761703. 
  6. ^ Monte AP, Waldman SR, Marona-Lewicka D, et al (September 1997). "Dihydrobenzofuran analogues of hallucinogens. 4. Mescaline derivatives". J. Med. Chem. 40 (19): 2997–3008. doi:10.1021/jm970219x. PMID 9301661. 
  7. ^ Béïque JC, Imad M, Mladenovic L, Gingrich JA, Andrade R (June 2007). "Mechanism of the 5-hydroxytryptamine 2A receptor-mediated facilitation of synaptic activity in prefrontal cortex". Proc. Natl. Acad. Sci. U.S.A. 104 (23): 9870–5. doi:10.1073/pnas.0700436104. PMID 17535909. 
  8. ^ United States Department of Justice. "Drug Scheduling". Retrieved on 2007-11-02.
  9. ^ "List of psychotropic substances under international control". International Narcotics Control Board. Retrieved on 2008-01-27.
  10. ^ "[http://www.erowid.org/plants/cacti/cacti_law2.shtml 2007 U.K. Trichocereus Cacti Legal Case Regina v. Saul Sette]".

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External links

Wikimedia Commons has media related to:
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Psychedelic phenethylamines

Aleph • 2C-B • 2C-B-FLY • 2C-C • 2C-D • 2C-E • 2C-F • 2C-G • 2C-I • 2C-N • 2C-O • 2C-O-4 • 2C-P • 2C-T • 2C-T-2 • 2C-T-4 • 2C-T-7 • 2C-T-8 • 2C-T-9 • 2C-T-13 • 2C-T-15 • 2C-T-17 • 2C-T-21 • 2C-TFM • 2C-YN • 25I-NBOH • 25I-NBOMe • 3C-E • 3C-P • Br-DFLY • DESOXY • DMMDA-2 • DOB • DOC • DOET • DOI • DOM • DON • DOPR • DOTFM • Escaline • Ganesha • HOT-2 • HOT-7 • HOT-17 • Isoproscaline • Lophophine • MDA • MMDA • MMDA-2 • MMDA-3a • MMDMA • Macromerine • Mescaline • Proscaline • TCB-2 • TMA Alexander and Ann Shulgin, in a photo from their book TiHKAL, c. ... A fractal pattern similar to the spiral patterns that may be seen as the result of some psychedelic drug experiences. ... Phenethylamine, or β-Phenylethylamine, is an alkaloid and monoamine. ... Aleph is a psychedelic hallucinogenic drug and a substituted amphetamine of the phenethylamine class of compounds, which can be used as an entheogen. ... 2C-B, or 4-bromo-2,5-dimethoxyphenethylamine (4-Bromo-2,5-dimethoxybenzeneethanamine) is a class of phenethylamine, a lesser-known psychedelic drug of the 2C family, an entactogen. ... 2C-B-FLY is a psychedelic phenethylamine first synthesized by Aaron P. Monte, and sometimes used as an entheogen. ... 2C-C is a psychedelic hallucinogenic drug first synthesized by Alexander Shulgin, sometimes used as an entheogen. ... 2C-D is a psychedelic hallucinogenic drug first synthesized by Alexander Shulgin, sometimes used as an entheogen. ... 2C-E (2,5-dimethoxy-4-ethylphenethylamine) is a psychedelic drug and phenethylamine of the 2C family. ... 2C-F, or 4-fluoro-2,5-dimethoxyphenethylamine, is a lesser-known psychedelic drug of the 2C family. ... Chemical structure of 2C-G 2C-G is a psychedelic phenethylamine of the 2C family. ... 2C-I is a psychedelic drug and phenethylamine that was developed and popularized by Alexander Shulgin. ... 2C-N is a psychedelic entheogen first synthesized by Alexander Shulgin. ... 2C-O (or β-2,4,5-trimethoxyphenethylamine) is a positional isomer of mescaline and was first synthesized by Jansen in 1931. ... 2C-O-4 (or 4-(i)-propoxy-2,5-dimethoxyphenethylamine) is a positional isomer of isoproscaline and was probably first synthesized by Alexander Shulgin. ... 2C-P is an entheogenic phenethylamine first synthesized by Alexander Shulgin. ... Chemical structure of 2C-T - CAS number 61638-09-3 2C-T (or 4-methylthio-2,5-DMPEA) is a psychedelic and hallucinogenic drug, used by some as an entheogen. ... 2C-T-2 is a psychedelic phenethylamine of the 2C family. ... 2C-T-4 or 2,5-dimethoxy-4-(i)-propylthiophenethylamine is a psychedelic phenethylamine of the 2C family. ... 2C-T-7 is a psychedelic phenethylamine and is sometimes used as an entheogen. ... 2C-T-8 is a psychedelic phenethylamine of the 2C family. ... 2C-T-9 is a psychedelic phenethylamine of the 2C family. ... 2C-T-13 or 2,5-dimethoxy-4-(β-methoxyethylthio)phenethylamine is a psychedelic phenethylamine of the 2C family. ... 2C-T-15 or 2,5-dimethoxy-4-(β-cyclopropylthio)phenethylamine is a psychedelic phenethylamine of the 2C family. ... 2C-T-17 or 2,5-dimethoxy-4-(β-isobutylthio)phenethylamine is a psychedelic phenethylamine of the 2C family. ... 2C-T-21 is a psychedelic phenethylamine of the 2C family. ... 2C-TFM is a psychedelic phenethylamine that may have first been synthesized by Daniel Trachsel. ... 2C-YN is an analogue of the phenethylamine derived hallucinogen 2C-E where the ethyl group has been replaced by an ethynyl group. ... 25I-NBOH or N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane is a derivative of the phenethylamine derived hallucinogen 2C-I, discovered in 2006 by a team at Purdue University. ... 25I-NBOMe or N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane is a derivative of the phenethylamine derived hallucinogen 2C-I, discovered in 2006 by a team at Purdue University. ... 3C-E is a psychedelic hallucinogenic drug and entheogen of the phenethylamine class of compounds. ... 3C-P is a psychedelic phenethylamine, sometimes used as an entheogen. ... Bromo-DragonFLY, also known as ABDF, is a psychedelic hallucinogenic drug related to the phenethylamine family. ... 4-desoxymescaline, or DESOXY, is a psychedelic phenethylamine and analogue with four times the potency of mescaline. ... DMMDA-2 is a psychedelic phenethylamine first synthesised by Alexander Shulgin and popularized by his book PiHKAL. Shulgin, Alexander. ... DOB (Brolamfetamine, Dr. Bob, Bob or Bromo-DMA) is a psychedelic hallucinogenic drug and a substituted amphetamine of the phenethylamine class of compounds, which can be used as an entheogen. ... DOC (or 4-Chloro-2,5-DMA) is a psychedelic hallucinogenic drug of the phenethylamine family. ... DOET, HECATE, or 2,5-dimethoxy-4-ethylamphetamine is an analogue of DOM, and is the three-carbon chain homologue to 2C-E. It produces hallucinogenic, psychedelic, and entheogenic effects. ... DOI or 2,5-dimethoxy-4-iodoamphetamine is a psychedelic hallucinogenic drug of the phenethylamine family. ... DOM (or STP, allegedly standing for Serenity, Tranquillity and Peace) is a psychedelic hallucinogenic drug of the phenethylamine class of compounds, sometimes used as an entheogen. ... DON 2,5-dimethoxy-4-nitroamphetamine is an analogue of DOM and DOB. It is also closely related to 2C-N, and produces hallucinogenic, psychedelic, and entheogenic effects. ... DOPR, or 2,5-dimethoxy-4-(n)-propylamphetamine, is a lesser-known psychedelic drug and a substituted Amphetamine. ... DOTFM is an analogue of the phenethylamine derived hallucinogen DOB where the bromine atom has been replaced by a trifluoromethyl group. ... Escaline is a psychedelic hallucinogenic drug and entheogen of the phenethylamine class of compounds. ... Ganesha, or 3,4-methyl-2,5-dimethoxyamphetamine, is a lesser-known psychedelic drug. ... HOT-2, or 2,5-dimethoxy-4-(β-ethylthio)-N-hydroxyphenethylamine is a psychedelic phenethylamine of the 2C family. ... HOT-7, or 2,5-dimethoxy-4-(β-propylthio)-N-hydroxyphenethylamine, is a psychedelic phenethylamine of the 2C family. ... HOT-17, or 2,5-dimethoxy-4-(β-isobutylthio)-N-hydroxyphenethylamine, is a psychedelic phenethylamine of the 2C family. ... Isoproscaline (or 4-(i)-propyl-3,5-dimethoxyphenethylamine) is an analogue of mescaline. ... Lophophine, homomyristicylamine, (or 3-methoxy-4,5-methylendioxyphenethylamine) is an homologue of MMDA. It is also related to mescaline and Alexander Shulgin suggests it could be a natural component in the peyote cactus because it is the only logical chemical intermediate for the biosynthesis of several of tetrahydroisoquinolines known to... 3,4-Methylenedioxyamphetamine (MDA or Tenamfetamine) is a psychedelic hallucinogenic drug and empathogen/entactogen of the phenethylamine family. ... The first prepared and first described positional isomer of methoxymethylenedioxyphenylisopropylamine was the 3,4,5-substituted compound MMDA (51, 3-methoxy-4,5-methylenedioxyphenylisopropylamine, 3-methoxy-4,5-methylenedioxyamphetamine). ... MMDA, or 3-methoxy-4,5-methylenedioxyamphetamine, is a stimulant, a psychedelic drug, an entheogen, and an entactogen. ... MMDA, or 3-methoxy-4,5-methylenedioxyamphetamine, is a stimulant, a psychedelic drug, an entheogen, and an entactogen. ... N-methyl-3-methoxy-4,5-methylenedioxyamphetamine (MMDMA) is a drug which is thought to have hallucinogenic and empathogenic effects. ... Macromerine is a psychedelic, hallucinogenic and entheogenic of the phenethylamine family. ... Proscaline (or 4-propoxy-3,5-DMPEA) is a psychedelic and hallucinogenic drug, used by some as an entheogen. ... TCB-2 or (R)-(4-Bromo-3,6-dimethoxybenzocyclobuten-1-yl)methylamine is a conformationally resticted derivative of the phenethylamine derived hallucinogen 2C-B, discovered in 2006 by a team at Purdue University. ... TMAs, also known as trimethoxyamphetamines, are a family of isomeric psychedelic hallucinogenic drugs. ...

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Drugs from PiHKAL

AEM · AL · Aleph · Aleph-2 · Aleph-4 · Aleph-6 · Aleph-7 · Ariadne · Asymbescaline · Buscaline · Beatrice · Bis-TOM · BOB · BOD · BOH · BOHD · BOM · 4-Bromo-3,5-dimethoxyamphetamine · 2-Bromo-4,5-methylenedioxyamphetamine · 2C-B · 3C-BZ · 2C-C · 2C-D · 2C-E · 3C-E · 2C-F · 2C-G · 2C-G-3 · 2C-G-4 · 2C-G-5 · 2C-G-N · 2C-H · 2C-I · 2C-N · 2C-O · 2C-O-4 · 2C-P · CPM · 2C-SE · 2C-T · 2C-T-2 · 2C-T-4 · psi-2C-T-4 · 2C-T-7 · 2C-T-8 · 2C-T-9 · 2C-T-13 · 2C-T-15 · 2C-T-17 · 2C-T-21 · 4-D · beta-D · DESOXY · 2,4-DMA · 2,5-DMA · 3,4-DMA · DMCPA · DME · DMMDA · DMMDA-2 · DMPEA · DOAM · DOB · DOBU · DOC · DOEF · DOET · DOI · DOM · psi-DOM · DON · DOPR · Escaline · EEE · EEM · EME · EMM · Ethyl-J (EBDB) · Ethyl-K · F-2 · F-22 · Flea · 3C-G-3 · 3C-G-4 · 3C-G-5 · 3C-G-N · Ganesha · HOT-2 · HOT-7 · HOT-17 · IDNNA · Isomescaline · Isoproscaline · Iris · J (BDB) · Lophophine · Mescaline · 4-MA · Madam-6 · Methallylescaline · MDA · MDAL · MDBU · MDBZ · MDCPM · MDDM · MDE · MDHOET · MDIP · MDMA · MDMC (EDMA) · MDMEO · MDMEOET · MDMP · MDOH · MDPEA · MDPH · MDPL · MDPR · Metaescaline · MEDA · MEE · MEM · MEPEA · Meta-DOB · Meta-DOT · Methyl-DMA · Methyl-DOB · Methyl-J (MBDB) · Methyl-K · Methyl-MA (PMMA) · Methyl-MMDA-2 · MMDA · MMDA-2 · MMDA-3a · MMDA-3b · MME · Metaproscaline · MPM · Ortho-DOT · Proscaline · Phenescaline · Phenethylamine · Propynyl · Symbescaline · 2,3,4,5-Tetramethoxyamphetamine · 3-TASB · 4-TASB · 5-TASB · Thiobuscaline · 3-TE · 4-TE · 3-TIM · 4-TIM · 5-TIM · 3-TM · 4-TM · TMA · TMA-2 · TMA-3 · TMA-4 · TMA-5 · TMA-6 · 3-TME · 4-TME · 5-TME · 2T-MMDA-3a · 4T-MMDA-2 · 2-TOET · 5-TOET · 2-TOM · 5-TOM · TOMSO · Thioproscaline · Trisescaline · 3-TSB · 4-TSB · 3-T-Trisescaline · 4-T-Trisescaline PiHKAL is a 1991 book by Dr. Alexander Shulgin and Ann Shulgin about psychedelic phenethylamines. ... AEM, or 3,4,5-trimethoxy-alpha-ethylphenethylamine, is a lesser-known psychedelic drug. ... Allyloxy, or 4-allyloxy-3,5-dimethoxyphenethylamine, is a lesser-known psychedelic drug. ... Aleph is a psychedelic hallucinogenic drug and a substituted amphetamine of the phenethylamine class of compounds, which can be used as an entheogen. ... Aleph is a psychedelic