Mescaline

from Wikipedia, the free encyclopedia
Structural formula
Structural formula of mescaline
General
Surname Mescaline
other names
  • mescaline
  • 2- (3,4,5-trimethoxyphenyl) ethanamine
  • 2- (3,4,5-trimethoxyphenyl) ethylamine
  • 3,4,5-trimethoxyphenethylamine
  • EA -1306
Molecular formula
  • C 11 H 17 NO 3 (mescaline)
  • C 11 H 17 NO 3 HCl (mescaline hydrochloride)
Brief description

colorless solid

External identifiers / databases
CAS number
  • 54-04-6 (mescaline)
  • 832-92-8 (mescaline hydrochloride )
  • 1152-76-7 (sulfate)
EC number 200-190-7
ECHA InfoCard 100,000.174
PubChem 4076
ChemSpider 3934
Wikidata Q193140
properties
Molar mass
  • 211.26 g · mol -1 (mescaline)
  • 247.72 g mol −1 (mescaline hydrochloride)
  • 556.63 g mol −1 [(mescaline) 2 sulfate dihydrate]
Melting point
  • 35–36 ° C (mescaline)
  • 181 ° C (mescaline hydrochloride)
  • 183–186 ° C (sulfate dihydrate)
boiling point

180.0 ° C (12 h Pa )

pK s value

9.56

solubility
  • soluble in acetone, chloroform, water and methanol (base)
  • soluble in water (mescaline hydrochloride)
  • ~ 3 mg / ml in PBS (pH 7.2), ~ 10 mg / ml in EtOH , ~ 3 mg / ml in DMSO , ~ 0.5 mg / ml in DMF (mescaline hydrochloride)
  • poorly soluble in methanol and water (sulfate dihydrate)
safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 302
P: no P-phrases
Toxicological data

880 mg kg −1 ( LD 50mouseoral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Mescaline or mescaline is a psychedelic and hallucinogenic effective alkaloid from the substance group of phenethylamines .

Occurrence

The peyote cactus Lophophora williamsii contains mescaline as its main active ingredient.
Biogenic , isolated crystalline mescaline

Mescaline is found in the Central American peyote cactus ( Lophophora williamsii ), in the cacti Echinopsis pachanoi , Echinopsis peruviana , Echinopsis lageniformis , Echinopsis santaensis and Echinopsis schoenii from the South American cactus genus Echinopsis as well as in many other small cacti species trace 0.1% Total salary).

history

In 1888 Louis Lewin described the cactus named after him "Anhalonium Lewinii" ( Lophophora williamsii , Peyote), whose chemical principle he extracted and investigated. He called this "anhalonin" (an alkaloid fraction containing mescaline ). At the same time Arthur Heffter also researched Lophophora williamsii , where he isolated the pure substance mescaline for the first time in 1896; Ernst Späth succeeded in determining the structure and the first total synthesis in 1919 .

chemistry

Mescaline cacti can be made by means of extraction are obtained, it can also but synthetically produced. Structurally related to mescaline is 3-methoxy-4,5-methylenedioxyamphetamine (MMDA), which may arise as a metabolic product after ingestion of myristicin , an ingredient in nutmeg oil . MMDA is the methoxy analogue of 3,4-methylenedioxyamphetamine (MDA). Also, 3,4,5-trimethoxyamphetamine (TMA) , 2,4,5-trimethoxyamphetamine (TMA-2) and 2,4,6-trimethoxyamphetamine (TMA-6) known amphetamine - analogues of mescaline with similar psychedelic effect. The mescaline body was the template for the development of the 2C group of substances and representatives of the dimethoxyamphetamines .

Pharmacodynamics

The pharmacodynamics of mescaline consists in the binding and activation of the serotonin receptor 5-HT 2A as a partial agonist with a relatively strong affinity (binding strength). There is also an effect on the serotonin receptor 5-HT 2C .

Pharmacokinetics

The orally effective dose is given as 200 to 400 mg (as mescaline sulfate) and 178 to 356 mg (as mescaline hydrochloride). The high itself then lasts for six to nine hours. Aftermath can be felt for up to twelve hours. The plasma half-life of mescaline is given as six hours.

Before the effects start, there is usually nausea and often vomiting. First, hyperactivity and inner restlessness set in, then slightly changed perception and an intensified color vision. Hallucinatory visions and dream images with loss of reality and feelings of happiness occur. Intensely bright colors are perceived. Subjectively, perception with all of the senses is clearly sharpened. Synesthesia is common .

Risks

Comparison of addiction potential and the ratio between the usual and fatal dose of various psychoactive substances and mescaline (according to RS Gable )

Mescaline can trigger substance-induced psychosis or persistent perception disorders ( hallucinogen persisting perception disorder , HPPD ). So-called " bad trips " can also occur; However, it was shown that depending on the set and setting, these were greatly reduced.

If the patient is very excited, medical treatment is indicated - "Goodman & Gilman's The Pharmacological Basis of Therapeutics" suggests 20 mg diazepam orally , but calming conversations have proven to be effective and are therefore the first step. Antipsychotics can enhance the experience and are therefore not indicated.

In a retrospective cross-sectional study (2013) of patient information in questionnaires from 2001 to 2004, a possible statistical relationship between medical treatment within the past year for psychological or psychiatric problems and at least one intake of mescaline / peyote throughout life was examined. The National Survey of Drug Use and Health (NSDUH) records, conducted by the U.S. Department of Health, provided data from 130,152 such patients for this period. Of these, 9,374 stated that they had taken mescaline / peyote at least once in their life. A statistically significant relationship between the examined variables was not found. The authors concluded that taking mescaline / peyote at least once throughout life was not an independent risk factor for mental health problems in the past year. However, they pointed out that a study of this type did not give any indications of possible causal relationships.

There is a particular risk in the combination with MAO inhibitors , which are contained in drugs such as antidepressants ( moclobemide ) and anti- Parkinson’s drugs with dopaminergic effects ( selegiline ) as well as in the hallucinogenic drug ayahuasca ( harmaline ). Since MAO inhibitors increase the effect of serotonergic substances, which include mescaline, to a considerable and unpredictable degree, there is an incalculable risk here, also in light of the fact that some MAO inhibitors continue to work for days. Typical consequences of the combination of mescaline with MAO inhibitors are symptoms of the serotonin syndrome , which can lead to death by disturbing the control of the respiratory muscles.

History of use

As a hallucinogen , mescaline, along with LSD , was widespread in the drug scene in the 1960s. It has been proposed repeatedly as an alternative to alcohol by some medical professionals and ethnologists , with a view to the social context of the American Indian reservations. Besides anthropologists (especially Richard Evans Schultes , Weston La Barre , JS Slotkin) and neuroscientists ( Heinrich Klüver ), the effect of mescaline has also been researched by some writers and artists in the 20th century , including Aldous Huxley , Antonin Artaud , Ernst Jünger , Carlos Castaneda and Henri Michaux .

Legal position

Mescaline was still legal in the 1950s and 1960s; many psychotherapists, philosophers and researchers experimented with it. With the fourth Narcotics Equal Opportunities Ordinance (4th BtMGlV) of February 21, 1967, which came into force on February 25, 1967, mescaline in the Federal Republic of Germany was made subject to the narcotics regulations of the Opium Act . It was made illegal worldwide in 1971 by the UN Convention on Psychotropic Substances . In the US, mescaline possession can be imprisoned for up to five years.

Mescaline is a non- marketable narcotic in Germany due to its listing in Appendix I BtMG . Handling without permission is generally a criminal offense.

In Austria and Germany, living cacti containing mescaline such as Lophophora williamsii or cacti of the cactus genus Echinopsis (formerly Trichocereus ) are not listed in the narcotics or addictive substances law . Possession and trade are permitted, provided that botanical purposes are pursued. Trade and possession of prepared plant parts for use as a drug are prohibited due to the mescaline it contains.

literature

Web links

Commons : Mescaline  - Album with pictures, videos and audio files

Individual evidence

  1. T. Passie, U. Benzenhöfer: MDA, MDMA, and other "mescaline-like" substances in the US military's search for a truth drug (1940s to 1960s). In: Drug testing and analysis. Volume 10, number 1, January 2018, pp. 72-80, doi: 10.1002 / dta.2292 , PMID 28851034 (review).
  2. Entry on mescaline. In: Römpp Online . Georg Thieme Verlag, accessed on April 4, 2019.
  3. a b c d The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, p. 1019, ISBN 978-0-911910-00-1 .
  4. a b c SWGDRUG Monographs: PEYOTE & MESCALINE Monograph (PDF; 484 kB), accessed on May 20, 2013.
  5. a b Entry on mescaline in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  6. Product information Mescaline (hydrochloride) . (PDF) from Cayman Chemicals, accessed April 21, 2014.
  7. a b data sheet Mescaline hydrochloride from Sigma-Aldrich , accessed on April 9, 2011 ( PDF ).
  8. ^ Albert Gossauer: Structure and reactivity of biomolecules , Verlag Helvetica Chimica Acta, Zurich, 2006, p. 247, ISBN 978-3-906390-29-1 .
  9. O. Ogunbodede, D. McCombs, K. Trout, P. Daley, M. Terry: New mescaline concentrations from 14 taxa / cultivars of Echinopsis spp. (Cactaceae) ("San Pedro") and their relevance to shamanic practice .  ( Page no longer available , search in web archivesInfo: The link was automatically marked as defective. Please check the link according to the instructions and then remove this notice. In: Journal of ethnopharmacology. Volume 131, Number 2, September 2010, pp. 356-362, doi: 10.1016 / j.jep.2010.07.021 . PMID 20637277 .@1@ 2Template: dead link / bitnest.ca  
  10. Yohei Hashimoto, Kazuko Kawanishi, Masataka Moriyasu: Forensic Chemistry of Alkaloids by Chromatographic Analysis . In: The Alkaloids: Chemistry and Pharmacology . Volume 32, 1988, p. 40 ( doi: 10.1016 / S0099-9598 (08) 60215-1 ).
  11. Keeper Trout: Cactus Chemistry by Species ( Memento of the original from July 11, 2016 in the Internet Archive ) Info: The archive link has been inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. (2014-e) doi: 10.13140 / RG.2.1.4715.8886 @1@ 2Template: Webachiv / IABot / sacredcacti.com
  12. ^ L. Lewin: Ueber Anhalonium Lewinii. In: Archives for Experimental Pathology and Pharmacology. 24, 1888, pp. 401-411, doi: 10.1007 / bf01923627 .
  13. Arthur Heffter: About Pellote. In: Archives of Experimental Pathology and Pharmacology. 34, 1894, p. 65, doi: 10.1007 / bf01864855 .
  14. A. Heffter: About Pellote. In: Archives of Experimental Pathology and Pharmacology. 40, 1898, p. 385, doi: 10.1007 / BF01825267 .
  15. Ernst Späth: About the anhalonium alkaloids: I. Anhaline and mezcaline. In: monthly Chem. 40, No. 2, 1919, pp. 129-154, doi: 10.1007 / BF01524590 .
  16. ^ AT Shulgin , MF Carter: Centrally active phenethylamines. In: Psychopharmacology communications. Volume 1, Number 1, 1975, pp. 93-98, PMID 1223994 .
  17. ^ A. Rickli, OD Moning, MC Hoener, ME Liechti: Receptor interaction profiles of novel psychoactive tryptamines compared with classic hallucinogens. In: European neuropsychopharmacology: the journal of the European College of Neuropsychopharmacology. Volume 26, Number 8, August 2016, pp. 1327-1337, doi: 10.1016 / j.euroneuro.2016.05.001 , PMID 27216487 .
  18. ^ DE Nichols: Psychedelics. In: Pharmacological reviews. Volume 68, number 2, April 2016, pp. 264–355, doi: 10.1124 / pr.115.011478 , PMID 26841800 , PMC 4813425 (free full text) (review).
  19. ^ Neuropharmacology of Hallucinogens . Erowid.org. Feb 2004. Retrieved February 21, 2012.
  20. ^ PiHKAL # 96 mescaline
  21. Erowid: Mescaline Dosage
  22. ^ KD Charalampous, KE Walker, John Kinross-Wright: Metabolic fate of mescaline in man. In: Psychopharmacologia. 9, 1966, pp. 48-63, doi: 10.1007 / BF00427703 .
  23. ^ Robert Gable: Drug Toxicity . Retrieved February 17, 2011.
  24. ^ Gable, RS (2006): Acute toxicity of drugs versus regulatory status. In JM Fish (Ed.), Drugs and Society: US Public Policy, pp. 149-162, Lanham, MD: Rowman & Littlefield Publishers.
  25. ^ JH Halpern, HG Pope: Hallucinogen persisting perception disorder: what do we know after 50 years? In: Drug and alcohol dependence. Volume 69, Number 2, March 2003, pp. 109-119, PMID 12609692 (review).
  26. ^ Richard Bunce: Social and political sources of drug effects: The case of bad trips on psychedelics. ( Memento of October 20, 2002 in the Internet Archive ) In: E. Zinberg, WM Harding: Control Over Intoxicant Use: Pharmacological, Psychological, and Social Considerations. In: Human Sciences Press. 1982, pp. 105-125.
  27. "Severe agitation may respond to diazepam (20 mg orally). “Talking down” by reassurance is also effective and is the management of first choice. Antipsychotic medications may intensify the experience and thus are not indicated. "Laurence Brunton, Bruce A. Chabner, Bjorn Knollman: Goodman and Gilman's Manual of Pharmacology and Therapeutics , Twelfth edition, McGraw-Hill 2011, p. 1537, ISBN 978-0- 07-176939-6 .
  28. Teri S. Krebs, Pål-Ørjan Johansen, Lin Lu: Psychedelics and Mental Health: A Population Study. In: PLoS ONE. 8, 2013, p. E63972, doi: 10.1371 / journal.pone.0063972 .
  29. F. Sjöqvist: Psychotropic drugs (2): Interaction between monoamine oxidase (MAO) inhibitors and other substances. In: Proceedings of the Royal Society of Medicine. Volume 58, Number 11 Part 2, November 1965, pp. 967-978, PMID 4952963 , PMC 1898666 (free full text) (review).
  30. ^ MG Livingston, HM Livingston: Monoamine oxidase inhibitors: An update on drug interactions. In: Drug safety. Volume 14, Number 4, April 1996, pp. 219-227, PMID 8713690 (review).
  31. JP Finberg: Update on the pharmacology of selective inhibitors of MAO-A and MAO-B: focus on modulation of CNS monoamine neurotransmitter release. In: Pharmacology & therapeutics. Volume 143, number 2, August 2014, pp. 133-152, doi: 10.1016 / j.pharmthera.2014.02.010 , PMID 24607445 (review).
  32. ^ DI Brierley, C. Davidson: Developments in harmine pharmacology: implications for ayahuasca use and drug-dependence treatment. In: Progress in neuro-psychopharmacology & biological psychiatry. Volume 39, Number 2, December 2012, pp. 263-272, doi: 10.1016 / j.pnpbp.2012.06.001 , PMID 22691716 (review).
  33. RS Gable: Risk assessment of ritual use of oral dimethyltryptamine (DMT) and harmala alkaloids. In: Addiction. Volume 102, Number 1, January 2007, pp. 24-34, doi: 10.1111 / j.1360-0443.2006.01652.x , PMID 17207120 (review).
  34. 4th BtMGlV of February 21, 1967 .
  35. cf. Law on the traffic in narcotics