リゼルグ酸、リゼルギン酸

WordNet

street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
having the characteristics of an acid; "an acid reaction"

PrepTutorEJDIC

酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/02/13 09:30:48」(JST)

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Lysergic acid, also known as D-lysergic acid and (+)-lysergic acid, is a precursor for a wide range of ergoline alkaloids that are produced by the ergot fungus and found in the Hawaiian Baby Woodrose and the seeds of Morning glory. Amides of lysergic acid, lysergamides, are widely used as pharmaceuticals and as psychedelic drugs (LSD). Lysergic acid received its name as it was a product of the lysis of various ergot alkaloids.^[1]

Synthesis

Lysergic acid is generally produced by hydrolysis^[2] of natural lysergamides, but can also be synthesized in the laboratory by a complex total synthesis for example by Woodward's team in 1956.^[3] An enantioselective total synthesis based on a palladium catalyzed domino cyclization reaction has been described in 2011 by Fujii and Ohno.^[4] Lysergic acid monohydrate crystallizes in very thin hexagonal leaflets when recrystallized from water. Lysergic acid monohydrate, when dried (140 °C at 2 mmHg or 270 Pa) forms anhydrous lysergic acid. The biosynthetic route is based on the alkylation of the amino acid tryptophan with dimethylallyl diphosphate (isoprene derived from 3R-mevalonic acid) giving 4-dimethylallyl-L-tryptophan which is N-methylated with S-adenosyl-L-methionine. Oxidative ring closure followed by decarboxylation, reduction, cyclization, oxidation, and allylic isomerization yields D-(+)-lysergic acid.^[1]

Isomers

Lysergic acid is a chiral compound with two stereocenters. The isomer with inverted configuration at carbon atom 8 close to the carboxy group is called isolysergic acid. Inversion at carbon 5 close to the nitrogen atom leads to L-lysergic acid and L-isolysergic acid, respectively. Lysergic acid is listed as a Table I precursor under the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances.^[5]

Chemical structures of lysergic acid isomers

References

^ ^a ^b Schiff PL (2006 Oct 15). "Ergot and its alkaloids". Am J Pharm Educ. 70 (5): 98. PMID 17149427.
^ Martínková L, Kren V, Cvak L, Ovesná M, Prepechalová I (2001 Nov 17). "Hydrolysis of lysergamide to lysergic acid by Rhodococcus equi A4". J Biotechnol. 84 (1): 63–6.
^ Edmund C. Kornfeld, E.J. Fornefeld, G. Bruce Kline, Marjorie J. Mann, Dwight E. Morrison, Reuben G. Jones and R.B. Woodward (1956). "The Total Synthesis of Lysergic Acid". Journal of the American Chemical Society 78: 3087–3114.
^ S. Inuki, A. Iwata, S. Oishi, N. Fujii and H. Ohno, J. Org. Chem. 2011, 76 (7), pp 2072–2083, doi:10.1021/jo102388e.
^ List of Precursors and Chemicals Frequently Used in the Illicit Manufacture of Narcotic Drugs and Psychotropic Substances Under International Control, International Narcotics Control Board

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1. LSDおよび他の一般的な幻覚剤による中毒 intoxication from lsd and other common hallucinogens
2. 薬物乱用検査（DOA） testing for drugs of abuse doa
3. キノコ中毒の臨床症状および評価 clinical manifestations and evaluation of mushroom poisoning
4. 小児における急性発症性精神病の救急外来による評価 emergency department evaluation of acute onset psychosis in children
5. 合成カンナビノイド：急性中毒 synthetic cannabinoids acute intoxication

English Journal

Cyclolization of d-lysergic Acid alkaloid peptides.

Havemann J1, Vogel D1, Loll B2, Keller U3.Author information 1Institut für Chemie, Arbeitsgruppe Biochemie und Molekulare Biologie, Technische Universität Berlin, Müller-Breslau-Strasse 10, Berlin-Charlottenburg 10623, Germany.2Institut für Chemie und Biochemie, Abteilung Strukturbiochemie, Freie Universität Berlin, Takusstrasse 6, Berlin 14195, Germany.3Institut für Chemie, Arbeitsgruppe Biochemie und Molekulare Biologie, Technische Universität Berlin, Müller-Breslau-Strasse 10, Berlin-Charlottenburg 10623, Germany. Electronic address: ullrich.keller@tu-berlin.de.AbstractThe tripeptide chains of the ergopeptines, a class of pharmacologically important D-lysergic acid alkaloid peptides, are arranged in a unique bicyclic cyclol based on an amino-terminal α-hydroxyamino acid and a terminal orthostructure. D-lysergyl-tripeptides are assembled by the nonribosomal peptide synthetases LPS1 and LPS2 of the ergot fungus Claviceps purpurea and released as N-(D-lysergyl-aminoacyl)-lactams. We show total enzymatic synthesis of ergopeptines catalyzed by a Fe(2+)/2-ketoglutarate-dependent dioxygenase (EasH) in conjunction with LPS1/LPS2. Analysis of the reaction indicated that EasH introduces a hydroxyl group into N-(D-lysergyl-aminoacyl)-lactam at α-C of the aminoacyl residue followed by spontaneous condensation with the terminal lactam carbonyl group. Sequence analysis revealed that EasH belongs to the wide and diverse family of the phytanoyl coenzyme A hydroxylases. We provide a high-resolution crystal structure of EasH that is most similar to that of phytanoyl coenzyme A hydroxylase, PhyH, from human.
Chemistry & biology.Chem Biol.2014 Jan 16;21(1):146-55. doi: 10.1016/j.chembiol.2013.11.008. Epub 2013 Dec 19.
The tripeptide chains of the ergopeptines, a class of pharmacologically important D-lysergic acid alkaloid peptides, are arranged in a unique bicyclic cyclol based on an amino-terminal α-hydroxyamino acid and a terminal orthostructure. D-lysergyl-tripeptides are assembled by the nonribosomal pepti
PMID 24361048

Hallucinogenic 5-HT2AR agonists LSD and DOI enhance dopamine D2R protomer recognition and signaling of D2-5-HT2A heteroreceptor complexes.

Borroto-Escuela DO1, Romero-Fernandez W2, Narvaez M3, Oflijan J4, Agnati LF5, Fuxe K6.Author information 1Department of Neuroscience, Karolinska Institutet, Stockholm, Sweden. Electronic address: Dasiel.Borroto-Escuela@ki.se.2Department of Neuroscience, Karolinska Institutet, Stockholm, Sweden. Electronic address: wromfdez@gmail.com.3Department of Physiology, School of Medicine, University of Málaga, Spain. Electronic address: mnarvaez@uma.es.4Department of Physiology, Faculty of Medicine, University of Tartu, Estonia. Electronic address: juliaofli@gmail.com.5IRCCS Lido, Venice, Italy. Electronic address: luigiagnati@tin.it.6Department of Neuroscience, Karolinska Institutet, Stockholm, Sweden. Electronic address: Kjell.Fuxe@ki.se.AbstractDopamine D2LR-serotonin 5-HT2AR heteromers were demonstrated in HEK293 cells after cotransfection of the two receptors and shown to have bidirectional receptor-receptor interactions. In the current study the existence of D2L-5-HT2A heteroreceptor complexes was demonstrated also in discrete regions of the ventral and dorsal striatum with in situ proximity ligation assays (PLA). The hallucinogenic 5-HT2AR agonists LSD and DOI but not the standard 5-HT2AR agonist TCB2 and 5-HT significantly increased the density of D2like antagonist (3)H-raclopride binding sites and significantly reduced the pKiH values of the high affinity D2R agonist binding sites in (3)H-raclopride/DA competition experiments. Similar results were obtained in HEK293 cells and in ventral striatum. The effects of the hallucinogenic 5-HT2AR agonists on D2R density and affinity were blocked by the 5-HT2A antagonist ketanserin. In a forskolin-induced CRE-luciferase reporter gene assay using cotransfected but not D2R singly transfected HEK293 cells DOI and LSD but not TCB2 significantly enhanced the D2LR agonist quinpirole induced inhibition of CRE-luciferase activity. Haloperidol blocked the effects of both quinpirole alone and the enhancing actions of DOI and LSD while ketanserin only blocked the enhancing actions of DOI and LSD. The mechanism for the allosteric enhancement of the D2R protomer recognition and signalling observed is likely mediated by a biased agonist action of the hallucinogenic 5-HT2AR agonists at the orthosteric site of the 5-HT2AR protomer. This mechanism may contribute to the psychotic actions of LSD and DOI and the D2-5-HT2A heteroreceptor complex may thus be a target for the psychotic actions of hallunicogenic 5-HT2A agonists.
Biochemical and biophysical research communications.Biochem Biophys Res Commun.2014 Jan 3;443(1):278-84. doi: 10.1016/j.bbrc.2013.11.104. Epub 2013 Dec 2.
Dopamine D2LR-serotonin 5-HT2AR heteromers were demonstrated in HEK293 cells after cotransfection of the two receptors and shown to have bidirectional receptor-receptor interactions. In the current study the existence of D2L-5-HT2A heteroreceptor complexes was demonstrated also in discrete regions o
PMID 24309097

The effects of benzofury (5-APB) on the dopamine transporter and 5-HT2-dependent vasoconstriction in the rat.

Dawson P, Opacka-Juffry J, Moffatt JD, Daniju Y, Dutta N, Ramsey J, Davidson C.Author information Pharmacology and Cell Physiology, Division of Biomedical Science, St George's University of London, London SW17 0RE, United Kingdom.Abstract5-APB, commonly marketed as 'benzofury' is a new psychoactive substance and erstwhile 'legal high' which has been implicated in 10 recent drug-related deaths in the UK. This drug was available on the internet and in 'head shops' and was one of the most commonly sold legal highs up until its recent UK temporary ban (UK Home Office). Despite its prominence, very little is known about its pharmacology. This study was undertaken to examine the pharmacology of 5-APB in vitro. We hypothesised that 5-APB would activate the dopamine and 5-HT systems which may underlie its putative stimulant and hallucinogenic effects. Autoradiographic studies showed that 5-APB displaced both [(125)I] RTI-121 and [(3)H] ketanserin from rat brain tissue suggesting affinity at the dopamine transporter and 5-HT2 receptor sites respectively. Voltammetric studies in rat accumbens brain slices revealed that 5-APB slowed dopamine reuptake, and at high concentrations caused reverse transport of dopamine. 5-APB also caused vasoconstriction of rat aorta, an effect antagonised by the 5-HT2A receptor antagonist ketanserin, and caused contraction of rat stomach fundus, which was reversed by the 5-HT2B receptor antagonist RS-127445. These data show that 5-APB interacts with the dopamine transporter and is an agonist at the 5-HT2A and 5-HT2B receptors in the rat. Thus 5-APB's pharmacology is consistent with it having both stimulant and hallucinogenic properties. In addition, 5-APB's activity at the 5-HT2B receptor may cause cardiotoxicity.
Progress in neuro-psychopharmacology & biological psychiatry.Prog Neuropsychopharmacol Biol Psychiatry.2014 Jan 3;48:57-63. doi: 10.1016/j.pnpbp.2013.08.013. Epub 2013 Sep 5.
5-APB, commonly marketed as 'benzofury' is a new psychoactive substance and erstwhile 'legal high' which has been implicated in 10 recent drug-related deaths in the UK. This drug was available on the internet and in 'head shops' and was one of the most commonly sold legal highs up until its recent U
PMID 24012617

Japanese Journal

The Synthesis of Alkaloids Using Transition-Metal-Catalyzed Intramolecular Amination Reactions

Ohno Hiroaki,Chiba Hiroaki,Inuki Shinsuke,Oishi Shinya,Fujii Nobutaka
Synlett 25(02), 179-192, 2014-01-13
… In this account, we report our recent studies on the use of a palladium-catalyzed cascade cyclization reaction and a gold(I)-catalyzed hydroamination reaction for the construction of the core structures of alkaloids, as well as their application to the total syntheses of lysergic acid, lysergol, isolysergol, and quinocarcin. …
NAID 120005587794

Discriminative Stimulus Effects of Hallucinogenic Drugs : a Possible Relation to Reinforcing and Aversive Effects

Mori Tomohisa,Yoshizawa Kazumi,Shibasaki Masahiro [他],SUZUKI Tsutomu
Journal of pharmacological sciences 120(2), 70-76, 2012-10-20
… Over the past two decades, the patterns of drug abuse have changed, so that club/recreational drugs such as phencyclidine (PCP), 3,4-methylenedioxymethamphetamine (MDMA), lysergic acid diethylamide (LSD), and ketamine, which induce perceptual distortions, like hallucinations, are now more commonly abused, especially in younger generations. …
NAID 10031123548

幻覚剤 (特集薬物依存症--薬物依存症のトレンド) -- (薬物依存症の臨床各論--最新動向)

森田展彰,嶋根卓也
日本臨床 68(8), 1486-1493, 2010-08
NAID 40017192455

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★リンクテーブル★

リンク元	「リゼルグ酸」「リゼルギン酸」
拡張検索	「lysergic acid diethylamide」

「リゼルグ酸」

Lysergic acid
	IUPAC name 7-Methyl- 4,6,6a,7,8,9- hexahydro- indolo [4,3-fg] quinoline- 9-carboxylic acid
	Other names 6-Methyl- 9,10- didehydroergoline- 8-carboxylic acid
Identifiers
CAS number	82-58-6 , ; [478-95-5],; [6915-32-8],; [23953-76-6],; [68985-97-7],; [68985-98-8]
ChemSpider	6461
ChEBI	CHEBI:6604
Jmol-3D images	Image 1
	SMILES O=C(O)[C@@H]3/C=C2/c4cccc1c4c(cn1)C[C@H]2N(C3)C ;
	InChI InChI=1S/C16H16N2O2/c1-18-8-10(16(19)20)5-12-11-3-2-4-13-15(11)9(7-17-13)6-14(12)18/h2-5,7,10,14,17H,6,8H2,1H3,(H,19,20)/t10-,14-/m1/s1 ; Key: ZAGRKAFMISFKIO-QMTHXVAHSA-N InChI=1/C16H16N2O2/c1-18-8-10(16(19)20)5-12-11-3-2-4-13-15(11)9(7-17-13)6-14(12)18/h2-5,7,10,14,17H,6,8H2,1H3,(H,19,20)/t10-,14-/m1/s1; Key: ZAGRKAFMISFKIO-QMTHXVAHBD ;
Properties
Molecular formula	C16H16N2O2
Molar mass	268.31 g mol−1
Melting point	238 - 240 °C
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references