Alkaloids are a group of naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.

Alkaloids are produced by a large variety of organisms, including bacteria, fungi, plants, and animals, and are part of the group of natural products (also called secondary metabolites). Many alkaloids can be purified from crude extracts by acid-base extraction. Many alkaloids are toxic to other organisms. They often have pharmacological effects and are used as medications, as recreational drugs, or in entheogenic rituals. Examples are the local anesthetic and stimulant cocaine; the psychedelic psilocin; the stimulant caffeine; nicotine; the analgesic morphine; the antibacterial berberine; the anticancer compound vincristine; the antihypertension agent reserpine; the cholinomimeric galatamine; the spasmolysis agent atropine; the vasodilator vincamine; the anti-arhythmia compound quinidine; the anti-asthma therapeutic ephedrine; and the antimalarial drug quinine. Although alkaloids act on a diversity of metabolic systems in humans and other animals, they almost uniformly invoke a bitter taste.

The boundary between alkaloids and other nitrogen-containing natural compounds is not clear-cut. Compounds like amino acid peptides, proteins, nucleotides, nucleic acid, amines, and antibiotics are usually not called alkaloids. Natural compounds containing nitrogen in the exocyclic position (mescaline, serotonin, dopamine, etc.) are usually attributed to amines rather than alkaloids. Some authors, however, consider alkaloids a special case of amines.

Naming[link]

The name "alkaloids" () was introduced in 1819 by the German chemist Carl F.W. Meissner, and is derived from late Latin root '''' (which, in turn, comes from the Arabic ''al-qalwī'' - "ashes of plants") and the suffix '''' - "like". However, the term came into wide use only after the publication of a review article by O. Jacobsen in the chemical dictionary of Albert Ladenburg in the 1880s.

There is no unique method of naming alkaloids. Many individual names are formed by adding the suffix "ine" to the species or genus name. For example, atropine is isolated from the plant Atropa belladonna, strychnine is obtained from the seed of Strychnine tree (''Strychnos nux-vomica'' L.).

History [link]

Alkaloid-containing plants were used by humans since ancient times for therapeutic and recreational purposes. For example, medicinal plants have been known in the Mesopotamia at least around 2000 BC. The ''Odyssey'' of Homer referred to a gift given to Helen by the Egyptian queen, a drug bringing oblivion. It is believed that the gift was an opium-containing drug. A Chinese book on houseplants written in 1st-3rd centuries BC mentioned a medical use of Ephedra and opium poppies. Also, coca leaves were used by South American Indians since ancient times.

Extracts from plants containing toxic alkaloids, such as aconitine and tubocurarine, were used since antiquity for poisoning arrows.

Studies of alkaloids began in the 19th century. In 1804, the German chemist Friedrich Sertürner isolated from opium a "soporific principle" (), which he called "morphium" in honor of Morpheus, the Greek god of dreams; in German and some other Central-European languages, this is still the name of the drug. The term "morphine", used in English and French, was given by the French physicist Joseph Louis Gay-Lussac).

A significant contribution to the chemistry of alkaloids in the early years of its development was made by the French researchers Pierre Joseph Pelletier and Joseph Bienaimé Caventou, who discovered quinine (1820) and strychnine (1818). Several other alkaloids were discovered around that time, including xanthine (1817), atropine (1819), caffeine (1820), coniine (1827), nicotine (1828), colchicine (1833), sparteine (1851), and cocaine (1860).

The first complete synthesis of an alkaloid was achieved in 1886 by the German chemist Albert Ladenburg. He produced coniine by reacting 2-methylpyridine with acetaldehyde and reducing the resulting 2-propenyl pyridine with sodium. The development of the chemistry of alkaloids was accelerated by the emergence of spectroscopic and chromatographic methods in the 20th century, so that by 2008 more than 12,000 alkaloids had been identified.

Classification [link]

Compared with most other classes of natural compounds, alkaloids are characterized by a great structural diversity and there is no uniform classification of alkaloids. First classification methods have historically combined alkaloids by the common natural source, e.g., a certain type of plants. This classification was justified by the lack of knowledge about the chemical structure of alkaloids and is now considered obsolete.

More recent classifications are based on similarity of the carbon skeleton (e.g., indole-, isoquinoline-, and pyridine-like) or biogenetic precursor (ornithine, lysine, tyrosine, tryptophan, etc.). and therefore can be assigned to both classes.

Alkaloids are often divided into the following major groups:

# "True alkaloids", which contain nitrogen in the heterocycle and originate from amino acids. Their characteristic examples are atropine, nicotine, and morphine. This group also includes some alkaloids that besides nitrogen heterocycle contain terpene (e.g., evonine) or peptide fragments (e.g. ergotamine). This group also includes piperidine alkaloids coniine and coniceine although they do not originate from amino acids. # "Protoalkaloids", which contain nitrogen and also originate from amino acids. Examples include mescaline, adrenaline and ephedrine. # Polyamine alkaloids – derivatives of putrescine, spermidine, and spermine. # Peptide and cyclopeptide alkaloids. #Pseudalkaloids – alkaloid-like compounds that do not originate from amino acids. This group includes, terpene-like and steroid-like alkaloids, as well as purine-like alkaloids such as caffeine, theobromine and theophylline. Some authors classify as pseudoalkaloids such compounds such as ephedrine and cathinone. Those originate from the amino acid phenylalanine, but acquire their nitrogen atom not from the amino acid but through transamination.

Some alkaloids do not have the carbon skeleton characteristic of their group. So, galantamine and homoaporphines do not contain isoquinoline fragment, but are, in general, attributed to isoquinoline alkaloids.

Main classes of monomeric alkaloids are listed in the table below: {| Class = "wikitable" |- ! Class !Major groups !Main synthesis steps !Examples |- | Colspan = "4" align = "center" bgcolor = "# DADADA" |''Alkaloids with nitrogen heterocycles (true alkaloids)'' |- | Pyrrolidine derivatives | | Ornithine or arginine → putrescine → N-methylputrescine → N-methyl-Δ¹-pyrroline | Cuscohygrine, hygrine, hygroline, stachydrine |- | Rowspan = "2"|Tropane derivatives | Atropine groupSubstitution in positions 3, 6 or 7 | Rowspan = "2"|Ornithine or arginine → putrescine → N-methylputrescine → N-methyl-Δ¹-pyrroline | Atropine, scopolamine, hyoscyamine |- | Cocaine group Substitution in positions 2 and 3 | Cocaine, ecgonine |- | Rowspan = "4"|Pyrrolizidine derivatives | Non-esters | Rowspan = "3"|In plants: ornithine or arginine → putrescine → homospermidine → retronecine | Retronecine, heliotridine, laburnine |- | Complex esters of monocarboxylic acids | Indicine, lindelophin, sarracine |- | Macrocyclic diesters | Platyphylline, trichodesmine |- | 1-aminopyrrolizidines (lolines) | In fungi: L-proline + L-homoserine → ''N''-(3-amino-3-carboxypropyl)proline → norloline |Loline, ''N''-formylloline, ''N''-acetylloline |- | Rowspan = "2"|Piperidine derivatives | | Lysine → cadaverine → Δ¹-piperideine | Sedamine, lobeline, anaferine, piperine |- | | Octanoic acid → coniceine → coniine | Coniine, coniceine |- | Rowspan = "5"|Quinolizidine derivatives | Lupinine group | Rowspan = "5"|Lysine → cadaverine → Δ¹-piperideine | Lupinine, nupharidin |- | Cytisine group | Cytisine |- | Sparteine group | Sparteine, lupanine, anahygrine |- | Matrine group | Matrine, oxymatrine, allomatridine |- | Ormosanine group | Ormosanine, piptantine |- | Indolizidine derivatives | | Lysine → δ-semialdehyde of α-aminoadipic acid → pipecolic acid → 1 indolizidinone | Swainsonine, castanospermine |- | Rowspan = "4"|Pyridine derivatives | Simple derivatives of pyridine | Rowspan = "3"|Nicotinic acid → dihydronicotinic acid → 1,2-dihydropyridine | Trigonelline, ricinine, arecoline |- | Polycyclic noncondensing pyridine derivatives | Nicotine, nornicotine, anabasine, anatabine |- | Polycyclic condensed pyridine derivatives | Actinidine, gentianine, pediculinine |- | Sesquiterpene pyridine derivatives | Nicotinic acid, isoleucine | Evonine, hippocrateine, triptonine |- | Rowspan = "26"|Isoquinoline derivatives and related alkaloids | Simple derivatives of isoquinoline | Rowspan = "26"|Tyrosine or phenylalanine → dopamine or tyramine (for alkaloids Amarillis) | Salsoline, lophocerine | N-methylcoridaldine, noroxyhydrastinine |- | Derivatives of 1- and 4-phenyltetrahydroisoquinolines |- | Derivatives of 5-naftil-isoquinoline | Ancistrocladine |- | Derivatives of 1- and 2-benzyl-izoquinolines | Papaverine, laudanosine, sendaverine |- | Cularine group | Cularine, yagonine |- | Pavines and isopavines | Argemonine, amurensin |- | Benzopyrrocolines | Cryptaustoline |- | Phthalidisoquinolines |- | Spirobenzylisoquinolines | Emetine, protoemetine, ipecoside |- | Benzophenanthridines |- | Aporphines |- | Proaporphines | Kreysiginine, multifloramine |- | Homoproaporphines | Bulbocodine |- | Morphines | Morphine, codeine, thebaine, sinomenine |- | Homomorphines | Kreysiginine, androcymbine |- | Tropoloisoquinolines |- | Amaryllis alkaloids | Lycorine, ambelline, tazettine, galantamine, montanine |- | Erythrite alkaloids | Erysodine, erythroidine |- | Phenanthrene derivatives | | Tyrosine → tyramine | Annuloline, halfordinol, texaline, texamine |- | Isoxazole derivatives | |Ibotenic acid → Muscimol |Ibotenic acid, Muscimol |- | Thiazole derivatives | | 1-Deoxy-D-xylulose 5-phosphate (DOXP), tyrosine, cysteine | Nostocyclamide, thiostreptone |- | Rowspan = "3"|Quinazoline derivatives | 3,4-Dihydro-4-quinazolone derivatives | Rowspan = "3"|Anthranilic acid or phenylalanine or ornithine | Febrifugine |- | 1,4-Dihydro-4-quinazolone derivatives | Glycorine, arborine, glycosminine |- | Pyrrolidine and piperidine quinazoline derivatives | Vazicine (peganine) |- | Acridine derivatives | | Anthranilic acid | Rutacridone, acronicine |- | Rowspan = "4"|Quinoline derivatives | Simple derivatives of quinoline derivatives of 2 - quinolones and 4-quinolone | Rowspan = "3"|Anthranilic acid → 3-carboxyquinoline | Cusparine, echinopsine, evocarpine |- | Tricyclic terpenoids | Flindersine |- | Furanoquinoline derivatives | Dictamnine, fagarine, skimmianine |- | Quinines | Tryptophan → tryptamine → strictosidine (with secologanin) → korinanteal → cinhoninon | Quinine quinidine cinchonine, cinhonidine |- | Rowspan = "10"|Indole derivatives | Colspan = "3" align = "center" |''Non-isoprene indole alkaloids'' |- | Simple indole derivatives | Rowspan = "3"|Tryptophan → tryptamine or 5-hydroxitriptofan | Serotonin, psilocybin, dimethyltryptamine (DMT), bufotenin |- | Simple derivatives of β-carboline | Harman, harmine, harmaline, eleagnine |- | Pyrroloindole alkaloids | Physostigmine (eserine), etheramine, physovenine, eptastigmine |- | Colspan = "3" align = "center" |''Semiterpenoid indole alkaloids'' |- | Ergot alkaloids | Tryptophan → chanoclavine → agroclavine → elimoclavine → paspalic acid → lysergic acid | Ergotamine, ergobasine, ergosine |- | Colspan = "3" align = "center" |''Monoterpenoid indole alkaloids'' |- | ''Corynanthe'' type alkaloids | Rowspan = "3"|Tryptophan → tryptamine → strictosidine (with secologanin) | Ajmalicine, sarpagine, vobasine, ajmaline, yohimbine, reserpine, mitragynine, group strychnine and (Strychnine brucine, aquamicine, vomicine ) |- | Iboga-type alkaloids | Ibogamine, ibogaine, voacangine |- | Aspidosperma-type alkaloids | Vincamine, vincotine, aspidospermine |- | Imidazole derivatives | | Directly from histidine | Histamine, pilocarpine, pilosine, stevensine |- | Purine derivatives | | Xanthosine (formed in purine biosynthesis) → 7 methylxantosine → 7-methyl xanthine → theobromine → caffeine | Caffeine theobromine theophylline saxitoxin |- | Colspan = "4" align = "center" bgcolor = "# DADADA" |''Alkaloids with nitrogen in the side chain (protoalkaloids)'' |- | β-Phenylethylamine derivatives | | Tyrosine or phenylalanine → dioxyphenilalanine → dopamine → adrenaline and mescaline tyrosine → tyramine phenylalanine → 1-phenylpropane-1,2-dione → cathinone → ephedrine and pseudoephedrine | Tyramine, ephedrine, pseudoephedrine, mescaline, cathinone, catecholamines (adrenaline, noradrenaline, dopamine) |- | Colchicine alkaloids | | Tyrosine or phenylalanine → dopamine → autumnaline → colchicine | Colchicine, colchamine |- | Muscarine | | Glutamic acid → 3-ketoglutamic acid → muscarine (with pyruvic acid) | Muscarine, allomuscarine, epimuscarine, epiallomuscarine |- | Benzylamine | | Phenylalanine with valine, leucine or isoleucine | Capsaicin, dihydrocapsaicin, nordihydrocapsaicin |- | Colspan = "4" align = "center" bgcolor = "# DADADA" |''Polyamines alkaloids'' |- | Putrescine derivatives | | Rowspan = "3"|ornithine → putrescine → spermidine → spermine | Paucine |- | Spermidine derivatives | | Lunarine, codonocarpine |- | Spermine derivatives | | Verbascenine, aphelandrine |- | Colspan = "4" align = "center" bgcolor = "# DADADA" |''Peptide (cyclopeptide) alkaloids'' |- | Rowspan = "2"|Peptide alkaloids with a 13-membered cycle | Numularine C type | Rowspan = "8"|From different amino acids | Numularine C, numularine S |- | Ziziphin type | Ziziphin A, sativanine H |- | Rowspan = "5"|Peptide alkaloids with a 14-membered cycle | Frangulanine type | Frangulanine, scutianine J |- | Scutianine A type | Scutianine A |- | Integerrine type | Integerrine, discarine D |- | Amphibine F type | Amphibine F, spinanine A |- | Amfibine B type | Amphibine B, lotusine C |- | Peptide alkaloids with a 15-membered cycle | Mucronine A type | Mucronine A |- | Colspan = "4" align = "center" bgcolor = "# DADADA" |''Pseudoalkaloids (terpenes and steroids)'' |- | Diterpenes | Licoctonine type | Mevalonic acid → izopentenilpyrophosfate → geranyl pyrophosphate | Aconitine, delphinine |- | Steroids | | Cholesterol, arginine | Solasodine, solanidine, veralkamine |}

Properties [link]

Most alkaloids contain oxygen; those compounds are usually colorless crystals at ambient conditions. Oxygen-free alkaloids, such as nicotine or coniine, Some alkaloids are colored, like berberine (yellow) and sanguinarine (orange).

Most alkaloids are weak bases, but some are amphoteric, for example theobromine and theophylline. Most alkaloids are poorly soluble in water but readily dissolve in organic solvents, such as diethyl ether, chloroform and 1,2-dichloroethane. However, caffeine dissolves well in boiling water. With acids, alkaloids form salts of various strengths. Those salts are usually soluble in water and alcohol and poorly soluble in most organic solvents. Exceptions include scopolamine hydrobromide, which is soluble in organic solvents and water-soluble quinine sulfate.

Most alkaloids have a bitter taste. It is believed that plants evolved the ability to produce these bitter substances, many of which are poisonous, in order to protect themselves from animals; however, animals in turn evolved the ability to detoxify alkaloids. Some alkaloids can produce developmental defects in the offspring of animals that consume them but cannot detoxify them. A characteristic example is the alkaloid cyclopamine, which is present in the leaves of corn lily. During the 1950s, up to 25% lambs born by sheep that had grazed on corn lily suffered serious facial defects. Those defects ranged from deformed jaws to cyclopia (see picture). After decades of research, in 1980s, the substance that was responsible for the deformities was identified as the alkaloid 11-deoxyjervine, which was renamed cyclopamine.

Distribution in nature[link]

Alkaloids are generated by various living organisms, especially by higher plants – about 10 to 25% of those contain alkaloids. Therefore, in the past the term "alkaloid" was associated with plants.

The alkaloids content in plants is usually within a few percent and is inhomogeneous over the plant tissues. Depending on the type of plants, the maximum concentration is observed in the leaves (black henbane), fruits or seeds (Strychnine tree), root (Rauwolfia serpentina) or bark (cinchona). Furthermore, different tissues of the same plants may contain different alkaloids.

Beside plants, alkaloids are found in certain types of fungi, such as psilocybin in the fungus of the genus Psilocybe, and in animals, such as bufotenin in the skin of some toads. Many marine organisms also contain alkaloids. Some amines, such as adrenaline and serotonin, which play an important role in higher animals, are similar to alkaloids in their structure and biosynthesis and are sometimes called alkaloids.

Extraction[link]

Because of the structural diversity of alkaloids, there is no single method of their extraction from natural raw materials. Most methods exploit the property of most alkaloids to be soluble in organic solvents but not in water, and the opposite tendency of their salts.

Most plants contain several alkaloids. Their mixture is extracted first and then individual alkaloids are separated. Plants are thoroughly ground before extraction. Most alkaloids are present in the raw plants in the form of salts of organic acids. The extracted alkaloids may remain salts or change into bases. Base extraction is achieved by processing the raw material with alkaline solutions and extracting the alkaloid bases with organic solvents, such as 1,2-dichloroethane, chloroform, diethyl ether or benzene. Then, the impurities are dissolved by weak acids; this converts alkaloid bases into salts that are washed away with water. If necessary, an aqueous solution of alkaloid salts is again made alkaline and treated with an organic solvent. The process is repeated until the desired purity is achieved.

In the acidic extraction, the raw plant material is processed by a weak acidic solution (e.g., acetic acid in water, ethanol, or methanol). A base is then added to convert alkaloids to basic forms that are extracted with organic solvent (if the extraction was performed with alcohol, it is removed first, and the remainder is dissolved in water). The solution is purified as described above.

Alkaloids are separated from their mixture using their different solubility in certain solvents and different reactivity with certain reagents or by distillation.

Biosynthesis[link]

Biological precursors of most alkaloids are amino acids, such as ornithine, lysine, phenylalanine, tyrosine, tryptophan, histidine, aspartic acid, and anthranilic acid. Nicotinic acid can be synthesized from tryptophan or aspartic acid. Ways of alkaloid biosynthesis are too numerous and cannot be easily classified. However, there are a few typical reactions involved in the biosynthesis of various classes of alkaloids, including synthesis of Schiff bases and Mannich reaction.

Synthesis of Schiff bases[link]

Schiff bases can be obtained by reacting amines with ketones or aldehydes. These reactions are a common method of producing C=N bonds.

In the biosynthesis of alkaloids, such reactions may take place within a molecule, such as in the synthesis of piperidine:

Mannich reaction[link]

An integral component of the Mannich reaction, in addition to an amine and a carbonyl compound, is a carbanion, which plays the role of the nucleophile in the nucleophilic addition to the ion formed by the reaction of the amine and the carbonyl.

The Mannich reaction can proceed both intermolecularly and intramolecularly:

Dimer alkaloids[link]

In addition to the described above monomeric alkaloids, there are also dimeric, and even trimeric and tetrameric alkaloids formed upon condensation of two, three, and four monomeric alkaloids. Dimeric alkaloids are usually formed from monomers of the same type through the following mechanisms:

Mannich reaction, resulting in, e.g., voacamine

Michael reaction (villalstonine)

Condensation of aldehydes with amines (toxiferine)

Oxidative addition of phenols (dauricine, tubocurarine)

Lactonization (carpaine).

The biological role[link]

The role of alkaloids for living organisms that produce them is still unclear. It was initially assumed that the alkaloids are the final products of nitrogen metabolism in plants, as urea in mammals. It was later shown that alkaloid concentrations varies over time, and this hypothesis was refuted.

Most of the known functions of alkaloids are related to protection. For example, aporphine alkaloid liriodenine produced by the tulip tree protects it from parasitic mushrooms. In addition, presence of alkaloids in the plant prevents insects and chordate animals from eating it. However, some animals adapted to alkaloids and even use them in their own metabolism. Such alkaloid-related substances as serotonin, dopamine and histamine are important neurotransmitters in animals. Alkaloids are also known to regulate plant growth.

Applications [link]

In medicine[link]

Medical use of alkaloid plants has a long history, and, thus, when the first alkaloids were synthesized in the 19th century, they immediately found application in clinical practice. Many alkaloids are still used in medicine, usually in the form of salts, including the following::

{| Class = "wikitable" ! Alkaloid ! Action |- | Ajmaline | antiarrhythmic |- | Atropine, scopolamine, hyoscyamine | anticholinergic |- | Vinblastine, vincristine | antitumor |- | Vincamine | vasodilating, antihypertensive |- | Codeine | cough medicine |- | Cocaine | anesthetic |- | Colchicine | remedy for gout |- | Morphine | analgesic |- | Reserpine | antihypertensive |- | Tubocurarine | Muscle relaxant |- | Physostigmine | inhibitor of acetylcholinesterase |- | Quinidine | antiarrhythmic |- | Quinine | antipyretics, antimalarial |- | Emetine | antiprotozoal agent |- | Ergot alkaloids | sympathomimetic, vasodilator, antihypertensive |}

Many synthetic and semisynthetic drugs are structural modifications of the alkaloids, which were designed to enhance or change the primary effect of the drug and reduce unwanted side-effects. For example, naloxone, an opioid receptor antagonist, is a derivative of thebaine that is present in opium.

In agriculture [link]

Prior to the development of a wide range of relatively low-toxic synthetic pesticides, some alkaloids, such as salts of nicotine and anabasine, were used as insecticides. Their use was limited by their high toxicity to humans.

Use as psychoactive drugs [link]

Preparations of plants containing alkaloids and their extracts, and later pure alkaloids, have long been used as psychoactive substances. Cocaine and cathinone are stimulants of the central nervous system. Mescaline and many of indole alkaloids (such as psilocybin, dimethyltryptamine and ibogaine) have hallucinogenic effect. Morphine and codeine are strong narcotic pain killers.

There are alkaloids that do not have strong psychoactive effect themselves, but are precursors for semi-synthetic psychoactive drugs. For example, ephedrine and pseudoephedrine are used to produce methcathinone and methamphetamine.

See also [link]

Amine

Base (chemistry)

Natural products

Secondary metabolite

Notes [link]

References [link]

Bibliography [link]

N. B. Veselovskaya, AE Kovalenko ''Drugs'', M.: Triada-X, 2000

*

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Dennis Jon McKenna (born December 17, 1950) is an American ethnopharmacologist, author and brother to well-known psychedelics proponent Terence McKenna.

Profile[link]

McKenna's research led to the development of natural products for Aveda Corporation as well as greater awareness of natural products and medicines. He has authored numerous scientific articles and books. He co-authored ''The Invisible Landscape'' with his brother Terence and ''Botanical Medicines: the Desk Reference for Major Herbal Supplements'' with Kenneth Jones and Kerry Hughes. McKenna spent a number of years as a senior lecturer for the Center for Spirituality and Healing, part of the Academic Health Center at the University of Minnesota, Twin Cities. He is now a senior research scientist for the Natural Health Products Research Group at the British Columbia Institute of Technology in the Vancouver area.

McKenna received his Master's degree in botany at the University of Hawaii in 1979. He received his Doctorate in Botanical Sciences in 1984 from the University of British Columbia, where he wrote a dissertation entitled ''Monoamine oxidase inhibitors in Amazonian hallucinogenic plants: ethnobotanical, phytochemical, and pharmacological investigations''. His research has included the pharmacology, botany, and chemistry of ayahuasca and oo-koo-hé, the subjects of his master's thesis. He has also conducted extensive fieldwork in the Peruvian, Colombian, and Brazilian Amazon.

He is currently working on a memoir entitled ''The Brotherhood of the Screaming Abyss'' about his and his brother Terence's journeys together.

See also[link]

Christian Rätsch

Christophe Wiart

External links [link]

Heffter Research Institute, biography and publications

Erowid's Dennis McKenna Vault

She Who Remembers Audio Archives of Terrence and Dennis McKenna interviews (MP3s).

Biography page for the Center for Spirituality and Healing

2009 - ''Cognition Factor'' (2009)

References [link]

http://magia.co/archivo/item/581-dmt-la-molécula-espiritual/581-dmt-la-molécula-espiritual.html

Category:1950 births Category:Living people Category:Psychedelic researchers Category:Psychedelic drug advocates

name	Maaya Sakamoto
background	solo_singer
birth date	March 31, 1980
origin	Itabashi, Tokyo, Japan
instrument	Vocals, guitar
genre	Pop
occupation	Singer, lyricist, actress, voice actress
years active	1995–present
label	Victor Entertainment, Flying Dog
associated acts	Yoko Kanno, Shōko Suzuki, Yūho Iwasato
spouse	Kenichi Suzumura (2011-present)
website
notable instruments	}}

}} is a Japanese singer-songwriter, actress, and voice actress. She made her debut as a voice actress in 1992 as the voice of Chifuru in the anime series ''Little Twins'', but is more well known for her role as Hitomi Kanzaki in the hit anime series ''The Vision of Escaflowne''. She released her debut single ''Yakusoku wa Iranai'', in collaboration with Yoko Kanno under Victor Entertainment on April 24, 1996.

Since her 1996 debut, she is among the more popular voice actresses who have also branched into singing, performing songs in both English and Japanese. As well as being a prolific seiyū, she has also had several successful releases; despite initially only modestly selling, her singles ''Tune the Rainbow'', ''Loop'', ''Ame ga Furu'', and ''Triangler'' have all reached the top 10 Oricon singles chart: ''Triangler'' in particular charted at #3 and remained charting for 26 weeks. Her albums have had similar success, with ''Shōnen Alice'' and ''Yūnagi Loop'' both reaching the top 10 Oricon albums chart; and her newest album, ''You Can't Catch Me'', released on January 12, 2011, became her first release to ever reach #1. She held a concert at the Nippon Budokan on March 31, 2010, her thirtieth birthday.

On August 8, 2011, Sakamoto married fellow voice actor and frequent co-star Kenichi Suzumura. She announced their marriage on her official site five days later.

Early life[link]

Born in Tokyo, Sakamoto grew up within a family of her parents and her older brother, who sustained a serious motorcycle accident in 1999 or 2000 (he married in 2002 and had a daughter in 2004). Sakamoto graduated from Toyo University with a Bachelor's degree in Sociology in the spring of 2002. Her favorite colors are blue and gold, while her hobbies are performing, reading, and singing. She was one half of the seiyū duo ''Whoops!!'', alongside Chieko Higuchi. She has been called , a respectful way of saying "older sister" by her ''Ouran High School Host Club'' co-star Ayaka Saitō.

Collaborations [link]

Sakamoto first teamed up with composer Yoko Kanno in her 1996 debut single, "''Yakusoku wa Iranai''" ("Promises Not Needed"), which was used as the opening theme for the anime series ''The Vision of Escaflowne''. Kanno collaborated with Sakamoto up until her fifth album, ''Yūnagi Loop'', which has no songs composed by Kanno. Sakamoto also performed three songs for the series ''Wolf's Rain'', for which Kanno was the composer: "Gravity" (which is sung completely in English), "Tell Me What The Rain Knows" (with lyrics by Chris Mosdell) and "Cloud 9". She performed "Hemisphere", the opening theme of the series ''RahXephon'', as well as two songs for the series' theatrical version ''RahXephon: Pluralitas Concentio'': "Tune the Rainbow" and "The Garden of Everything" (duet with Steve Conte). In 2008, Sakamoto and Kanno collaborated again for "Triangler", the opening theme song for the series ''Macross Frontier''. She also performed the song "cream" with HIDE, which was featured in the ''Ghost in the Shell: Stand Alone Complex'' mini album ''be Human''.

Awards and nominations [link]

In the 23rd Anime Grand Prix, she ranked tenth place under the seiyū category with 126 votes.

In addition, in the first ''Seiyū Awards'', she was nominated for "Best Actress in a leading role" for her portrayal of Haruhi Fujioka in ''Ouran High School Host Club'' as well as "Best Musical Performance" for ''Tsubasa Chronicle'''s ending theme ''Loop''.

Discography [link]

Studio albums [link]

1997: ''Grapefruit''

1998: ''Dive''

2001: ''Lucy''

2003: ''Shōnen Alice''

2005: ''Yūnagi Loop''

2009: ''Kazeyomi''

2011: ''You Can't Catch Me''

Compilation albums [link]

1999: ''Single Collection+ Hotchpotch''

2003: ''Single Collection+ Nikopachi''

2010: ''Everywhere''

Filmography [link]

''Canaan'' - Alphard

''Cobra the Animation'' - Secret

''Cowboy Bebop'' - Stella

''Death Note'' - Kiyomi Takada

''D.Gray-man'' - Lou Fa

''El-Hazard'' - Qawoor Towles

''Fantastic Children'' - Mel

''Geneshaft'' - Beatrice Ratio

''Ghost in the Shell: Stand Alone Complex'' - Motoko Kusanagi (young)

''Ghost in the Shell: S.A.C. 2nd GIG'' - Motoko Kusanagi (young)

''Ghost Stories'' - Miyuki Watanabe

''Gunslinger Girl -Il Teatrino-'' - Elizaveta

''Heat Guy J'' - Hime

''Jing: King of Bandits'' - Mimosa

''Kanon'' - Mishio Amano

''Kokoro Library'' - June, Shuri

''Kuroshitsuji'' - Ciel Phantomhive

''Kuroshitsuji II'' - Ciel Phantomhive

''Macross Frontier'' - Mei Ranshe

''Medabots'' - Karin

''Mizuiro Jidai'' - Natsumi Kugayama

''Mobile Suit Gundam SEED Destiny'' - Lunamaria Hawke, Mayu Asuka

''Mushishi'' - Amane

''Naruto'' - Matsuri

''Naruto Shippūden'' - Matsuri

''Nightwalker: The Midnight Detective'' - Riho Yamazaki

''Nisemonogatari'' - Shinobu Oshino

''Omishi Magical Theater: Risky Safety'' - Moe Katsuragi

''Ouran High School Host Club'' - Haruhi Fujioka

''Petite Princess Yucie'' - Aries

''RahXephon'' - Reika Mishima

''Record of Lodoss War: Chronicles of the Heroic Knight'' - Leaf

''Star Driver'' - Sarina Endō

''Star Wars: The Clone Wars'' - Padmé Amidala

''Soul Eater'' - Crona

''Takane no Jitensha'' - Takane

''Tiger & Bunny'' - Tomoe Kaburagi

''Tsubasa: Reservoir Chronicle'' - Princess Tomoyo ''The Vision of Escaflowne'' - Hitomi Kanzaki

''Wolf's Rain'' - Hamona

''Yojō-Han Shinwa Taikei'' - Akashi

OVA [link]

''.hack//Sign'' - Aura

''.hack//GIFT'' - Aura, Molti

''Diebuster'' - Lal'C

''El Hazard - The Magnificent World'' - Qawoor Towles

''Hellsing Ultimate'' - Rip van Winkle

''Kenomoto no Chat'' - Chacha Kenomoto

''Kita e. Pure Session'' - Tanya Lipinsky

''Little Twins'' - Chifuru

''Mobile Suit Gundam Seed Destiny Final Plus: The Chosen Future'' - Lunamaria Hawke

''Mobile Suit Gundam Seed Destiny Special Edition'' - Lunamaria Hawke

''Nasu: A Migratory Bird with Suitcase'' - Hikaru Toyoki

''Saint Seiya: The Hades Chapter – Elysion'' - Pandora

''Saint Seiya: The Hades Chapter – Inferno'' - Pandora

''Saint Seiya: The Hades Chapter – Sanctuary'' - Pandora

''Saint Seiya: The Lost Canvas'' - Previous Generation of Athena

''Shin Kyūseishu Densetsu Hokuto no Ken: Toki-den'' - Lin

''Tsubasa Shunraiki'' - Princess Tomoyo

''Final Fantasy VII Advent Children'' - Aerith Gainsborough

''Fullmetal Alchemist: The Sacred Star of Milos'' - Julia Crichton

''Ghost in the Shell'' - Motoko Kusanagi (young)

''Ghost in the Shell 2: Innocence'' - Motoko Kusanagi (young)

''Kara no Kyōkai: The Garden of Sinners series'' - Shiki Ryōgi

''RahXephon: Pluralitas Concentio'' - Haruka Mishima, Reika Kamina

''Tsubasa Chronicle the Movie: The Princess of the Country of Birdcages'' - Princess Tomoyo

''Shin Kyūseishu Densetsu Hokuto no Ken: Raoh-den Gekitō no Shō'' - Lin

''Shin Kyūseishu Densetsu Hokuto no Ken: Raoh-den Junai no Shō'' - Lin

''Sword of the Stranger'' - Hagihime

''xxxHOLiC the Movie: A Midsummer Night's Dream'' - Princess Tomoyo

''Tekken: Blood Vengeance'' - Ling Xiaoyu

''Trigun: Badlands Rumble'' - Ameila

Web animation [link]

''Chocolate Underground'' - Carol Hunter

DVD [link]

''Panda de Mafumafu'' - Narrator

Dubbing [link]

''Barbie: Fairytopia'' - Barbie

''Brandy & Mr. Whiskers'' - Brandy Harrington

''Brilliant Legacy'' - Go Eun Sung

''Casper'' - Katt (TV Edition)

''Star Wars: Clone Wars'' - Padmé Amidala

''Doctor Who'' - Rose Tyler

''Dark Angel'' - Max

''Fantastic Four'' - Susan Storm (TV movie)

''Flight 29 Down'' - Taylor Hagan

''Glee'' - Rachel Berry

''Grey's Anatomy'' - Bonnie (Season 3)

''High School Musical'' - Taylor McKessie

''Jumong'' - Lady Soseono

''Jurassic Park'' - Lex Murphy

''Mr. Magorium's Wonder Emporium'' - Molly

''Paris, je t'aime'' - Francine (DVD release)

''Piranha 3D'' - Kelly Driscoll

''Prince of Persia: The Sands of Time'' - Princess Tamina

''Romeo and Juliet'' - Juliet

''Terminator 3: Rise of the Machines'' - Kate Brewster

''The Land Before Time'' - Cera

''The Land Before Time II: The Great Valley Adventure'' - Cera

''Thor'' - Jane Foster

''Under Siege 2: Dark Territory'' - Sarah Ryback

TV drama [link]

''Suekko Chōan Ane Sannin'' - Emi

Short films [link]

''03†'' - Zero Saint Cross

Appearances in other media [link]

''Kanon'' - Mishio Amano

''Kingdom Hearts II'' - Aerith Gainsborough

''Kōyasai'' - Risa Hashinoto

''Kita e. ~White Illumination~'' - Tanya Lipinsky

''Kita e. Photo Memories'' - Tanya Lipinsky

''Kuroshitsuji: Phantom & Ghost'' - Ciel Phantomhive

''Little Lovers'' - Yui

''Little Lovers - 2nd -'' - Yui

''Melty Blood: Actress Again'' (PlayStation 2 version) - Shiki Ryōgi

''Mahoroba Stories'' - Suzu

''Missing Blue'' - Siena Areel

''Mobile Suit Gundam series'' - Lunamaria Hawke

''Napple Tale'' - Poach, Arsia

''Okaeri!~Yūnagiiro no Koimonogatari~'' - Nagisa Shinohara

''Ouran High School Host Club'' - Haruhi Fujioka

''Panzer Dragoon Saga'' - Azel

''Persona 3'' - Aigis

''Persona 3 FES'' - Aigis

''Persona 3 Portable'' - Aigis

''Panzer Dragoon Orta'' - Azel

''Project X Zone'' - Ling Xiaoyu

''RahXephon Sokyu Gensokyoku'' - Reika Mishima

''Rune Factory 2: A Fantasy Harvest Moon'' - Kyle

''Saint Seiya: The Hades'' - Pandora

''Shin Megami Tensei: Persona 3'' - Aegis

''Suikoden Tierkreis'' - Marika

''Sonic the Hedgehog'' - Princess Elise

''Super Robot Wars series'' - Reika Mishima, Lunamaria Hawke

''Tail Concerto'' - Telia-hime

''Tekken Tag Tournament 2'' - Ling Xiaoyu

''The 3rd Birthday'' - Aya Brea

''The Vision of Escaflowne'' - Hitomi Kanzaki

''White Knight Chronicles'' - Princess Cisna

''World Destruction'' - Morte Āshera

- TBS Radio

* Broadcast date: April 7, 2007 ~ March 28, 2009

''Konica Minolta presents Night on the Planet'' - Tokyo FM

''Yellow tail music tail'' - Tokyo FM

''Sapporo Beer Key of Dish'' - Tokyo FM

- Nack5

''Girls' School Fantasy'' – NACK5

- Nack5, FM Osaka, FM Aichi – FM Fukuoka, Sendai City-FM, FM-Nigata, K-Mix - Nack5, FM Osaka, North Wave, Cross FM - Nippon Cultural Broadcasting - Nippon Cultural Broadcasting

Webcast [link]

Maaya Sakamoto's Full Moon Recital Hall (September 23, October 23, November 22, December 21, 2010) -Ustream

reading of Japanese literary works

* one of the special projects offered by a Japanese online magazine "''Saizensen''"

Publications [link]

Serialization [link]

Sakamoto Maaya no Manpukuron – Currently in Newtype. - A monthly column

Books [link]

– December 9, 2005 - An essay collection (out of print) – April 18, 2008 - A photo and lyrics book compilation ''from everywhere.'' – February 21, 2011 - An essay collection

References [link]

External links [link]

Maaya Sakamoto's Official Homepage Idling Stop ~ Official Fansite "''Saizensen''" Maaya Sakamoto's Full moon Recital

Category:1980 births Category:Living people Category:People from Tokyo Category:Japanese female singers Category:Japanese musicians Category:Japanese voice actors Category:Japanese-language singers

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