Psychoactive Alkaloids
Get flash to fully experience Pearltrees
Yuremamine is a phytoindole alkaloid which was isolated and identified from the bark of Mimosa tenuiflora in 2005. [ 1 ] It may explain the oral psychoactivity of traditional preparations from Mimosa tenuiflora , which also contains DMT ( dimethyltryptamine ). [ citation needed ] As a pure compound, yuremamine is a purple amorphous solid. It represents an entirely new family of indole derivatives. This compound contains dimethyltryptamine within its molecular structure. Perhaps yuremamine acts as an MAOI, being metabolically protected itself through intra-molecular hydrogen bonding of its tertiary amine , or perhaps yuremamine acts as a prodrug and releases DMT closer to its site of action. [ 2 ]
Yuremamine
Muscimol
Muscimol ( agarin , pantherine ) is the major psychoactive alkaloid present in many mushrooms of the Amanita genus. Muscimol is a potent, selective agonist for the GABA A receptors and displays sedative-hypnotic and dissociative psychoactive effects. [ edit ] Chemistry
Aporphine
Aporphine is one of a class of quinoline alkaloids . Many different relatives of this compound have been purified from plants. [ 1 ] One commonly-used aporphine derivative is apomorphine , although it does not occur naturally. Aporphine is a 5-HT1a partial agonist with a ki of 80nM and a 5-HT7 antagonist with a ki of 88nM. [ 2 ] Aporphine is a Dopamine D1 antagonist with a ki of 717nM [ 3 ] and a dopamine D2 antagonist with a ki of 527nM. [ 4 ] Aporphine and its related alkaloids bulbocapnine, boldine, glaucine and corytuberine are antipsychotic, exert naloxone -reversible antinociceptive activity and with the exception of corytuberine are anticonvulsant. [ 5 ] Some derivatives of aporphine such as S(+)-N-propylnorapomorphine have potential as low side effect profile antipsychotics. S(+)-N-propylnorapomorphine is highly selective for meso-limbic dopaminergic tracts and function as efficacious partial agonists, with no elevation in prolactin. [ 6 ]
Tryptamine is a monoamine alkaloid found in plants , fungi , and animals . It contains an indole ring structure, and is structurally similar to the amino acid tryptophan , from which it derives its name. Tryptamine is found in trace amounts in the brains of mammals and is believed to play a role as a neuromodulator or neurotransmitter . [ 1 ] The tryptamine chemical structure is the backbone for a group of compounds termed collectively tryptamines . This group includes many biologically active compounds , including neurotransmitters and psychedelic drugs . The concentration of tryptamine in rat brains is about 3.5 pmol /g. [ 2 ]
Tryptamine
Psilocybin [ nb 1 ] ( pron.: / ˌ s ɪ l ə ˈ s aɪ b ɪ n / SIL -ə- SY -bin ) is a naturally occurring psychedelic compound produced by more than 200 species of mushrooms , collectively known as psilocybin mushrooms . The most potent are members of the genus Psilocybe , such as P. azurescens , P. semilanceata , and P. cyanescens , but psilocybin has also been isolated from about a dozen other genera . As a prodrug , psilocybin is quickly converted by the body to psilocin , which has mind-altering effects similar to those of LSD and mescaline .
Psilocybin
Psilocin (also known as 4-HO-DMT , psilocine , psilocyn , or psilotsin ), is a substituted tryptamine alkaloid and a serotonergic psychedelic drug . It is present in most psychedelic mushrooms together with its phosphorylated counterpart psilocybin . Psilocin is a Schedule I drug under the Convention on Psychotropic Substances . [ 2 ] The mind-altering effects of psilocin are highly variable and subjective and resemble those of LSD and mescaline . [ edit ] Chemistry
Psilocin
Dimethyltryptamine
N , N -Dimethyltryptamine ( DMT or N , N -DMT ) is a psychedelic compound of the tryptamine family. Its presence is widespread throughout the plant kingdom . [ 3 ] [ 4 ] DMT occurs in trace amounts in mammals, including humans, where it putatively functions as a trace amine neurotransmitter / neuromodulator . [ 5 ] It is originally derived from the essential amino acid tryptophan and ultimately produced by the enzyme INMT during normal metabolism . [ 6 ] The significance of its widespread natural presence remains undetermined. Structurally , DMT is analogous to the neurotransmitter serotonin (5-HT), the hormone melatonin , and other psychedelic tryptamines, such as 5-MeO-DMT , bufotenin , psilocin and psilocybin .5-MeO-DMT
5-MeO-DMT ( 5-methoxy- N , N -dimethyltryptamine ) is a powerful psychedelic tryptamine . It is found in a wide variety of plant and psychoactive toad species and, like its close relatives DMT and bufotenin (5-HO-DMT) , it has been used as an entheogen by South American shamans for thousands of years . [ edit ] Chemistry
Bufotenin
Bufotenin ( 5-OH-DMT ), is a tryptamine related to the neurotransmitter serotonin . It is an alkaloid found in the skin of some species of toads ; in mushrooms , higher plants , and mammals . [ 1 ] The name bufotenin originates from the Bufo genus of toads, which includes several species of psychoactive toads , most notably Bufo alvarius , that secrete bufotoxins from their parotoid glands . [ 2 ] Bufotenin is similar in chemical structure to the psychedelics psilocin (4-OH-DMT) , 5-MeO-DMT , and DMT , chemicals which also occur in some of the same fungus, plant, and animal species as bufotenin. The psychoactivity of bufotenin has been disputed, though recent studies suggest it is similar in nature to 5-MeO-DMT . [ edit ] Nomenclature Bufotenin (bufotenine) is also known by the chemical names 5-hydroxy- N , N -dimethyltryptamine (5-OH-DMT), N , N -dimethyl-5-hydroxytryptamine, dimethyl serotonin, [ 3 ] and mappine. [ 3 ]
N-Methyltryptamine
N -Methyltryptamine ( NMT ), or methyltryptamine , is a member of the tryptamine chemical class . It is an alkaloid , probably derived from L -tryptophan , that has been found in the bark , shoots and leaves of several plant species , including Virola , Acacia , Mimosa and Desmanthus often together with the related compounds N , N -dimethyltryptamine (DMT) and 5-methoxy- N , N -dimethyltryptamine (5-MeO-DMT). [ 1 ] It is also synthesized in the human body as a metabolic endproduct of the amino acid L -tryptophan . [ 2 ] It was found to be a natural trace component in human urine. [ 3 ] Orally administered NMT appears to produce no psychoactive effects, likely as a result of extensive first-pass metabolism . [ 4 ] However, it may become active upon combination with a MAO A inhibitor (MAOI). [ 4 ] By vaporization NMT shows activity at 50–100 mg, with a duration of 45–70 minutes; duration of visual effects 15–30 seconds. [ 5 ] [ 6 ]DET , also known under its chemical name N , N -diethyltryptamine and as T-9 , [ 1 ] is a psychedelic drug closely related to DMT and 4-HO-DET . However, despite its structural similarity to DMT it is active orally around 50–100 mg without the aid of MAO inhibitors lasting about 2–4 hours. [ edit ] Chemistry
Diethyltryptamine
Indole alkaloids are a class of alkaloids containing a structural moiety of indole ; many indole alkaloids also include isoprene groups. Containing more than 4100 known different compounds, it is one of the largest classes of alkaloids. [ 1 ] Many of them possess significant physiological activity and some of them are used in medicine. The amino acid tryptophan is the biochemical precursor of indole alkaloids. [ 2 ] [ edit ] History
Indole alkaloid
Tryptophan (IUPAC-IUBMB abbreviation: Trp or W ; IUPAC abbreviation: L-Trp or D-Trp; sold for medical use as Tryptan ) [ 2 ] is one of the 22 standard amino acids and an essential amino acid in the human diet. It is encoded in the standard genetic code as the codon UGG . Only the L- stereoisomer of tryptophan is used in structural or enzyme proteins, but the D- stereoisomer is occasionally found in naturally produced peptides (for example, the marine venom peptide contryphan ). [ 3 ] The distinguishing structural characteristic of tryptophan is that it contains an indole functional group. It is an essential amino acid, as demonstrated by its growth effects on rats . [ edit ] Isolation
Tryptophan
Melatonin
Melatonin i / ˌ m ɛ l ə ˈ t oʊ n ɪ n / , also known chemically as N -acetyl-5-methoxytryptamine , [ 1 ] is a naturally occurring compound found in animals, plants, and microbes. [ 2 ] [ 3 ] In animals, circulating levels of the hormone melatonin vary in a daily cycle, thereby allowing the entrainment of the circadian rhythms of several biological functions. [ 4 ] Many biological effects of melatonin are produced through activation of melatonin receptors , [ 5 ] while others are due to its role as a pervasive and powerful antioxidant , [ 6 ] with a particular role in the protection of nuclear and mitochondrial DNA . [ 7 ]Myristicin
Myristicin is a phenylpropene , a natural organic compound present in small amounts in the essential oil of nutmeg and to a lesser extent in other spices such as parsley and dill . It is insoluble in water, but soluble in ethanol and acetone . [ 1 ] [ edit ] Uses Nutmeg has psychoactive properties at doses much higher than used in cooking .MDMA