background preloader

Psychoactive Alkaloids

Facebook Twitter

Online Books : "TIHKAL" - The Continuation" by Alexander and Ann Shulgin. Yuremamine. Yuremamine is a phytoindole alkaloid which was isolated and identified from the bark of Mimosa tenuiflora in 2005.[1] As a pure compound, yuremamine is a purple amorphous solid. It represents an entirely new family of indole derivatives.

Jump up ^ Vepsäläinen, J. J.; Auriola, S.; Tukiainen, M.; Ropponen, N. & Callaway, J. (2005). "Isolation and characterization of Yuremamine, a new phytoindole". Planta Medica 71 (11): 1049–1053. 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 GABAA receptors and displays sedative-hypnotic effects. Chemistry[edit] Muscimol is the psychoactive compound responsible for the effects of Amanita muscaria intoxication. Ibotenic acid, a neurotoxic secondary metabolite of Amanita muscaria, serves as a prodrug to muscimol when the mushroom is ingested or dried, converting to muscimol via decarboxylation.

Biology[edit] Pharmacology[edit] While muscimol is conventionally thought of as a selective GABAA agonist, it is also a partial agonist at the GABAA-rho receptor, and so its range of effects results from a combined action at both targets.[7] In patients with Huntington's disease and chronic schizophrenia, oral doses of muscimol have been found to cause a rise of both prolactin and growth hormone.[8] Toxicity[edit] Effects[edit] See also[edit] Notes[edit] References[edit] Neurotransmitters and Drugs Chart. Nuciferine. References[edit] Jump up ^ Bhattacharya SK, Bose R, Ghosh P, Tripathi VJ, Ray AB, Dasgupta B (Sep 1978). "Psychopharmacological studies on (—)-nuciferine and its Hofmann degradation product atherosperminine". Psychopharmacology (Berl.) 59 (1): 29–33. doi:10.1007/BF00428026. PMID 100809. Jump up ^ Spess, David L. See also[edit] 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] See also[edit] References[edit] Tryptamine. 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.[2] 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.[3] Plants containing tryptamine[edit] Many plants contain small amounts of tryptamine, for example, as a possible intermediate in one biosynthetic pathway to the plant hormone indole-3-acetic acid.[4] Higher concentrations can be found in many Acacia species.

Role in vertebrates[edit] Tryptamine derivatives[edit] General structure of substituted tryptamines Synthesis [edit] Psilocybin. Psilocybin[nb 1] (/ˌsɪləˈsaɪbɪn/ 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 (in some aspects) to those of LSD, mescaline, and DMT. In general, the effects include euphoria, visual and mental hallucinations, changes in perception, a distorted sense of time, and spiritual experiences, and can include possible adverse reactions such as nausea and panic attacks.

History[edit] Early[edit] Modern[edit] Albert Hofmann (shown here in 1993) purified psilocybin and psilocin from Psilocybe mexicana in the late 1950s. Occurrence[edit] Baeocystin. Baeocystin was first isolated from the mushroom Psilocybe baeocystis,[1] and later from P. semilanceata,[2] Panaeolus renenosus, Panaeolus subbalteatus, and Copelandia chlorocystis.[3] It was first synthesized by Troxler et al. (1959).[4] Little information exists with regard to human pharmacology, but in the book Magic Mushrooms Around the World, author Jochen Gartz reports being aware of a study in which "10 mg of baeocystin were found to be about as psychoactive as a similar amount of psilocybin.

"[citation needed] Gartz also reported in a research paper that a self-administered assay of 4 mg of baeocystin caused "a gentle hallucinogenic experience".[5] Psilocin. Psilocin (also known as 4-OH-DMT, psilocine, psilocyn, or psilotsin), is a substituted tryptamine alkaloid and a serotonergic psychedelic substance. 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 DMT. Chemistry[edit] Psilocin and its phosphorylated cousin, psilocybin, were first isolated and named in 1958 by Swiss chemist Albert Hofmann. Hofmann obtained the chemicals from laboratory-grown specimens of the entheogenic mushroom Psilocybe mexicana. Psilocin is relatively unstable in solution due to its phenolic hydroxy (-OH) group. Structural analogs[edit] Pharmacology[edit] Psilocin is the pharmacologically active agent in the body after ingestion of psilocybin or some species of psychedelic mushrooms.

Psilocin's half-life ranges from 1 to 3 hours.[1] Dimethyltryptamine. History[edit] Another historical milestone is the discovery of DMT in plants frequently used by Amazonian natives as additive to the vine Banisteriopsis caapi to make ayahuasca decoctions. Biosynthesis[edit] Biosynthetic pathway for N,N-dimethyltryptamine This transmethylation mechanism has been repeatedly and consistently proven by radiolabeling of SAM methyl group with carbon-14 (14C-CH3)SAM).[22][20][24][25][26] Evidence in mammals[edit] In 2013, researchers first reported DMT in the pineal gland microdialysate of rodents.[28] A study published in 2014 reported the biosynthesis of N,N-dimethyltryptamine (DMT) in the human melanoma cell line SK-Mel-147 including details on its metabolism by peroxidases. [29] In a 2014 paper, a group first demonstrated the immunomodulatory potential of DMT and 5-MeO-DMT through the Sigma-1_receptor of human immune cells.

INMT[edit] Endogenous DMT[edit] The first claimed detection of mammalian endogenous DMT was published in June 1965: German researchers F. 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. [citation needed] Chemistry[edit] History[edit] Traditionally 5-MeO-DMT has been used in psychedelic snuff made from virola bark resin, and may be a trace constituent of ayahuasca when plants such as Diplopterys cabrerana are used as an admixture. 5-MeO-DMT is also found in the venom of the Colorado River toad (Bufo alvarius), although there is no direct evidence this was used as a hallucinogen until recent times.

Religious use[edit] 5-MeO-DMT is a sacrament of the Church of the Tree of Life. Pharmacology[edit] Use and effects[edit] Although similar in many respects to its close relatives DMT and bufotenin (5-OH-DMT), the effects are typically not as visual. Positive[edit] Neutral[edit] Negative[edit] S. Bufotenin. Bufotenin (5-HO-DMT, N,N-dimethylserotonin), 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 Incilius alvarius, that secrete bufotoxins from their parotoid glands.[2] Bufotenin is similar in chemical structure to the psychedelics psilocin (4-HO-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. Nomenclature[edit] Bufotenin (bufotenine) is also known by the chemical names 5-hydroxy-N,N-dimethyltryptamine (5-HO-DMT), N,N-dimethyl-5-hydroxytryptamine, dimethyl serotonin,[3] and mappine.[3] History[edit] Sources[edit] Toads[edit] Anadenanthera seeds[edit] In 1956, Dr. 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] NMT has been shown to act as an agonist of the TAAR1, similarly to its relatives tryptamine and N,N-dimethyltryptamine.[7] See also[edit] N-Ethyltryptamine (NET)N,N,-Dimethyltryptamine (DMT)Acacia confusa (a natural source of NMT, with other tryptamines, 1.63%.

References[edit] External links[edit] Diethyltryptamine. Chemistry[edit] DET is an analogue of the common tryptamine hallucinogen N,N-Dimethyltryptamine or DMT. Pharmacology[edit] The mechanism of action is thought to be serotonin receptor agonism, much like other classic psychedelics.[2] DET is sometimes preferred over DMT because it can be taken orally whereas DMT cannot.

Biochemistry[edit] Though DET is a synthetic compound with no known natural sources it has been used with mycelium of Psilocybe cubensis to produce the synthetic chemicals 4-PO-DET (Ethocybin) and 4-HO-DET (Ethocin), as opposed to the naturally occurring 4-PO-DMT (Psilocybin) and 4-HO-DMT (Psilocin). Psychosis model[edit] See also[edit] References[edit] External links[edit] Indole alkaloid. History[edit] The action of some indole alkaloids has been known for ages. Aztecs used the psilocybin mushrooms which contain alkaloids psilocybin and psilocin. The flowering plant Rauwolfia serpentina which contains reserpine was a common medicine in India around 1000 BC. Africans used the roots of the perennial rainforest shrub Iboga, which contain ibogaine, as a stimulant. An infusion of Calabar bean seeds was given to people accused of crime in Nigeria: its rejection by stomach was regarded as a sign of innocence, otherwise, the person was killed via the action of physostigmine, which is present in the plant and which causes paralysis of the heart and lungs.[3] Consumption of rye and related cereals contaminated with the fungus Claviceps purpurea causes ergot poisoning and ergotism in humans and other mammals.

The first indole alkaloid, strychnine, was isolated by Pierre Joseph Pelletier and Joseph Bienaimé Caventou in 1818 from the plants of the Strychnos genus. Classification[edit] Tryptophan. 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, as demonstrated by its growth effects on rats. 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 R -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. Isolation[edit] The isolation of tryptophan was first reported by Frederick Hopkins in 1901[4] through hydrolysis of casein. From 600 grams of crude casein one obtains 4-8 grams of tryptophan.[5] Biosynthesis and industrial production[edit] Function[edit] Metabolism of L-tryptophan into serotonin and melatonin (left) and niacin (right).

Dietary sources[edit] [edit] Melatonin. Myristicin. Beta-Carboline. Tryptoline. Pinoline. Harmala alkaloid. Harmine. Harmaline. Tranylcypromine. Iproniazid. Phenelzine. Indole alkaloid. Ibogaine. Voacangine. Cannabinoid. Tetrahydrocannabinol. Anandamide. Salvinorin A. Elemicin. Ergotamine. Ergine. Lisuride. Pergolide. Methysergide. Methylergometrine. Lysergic acid hydroxyethylamide. Ergometrine. Ergoline. Lysergic acid diethylamide. Triterpenoid saponins. Mescaline. Gramine. Hordenine. Tropane alkaloid. Hyoscyamine. Atropine. Scopolamine. Nicotine. Arecoline. Piracetam. MDMA. Too much Ecstasy? The man who took 40,000 MDMA pills in 9 years. PiHKAL. MDMA. Ethanol. Thujone. Tiagabine. Ketamine. Phencyclidine. Caffeine. Theophylline. Theobromine. Mirtazapine. Doxylamine. Diphenhydramine. Morphine. Heroin. Codeine. Oxycodone. Cocaine. Amphetamine. Bupropion. Methylphenidate.