NCBI Taxonomy: 181775

Psilocybe semilanceata (ncbi_taxid: 181775)

found 8 associated metabolites at species taxonomy rank level.

Ancestor: Psilocybe

Child Taxonomies: none taxonomy data.

Psilocin

3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol

C12H16N2O (204.1263)


Psilocin (4-OH-DMT), an aromatic compound, sometimes also spelled psilocine, psilocyn, or psilotsin, is a psychedelic mushroom alkaloid. It is found in most psychedelic mushrooms together with its phosphorylated counterpart psilocybin. Psilocin is a Schedule I drug under the Convention on Psychotropic Substances. The mind-altering effects of psilocin are highly variable and subjective, but resemble those caused by LSD and mescaline. The effects typically last anywhere from three to eight hours depending on certain variables (such as metabolism, food interaction); however the effects can seem to last much longer due to psilocins ability to distort the perception of time. Sulfur analogs are known with a benzothienyl replacement as well as 4-SH-DMT. N1-methylpsilocin is a functionally 5-HT2C receptor preferring agonists. 4-fluoro-N,N-dimethyltryptamine is known. O-Acetylpsilocin is an acetylized analog of psilocin, also known as 4-AcO-DMT. Additionally, substitution of a methyl group at the dimethylated nitrogen with an isopropyl or ethyl group yields 4-HO-MIPT (4-Hydroxy-N-Methyl-N-Isopropyltryptamine) and 4-HO-MET (4-Hydroxy-N-Methyl-N-Ethyltryptamine), respectively. D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D006213 - Hallucinogens

   

Phenylethylamine

Phenethylamine, beta-(14)C-labeled CPD

C8H11N (121.0891)


Phenylethylamine (PEA) is an aromatic amine, which is a colorless liquid at room temperature. It is soluble in water, ethanol, and ether. Similar to other low-molecular-weight amines, it has a fishy odor. Upon exposure to air, it forms a solid carbonate salt with carbon dioxide. Phenethylamine is strongly basic and forms a stable crystalline hydrochloride salt with a melting point of 217 °C. Phenethylamine is also a skin irritant and possible sensitizer. Phenethylamine also has a constitutional isomer (+)-phenylethylamine (1-phenylethylamine), which has two stereoisomers: (R)-(+)-1-phenylethylamine and (S)-(-)-1-phenylethylamine. In the human brain, 2-phenethylamine is believed to function as a neuromodulator or neurotransmitter (a trace amine). Phenethylamine can be biosynthesized from the amino acid phenylalanine by enzymatic decarboxylation. It is also found in many foods such as chocolate, especially after microbial fermentation. However trace amounts from food are quickly metabolized by the enzyme MAO-B (into phenylacetic acid), preventing significant concentrations from reaching the brain. Phenylethylamine is a precursor to the neurotransmitter phenylethanolamine. High levels of PEA have been found in the urine of schizophrenics but it is not significantly elevated in the serum or CSF of schizophrenics (PMID:7906896, PMID:7360842).¬† Urinary levels of PEA are significantly lower in children with attention deficit hyperactivity disorder (ADHD) (PMID:12205654).¬† It has been found that PEA is the primary compound found in carnivore (especially cat) urine that leads to rodent (mouse and rat) avoidance. In other words, phenylethylamine is useful for scaring off rodent pests.¬† Quantitative HPLC analysis across 38 mammalian species has shown that PEA production in urine is especially enhanced in carnivores, with some producing >3,000-fold more than herbivores (PMID:21690383). Phenethylamine has been found to be a metabolite of Bacillus, Enterococcus and Lactobacillus (PMID:22953951; PMID:17307265; PMID:16630269). Present in cooked cabbage, cheeses, sherry, wine, processed lean fish, cocoa, raw cauliflower, raw beetroot and raw radish. Flavouring ingredient

   

Baeocystin

Baeocystin

C11H15N2O4P (270.0769)


A tryptamine alkaloid that is N-methyltryptamine carrying an additional phosphoryloxy substituent at position 4.

   

Phenethylamine

2-Phenylethanamine

C8H11N (121.0891)


D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs

   

Phenethylamine

2-phenylethanamine

C8H11N (121.0891)


2-phenylethylamine is a phenylethylamine having the phenyl substituent at the 2-position. It has a role as a human metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a phenylethylamine, an aralkylamine and an alkaloid. It is a conjugate base of a 2-phenylethanaminium. Phenylethylamine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Phenethylamine has been reported in Senegalia berlandieri, Sedum lydium D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs

   

PSILOCIN

PSILOCIN

C12H16N2O (204.1263)


A tryptamine alkaloid that is N,N-dimethyltryptamine carrying an additional hydroxy substituent at position 4. A hallucinogenic alkaloid isolated in trace amounts from Psilocybe mushrooms (also known as Teonanacatl or "magic mushrooms"). D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D006213 - Hallucinogens

   

2-Phenylethylamine

2-Phenylethylamine

C8H11N (121.0891)


A phenylethylamine having the phenyl substituent at the 2-position.

   

Psilocybin

Psilocybin

C12H17N2O4P (284.0926)


A tryptamine alkaloid that is N,N-dimethyltryptamine carrying an additional phosphoryloxy substituent at position 4. The major hallucinogenic alkaloid isolated from Psilocybe mushrooms (also known as Teonanacatl or "magic mushrooms").