SerotoninMonoamine neurotransmitterPharmaceutical compoundChemical compoundSerotonin (), also known as 5-hydroxytryptamine (5-HT), is a monoamine neurotransmitter with a wide range of functions in both the central nervous system (CNS) and also peripheral tissues. It is involved in mood, cognition, reward, learning, memory, and physiological processes such as vomiting and vasoconstriction. In the CNS, serotonin regulates mood, appetite, and sleep.
BufoteninBufotenin, also known as dimethylserotonin or as 5-hydroxy-N,N-dimethyltryptamine (5-HO-DMT), is a serotonergic psychedelic of the tryptamine family. It is a derivative of the psychedelic dimethyltryptamine (DMT) and of the neurotransmitterserotonin (5-hydroxytryptamine; 5-HT). The compound is an alkaloid found in some species of mushrooms, plants, and toads. It is also found naturally in the human body in small amounts.
DimethyltryptaminePsychedelic drugPharmaceutical compoundDimethyltryptamine (DMT), also known as N,N-dimethyltryptamine (N,N-DMT), is a serotonergic hallucinogen and investigational drug of the tryptamine family that occurs naturally in many plants and animals. DMT is used as a psychedelic drug and prepared by various cultures for ritual purposes as an entheogen.DMT has a rapid onset, intense effects, and a relatively short duration of action.
TryptophanNames IUPAC nameTryptophanSystematic IUPAC name2-Amino-3-(1H-indol-3-yl)propanoic acidOther names 2-Amino-3-(1H-indol-3-yl)propionic acidIdentifiers CAS Number73-22-33D model (JSmol)Interactive imageZwitterion: Interactive imageChEBICHEBI:16828ChEMBLChEMBL54976ChemSpider6066DrugBankDB00150ECHA InfoCard100.000.723IUPHAR/BPS717KEGGD00020PubChemCID6305UNII8DUH1N11BXCompTox Dashboard(EPA)DTXSID5021419InChIInChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m0/s1Key: QIVBCDIJIAJPQS-VIFPVBQESA-NSMILESc1[nH]c2ccccc2c1C[C@H](N)C(=O)OZwitterion: c1[nH]c2ccccc2c1C[C@H]([NH3+])C(=O)[O-]Properties Chemical formulaC11H12N2O2Molar mass204.229 g·mol Solubility in waterSoluble: 0.23 g/L at 0 °C,11.4 g/L at 25 °C, 17.1 g/L at 50 °C, 27.95 g/L at 75 °C SolubilitySoluble in hot alcohol, alkali hydroxides; insoluble in chloroform.
PsilocybinPsilocybin, also known as 4-phosphoryloxy-N,N-dimethyltryptamine (4-PO-DMT), is a naturally occurringtryptaminealkaloid and investigational drug found in more than 200 species of mushrooms, with hallucinogenic and serotonergic effects. Effects include euphoria, changes in perception, a distorted sense of time, and perceived spiritual experiences. Psilocin is the metabolite of psilocybin.
IndoleChemical compoundChemical compoundIndole is an organic compound with the formula C6H4CCNH3. Indole is classified as an aromaticheterocycle. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered pyrrole ring. Indoles are derivatives of indole where one or more of the hydrogen atoms have been replaced by substituent groups. Indoles are widely distributed in nature, most notably as amino acidtryptophan and neurotransmitterserotonin.
IndolaminesIndolamines are a family of neurotransmitters that share a common molecular structure. Indolamines are a classification of monoamine neurotransmitter, along with catecholamines and ethylamine derivatives. A common example of an indolamine is the tryptophan derivative serotonin, a neurotransmitter involved in mood and sleep. Another example of an indolamine is melatonin. In biochemistry, indolamines are substituted indole compounds that contain an amino group.
MelatoninMelatonin is an indoleamine compound produced by various organisms, including bacteria and eukaryotes. It was discovered in 1958 by Aaron B. Lerner and colleagues in substance from the pineal gland of cows that could induce skin lightening in common frogs. The secretion of melatonin is influenced by the circadian rhythm, and it plays a role in regulating the sleep-wake cycle in vertebrates.
NeuromodulationNeuromodulation is the physiological process by which a given neuron uses one or more chemicals to regulate diverse populations of neurons. Neuromodulators typically bind to metabotropic, G-protein coupled receptors (GPCRs) to initiate a second messenger signaling cascade that induces a broad, long-lasting signal. This modulation can last for hundreds of milliseconds to several minutes.
MetaboliteIn biochemistry, a metabolite is an intermediate or end product of metabolism. The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, catalytic activity of their own (usually as a cofactor to an enzyme), defense, and interactions with other organisms (e.g. pigments, odorants, and pheromones).
BenzeneHydrocarbon compound (C6H6)Sample of benzeneBenzene at room temperatureNames Preferred IUPAC nameBenzeneOther names Benzol (historic/German)Cyclohexa-1,3,5-triene; 1,3,5-Cyclohexatriene (theoretical resonance isomers)[6]Annulene (not recommended)Phene (historic)Identifiers CAS Number71-43-23D model (JSmol)Interactive imageChEBICHEBI:16716ChEMBLChEMBL277500ChemSpider236ECHA InfoCard100.000.685EC Number200-753-7KEGGC01407PubChemCID241RTECS numberCY1400000UNIIJ64922108FCompTox Dashboard(EPA)DTXSID3039242InChIInChI=1S/C6H6/c1-2-4-6-5-3-1/h1-6HKey: UHOVQNZJYSORNB-UHFFFAOYSA-NSMILESc1ccccc1Properties Chemical formulaC6H6Molar mass78.114 g·mol Appearance Colorless liquid Odorsweet aromatic Density0.8765(20) g/cm Melting point5.53 °C (41.95 °F; 278.68 K) Boiling point80.1 °C (176.2 °F; 353.2 K) Critical point (T, P) 562 K (289 °C), 4.89 MPa Solubility in water1.53 g/L (0 °C) 1.81 g/L (9 °C) 1.79 g/L (15 °C) 1.84 g/L (30 °C) 2.26 g/L (61 °C) 3.94 g/L (100 °C) 21.7 g/kg (200 °C, 6.5 MPa) 17.8 g/kg (200 °C, 40 MPa) SolubilitySoluble in alcohol, CHCl3, CCl4, diethyl ether, acetone, acetic acidSolubility in ethanediol5.83 g/100 g (20 °C) 6.61 g/100 g (40 °C) 7.61 g/100 g (60 °C) Solubility in diethylene glycol52 g/100 g (20 °C) log P2.13 Vapor pressure12.7 kPa (25 °C) 24.4 kPa (40 °C) 181 kPa (100 °C) Conjugate acidBenzeniumConjugate baseBenzenideUV-vis (λmax) 255 nm Magnetic susceptibility (χ)−54.8·10 cm/mol Refractive index (nD)1.5011 (20 °C) 1.4948 (30 °C) Viscosity0.7528 cP (10 °C) 0.6076 cP (25 °C) 0.4965 cP (40 °C) 0.3075 cP (80 °C) Structure Molecular shapeTrigonal planarDipole moment0 DThermochemistry Heat capacity(C)134.8 J/mol·K Std molarentropy(S298)173.26 J/mol·K Std enthalpy offormation(ΔfH298)48.7 kJ/mol Std enthalpy ofcombustion(ΔcH298)−3267.6 kJ/mol Enthalpy of fusion(ΔfHfus)9.9 kJ/mol Enthalpy of vaporization(ΔfHvap)33.9 kJ/mol Hazards Occupational safety and health (OHS/OSH): Main hazardspotential occupational carcinogen, flammable GHS labelling: PictogramsSignal wordDangerHazard statementsH225, H302, H304, H305, H315, H319, H340, H350, H372, H410Precautionary statementsP201, P210, P301+P310, P305+P351+P338, P308+P313, P331NFPA 704 (fire diamond) 230Flash point−11.63 °C (11.07 °F; 261.52 K) Autoignitiontemperature497.78 °C (928.00 °F; 770.93 K) Explosive limits1.2–7.8% Lethal dose or concentration (LD, LC): LD50 (median dose)930 mg/kg (rat, oral) LCLo (lowest published)44,000 ppm (rabbit, 30 min)44,923 ppm (dog)52,308 ppm (cat)20,000 ppm (human, 5 min) NIOSH (US health exposure limits): PEL (Permissible)TWA 1 ppm, ST 5 ppm REL (Recommended)Ca TWA 0.1 ppm ST 1 ppm IDLH (Immediate danger)500 ppm Safety data sheet (SDS) HMDBRelated compounds Related compoundsTolueneBorazineSupplementary data page Benzene (data page)Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).Y verify ( ?)
Essential amino acidAn essential amino acid, or indispensable amino acid, is an amino acid that cannot be synthesized from scratch by the organism fast enough to supply its demand, and must therefore come from the diet. Of the 21 amino acids common to all life forms, the nine amino acids humans cannot synthesize are valine, isoleucine, leucine, methionine, phenylalanine, tryptophan, threonine, histidine, and lysine.
PyrroleNames Preferred IUPAC name1H-PyrroleOther names AzoleImidoleIdentifiers CAS Number109-97-73D model (JSmol)Interactive imageInteractive imageBeilstein Reference1159 ChEBICHEBI:19203ChEMBLChEMBL16225ChemSpider7736ECHA InfoCard100.003.387EC Number203-724-7Gmelin Reference1705 PubChemCID8027RTECS numberUX9275000UNII86S1ZD6L2CUN number1992, 1993 CompTox Dashboard(EPA)DTXSID5021910InChIInChI=1S/C4H5N/c1-2-4-5-3-1/h1-5HKey: KAESVJOAVNADME-UHFFFAOYSA-NInChI=1/C4H5N/c1-2-4-5-3-1/h1-5HSMILESN1C=CC=C1[nH]1cccc1Properties Chemical formulaC4H5NMolar mass67.091 g·mol Appearance colorless volatile liquid Density0.967 g cm Melting point−23 °C (−9 °F; 250 K) Boiling point129 to 131 °C (264 to 268 °F; 402 to 404 K) Vapor pressure7 mmHg at 23 °C Acidity (pKa) 17.5 (for the N−H proton) Basicity (pKb) 13.6 (pKa 0.4 for C.A.) Magnetic susceptibility (χ)−47.6×10 cm molViscosity0.001225 Pa s Thermochemistry Heat capacity(C)1.903 J K mol Std enthalpy offormation(ΔfH298)108.2 kJ mol (gas) Std enthalpy ofcombustion(ΔcH298)2242 kJ mol Hazards NFPA 704 (fire diamond) 220Flash point33.33 °C (91.99 °F; 306.48 K) Autoignitiontemperature550 °C (1,022 °F; 823 K) Explosive limits3.1–14.8% Safety data sheet (SDS) Chemical Safety DataRelated compounds Related compoundsPhosphole, arsole, bismole, stiboleExcept where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).Yverify ( ?)*As an Amazon Associate I earn from qualifying purchases.