{"Abbreviation":"5-HO-DMT","Aliases":["Bufotenine","3-[2-(Dimethylamino)ethyl]-1H-indol-5-ol","N,N-Dimethyl-5-HT","5-OH-DMT","3-(2-(Dimethylamino)ethyl)-1H-indol-5-ol","3-(2-dimethylaminoethyl)-1H-indol-5-ol","5-22-12-00026","1,5-benzoxazepin-4(5H)-one, 2,3-dihydro-8-methoxy-2,2,5,6-tetramethyl-","8-methoxy-2,2,5,6-tetramethyl-2,3-dihydro-1,5-benzoxazepin-4(5H)-one","3-(b-(Dimethylamino)ethyl)-5-hydroxyindole"],"CAS":"487-93-4","ChEBI":"CHEBI:3210","ChEMBL":"CHEMBL416526","ChemicalClasses":["tryptamine"],"Chirality":"achiral","Classes":["Psychedelic"],"DEA no":7433,"Dosing Info":[],"DrugClasses":["hallucinogens"],"DurationOfAction":"Oral administration: ~2\u0026nbsphours Intranasal administration: 30–90\u0026nbspmin Sublingual administration: 30–90\u0026nbspmin Rectal administration: ~1\u0026nbsphour Inhalational administration: 60–90\u0026nbspmin Intravenous injection: ~5–120\u0026nbspmin","EINECS":"207-667-9","EliminationHalfLife":"","European Community (EC) Number":"207-667-9","HMDB ID":"HMDB0041842","HeavyAtomCount":15,"Human Drugs":"Pharmaceuticals","IUPACName":"3-[2-(dimethylamino)ethyl]-1H-indol-5-ol","InChI":"InChI=1S/C12H16N2O/c1-14(2)6-5-9-8-13-12-4-3-10(15)7-11(9)12/h3-4,7-8,13,15H,5-6H2,1-2H3","InChIKey":"VTTONGPRPXSUTJ-UHFFFAOYSA-N","MeSH Pharmacological Classification":"Drugs capable of inducing illusions, hallucinations, delusions, paranoid ideations, and other alterations of mood and thinking. Despite the name, the feature that distinguishes these agents from other classes of drugs is their capacity to induce states of altered perception, thought, and feeling that are not experienced otherwise. (See all compounds classified as Hallucinogens.)","Melting Point":"146.5 °C","MolecularFormula":"C\u003csub\u003e12\u003c/sub\u003eH\u003csub\u003e16\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eO","MolecularWeight":"204.27 g/mol","Pharmacodynamics":"Bufotenin is a tryptamine related to the neurotransmitter serotonin.","Physical Description":"Solid","PrevSalts":[],"PubChemId":10257,"Record Description":["Bufotenin is a tertiary amine that consists of N,N-dimethyltryptamine bearing an additional hydroxy substituent at position 5. It has a role as a hallucinogen and a coral metabolite. It is a tryptamine alkaloid and a tertiary amine. It is functionally related to a N,N-dimethyltryptamine.","Bufotenine is a DEA Schedule I controlled substance. Substances in the DEA Schedule I have no currently accepted medical use in the United States, a lack of accepted safety for use under medical supervision, and a high potential for abuse. It is a Hallucinogenic substances substance.","A hallucinogenic serotonin analog found in frog or toad skins, mushrooms, higher plants, and mammals, especially in the brains, plasma, and urine of schizophrenics. Bufotenin has been used as a tool in CNS studies and misused as a psychedelic.","Bufotenine has been reported in Bufo gargarizans, Citrus reticulata, and other organisms with data available.","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. Bufotenin is a chemical constituent in the venom and eggs of several species of toads belonging to the Bufo genus, but most notably in the Colorado River toad (Bufo alvarius) as it is the only toad species in which bufotenin is present in large enough quantities for a psychoactive effect. Extracts of toad venom, containing bufotenin and other bioactive compounds, have been used in some traditional medicines (probably derived from Bufo gargarizans), which has been used medicinally for centuries in China. Bufotenin is a constituent of the seeds of Anadenanthera colubrina and Anadenanthera peregrina trees. Anadenanthera seeds have been used as an ingredient in psychedelic snuff preparations by indigenous cultures of the Caribbean, Central and South America. The acute toxicity (LD50) of bufotenin in rodents has been estimated at 200 to 300 mg/kg. Death occurs by respiratory arrest.","A hallucinogenic serotonin analog found in frog or toad skins, mushrooms, higher plants, and mammals, especially in the brains, plasma, and urine of schizophrenics. Bufotenin has been used as a tool in CNS studies and misused as a psychedelic.","Bufotenin is a tertiary amine that consists of N,N-dimethyltryptamine bearing an additional hydroxy substituent at position 5. It has a role as a hallucinogen and a coral metabolite. It is a tryptamine alkaloid and a tertiary amine. It is functionally related to a N,N-dimethyltryptamine.","Wikipedia|TiHKAL|Tryptamines"],"References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Bufotenin","Name":"Bufotenin","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q408915","Name":"Bufotenin","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/drugs/DB01445","Name":"Bufotenin","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/10257","Name":"Bufotenin","Sub":false}]},{"Name":"ChEMBL","Urls":[{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL416526","Name":"Bufotenin","Sub":false}]},{"Name":"ChEBI","Urls":[{"Link":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3210","Name":"Bufotenin","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=487-93-4","Name":"Bufotenin","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0041842","Name":"Bufotenin","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/C08299","Name":"Bufotenin","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/0A31347TZK","Name":"Bufotenin","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID0048894","Name":"Bufotenin","Sub":false}]}],"SMILES":"CN(C)CCC1=CNC2=C1C=C(C=C2)O","Scheduling":[{"gov":"Australia","schedule":"S9 substance"},{"gov":"Canada","schedule":"Unscheduled substance"},{"act":"Neue-psychoaktive-Stoffe-Gesetz (NpSG)","gov":"Germany","schedule":"Neuer-Psychoaktiver-Stoff"},{"gov":"United Kingdom","schedule":"Class A substance"},{"gov":"United States","schedule":"Schedule I substance"}],"StoreUNII":["0A31347TZK"],"StructureBase64":"PHN2ZyB4bWxucz0iaHR0cDovL3d3dy53My5vcmcvMjAwMC9zdmciIHhtbG5zOnhsaW5rPSJodHRwOi8vd3d3LnczLm9yZy8xOTk5L3hsaW5rIiBoZWlnaHQ9IjYyLjc4Mm1tIiB2ZXJzaW9uPSIxLjIiIHZpZXdCb3g9IjAgMCA5OS4yMTkgNjIuNzgyIiB3aWR0aD0iOTkuMjE5bW0iPgogICAgICAKICAgIDxkZXNjPkdlbmVyYXRlZCBieSB0aGUgQ2hlbWlzdHJ5IERldmVsb3BtZW50IEtpdCAoaHR0cDovL2dpdGh1Yi5jb20vY2RrKTwvZGVzYz4KICAgICAgCiAgICA8ZyBmaWxsPSIjMzA1MEY4IiBzdHJva2U9IiMwMDAwMDAiIHN0cm9rZS1saW5lY2FwPSJyb3VuZCIgc3Ryb2tlLWxpbmVqb2luPSJyb3VuZCIgc3Ryb2tlLXdpZHRoPSIuNyI+CiAgICAgICAgICAgIAogICAgICAgIDxyZWN0IGZpbGw9IiNGRkZGRkYiIGhlaWdodD0iNjMuMCIgc3Ryb2tlPSJub25lIiB3aWR0aD0iMTAwLjAiIHg9Ii4wIiB5PSIuMCIvPgogICAgICAgICAgICAKICAgICAgICA8ZyBjbGFzcz0ibW9sIiBpZD0ibW9sMSI+CiAgICAgICAgICAgICAgICAgIAogICAgICAgICAgICA8bGluZSBjbGFzcz0iYm9uZCIgaWQ9Im1vbDFibmQxIiB4MT0iOTguMTgxIiB4Mj0iODguMTQ0IiB5MT0iNDEuNTY1IiB5Mj0iMzUuNzU0Ii8+CiAgICAgICAgICAgICAgICAgIAogICAgICAgICAgICA8bGluZSBjbGFzcz0iYm9uZCIgaWQ9Im1vbDFibmQyIiB4MT0iODQuOTk2IiB4Mj0iODUuMDEiIHkxPSIzMC4wNzkiIHkyPSIxOC42ODkiLz4KICAgICAgICAgICAgICAgICAgCiAgICAgICAgICAgIDxsaW5lIGNsYXNzPSJib25kIiBpZD0ibW9sMWJuZDMiIHgxPSI4MS44MzgiIHgyPSI3MS43ODQiIHkxPSIzNS43NDUiIHkyPSI0MS41MzMiLz4KICAgICAgICAgICAgICAgICAgCiAgICAgICAgICAgIDxsaW5lIGNsYXNzPSJib25kIiBpZD0ibW9sMWJuZDQiIHgxPSI3MS43ODQiIHgyPSI1OC41OTUiIHkxPSI0MS41MzMiIHkyPSIzMy44OTYiLz4KICAgICAgICAgICAgICAgICAgCiAgICAgICAgICAgIDxsaW5lIGNsYXNzPSJib25kIiBpZD0ibW9sMWJuZDUiIHgxPSI1OC41OTUiIHgyPSI0NS4zODgiIHkxPSIzMy44OTYiIHkyPSI0MS41Ii8+CiAgICAgICAgICAgICAgICAgIAogICAgICAgICAgICA8ZyBjbGFzcz0iYm9uZCIgaWQ9Im1vbDFibmQ2Ij4KICAgICAgICAgICAgICAgICAgICAgICAgCiAgICAgICAgICAgICAgICA8bGluZSB4MT0iNDMuODA2IiB4Mj0iNDUuMzg4IiB5MT0iNTYuNjE5IiB5Mj0iNDEuNSIvPgogICAgICAgICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgICAgIDxsaW5lIHgxPSI0MS41NjUiIHgyPSI0Mi43NzkiIHkxPSI1NC42MDEiIHkyPSI0My4wMDIiLz4KICAgICAgICAgICAgICAgICAgICAgIAogICAgICAgICAgICA8L2c+CiAgICAgICAgICAgICAgICAgIAogICAgICAgICAgICA8bGluZSBjbGFzcz0iYm9uZCIgaWQ9Im1vbDFibmQ3IiB4MT0iNDMuODA2IiB4Mj0iMzIuMjQ2IiB5MT0iNTYuNjE5IiB5Mj0iNTkuMDciLz4KICAgICAgICAgICAgICAgICAgCiAgICAgICAgICAgIDxsaW5lIGNsYXNzPSJib25kIiBpZD0ibW9sMWJuZDgiIHgxPSIyNi44MDgiIHgyPSIyMS4yNjYiIHkxPSI1Ni4xMTIiIHkyPSI0Ni41NzciLz4KICAgICAgICAgICAgICAgICAgCiAgICAgICAgICAgIDxnIGNsYXNzPSJib25kIiBpZD0ibW9sMWJuZDkiPgogICAgICAgICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgICAgIDxsaW5lIHgxPSIyMS4yNjYiIHgyPSIzMS40NjMiIHkxPSI0Ni41NzciIHkyPSIzNS4yNTIiLz4KICAgICAgICAgICAgICAgICAgICAgICAgCiAgICAgICAgICAgICAgICA8bGluZSB4MT0iMjAuMzk2IiB4Mj0iMjguNzA5IiB5MT0iNDMuODk5IiB5Mj0iMzQuNjY3Ii8+CiAgICAgICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgPC9nPgogICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgPGxpbmUgY2xhc3M9ImJvbmQiIGlkPSJtb2wxYm5kMTAiIHgxPSI0NS4zODgiIHgyPSIzMS40NjMiIHkxPSI0MS41IiB5Mj0iMzUuMjUyIi8+CiAgICAgICAgICAgICAgICAgIAogICAgICAgICAgICA8bGluZSBjbGFzcz0iYm9uZCIgaWQ9Im1vbDFibmQxMSIgeDE9IjMxLjQ2MyIgeDI9IjI2Ljc0NyIgeTE9IjM1LjI1MiIgeTI9IjIwLjc1MSIvPgogICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgPGcgY2xhc3M9ImJvbmQiIGlkPSJtb2wxYm5kMTIiPgogICAgICAgICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgICAgIDxsaW5lIHgxPSIyNi43NDciIHgyPSIxMS44MzMiIHkxPSIyMC43NTEiIHkyPSIxNy41NzYiLz4KICAgICAgICAgICAgICAgICAgICAgICAgCiAgICAgICAgICAgICAgICA8bGluZSB4MT0iMjQuODYzIiB4Mj0iMTIuNzAyIiB5MT0iMjIuODQzIiB5Mj0iMjAuMjU0Ii8+CiAgICAgICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgPC9nPgogICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgPGxpbmUgY2xhc3M9ImJvbmQiIGlkPSJtb2wxYm5kMTMiIHgxPSIxMS44MzMiIHgyPSIxLjYzNSIgeTE9IjE3LjU3NiIgeTI9IjI4LjkwMiIvPgogICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgPGcgY2xhc3M9ImJvbmQiIGlkPSJtb2wxYm5kMTQiPgogICAgICAgICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgICAgIDxsaW5lIHgxPSIxLjYzNSIgeDI9IjYuMzUyIiB5MT0iMjguOTAyIiB5Mj0iNDMuNDAyIi8+CiAgICAgICAgICAgICAgICAgICAgICAgIAogICAgICAgICAgICAgICAgPGxpbmUgeDE9IjQuMzg5IiB4Mj0iOC4yMzUiIHkxPSIyOS40ODciIHkyPSI0MS4zMSIvPgogICAgICAgICAgICAgICAgICAgICAgCiAgICAgICAgICAgIDwvZz4KICAgICAgICAgICAgICAgICAgCiAgICAgICAgICAgIDxsaW5lIGNsYXNzPSJib25kIiBpZD0ibW9sMWJuZDE1IiB4MT0iMjEuMjY2IiB4Mj0iNi4zNTIiIHkxPSI0Ni41NzciIHkyPSI0My40MDIiLz4KICAgICAgICAgICAgICAgICAgCiAgICAgICAgICAgIDxsaW5lIGNsYXNzPSJib25kIiBpZD0ibW9sMWJuZDE2IiB4MT0iMTEuODMzIiB4Mj0iOC4zNjQiIHkxPSIxNy41NzYiIHkyPSI2Ljg5NyIvPgogICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgPHBhdGggY2xhc3M9ImF0b20iIGQ9Ik04Ni45MzIgMzYuMzc5aC0uNzJsLTIuNjE5IC00LjA2NmgtLjAzcS4wMTIgLjIzOCAuMDMgLjU5NXEuMDI0IC4zNTcgLjAyNCAuNzMydjIuNzM5aC0uNTY2di00LjloLjcxNGwyLjYwOCA0LjA1NGguMDNxLS4wMDYgLS4xMDcgLS4wMTggLS4zMjdxLS4wMTIgLS4yMiAtLjAyNCAtLjQ3NnEtLjAwNiAtLjI2MiAtLjAwNiAtLjQ4M3YtMi43NjhoLjU3N3Y0Ljl6IiBpZD0ibW9sMWF0bTIiIHN0cm9rZT0ibm9uZSIvPgogICAgICAgICAgICAgICAgICAKICAgICAgICAgICAgPGcgY2xhc3M9ImF0b20iIGlkPSJtb2wxYXRtOCI+CiAgICAgICAgICAgICAgICAgICAgICAgIAogICAgICAgICAgICAgICAgPHBhdGggZD0iTTMwLjg3NiA2Mi4yMjJoLS43MmwtMi42MTkgLTQuMDY2aC0uMDNxLjAxMiAuMjM4IC4wMyAuNTk1cS4wMjMgLjM1NyAuMDIzIC43MzJ2Mi43MzloLS41NjV2LTQuOWguNzE0bDIuNjA4IDQuMDU0aC4wM3EtLjAwNiAtLjEwNyAtLjAxOCAtLjMyN3EtLjAxMiAtLjIyIC0uMDI0IC0uNDc2cS0uMDA2IC0uMjYyIC0uMDA2IC0uNDgydi0yLjc2OWguNTc3djQuOXoiIHN0cm9rZT0ibm9uZSIvPgogICAgICAgICAgICAgICAgICAgICAgICAKICAgICAgI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Effects":null,"Title":"Bufotenin","UNII":"0A31347TZK","Wikidata":"Q408915","Wikipedia":"Bufotenin","XLogP":1.2}