3-[2-(dimethylamino)ethyl]-1H-indol-5-ol

• ChemBase ID: 1251
• Molecular Formular: C12H16N2O
• Molecular Mass: 204.26824
• Monoisotopic Mass: 204.12626314
• SMILES: Oc1cc2c(CCN(C)C)c[nH]c2cc1
• Canonical SMILES: CN(CCc1c[nH]c2c1cc(O)cc2)C
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[2-(dimethylamino)ethyl]-1H-indol-5-ol
• IUPAC Traditional name: mappin
• Synonyms: 3-[2-(Dimethylamino)ethyl]-1H-indol-5-ol; 3-(β-Dimethylaminoethyl)-5-hydroxyindole; 5-Hydroxy-N,N-dimethyltryptamine; Bufotenin; Cinobufotenine; Dimethylserotonin; Mappin; Mappine; N,N-Dimethylserotonin; NSC 89593; Bufotenine; Bufotenine; N,N-dimethyl-5-hydroxytryptamine; 5-hydroxy-dimethyltryptamine; cebilcin; Bufotenin

Database IDs

• CAS Number: 487-93-4
• PubChem SID: 160964711; 46507174
• PubChem CID: 10257
• CHEBI ID: 3210
• CHEMBL: 416526
• Chemspider ID: 9839
• DrugBank ID: DB01445
• IUPHAR ligand ID: 144
• KEGG ID: C08299
• Wikipedia Title: Bufotenin

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.232412
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -1.3982623
• LogD (pH = 7.4): -0.15401816
• Log P: 1.2922695
• Molar Refractivity: 62.4231 cm^3
• Polarizability: 24.996414 Å^3
• Polar Surface Area: 39.26 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.04
• LOG S: -1.81
• Solubility (Water): 3.20e+00 g/l

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Yellow Solid
• Melting Point: 146-147 °C (294.8-296.6°F); 62-64°C
• Boiling Point: 320°C (608°F)

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

Pharmacology Properties

• Admin Routes: Parenteral
• Legal Status: Schedule I (US)

DETAILS

DrugBank - DB01445

• Drug Groups: illicit; experimental
• Description: 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.
• Pharmacology: Bufotenin is a tryptamine related to the neurotransmitter serotonin.
• Toxicity: Ingestion of Bufo toad venom and eggs by humans has resulted in several reported cases of poisoning, some of which resulted in death. The acute toxicity of bufotenin in rodents has been calculated to have an LD50 of between 200 and 300 mg/kg, which by comparison, is comparable to the LD50 for intravenous morphine (200-300 mg/kg) in mice. Death occurs by respiratory arrest.
• Affected Organisms: Humans and other mammals
• Biotransformation: Orally administered bufotenine undergoes extensive first-pass metabolism by the enzyme monoamine oxidase.
• Absorption: Rapidly absorbed following intravenous administration.
• References: Pomilio AB, Vitale AA, Ciprian-Ollivier J, Cetkovich-Bakmas M, Gomez R, Vazquez G: Ayahoasca: an experimental psychosis that mirrors the transmethylation hypothesis of schizophrenia. J Ethnopharmacol. 1999 Apr;65(1):29-51. [Pubmed] ; Ciprian-Ollivier J, Cetkovich-Bakmas MG: Altered consciousness states and endogenous psychoses: a common molecular pathway? Schizophr Res. 1997 Dec 19;28(2-3):257-65. [Pubmed] ; Carpenter WT Jr, Fink EB, Narasimhachari N, Himwich HE: A test of the transmethylation hypothesis in acute schizophrenic patients. Am J Psychiatry. 1975 Oct;132(10):1067-71. [Pubmed] ; Takeda N, Ikeda R, Ohba K, Kondo M: Bufotenine reconsidered as a diagnostic indicator of psychiatric disorders. Neuroreport. 1995 Nov 27;6(17):2378-80. [Pubmed] ; Sponheim E, Myhre AM, Reichelt KL, Aalen OO: [Urine peptide patterns in children with milder types of autism] Tidsskr Nor Laegeforen. 2006 May 25;126(11):1475-7. [Pubmed]
• External Links: Wikipedia

Toronto Research Chemicals - B689525

Controlled substance (hallucinogen).

REFERENCES

• Pomilio AB, Vitale AA, Ciprian-Ollivier J, Cetkovich-Bakmas M, Gomez R, Vazquez G: Ayahoasca: an experimental psychosis that mirrors the transmethylation hypothesis of schizophrenia. J Ethnopharmacol. 1999 Apr;65(1):29-51. Pubmed
• Ciprian-Ollivier J, Cetkovich-Bakmas MG: Altered consciousness states and endogenous psychoses: a common molecular pathway? Schizophr Res. 1997 Dec 19;28(2-3):257-65. Pubmed
• Carpenter WT Jr, Fink EB, Narasimhachari N, Himwich HE: A test of the transmethylation hypothesis in acute schizophrenic patients. Am J Psychiatry. 1975 Oct;132(10):1067-71. Pubmed
• Takeda N, Ikeda R, Ohba K, Kondo M: Bufotenine reconsidered as a diagnostic indicator of psychiatric disorders. Neuroreport. 1995 Nov 27;6(17):2378-80. Pubmed
• Sponheim E, Myhre AM, Reichelt KL, Aalen OO: [Urine peptide patterns in children with milder types of autism] Tidsskr Nor Laegeforen. 2006 May 25;126(11):1475-7. Pubmed
• Stoll, et al.: Helv. Chim. Acta, 38, 1452 (1955)
• Bhattacharya, S., et al.: Indian. J. Physiol. Pharmacol., 15, 133 (1955)
• Falkenberg, G., et al.: Acta Crystallogr., 28B, 3219 (1955)