Bufotenine
Title: Bufotenine
CAS Registry Number: 487-93-4
CAS Name: 3-[2-(Dimethylamino)ethyl]-1H-indol-5-ol
Additional Names: 3-(2-dimethylaminoethyl)-5-indolol; 5-hydroxy-N,N-dimethyltryptamine; N,N-dimethylserotonin; 3-(b-dimethylaminoethyl)-5-hydroxyindole; mappine
Molecular Formula: C12H16N2O
Molecular Weight: 204.27
Percent Composition: C 70.56%, H 7.89%, N 13.71%, O 7.83%
Literature References: Isoln from toads: Wieland et al., Ann. 513, 1 (1934); Wieland, Wieland, ibid. 528, 239 (1937); from toadstools: Wieland, Motzel, ibid. 581, 10 (1953). Isoln from Piptadenia peregrina Benth., Leguminosae: Stromberg, J. Am. Chem. Soc. 76, 1707 (1954). Synthesis: Hoshino, Shimodaira, Ann. 520, 19 (1935); Harley-Mason, Jackson, Chem. Ind. (London) 1952, 954; see also Serotonin; and Speetor, US 2708197 (1955 to Upjohn); Stoll et al., Helv. Chim. Acta 38, 1452 (1955). Activity: Bhattacharya, Sanyal, Indian J. Physiol. Pharmacol. 15, 133 (1971). Crystal and molecular structure: G. Falkenberg, Acta Crystallogr. 28B, 3219 (1972).
Properties: Stout prisms from ethyl acetate, mp 146-147°. bp0.1 320°. uv max: 220, 265 nm (log e 4.0, 3.7). Almost insol in water. Freely sol in alcohol, less sol in ether. Sol in dil acids and alkalies.
Melting point: mp 146-147°
Boiling point: bp0.1 320°
Absorption maximum: uv max: 220, 265 nm (log e 4.0, 3.7)
 
Derivative Type: Methyliodide
Molecular Formula: C13H19IN2O
Molecular Weight: 346.21
Percent Composition: C 45.10%, H 5.53%, I 36.66%, N 8.09%, O 4.62%
Properties: Stout prisms from methanol, dec 214-215°.
 
NOTE: This is a controlled substance (hallucinogen): 21 CFR, 1308.11.

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