1478. Bufotenine

Nomenclature

CAS number: 487-93-4
3-[2-(Dimethylamino)ethyl]-1H-indol-5-ol; 3-(2-dimethylaminoethyl)-5-indolol; 5-hydroxy-N,N-dimethyltryptamine; N,N-dimethylserotonin; 3-(β-dimethylaminoethyl)-5-hydroxyindole; mappine.
C12H16N2O; mol wt 204.27.
C 70.56%, H 7.89%, N 13.71%, O 7.83%.

Description and 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).

Chemical structure

Properties

Stout prisms from ethyl acetate, mp 146-147°. bp0.1 320°. uv max: 220, 265 nm (log ε 4.0, 3.7). Almost insol in water. Freely sol in alcohol, less sol in ether. Sol in dil acids and alkalies.

Derivative

Methyliodide.
C13H19IN2O; mol wt 346.21.
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.