Bufoviridine

Last updated
Bufoviridine
Bufoviridine.svg
Names
IUPAC name
[3-[2-(dimethylamino)ethyl]-1H-indol-5-yl] hydrogen sulfate
Other names
Bufotenine O-sulfate; Dihydrobufothionine; 5-Sulfooxy-N,N-dimethyltryptamine; 5-Sulfooxy-DMT; 5-SO-DMT
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C12H16N2O4S/c1-14(2)6-5-9-8-13-12-4-3-10(7-11(9)12)18-19(15,16)17/h3-4,7-8,13H,5-6H2,1-2H3,(H,15,16,17)
    Key: OYOOWLVMRZQOMJ-UHFFFAOYSA-N
  • CN(C)CCC1=CNC2=C1C=C(C=C2)OS(=O)(=O)O
Properties
C12H16N2O4S
Molar mass 284.33 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Bufoviridine, also known as bufotenine O-sulfate, dihydrobufothionine, or 5-sulfooxy-N,N-dimethyltryptamine (5-sulfooxy-DMT or 5-SO-DMT), is a naturally occurring tryptamine found in Bufo species such as Bufo viridis and Bufo calamita . [1] [2] [3] [4] [5] [6] It is the O-sulfate ester of bufotenin (5-HO-DMT). [1] [3] The compound shows very weak serotonergic activity. [7] Bufoviridine is not known to have been evaluated in humans, but is suggested to be inactive based on animal studies. [1] The 4-O-acetate, 4-O-phosphate, and 4-O-benzoate esters of psilocin (4-HO-DMT) are all active, but the 4-O-sulfate ester is inactive, suggesting that bufoviridine may be inactive as well. [1] It was first described in the 1950s. [2]

Contents

See also

References

  1. 1 2 3 4 Keeper of the Trout and Friends (2007). "Bufoviridine". Some Simple Tryptamines (2 ed.). Austin, Texas: Mydriatric Productions. p. 114. ISBN   978-0977087655. OCLC   948674100.
  2. 1 2 Deulofeu, Venancio; RúVeda, Edmundo A. (1971). "The Basic Constituents of Toad Venoms". Venomous Animals and their Venoms. Elsevier. pp. 475–495. doi:10.1016/b978-0-12-138902-4.50025-8. ISBN   978-0-12-138902-4. Archived from the original on 28 March 2025. 5. N,N-Dimethyl-5-hydroxytryptamine-O-sulfate (Bufoviridine) (XX) From the many species of amphibians investigated by Erspamer and Vialli (1951, 1952) bufoviridine (X VIII) was detected only in B. viridis and B. calamita. Later it was isolated from B. viridis by Erspamer (1959). On acid hydrolysis, bufotenine (X VII) and sulfuric acid were produced, showing that bufoviridine was the sulfuric ester of the base."
  3. 1 2 John Buckingham (2 December 1993). Dictionary of Natural Products. CRC Press. p. 762. ISBN   978-0-412-46620-5. [Bufotenine] O-Sulfate: [16369-08-7]. Bufoviridine. Dihydrobufothionine C12H16N2O4S M 284.335 Isol. from the skins of various amphibia incl. B. viridis.
  4. ↑ Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN   0-9630096-9-9. OCLC   38503252.
  5. ↑ Erspamer V (November 1959). "Isolation of bufoviridine from the skin of Bufo viridis and its identification as dihydrobufothionine". Biochem Pharmacol. 2 (4): 270–275. doi:10.1016/0006-2952(59)90040-1. PMID   13820720.
  6. ↑ Roseghini M, Falconieri Erspamer G, Severini C, Simmaco M (1989). "Biogenic amines and active peptides in extracts of the skin of thirty-two European amphibian species". Comp Biochem Physiol C Comp Pharmacol Toxicol. 94 (2): 455–460. doi:10.1016/0742-8413(89)90097-2. PMID   2576781.
  7. ↑ Erspamer, Vittorio (1966). "Bioassay of indolealkylamines". 5-Hydroxytryptamine and Related Indolealkylamines. Berlin, Heidelberg: Springer Berlin Heidelberg. pp. 113–131. doi:10.1007/978-3-642-85467-5_3. ISBN   978-3-642-85469-9.



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