Dehydrobufotenine

Dehydrobufotenine
Clinical data
Other namesDehydrobufotenin
ATC code
  • None
Identifiers
  • 7,7-dimethyl-2-aza-7-azoniatricyclo[6.3.1.04,12]dodeca-1(12),3,8,10-tetraen-9-olate
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC12H14N2O
Molar mass202.257 g·mol−1
3D model (JSmol)
  • C[N+]1(CCC2=CNC3=C2C1=C(C=C3)[O-])C
  • InChI=1S/C12H14N2O/c1-14(2)6-5-8-7-13-9-3-4-10(15)12(14)11(8)9/h3-4,7,13H,5-6H2,1-2H3
  • Key:XRZDSPVDZKCARG-UHFFFAOYSA-N

Dehydrobufotenine is a cyclized tryptamine alkaloid related to bufotenin which is found in several toads and a few giant reeds.[1][2][3][4][5] It was first described in the scientific literature by at least the 1940s.[6]

See also

References

  1. ^ Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. "Dehydrobufotenine: There is a covalent bond formed between the dimethylated nitrogen atom and the indolic 4-position, by the theoretical removal of a molecule of hydrogen. It is no longer a simple tryptamine but as it is a commonly found component of the chemistry of several toads, and a few giant reeds as well, it is included here. It is, by definition, a quaternary amine salt. The original structure assigned it was that of a vinylamine (with the loss of a hydrogen molecule from the alpha/beta chain positions. This was shown to be incorrect."
  2. ^ Smith TA (1977). "Tryptamine and related compounds in plants". Phytochemistry. 16 (2): 171–175. Bibcode:1977PChem..16..171S. doi:10.1016/S0031-9422(00)86778-3. Retrieved 26 November 2025.
  3. ^ Asrorov AM, Kayumov M, Mukhamedov N, Yashinov A, Mirakhmetova Z, Huang Y, et al. (August 2023). "Toad venom bufadienolides and bufotoxins: An updated review". Drug Development Research. 84 (5): 815–838. doi:10.1002/ddr.22072. PMID 37154099.
  4. ^ Lyttle T, Goldstein D, Gartz J (1996). "Bufo toads and bufotenine: fact and fiction surrounding an alleged psychedelic". Journal of Psychoactive Drugs. 28 (3): 267–290. doi:10.1080/02791072.1996.10472488. PMID 8895112.
  5. ^ McKenna DJ, Towers GH (1984). "Biochemistry and pharmacology of tryptamines and beta-carbolines. A minireview". Journal of Psychoactive Drugs. 16 (4): 347–358. doi:10.1080/02791072.1984.10472305. PMID 6394730.
  6. ^ Deulofeu V, Duprat E (1944). "The Basic Constituents of the Venom of Some South American Toads". Journal of Biological Chemistry. 153 (2): 459–463. doi:10.1016/S0021-9258(18)71987-X.
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