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Cinobufotenine

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Cinobufotenine
Names
IUPAC name
2-(5-hydroxy-1H-indol-3-yl)ethyl-trimethylazanium
Other names
Bufotenium; Bufoteninium; 5-HTQ; 5-Hydroxy-N,N,N-trimethyltryptaminium
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
  • InChI=1S/C13H18N2O/c1-15(2,3)7-6-10-9-14-13-5-4-11(16)8-12(10)13/h4-5,8-9,14H,6-7H2,1-3H3/p+1
    Key: HIYGARYIJIZXGW-UHFFFAOYSA-O
  • C[N+](C)(C)CCC1=CNC2=C1C=C(C=C2)O
Properties
C13H19N2O
Molar mass 219.308 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Cinobufotenine, also known as bufotenium, bufoteninium, or 5-hydroxy-N,N,N-trimethyltryptaminium, is a quaternary ammonium cation as well as a derivative of 5-hydroxytryptamine, It is the parent compound for bufotenidine. The compound is a powerful stimulant of the parasympathetic ganglia, activates nicotine-sensitive acetylcholine receptors, сinobufotenine is highly active on the ileum.[1] It is contained within the skin of certain toads (Bufo gargarizans).[2][3]

Bufotenidine, also known as 5-hydroxy-N,N,N-trimethyltryptammonium (5-HTQ) or as cinobufagine, is an indole toxin related to bufotenin, serotonin, and other tryptamines which is found in the venom of a variety of toads.[4][5] It acts as a selective serotonin 5-HT3 receptor agonist, and has been used in scientific research to study the function of the serotonin 5-HT3 receptor, though this use has been limited by the fact that, as a quaternary amine, it is unable to readily cross the blood-brain-barrier and hence is peripherally selective.[6]

Bufotenium or as cinobufotenine is the quaternary ammonium cation form of bufotenidine, exhibits nicotine-like activity; activates nicotine-sensitive acetylcholine receptors.[7][8]

Differences

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Cinobufotenine is similar to bufotenidine in that it does not readily cross the blood-brain barrier and is therefore peripherally selective. Cinobufotenine has very little activity or low affinity at the 5-hydroxytryptamine receptor, possessing less than one thousandth the potency of 5-hydroxytryptamine.[9][10] and also has a stimulation of cardiac activity, ten times less than the activity of adrenaline chloride, has a low miotic effect and increases the tone of the isolated intestine and uterus.[2]

Bufotenidine
Names
Preferred IUPAC name
3-[2-(Trimethylazaniumyl)ethyl]-1H-indol-5-olate
Other names
Bufotenidin; Cinobufagine; N,N,N-Trimethylserotonin; 5-Hydroxy-N,N,N-trimethyltryptammonium; 5-HTQ
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C13H18N2O/c1-15(2,3)7-6-10-9-14-13-5-4-11(16)8-12(10)13/h4-5,8-9,14H,6-7H2,1-3H3 X markN
    Key: HIYGARYIJIZXGW-UHFFFAOYSA-N X markN
  • InChI=1/C13H18N2O/c1-15(2,3)7-6-10-9-14-13-5-4-11(16)8-12(10)13/h4-5,8-9,14H,6-7H2,1-3H3
    Key: HIYGARYIJIZXGW-UHFFFAOYAI
  • C[N+](C)(C)CCC1=CNC2=C1C=C(C=C2)[O-]
Properties
C13H18N2O
Molar mass 218.300 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X markN verify (what is checkYX markN ?)

See also

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References

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  1. ↑ Barlow, R. B.; Burston, K. N. (1980). "A comparison of cinobufotenine (the quaternary derivative of 5-HT) and some related compounds with coryneine (the quaternary derivative of dopamine) on the frog rectus, guinea-pig ileum and rat fundus strip preparations". British Journal of Pharmacology. 69 (4): 597–600. doi:10.1111/j.1476-5381.1980.tb07909.x. ISSN 0007-1188. PMC 2044297. PMID 6449223.
  2. 1 2 Chen, K. K.; Jensen, H.; Chen, A. LING (1931-09-01). "The Pharmacological Action of the Principles Isolated from Ch'an Su, the Dried Venom of the Chinese Toad". The Journal of Pharmacology and Experimental Therapeutics. 43 (1): 13–50. doi:10.1016/S0022-3565(25)08619-7. ISSN 0022-3565.
  3. ↑ Wu, Qi; Ge, Xue-li; Geng, Zi-kai; Wu, Hao; Yang, Jing-yi; Cao, Shi-rong; Yang, Ai-lin (2024-02-15). "HuaChanSu suppresses the growth of hepatocellular carcinoma cells by interfering with pentose phosphate pathway through down-regulation of G6PD enzyme activity and expression". Heliyon. 10 (3) e25144. doi:10.1016/j.heliyon.2024.e25144. ISSN 2405-8440. PMID 38322888.
  4. ↑ Wieland, Heinrich; Konz, Wilhelm; Mittasch, Heinz (1934). "Toad poisons. VII. Constitution of bufotenin and bufotenidine". Justus Liebigs Annalen der Chemie. 513: 1–25. doi:10.1002/jlac.19345130102.
  5. ↑ Raymond-Hamet (1943). "Bufotenidine, an extremely active principle of the venom of the common toad (Bufo bufo)". Comptes rendus des séances de la Société de biologie et de ses filiales. 137: 74–75.
  6. ↑ Bryan L. Roth (17 August 2008). The Serotonin Receptors: From Molecular Pharmacology to Human Therapeutics. Springer Science & Business Media. pp. 108–. ISBN 978-1-59745-080-5.
  7. ↑ PubChem. "Bufotenium". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-02-24.
  8. ↑ Barlow, R. B.; Burston, K. N. "A comparison of cinobufotenine (the quaternary derivative of 5-HT) and some related compounds with coryneine (the quaternary derivative of dopamine) on the frog rectus, guinea-pig ileum and rat fundus strip preparations". British Journal of Pharmacology. 69 (4): 597–600. doi:10.1111/j.1476-5381.1980.tb07909.x. ISSN 0007-1188. PMC 2044297. PMID 6449223.
  9. ↑ Barlow, R.B.; Burston, K.N. (1980). "A COMPARISON OF CINOBUFOTENINE (THE QUATERNARY DERIVATIVE OF 5-HT) AND SOME RELATED COMPOUNDS WITH CORYNEINE (THE QUATERNARY DERIVATIVE OF DOPAMINE) ON THE FROG RECTUS, GUINEA-PIG ILEUM AND RAT FUNDUS STRIP PREPARATIONS". British Journal of Pharmacology. 69 (4): 597–600. doi:10.1111/j.1476-5381.1980.tb07909.x. ISSN 0007-1188. PMC 2044297. PMID 6449223.
  10. ↑ Powell, C. E.; Swanson, E. E.; Chen, K. K. (1955-07-01). "The Pharmacologic Action of Indole Compounds*". Journal of the American Pharmaceutical Association (Scientific Ed.). 44 (7): 399–404. doi:10.1002/jps.3030440704. ISSN 0095-9553. PMID 13242423.
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