Cinobufotenine

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).
Infobox references
Not to be confused with Bufotenidine or Bufotenin.

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 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.[2][3] 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.[4]

Occurrence

Contained within the skin of certain toads (Bufo gargarizans).[4][5]

See also

References

  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. ^ 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.
  3. ^ 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.
  4. ^ a b 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.
  5. ^ 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.
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