Bufotenidine | CAS#487-91-2 | alkaloid

MedKoo Cat#: 145454 | Name: Bufotenidine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Bufotenidine is an alkaloid that can be isolated from the Bufo viridis toad venom. BUFOTENIDINE is speculated to play a pivotal role in self-defense and increasing venom toxicity and could also offer promising biotechnological applications as a small bioactive molecule.

Chemical Structure

Bufotenidine

CAS#487-91-2

Theoretical Analysis

MedKoo Cat#: 145454

Name: Bufotenidine

CAS#: 487-91-2

Chemical Formula: C13H18N2O

Exact Mass: 218.1400

Molecular Weight: 218.30

Elemental Analysis: C, 71.53; H, 8.31; N, 12.83; O, 7.33

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

Bufotenidine; Bufotenidin;

IUPAC/Chemical Name

3-(2-(trimethylammonio)ethyl)-1H-indol-5-olate

InChi Key

HIYGARYIJIZXGW-UHFFFAOYSA-N

InChi Code

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

SMILES Code

C[N+](C)(C)CCC1=CNC2=C1C=C([O-])C=C2

Appearance

To be determined

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 218.30 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Bhattacharya SK, Sanyal AK. Neuromuscular blocking activity of bufotenidine isolated from Arundo donax L. Naturwissenschaften. 1972 Dec;59(12):650-1. doi: 10.1007/BF00609561. PMID: 4266530. 2: De Oliveira LF, Bretas AD. Blockade by bufotenidine of the serotonin- and narcotic-analgesics-induced contraction of dog intestine in vivo. Eur J Pharmacol. 1973 Mar;21(3):369-71. doi: 10.1016/0014-2999(73)90140-4. PMID: 4708072. 3: Ibarra-Vega R, Jiménez-Vargas JM, Pineda-Contreras A, Martínez-Martínez FJ, Barajas-Saucedo CE, García-Ortega H, Magaña-Vergara NE, Possani LD, Corzo G, Gaitan-Hinojosa MA, Vázquez-Vuelvas OF, Zamudio F, Valdez-Velazquez LL. Indolealkylamines in the venom of the scorpion Thorellius intrepidus. Toxicon. 2023 Sep;233:107232. doi: 10.1016/j.toxicon.2023.107232. Epub 2023 Aug 1. PMID: 37536653. 4: Zhang Y, Ding YH, Wei XL, Zhou YY, Si N, Yang J, Wang HJ, Zhao HY, Bian BL. [Study on anti-inflammatory activity and mechanism of indolealkylamines in toad skin on LPS-activated neutrophils]. Zhongguo Zhong Yao Za Zhi. 2021 Sep;46(18):4774-4781. Chinese. doi: 10.19540/j.cnki.cjcmm.20210616.401. PMID: 34581088. 5: Dong Q, Liu L, Yuan Y, Turdu G, Mirzaakhmedov S, Aisa HA, Yili A. Two new polyamine alkaloids from the Bufo viridis toad venom. Nat Prod Res. 2023 Oct-Nov;37(20):3538-3542. doi: 10.1080/14786419.2022.2086545. Epub 2022 Jun 8. PMID: 35675547. 6: Pham DNK, Chadeayne AR, Golen JA, Manke DR. 2,5-Di-methyl-bufo-tenine and 2,5-di-methyl-bufo-teni-dine: novel derivatives of natural tryptamines found in Bufo alvarius toads. Acta Crystallogr E Crystallogr Commun. 2021 Jan 29;77(Pt 2):190-194. doi: 10.1107/S2056989021000803. PMID: 33614152; PMCID: PMC7869544. 7: Chen YL, Dai YH, Wang AD, Zhou ZY, Lei M, Liu J, Lin B, Xia MY, Wang D. Two New Indole Alkaloids from Toad Venom of Bufo bufo gargarizans. Molecules. 2020 Oct 1;25(19):4511. doi: 10.3390/molecules25194511. PMID: 33019706; PMCID: PMC7582642. 8: Servillo L, Giovane A, Casale R, D'Onofrio N, Ferrari G, Cautela D, Balestrieri ML, Castaldo D. Serotonin 5-O-β-Glucoside and Its N-Methylated Forms in Citrus Genus Plants. J Agric Food Chem. 2015 Apr 29;63(16):4220-7. doi: 10.1021/acs.jafc.5b01031. Epub 2015 Apr 20. PMID: 25893818. 9: Li Q, DU H, Wen HS, Xu T, Wang YJ, Lai XR, Fan G. [Determination of six compounds in Berberidis Cortex and comparative study of its different species]. Zhongguo Zhong Yao Za Zhi. 2019 Mar;44(5):968-974. Chinese. doi: 10.19540/j.cnki.cjcmm.20181226.014. PMID: 30989857. 10: Servillo L, Giovane A, Balestrieri ML, Casale R, Cautela D, Castaldo D. Citrus genus plants contain N-methylated tryptamine derivatives and their 5-hydroxylated forms. J Agric Food Chem. 2013 May 29;61(21):5156-62. doi: 10.1021/jf401448q. Epub 2013 May 17. PMID: 23682903. 11: PEREIRA NA, MARINS IC, MOUSSATCHE H. SOME PHARMACOLOGICAL STUDIES ON BUFOTENINE AND BUFOTENIDINE. Rev Bras Biol. 1963 Oct;23:211-22. PMID: 14119800. 12: Dai YH, Shen B, Xia MY, Wang AD, Chen YL, Liu DC, Wang D. A New Indole Alkaloid from the Toad Venom of Bufo bufo gargarizans. Molecules. 2016 Mar 16;21(3):349. doi: 10.3390/molecules21030349. PMID: 26999086; PMCID: PMC6273675. 13: Jensen N, Gartz J, Laatsch H. Aeruginascin, a trimethylammonium analogue of psilocybin from the hallucinogenic mushroom Inocybe aeruginascens. Planta Med. 2006 Jun;72(7):665-6. doi: 10.1055/s-2006-931576. Epub 2006 Apr 28. PMID: 16673333. 14: RAYMOND-HAMET. Sur les effets vasoconstricteurs directs de l'iodure de bufoténidine pure de Wieland [Direct vasoconstrictive effects of Wieland's pure bufotenidine iodide]. C R Seances Soc Biol Fil. 1954 Oct;148(19-20):1613-4. French. PMID: 14364958. 15: Gang F, Qi LI, Xin-Mei XU, Huan DU, Tong XU, Xian-Rong L, Lei-Lei DU. [Quality evaluation of different Berberidis Cortex species based on ~1H-NMR metabolomics and anti-diabetic activity]. Zhongguo Zhong Yao Za Zhi. 2020 Oct;45(19):4677-4685. Chinese. doi: 10.19540/j.cnki.cjcmm.20200620.201. PMID: 33164432. 16: Liu Y, Luo Y, Li M, Li Z, Lan J, Lu L, Zhang T, Ding Y. Comparative study on pharmacokinetics of extract from Bufonis venenum and its liposomes. J Pharm Biomed Anal. 2024 Jul 21;249:116375. doi: 10.1016/j.jpba.2024.116375. Epub ahead of print. PMID: 39083920. 17: Xu D, Wang J, Chen W, Yang X, Zhou J, Ma H, Di L, Duan J. Evaluation of analgesic and anti-inflammatory actions of indolealkylamines from toad venom in mice using lipidomics and molecular docking. J Ethnopharmacol. 2021 Apr 6;269:113677. doi: 10.1016/j.jep.2020.113677. Epub 2020 Dec 13. PMID: 33321188. 18: RAYMOND-HAMET. Influence de la cocaïnisation sur l'action hypertensive et vasoconstrictive rénale de la bufoténidine [Influence of cocaine on the hypertensive and renal vasoconstrictor action of bufotenidine]. C R Hebd Seances Acad Sci. 1954 Dec 20;239(25):1881-3. French. PMID: 14352461. 19: Li Q, Zhao C, Zhang Y, Du H, Xu T, Xu X, Zhang J, Kuang T, Lai X, Fan G, Zhang Y. 1H NMR-Based Metabolomics Coupled With Molecular Docking Reveal the Anti-Diabetic Effects and Potential Active Components of Berberis vernae on Type 2 Diabetic Rats. Front Pharmacol. 2020 Jun 19;11:932. doi: 10.3389/fphar.2020.00932. PMID: 32636751; PMCID: PMC7317004. 20: Kryukova EV, Lebedev DS, Ivanov IA, Ivanov DA, Starkov VG, Tsetlin VI, Utkin YN. N-methyl serotonin analogues from the Bufo bufo toad venom interact efficiently with the α7 nicotinic acetylcholine receptors. Dokl Biochem Biophys. 2017 Jan;472(1):52-55. doi: 10.1134/S1607672917010136. Epub 2017 Apr 19. PMID: 28421441.