Bufotenin

• CAT Number: I023792
• CAS Number: 487-93-4
• Molecular Formula: C12H16N2O
• Molecular Weight: 204.27
• Purity: 98%
• Synonyms: Bufotenin; Bufotenine; Cinobufotenine; Cohoba; Mappin; Mappine
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: 1H-Indol-5-ol, 3-(2-(dimethylamino)ethyl)-
• InChI: InChI=1S/C12H16N2O/c1-14(2)6-5-9-8-13-12-4-3-10(15)7-11(9)12/h3-4,7-8,13,15H,5-6H2,1-2H3
• InChIKey: VTTONGPRPXSUTJ-UHFFFAOYSA-N
• SMILES: OC1=CC2=C(NC=C2CCN(C)C)C=C1

Bufotenin (5-HO-DMT, bufotenine) is discontinued (DEA controlled substance, Schedule I). It is a tryptamine related to the neurotransmitter serotonin. A hallucinogenic serotonin analog found in frog or toad skins, mushrooms, higher plants, and mammals, especially in the brains, plasma, and urine of schizophrenics. Bufotenin has been used as a tool in CNS studies and misused as a psychedelic.

Reference

1: Peng C, Yang ZD. [Chemical Constituents of the Endophytic Fungus Rhinocladiella sp. lgt-3 from Tripterygium wilfordii]. Zhong Yao Cai. 2016 Aug;39(8):1775-8. Chinese. PubMed PMID: 30204382.
2: Lim WJ, Yap AT, Mangudi M, Hu CY, Yeo CY, Eyo ZW, Chia SX, Chan KB. Gambir, "Gambir Sarawak" and toad venom. Drug Test Anal. 2017 Mar;9(3):491-499. doi: 10.1002/dta.2034. Epub 2016 Jul 26. PubMed PMID: 27367276.
3: Jiang XL, Shen HW, Yu AM. Modification of 5-methoxy-N,N-dimethyltryptamine-induced hyperactivity by monoamine oxidase A inhibitor harmaline in mice and the underlying serotonergic mechanisms. Pharmacol Rep. 2016 Jun;68(3):608-15. doi: 10.1016/j.pharep.2016.01.008. Epub 2016 Feb 5. PubMed PMID: 26977821; PubMed Central PMCID: PMC4848137.
4: Halberstadt AL. Behavioral and pharmacokinetic interactions between monoamine oxidase inhibitors and the hallucinogen 5-methoxy-N,N-dimethyltryptamine. Pharmacol Biochem Behav. 2016 Apr;143:1-10. doi: 10.1016/j.pbb.2016.01.005. Epub 2016 Jan 15. PubMed PMID: 26780349; PubMed Central PMCID: PMC5403252.
5: Riga MS, Bortolozzi A, Campa L, Artigas F, Celada P. The serotonergic hallucinogen 5-methoxy-N,N-dimethyltryptamine disrupts cortical activity in a regionally-selective manner via 5-HT(1A) and 5-HT(2A) receptors. Neuropharmacology. 2016 Feb;101:370-8. doi: 10.1016/j.neuropharm.2015.10.016. Epub 2015 Oct 23. PubMed PMID: 26477571.
6: Moreira LA, Murta MM, Gatto CC, Fagg CW, dos Santos ML. Concise synthesis of N,N-dimethyltryptamine and 5-methoxy-N,N-dimethyltryptamine starting with bufotenine from Brazilian Anadenanthera ssp.. Nat Prod Commun. 2015 Apr;10(4):581-4. PubMed PMID: 25973481.
7: Jeckel AM, Grant T, Saporito RA. Sequestered and Synthesized Chemical Defenses in the Poison Frog Melanophryniscus moreirae. J Chem Ecol. 2015 May;41(5):505-12. doi: 10.1007/s10886-015-0578-6. Epub 2015 Apr 23. PubMed PMID: 25902958.
8: Queiroz MM, Marti G, Queiroz EF, Marcourt L, Castro-Gamboa I, Bolzani VS, Wolfender JL. LC-MS/MS quantitative determination of Tetrapterys mucronata alkaloids, a plant occasionally used in ayahuasca preparation. Phytochem Anal. 2015 May-Jun;26(3):183-8. doi: 10.1002/pca.2548. Epub 2015 Jan 26. PubMed PMID: 25620461.
9: Martin R, Schürenkamp J, Gasse A, Pfeiffer H, Köhler H. Analysis of psilocin, bufotenine and LSD in hair. J Anal Toxicol. 2015 Mar;39(2):126-9. doi: 10.1093/jat/bku141. Epub 2014 Dec 23. PubMed PMID: 25540060.
10: Jiang XL, Shen HW, Yu AM. Potentiation of 5-methoxy-N,N-dimethyltryptamine-induced hyperthermia by harmaline and the involvement of activation of 5-HT1A and 5-HT2A receptors. Neuropharmacology. 2015 Feb;89:342-51. PubMed PMID: 25446678; PubMed Central PMCID: PMC4310233.
11: Szabo A, Kovacs A, Frecska E, Rajnavolgyi E. Psychedelic N,N-dimethyltryptamine and 5-methoxy-N,N-dimethyltryptamine modulate innate and adaptive inflammatory responses through the sigma-1 receptor of human monocyte-derived dendritic cells. PLoS One. 2014 Aug 29;9(8):e106533. doi: 10.1371/journal.pone.0106533. eCollection 2014. PubMed PMID: 25171370; PubMed Central PMCID: PMC4149582.
12: Zhi KK, Yang ZD, Shi DF, Yao XJ, Wang MG. Desmodeleganine, a new alkaloid from the leaves of Desmodium elegans as a potential monoamine oxidase inhibitor. Fitoterapia. 2014 Oct;98:160-5. doi: 10.1016/j.fitote.2014.07.022. Epub 2014 Aug 4. PubMed PMID: 25102471.
13: Riga MS, Soria G, Tudela R, Artigas F, Celada P. The natural hallucinogen 5-MeO-DMT, component of Ayahuasca, disrupts cortical function in rats: reversal by antipsychotic drugs. Int J Neuropsychopharmacol. 2014 Aug;17(8):1269-82. doi: 10.1017/S1461145714000261. Epub 2014 Mar 20. PubMed PMID: 24650558.
14: Jiang XL, Shen HW, Mager DE, Yu AM. Pharmacokinetic interactions between monoamine oxidase A inhibitor harmaline and 5-methoxy-N,N-dimethyltryptamine, and the impact of CYP2D6 status. Drug Metab Dispos. 2013 May;41(5):975-86. doi: 10.1124/dmd.112.050724. Epub 2013 Feb 7. PubMed PMID: 23393220; PubMed Central PMCID: PMC3629804.
15: Martin R, Schürenkamp J, Gasse A, Pfeiffer H, Köhler H. Determination of psilocin, bufotenine, LSD and its metabolites in serum, plasma and urine by SPE-LC-MS/MS. Int J Legal Med. 2013 May;127(3):593-601. doi: 10.1007/s00414-012-0796-1. Epub 2012 Nov 27. PubMed PMID: 23183899.
16: Owens J, Provenza FD, Wiedmeier RD, Villalba JJ. Influence of saponins and tannins on intake and nutrient digestion of alkaloid-containing foods. J Sci Food Agric. 2012 Aug 30;92(11):2373-8. doi: 10.1002/jsfa.5643. Epub 2012 Mar 19. PubMed PMID: 22430569.
17: Barker SA, McIlhenny EH, Strassman R. A critical review of reports of endogenous psychedelic N, N-dimethyltryptamines in humans: 1955-2010. Drug Test Anal. 2012 Jul-Aug;4(7-8):617-35. doi: 10.1002/dta.422. Epub 2012 Feb 28. Review. PubMed PMID: 22371425.
18: Halberstadt AL, Nichols DE, Geyer MA. Behavioral effects of α,α,β,β-tetradeutero-5-MeO-DMT in rats: comparison with 5-MeO-DMT administered in combination with a monoamine oxidase inhibitor. Psychopharmacology (Berl). 2012 Jun;221(4):709-18. doi: 10.1007/s00213-011-2616-6. Epub 2012 Jan 6. PubMed PMID: 22222861; PubMed Central PMCID: PMC3796951.
19: Winter JC, Amorosi DJ, Rice KC, Cheng K, Yu AM. Stimulus control by 5-methoxy-N,N-dimethyltryptamine in wild-type and CYP2D6-humanized mice. Pharmacol Biochem Behav. 2011 Sep;99(3):311-5. doi: 10.1016/j.pbb.2011.05.015. Epub 2011 May 23. PubMed PMID: 21624387; PubMed Central PMCID: PMC3129464.
20: van den Buuse M, Ruimschotel E, Martin S, Risbrough VB, Halberstadt AL. Enhanced effects of amphetamine but reduced effects of the hallucinogen, 5-MeO-DMT, on locomotor activity in 5-HT(1A) receptor knockout mice: implications for schizophrenia. Neuropharmacology. 2011 Jul-Aug;61(1-2):209-16. doi: 10.1016/j.neuropharm.2011.04.001. Epub 2011 Apr 12. PubMed PMID: 21501627; PubMed Central PMCID: PMC3866100.