Bufotenin
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Basic Info
| Common Name | Bufotenin(F04710) |
| 2D Structure | |
| Description | Bufotenin (5-OH-DMT), is a tryptamine related to the neurotransmitter serotonin. It is an alkaloid found in the skin of some species of toads; in mushrooms, higher plants, and mammals. Bufotenin is a chemical constituent in the venom and eggs of several species of toads belonging to the Bufo genus, but most notably in the Colorado River toad (Bufo alvarius) as it is the only toad species in which bufotenin is present in large enough quantities for a psychoactive effect. Extracts of toad venom, containing bufotenin and other bioactive compounds, have been used in some traditional medicines (probably derived from Bufo gargarizans), which has been used medicinally for centuries in China. Bufotenin is a constituent of the seeds of Anadenanthera colubrina and Anadenanthera peregrina trees. Anadenanthera seeds have been used as an ingredient in psychedelic snuff preparations by indigenous cultures of the Caribbean, Central and South America. The acute toxicity (LD50) of bufotenin in rodents has been estimated at 200 to 300 mg/kg. Death occurs by respiratory arrest. |
| FRCD ID | F04710 |
| CAS Number | 487-93-4 |
| PubChem CID | 10257 |
| Formula | C12H16N2O |
| IUPAC Name | 3-[2-(dimethylamino)ethyl]-1H-indol-5-ol |
| InChI Key | VTTONGPRPXSUTJ-UHFFFAOYSA-N |
| 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 |
| Canonical SMILES | CN(C)CCC1=CNC2=C1C=C(C=C2)O |
| Isomeric SMILES | CN(C)CCC1=CNC2=C1C=C(C=C2)O |
| Wikipedia | Bufotenin |
| Synonyms |
Bufotenine
Bufotenin
N,N-Dimethylserotonin
N,N-Dimethyl-5-hydroxytryptamine
Mappin
Cinobufotenine
Cohoba
Mappine
Dimethylserotonin
487-93-4
|
| Classifies |
Animal Toxin
Fungal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Indoles and derivatives |
| Subclass | Tryptamines and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Serotonins |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Serotonin - Hydroxyindole - 3-alkylindole - Indole - Alkaloid or derivatives - 1-hydroxy-2-unsubstituted benzenoid - Aralkylamine - Substituted pyrrole - Benzenoid - Pyrrole - Heteroaromatic compound - Tertiary aliphatic amine - Tertiary amine - Azacycle - Hydrocarbon derivative - Organopnictogen compound - Organic oxygen compound - Amine - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as serotonins. These are compounds containing a serotonin moiety, which consists of an indole that bears an aminoethyl a position 2 and a hydroxyl group at position 5. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 204.273 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 3 |
| Complexity | 208 |
| Monoisotopic Mass | 204.126 |
| Exact Mass | 204.126 |
| XLogP | 1.2 |
| Formal Charge | 0 |
| Heavy Atom Count | 15 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9604 |
| Human Intestinal Absorption | HIA+ | 0.9957 |
| Caco-2 Permeability | Caco2+ | 0.5521 |
| P-glycoprotein Substrate | Substrate | 0.7363 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9844 |
| Non-inhibitor | 0.6343 | |
| Renal Organic Cation Transporter | Inhibitor | 0.6362 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6948 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7941 |
| CYP450 2D6 Substrate | Substrate | 0.5684 |
| CYP450 3A4 Substrate | Substrate | 0.6268 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.6444 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9218 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.5464 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9190 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8388 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7531 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.7984 |
| Non-inhibitor | 0.7167 | |
| AMES Toxicity | Non AMES toxic | 0.6702 |
| Carcinogens | Non-carcinogens | 0.9596 |
| Fish Toxicity | High FHMT | 0.6973 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.6621 |
| Honey Bee Toxicity | Low HBT | 0.6322 |
| Biodegradation | Not ready biodegradable | 0.9933 |
| Acute Oral Toxicity | III | 0.5693 |
| Carcinogenicity (Three-class) | Non-required | 0.7019 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.9660 | LogS |
| Caco-2 Permeability | 0.8190 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.5986 | LD50, mol/kg |
| Fish Toxicity | 1.3636 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.1996 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Concise synthesis of N,N-dimethyltryptamine and 5-methoxy-N,N-dimethyltryptamine starting with bufotenine from Brazilian Anadenanthera ssp.. | Nat Prod Commun | 2015 Apr | 25973481 |
| Isolation of N,N-dimethyl and N-methylserotonin 5-O-β-glucosides from immature Zanthoxylum piperitum seeds. | Biosci Biotechnol Biochem | 2010 | 20834148 |
| Urinary excretion of dietary contaminants in horses. | Equine Vet J Suppl | 2006 Aug | 17402502 |
| Pharmañopo-psychonautics: human intranasal, sublingual, intrarectal, pulmonary and oral pharmacology of bufotenine. | J Psychoactive Drugs | 2001 Jul-Sep | 11718320 |
| GC/MS comparison of the West Indian aphrodisiac "Love Stone" to the Chinese medication "chan su": bufotenine and related bufadienolides. | J Forensic Sci | 1996 Nov | 8914298 |
| SOME PHARMACOLOGICAL STUDIES ON BUFOTENINE AND BUFOTENIDINE. | Rev Bras Biol | 1963 Oct | 14119800 |
Targets
- General Function:
- Serotonin receptor activity
- Specific Function:
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-iodophenyl-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling activates a phosphatidylinositol-calcium second messenger system that modulates the activity of phosphatidylinositol 3-kinase and down-stream signaling cascades and promotes the release of Ca(2+) ions from intracellular stores. Regulates neuronal activity via the activation of short transient receptor potential calcium channels in the brain, and thereby modulates the activation of pro-opiomelacortin neurons and the release of CRH that then regulates the release of corticosterone. Plays a role in the regulation of appetite and eating behavior, responses to anxiogenic stimuli and stress. Plays a role in insulin sensitivity and glucose homeostasis.
- Gene Name:
- HTR2C
- Uniprot ID:
- P28335
- Molecular Weight:
- 51820.705 Da
- Mechanism of Action:
- Bufotenin is a neurotoxin similar to the mushroom toxin psilocin. Thus it likely acts as a partial agonist at the 5-HT2A serotonin receptor in the brain where it mimics the effects of serotonin (5-HT). It is likely also a 5-HT1A and 5-HT2A/2C agonist.
References
- Glennon RA: Central serotonin receptors as targets for drug research. J Med Chem. 1987 Jan;30(1):1-12. [3543362 ]
- General Function:
- Serotonin receptor activity
- Specific Function:
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling inhibits adenylate cyclase activity and activates a phosphatidylinositol-calcium second messenger system that regulates the release of Ca(2+) ions from intracellular stores. Plays a role in the regulation of 5-hydroxytryptamine release and in the regulation of dopamine and 5-hydroxytryptamine metabolism. Plays a role in the regulation of dopamine and 5-hydroxytryptamine levels in the brain, and thereby affects neural activity, mood and behavior. Plays a role in the response to anxiogenic stimuli.
- Gene Name:
- HTR1A
- Uniprot ID:
- P08908
- Molecular Weight:
- 46106.335 Da
- Mechanism of Action:
- Bufotenin is a neurotoxin similar to the mushroom toxin psilocin. Thus it likely acts as a partial agonist at the 5-HT2A serotonin receptor in the brain where it mimics the effects of serotonin (5-HT). It is likely also a 5-HT1A and 5-HT2A/2C agonist.
References
- Wikipedia. Bufotenin. Last Updated 28 June 2009. : http://en.wikipedia.org/wiki/Bufotenin
- General Function:
- Serotonin:sodium symporter activity
- Specific Function:
- Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into the pre-synaptic terminal for re-utilization. Plays a key role in mediating regulation of the availability of serotonin to other receptors of serotonergic systems. Terminates the action of serotonin and recycles it in a sodium-dependent manner.
- Gene Name:
- SLC6A4
- Uniprot ID:
- P31645
- Molecular Weight:
- 70324.165 Da
References
- Schmitz WD, Denhart DJ, Brenner AB, Ditta JL, Mattson RJ, Mattson GK, Molski TF, Macor JE: Homotryptamines as potent and selective serotonin reuptake inhibitors (SSRIs). Bioorg Med Chem Lett. 2005 Mar 15;15(6):1619-21. [15745809 ]
- General Function:
- Virus receptor activity
- Specific Function:
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling activates phospholipase C and a phosphatidylinositol-calcium second messenger system that modulates the activity of phosphatidylinositol 3-kinase and promotes the release of Ca(2+) ions from intracellular stores. Affects neural activity, perception, cognition and mood. Plays a role in the regulation of behavior, including responses to anxiogenic situations and psychoactive substances. Plays a role in intestinal smooth muscle contraction, and may play a role in arterial vasoconstriction.(Microbial infection) Acts as a receptor for human JC polyomavirus/JCPyV.
- Gene Name:
- HTR2A
- Uniprot ID:
- P28223
- Molecular Weight:
- 52602.58 Da
- Mechanism of Action:
- Bufotenin is a neurotoxin similar to the mushroom toxin psilocin. Thus it likely acts as a partial agonist at the 5-HT2A serotonin receptor in the brain where it mimics the effects of serotonin (5-HT). It is likely also a 5-HT1A and 5-HT2A/2C agonist.
References
- Egan C, Grinde E, Dupre A, Roth BL, Hake M, Teitler M, Herrick-Davis K: Agonist high and low affinity state ratios predict drug intrinsic activity and a revised ternary complex mechanism at serotonin 5-HT(2A) and 5-HT(2C) receptors. Synapse. 2000 Feb;35(2):144-50. [10611640 ]