Record Information |
---|
Version | 1.0 |
---|
Created at | 2021-06-20 19:31:43 UTC |
---|
Updated at | 2021-06-30 00:07:55 UTC |
---|
NP-MRD ID | NP0036326 |
---|
Secondary Accession Numbers | None |
---|
Natural Product Identification |
---|
Common Name | bufotenine |
---|
Provided By | JEOL Database |
---|
Description | Bufotenin, also known as DM5-HT or mappin, belongs to the class of organic compounds known as serotonins. Serotonins 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. Bufotenin has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make bufotenin a potential biomarker for the consumption of these foods. Bufotenin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. bufotenine is found in Amanita citrina, Anadenanthera colubrina, Anadenanthera peregrina, Bufo bufo, Citrus reticulata, Mimosa somnians, Ohwia caudata, Paramuricea clavata, Phalaris aquatica, Phyllodium pulchellum and Umbellularia californica. It was first documented in 1975 (PMID: 1058643). Based on a literature review a significant number of articles have been published on Bufotenin (PMID: 8747157) (PMID: 9468359) (PMID: 10350367) (PMID: 16732341). |
---|
Structure | [H]OC1=C([H])C2=C(N([H])C([H])=C2C([H])([H])C([H])([H])N(C([H])([H])[H])C([H])([H])[H])C([H])=C1[H] 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 |
---|
Synonyms | Value | Source |
---|
3-[2-(Dimethylamino)ethyl]-5-indolol | ChEBI | 3-[2-(Dimethylamino)ethyl]indol-5-ol | ChEBI | 3-[beta-(Dimethylamino)ethyl]-5-hydroxyindole | ChEBI | 5-Hydroxy-N,N-dimethyltryptamine | ChEBI | Bufotenine | ChEBI | DM5-HT | ChEBI | N,N-Dimethylserotonin | ChEBI | 3-[b-(Dimethylamino)ethyl]-5-hydroxyindole | Generator | 3-[Β-(dimethylamino)ethyl]-5-hydroxyindole | Generator | 1H-indol-5-Ol, {3-[2-(dimethylamino)ethyl]-} | HMDB | 3-(2-(Dimethylamino)ethyl)-1H-indol-5-ol (acd/name 4.0) | HMDB | 3-(2-Dimethylaminoethyl)-5-indolol | HMDB | 3-(2-Dimethylaminoethyl)indol-5-ol | HMDB | 3-(beta-Dimethylaminoethyl)-5-hydroxyindole | HMDB | 3-[2-(Dimethylamino)ethyl]-1H-indol-5-ol | HMDB | 3-[2-(Dimethylamino)ethyl]-indol-5-ol | HMDB | 5-Hydroxy-N, N-dimethyltryptamine | HMDB | Cinobufotenine | HMDB | Cohoba | HMDB | Dimethylserotonin | HMDB | indol-5-Ol, {3-[2-(dimethylamino)ethyl]-} | HMDB | Mapine | HMDB | Mappin | HMDB | Mappine | HMDB | N, N-Dimethylserotonin | HMDB | N,N-Dimethyl-5-hydroxytryptamine | HMDB | {3-[(2-dimethylamino)ethyl]-5-indolol} | HMDB | {3-[(beta-dimethylamino)ethyl]-5-hydroxyindole} | HMDB | N,N Dimethyl 5 hydroxytryptamine | HMDB | 5 Hydroxy N,N dimethyltryptamine | HMDB | Bufotenin | KEGG |
|
---|
Chemical Formula | C12H16N2O |
---|
Average Mass | 204.2682 Da |
---|
Monoisotopic Mass | 204.12626 Da |
---|
IUPAC Name | 3-[2-(dimethylamino)ethyl]-1H-indol-5-ol |
---|
Traditional Name | bufotenine |
---|
CAS Registry Number | Not Available |
---|
SMILES | [H]OC1=C([H])C2=C(N([H])C([H])=C2C([H])([H])C([H])([H])N(C([H])([H])[H])C([H])([H])[H])C([H])=C1[H] |
---|
InChI Identifier | 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 |
---|
InChI Key | VTTONGPRPXSUTJ-UHFFFAOYSA-N |
---|
Experimental Spectra |
---|
|
| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
---|
1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
---|
|
| Not Available | Chemical Shift Submissions |
---|
|
| Not Available | Species |
---|
Species of Origin | |
---|
Species Where Detected | |
---|
Chemical Taxonomy |
---|
Description | Belongs to the class of organic compounds known as serotonins. Serotonins 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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organoheterocyclic compounds |
---|
Class | Indoles and derivatives |
---|
Sub Class | Tryptamines and derivatives |
---|
Direct Parent | Serotonins |
---|
Alternative Parents | |
---|
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
|
---|
Molecular Framework | Aromatic heteropolycyclic compounds |
---|
External Descriptors | |
---|
Physical Properties |
---|
State | Not Available |
---|
Experimental Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
|
---|
Predicted Properties | |
---|
General References | - Takeda N, Ikeda R, Ohba K, Kondo M: Bufotenine reconsidered as a diagnostic indicator of psychiatric disorders. Neuroreport. 1995 Nov 27;6(17):2378-80. doi: 10.1097/00001756-199511270-00024. [PubMed:8747157 ]
- Carpenter WT Jr, Fink EB, Narasimhachari N, Himwich HE: A test of the transmethylation hypothesis in acute schizophrenic patients. Am J Psychiatry. 1975 Oct;132(10):1067-71. doi: 10.1176/ajp.132.10.1067. [PubMed:1058643 ]
- Ciprian-Ollivier J, Cetkovich-Bakmas MG: Altered consciousness states and endogenous psychoses: a common molecular pathway? Schizophr Res. 1997 Dec 19;28(2-3):257-65. doi: 10.1016/s0920-9964(97)00116-3. [PubMed:9468359 ]
- Pomilio AB, Vitale AA, Ciprian-Ollivier J, Cetkovich-Bakmas M, Gomez R, Vazquez G: Ayahoasca: an experimental psychosis that mirrors the transmethylation hypothesis of schizophrenia. J Ethnopharmacol. 1999 Apr;65(1):29-51. doi: 10.1016/s0378-8741(98)00163-9. [PubMed:10350367 ]
- Sponheim E, Myhre AM, Reichelt KL, Aalen OO: [Urine peptide patterns in children with milder types of autism]. Tidsskr Nor Laegeforen. 2006 May 25;126(11):1475-7. [PubMed:16732341 ]
- Penez, N., et al. (2011). Penez, N., et al, J. Nat. Prod. 74, 2304 (2011). J. Nat. Prod..
|
---|