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| CAS No.: | 487-93-4 |
|---|---|
| Name: | BUFOTENINE |
| Article Data: | 25 |
| Molecular Structure: | |
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| Formula: | C12H16 N2 O |
| Molecular Weight: | 204.272 |
| Synonyms: | Bufotenine(6CI); Indol-5-ol, 3-[2-(dimethylamino)ethyl]- (7CI,8CI);3-(2-Dimethylaminoethyl)indol-5-ol; 3-(b-Dimethylaminoethyl)-5-hydroxyindole;5-Hydroxy-N,N-dimethyltryptamine; Bufotenin; Cinobufotenine; Dimethylserotonin;Mappin; Mappine; N,N-Dimethyl-5-hydroxytryptamine; N,N-Dimethylserotonin; NSC89593 |
| Density: | 1.178g/cm3 |
| Melting Point: | 62-64oC |
| Boiling Point: | 392.8°C at 760 mmHg |
| Flash Point: | 191.3°C |
| Safety: | Poison by intraperitoneal route. Human systemic effects with very small amounts taken by intravenous route: psychotropic effects. A modified natural neurotransmitter. When heated to decomposition it emits toxic fumes of NOx. |
| PSA: | 39.26000 |
| LogP: | 1.97760 |
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Chemistry
Chemistry informtion about 3-(2-Dimethylaminoethyl)-5-Indolol (CAS NO.487-93-4) is:
IUPAC Name: 3-(2-Dimethylaminoethyl)-1h-Indol-5-Ol
Synonyms: Bufotenine ; 1h-Indol-5-Ol, 3-[2-(Dimethylamino)Ethyl]- ; 3-(2-(Dimethylamino)Ethyl)-Indol-5-O ; 3-(2-Dimethylaminoethyl)-5-Indolol ; 3-(Beta-Dimethylaminoethyl)-5-Hydroxyindole ; 3-[2-(Dimethylamino)Ethyl]-1h-Indol-5-Ol ; 3-[2-(Dimethylamino)Ethyl]-5-Indolol ; 3-[2-(Dimethylamino)Ethyl]Indol-5-Ol
MF: C12H16N2O
MW: 204.27
EINECS: 207-667-9
Density: 1.178 g/cm3
Flash Point: 191.3 °C
Boiling Point: 392.8 °C at 760 mmHg
Vapour Pressure: 9.89E-07 mmHg at 25°C
Enthalpy of Vaporization: 66.76 kJ/mol
Following is the molecular structure of 3-(2-Dimethylaminoethyl)-5-Indolol (CAS NO.487-93-4) is:
History
It was first isolated, from toad skin, and named by the Austrian chemist Handovsky at the University of Prague during World War I. The structure of bufotenine was first confirmed in 1934 by Heinrich Wieland's laboratory in Munich, and the first reported synthesis of bufotenine was by Toshio Hoshino in 1936.
Uses
3-(2-Dimethylaminoethyl)-5-Indolol (CAS NO.487-93-4) has been used as a street drug; that is, as an aphrodisiac, ingested orally in the form of ch'an su, and as a psychedelic, by smoking or orally ingesting Bufo toad venom or dried Bufo skins. The use of chan'su and love stone (a related toad venom preparation used as an aphrodisiac in the West Indies) has resulted in several cases of poisoning and at least one death. The practice of orally ingesting toad venom has been referred to in popular culture and in the scientific literature as toad licking and has drawn media attention. Albert Most, founder of the Church of the Toad of Light and a proponent of recreational use of Bufo alvarius venom, published a booklet titled Bufo avlarius: The Psychedelic Toad of the Sonoran Desert in 1983 which explained how to extract and smoke the secretions.
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| frog | LDLo | parenteral | 2500mg/kg (2500mg/kg) | cardiac: other changes | Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 86, Pg. 138, 1920. |
| human | TDLo | intravenous | 57ug/kg (0.057mg/kg) | peripheral nerve and sensation: sensory change involving peripheral nerve lungs, thorax, or respiration: other changes gastrointestinal: other changes | Science. Vol. 123, Pg. 886, 1956. |
| mouse | LD50 | intraperitoneal | 290mg/kg (290mg/kg) | Psychopharmacologia Vol. 16, Pg. 385, 1970. | |
| mouse | LD50 | intravenous | 25mg/kg (25mg/kg) | Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 64, Pg. 144, 1968. |
Safety Profile
Poison by intraperitoneal route. Human systemic effects with very small amounts taken by intravenous route: psychotropic effects. A modified natural neurotransmitter. When heated to decomposition it emits toxic fumes of NOx.
RIDADR: 1544
HazardClass: 6.1(b)
PackingGroup: III
Specification
3-(2-Dimethylaminoethyl)-5-Indolol (CAS NO.487-93-4) 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.