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3,4,5-Trimethoxyphenethylamin
TMPEA · 3,4,5-Trimethoxyphenethylamine · 2-(3,4,5-Trimethoxyphenyl)ethanamine · 2-(3,4,5-Trimethoxyphenyl)ethylamine · 1-amino-2-(3,4,5-trimethoxyphenyl)-ethan · Mezcalin · Mescline · Mescalin
Identifikatoren & physikalische Daten
| CAS No. | 54-04-6 |
|---|---|
| Summenformel | C11H17NO3 |
| Durchschnittliche Molmasse | 211,26 g/mol |
| Monoisotopische Masse | 211,1208434 g/mol |
| SMILES | COc1cc(CCN)cc(OC)c1OC |
| InChIKey | RHCSKNNOAZULRK-UHFFFAOYSA-N |
| PubChem CID | 4076 |
| ChEMBL | CHEMBL26687 |
| ChEBI | CHEBI:28346 |
| EC No. | 200-190-7 |
| DTXSID | DTXSID80202303 |
| Lokaler Name | 3,4,5-Trimethoxyphenethylamin |
Chemische & physikalische Eigenschaften
| XLogP | 0,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 53,7 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 5 |
| Schwere Atome | 15 |
| Formalladung | 0 |
| Komplexität | 163 |
| Arzneimittel | DEA Schedule I Controlled Substance -> Hallucinogenic substancesPharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds |
| LogP (Verteilungskoeffizient) | log Kow = 0.78 |
| Color/Form | Crystals. ... Takes up CO2 from the air and forms crystalline carbonate |
| Löslichkeit | Moderately soluble in watersoluble in chloroform, benzene. Practically insoluble in ether, petroleum ether.Soluble in ethanolslightly soluble in lignin |
| Siedepunkt | 180 °C at 12 mm Hgbp12 180° |
| Schmelzpunkt | 35-36 °C35-36° |
| Dissociation Constants | pKa = 9.56 |
| Other Experimental Properties | Needles, mp 181 °C. Soluble in water, alcohol /Hydrochloride/Prisms, mp 183-186 °C. Soluble in hot water, methanolsparingly soluble in cold water, ethanol. /Sodium dihydrate/Crystals, mp 158 °C /Acid sulfate/Needles from aqueous alcohol, mp 121 °C. Very soluble in alcohol, ether /N-Benzoylmescaline/For more Other Experimental Properties (Complete) data for 3,4,5-TRIMETHOXYPHENETHYLAMINE (7 total), please visit the HSDB record page. |
| Dichte | 1.1240 (rough estimate) |
| Brechungsindex | 1.5718 (estimate) |
| pKa (Säurekonstante) | 9.57±0.10(Predicted) |
| CAS Datenbank | 54-04-6 |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory. |
|---|---|
| Regulatorische Informationen | DEA schedule I controlled substance |
| FDA-Anforderungen | Schedule I shall consist of the drugs and other substances, by whatever official name, common or usual name, chemical name, or brand name designated, listed in this section. ... Hallucinogenic substances. Unless specifically excepted or unless listed in another schedule, any material, compound, mixture, or preparation, which contains any quantity of the following hallucinogenic substances, or which contains any of its salts, isomers, and salts of isomers whenever the existence of such salts, isomers, and salts of isomers is possible within the specific chemical designation (for purposes of this paragraph only, the term "isomer" includes the optical, position and geometric isomers): Mescaline, DEA Code: 7381. |
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| Wechselwirkungen | Mescaline (25 mg/kg66 muc/kg) was injected (ip) in mice 45 min before chlorpromazine (2.5, 5, 15 mg/kg), thioridazine (10, 30, 45 mg/kg), or chlorpromazine-sulfoxide (15 mg/kg). Excitement, agitation, slight increase in ventilation and occasional head-shaking were seen 30 min after mescaline and continued for 30-45 min thereafterlocomotor activity and the number of scratching events were significantly increased during this period. chlorpromazine (2.5, 5, 15 mg/kg) and thioridazine (10, 30, 45 mg/kg) partially or completely blocked mescaline-induced gross behaviorchlorpromazine-sulfoxide (15 mg/kg) was not effective. Increased scratching responses and locomotor activity induced by mescaline were antagonized by all doses of chlorpromazine and thioridazineat higher doses, both chlorpromazine (7.5, 15 mg/kg) and thioridazine (45 mg/kg) induced cataleptic-like condition and marked hypothermia. Tissue levels of mescaline, examined 3 hr after its administration, were increased by all doses of chlorpromazine and a higher dose of thioridazine (45 mg/kg)chlorpromazine-sulfoxide and lower doses of thioridazine had no effect. |
| Natural Pollution Sources | Psychotomimetic alkaloid isolated from peyote (mescal buttons), the flowering heads of Lophophora williamsii (Lemaire) Cout., Cactaceae |
| Human Toxicity Excerpts | /HUMAN EXPOSURE STUDIES/ The psychological, neuropsychological, and neurometabolic effects of the hallucinogenic agent mescaline were investigated in 12 normal men who were volunteers. Mescaline produced an acute psychotic state 3 1/2-4 hr after drug intake, as measured by the Brief Psychiatric Rating Scale (BPRS) and Paranoid Depression Scale (PDS). The Assessment of Altered States of Consciousness (APZ) questionnaire revealed specific effects of mescaline in the visual system. Neuropsychological effects were studied with a face/nonface decision task with known right-hemisphere advantage, in which mescaline induced a decrease of functioning of the right hemisphere. In functional brain imaging using single photon emission computed tomography (SPECT), mescaline produced a "hyperfrontal" pattern with an emphasis on the right hemisphere, which was correlated with mescaline-induced psychotic psychopathology. These findings question the validity of the concept of hypofrontality as an explanation for schizophrenic symptomatology. The study of psychoactive substances under controlled laboratory conditions has the methodological advantage of intraindividual control, and hence, minimal variability of data./SIGNS AND SYMPTOMS/ Mescaline produces hallucinations and symptoms of CNS and sympathetic stimulation. Mild elevations in pulse, blood pressure, respiratory rate, and temperature may be noted. Nausea and vomiting commonly precede the hallucinogenic effects. The clinical presentation may mimic an anticholinergic syndrome. Mydriasis, salivation, and blurred vision are common. Palpitations may occur. Nausea and vomiting, abdominal cramps, and diarrhea are common. GI effects may persist for several days. Antidiuretic effects and polyuria have been noted. Headaches, dizziness, ataxia, tremors, weakness, hallucinations, and paresthesias have been noted. Anxiety auditory and visual hallucinations, emotional instability, paranoia, and flashbacks may occur. Piloerection, flushing, and diaphoresis can occur. Shivering, tremors, increased muscle tone, hyperreflexia, and weakness may occur./SIGNS AND SYMPTOMS/ The clinical effects usually occur approximately one hour following ingestions, and begin with a gastrointestinal phase, predominantly nausea and vomiting, and may be accompanied by diaphoresis, hypertension, mydriasis, and ataxia. This is followed by the psychoactive phase, which generally peaks at 4 to 6 hours and resembles LSD intoxication. This temporal pattern of transition from the gastrointestinal phase to the psychoactive phase is markedly uniform and is characteristic of mescaline intoxication. Symptoms usually resolve within 12 hours of ingestion. Deaths are rare, and are usually associated with accidents due to the user's altered perception./CASE REPORTS/ The death of an individual under the influence of mescaline is presented. Concentrations of the drug were 9.7, 70.8, and 1163 micrograms/mL or micrograms/g in blood, liver, and urine respectively.For more Human Toxicity Excerpts (Complete) data for 3,4,5-TRIMETHOXYPHENETHYLAMINE (7 total), please visit the HSDB record page. |
| Non-Human Toxicity Excerpts | /LABORATORY ANIMALS: Acute Exposure/ The central effect of mescaline and of its derivative N-(3,4,5- trimethoxyphenylethyl)-aziridine after their stereotaxic administration into the lateral ventricle of the brain was studied in behavioral experiments on rats. The effect of the two substances was tested by a method studying memory elicitation in response to appetitive motivation in a multiple T-maze. The results show that both substances worsened the behavior in question. The negative effect of mescaline (lengthening of the time of passage through the maze) was manifested both immediately and several weeks after a single dose. N-(3,4,5- trimethoxyphenylethyl)-aziridine likewise worsened the test reaction, but its effect was less pronounced than that of mescaline./LABORATORY ANIMALS: Acute Exposure/ Motor impairment, especially ataxia, is often mentioned as a 'side effect' of doses of psychoactive drugs which depress animal behaviorit is difficult to determine it accurately from visual observation, but relatively few attempts have been made to measure it objectively and quantitatively. Mescaline, in moderate to large doses, can induce biphasic--depressant followed by stimulant--effects on learned and other performance of laboratory rodents. Motor impairment, using three doses, was accordingly measured during the depressant phase by two methods. An 'ataxia' test, involving analyses of footprints, showed few irregularities of gait splay due to mescaline, but the drug markedly reduced the length of steps ('stride') in a dose-related manner. In a 'tilt plane' test for general motor control, the animals' ability to cling to a tilted plane decreased with 25 mg/kg mescaline, at 30 and 40 minutes after administration. Deficits of this kind can be relevant to interpreting drug actions on forms of behavior which involve movements for responding, and they also have interesting potential in their own right./LABORATORY ANIMALS: Acute Exposure/ The authors/ evaluated the behavioral response of guinea pigs to hallucinogenic agents in order to characterize the response of this species to a variety of known hallucinogenic drugs. The systemic injection of LSD in the guinea pig elicited a "myoclonic-like" response the frequency of which was dose-dependent. This behavior exhibited rapid tolerance which was more prominent at higher doses. Subacute mescaline pretreatment reduced the myoclonic response to LSD suggesting cross-tolerance. Mescaline, DOM, TMA, DMA and 5 Me-ODMT also elicited myoclonus in a dose-dependent manner and in potency ratios which approximate the human experience for hallucinogenic activity. .../LABORATORY ANIMALS: Acute Exposure/ The modifications of behavior caused in the rat by a chronic oral administration of mescaline have been studied in three experimental situations. In the staircase maze mescaline accelerated the spontaneous decay on the conditioned reflex (memory decay) during the period without daily training. Only the results observed at 30 mg/kg/day of mescaline were statistically significant. In a T maze two lateral alleys closed by two swinging doors, 30 mg/kg/day of mescaline increased the time spent in opening the first door. When the two doors of the lateral alleys were closed with a latch, mescaline 30 mg/kg/day, caused an increase in the time spent by the rat in opening the doors. Mescaline caused an increase in food consumption. The increase at 30 mg/kg/day is statistically significant.For more Non-Human Toxicity Excerpts (Complete) data for 3,4,5-TRIMETHOXYPHENETHYLAMINE (7 total), please visit the HSDB record page. |
| Antidote and Emergency Treatment | For patient with a "bad trip" or panic reaction, provide gentle reassurance and relaxation techniques in a quiet environment. Treat agitation or severe anxiety states with diazepam or midazolam. Butyrophenones such as haloperidol are useful despite a small theoretic risk of lowering seizure threshold. Treat seizures, hyperthermia, rhabdomyolysis, hypertension, and cardiac arrhythmias if they occur. /LSD and other hallucinogens/Specific Drugs and Antidotes: There are no specific antidote. Sedating doses of diazepam may alleviate anxiety, and hypnotic doses can induce sleep for the duration of the "trip". /LSD and other hallucinogens/Decontamination: Most of these drugs are taken orally in small doses, and decontamination procedures are relatively ineffective and likely to aggravate psychological distress. Consider the use of activated charcoal ... only after recent (within 30-60 minutes) large ingestions. /LSD and other hallucinogens/Enhanced Elimination: These procedures are not useful. Although urinary acidification may increase the urine concentrations of some agents, it does not significantly enhance total-body elimination and may aggravate myoglobinuric renal failure. /LSD and other hallucinogens/ |
| Toxizität | LD50 i.p. in rats: 370 mg/kg (Speck) |
| Gefahrstoffdaten | 54-04-6(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
Mescaline is one of the main active ingredients in the peyote plant, Lophophora williamsii. It is also found in several other cacti including the South American Trichocereus otherwise known as the Peruvian torch species. Mescaline can also be synthesized in the laboratory. It is one of the oldest known hallucinogenic drugs. Ingestion of mescaline via use of the peyote cactus has been used in rituals by North American Indians dating back thousands of years. Ingestion of peyote was also common among the Aztec, Apache, and Pima Indians for religious, ceremonial, and medicinal purposes. Mescaline was isolated from peyote in 1896 by the chemist Hefter and in 1919, the chemical structure was confirmed by Spath. There are many analogs of mescaline with over 250 being prepared and self-tested by the chemist and pharmacologist, Alexander Shulgin (aka Sasha Shulgin). Mescaline became a Schedule I drug and was placed in Controlled Substances Act in 1970. Many of the related chemicals or analogs of mescaline were also placed in Schedule I of the Controlled Substances Act.
Verwenden
Psychedelic Alkoloid