メスカリン
2-(3,4,5-トリメトキシフェニル)エチルアミン · 3,4,5-トリメトキシフェネチルアミン · 2-(3,4,5-トリメトキシフェニル)エタンアミン · メズカリン · メスカリン · TMPEA · 3,4,5-Trimethoxyphenethylamine · 2-(3,4,5-Trimethoxyphenyl)ethanamine
識別子と物理属性
| CAS No. | 54-04-6 |
|---|---|
| 分子式 | C11H17NO3 |
| 平均分子量 | 211.26 g/mol |
| 単同位体質量 | 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 |
| 現地名 | メスカリン |
化学・物理的性質
| XLogP | 0.7 |
|---|---|
| 極性表面積 | 53.7 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 4 |
| 回転可能結合数 | 5 |
| 重原子数 | 15 |
| 形式電荷 | 0 |
| 複雑度 | 163 |
| 医薬品 | DEA Schedule I Controlled Substance -> Hallucinogenic substancesPharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds |
| LogP（分配係数） | log Kow = 0.78 |
| Color/Form | Crystals. ... Takes up CO2 from the air and forms crystalline carbonate |
| 溶解度 | Moderately soluble in watersoluble in chloroform, benzene. Practically insoluble in ether, petroleum ether.Soluble in ethanolslightly soluble in lignin |
| 沸点 | 180 °C at 12 mm Hgbp12 180° |
| 融点 | 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. |
| 密度 | 1.1240 (rough estimate) |
| 屈折率 | 1.5718 (estimate) |
| pKa（酸解離定数） | 9.57±0.10(Predicted) |
| CAS データベース | 54-04-6 |
化学的特性
White Powder
安全性と法規制
| GHS 分類 | 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. |
|---|---|
| 規制情報 | DEA schedule I controlled substance |
| FDA 要件 | 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%) |
| 相互作用 | 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 |
用途
解説
メスカリン，融点35～36 ℃，沸点180 ℃(1.6 kPa)．水，アルコール類，クロロホルムに易溶，エーテルにほとんど不溶．空気中で二酸化炭素を吸収して炭酸塩となる．硫酸塩(C11H17NO3)2·H2SO4·2H2O(融点183～186 ℃)として容易に精製できる．0.3～0.5 g の摂取で，とくに色彩に関する強烈な幻覚が現れ，5～10時間程度多幸感を与えるので，精神医学分野で利用される．LD50 212 mg/kg(マウス，静注)．森北出版「化学辞典（第2版）
用途
0.3～0.5 g の摂取で，とくに色彩に関する強烈な幻覚が現れ，5～10時間程度多幸感を与えるので，精神医学分野で利用される．
説明
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.
使用
Psychedelic Alkoloid