Mescaline-obtained from Peyote (Mescal Buttons)

C. Mescaline:

Synonym Mezcaline

Biological Sources It is obtained from Peyote (Mescal Buttons) the flowering heads of Lophophore williamsii (Lemaire) Coult. (Coctaceae) and the cactus Trichocereus pachanoi Britton and Rose (Cactaceae) (Achuma, San Pedro Aguacolli).

Chemical Structure

3, 4, 5-Trimethoxybenzeneethanamine; (C₁₁H₁₇NO₃).

Isolation Mescaline has been successfully isolated from the plant source by Banholzer et al.* (1952).

Characteristic Features

1. The crystals have mp 35-36°C and bp₁₂ 180°C.

2. It is moderately soluble in water; freely soluble in ethanol, chloroform and benzene; and practically insoluble in ether and petroleum ether.

Identification Tests It forms readily a variety of salts, such as:

1. Mescaline Hydrochloride (C₁₁H₁₇NO₃C₁₁H₁₇NO₃.HCl): The needles have mp 181°C and freely soluble both in ethanol and water.

2. Mescaline Sulphate Dihydrate [(C₁₁H₁₇NO₃)₂.H₂SO₄.2H₂O)]: It is obtained as prisms having mp 183-186°C; soluble freely in methanol and hot water; and sparingly soluble in ethanol and cold water.

3. Mescaline Acid Sulphate (C₁₁H₁₇NO₃.H₂SO₄): The crystals have mp 158°C.

4. N-Acetylmescaline: It mostly occurs naturally, mp 94°C.

5. N-Methylmescaline: It occurs naturally, bp 130-140°C.

6. N-Benzoylmescaline: It is obtained as needles from aqueous ethanol having mp 121°C; and is found to be very soluble in ether and ethanol.

Note: This is a controlled substance (hallucinogen) listed in the US code of Federal Regulations

[Title 21 Part 1308.11 (1995)].

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* Erspamer and Falconieri, Naturniss, 39, 431 (1952).