Mescaline

Mescaline:

Mescaline ( 3,4,5 - trimethoxyphenethylamine ) is both one of the most widely studied of the hallucinogens, and one of the weakest (by volume). Quantitatively, mescaline serves as a sort of a standard among hallucinogens.

Mescaline has a melting point of 320 C at STP, is a white crystalline substance, taking the form of long, needle shaped structures. Will form a carbonate after absorbing CO2 from the air. The molecular weight of mescaline is 211.25, it is composed of C 62.54%, H 8.11%, N 6.63%, O 22.72%, chemically C11H17NO3. Mescaline is moderately soluble in water; soluble in alcohol, chloroform or benzene. Practically insoluble in ether or petroleum ether.

Botanical Background:

Peyote (Lophophora Williamsii) is a spineless cactus with a long root. It grows in the southwesterm United States and Mexico. Its crown, or 'button', is used for psychedelic purposes. It is cut from the cactus and dried into a hard brown disc. The disc, sometimes referred to as a 'mescal button', contains a methoxylated amphetamine: mescaline (C₁₁H₁₇NO₃) (3,4,5-trimethoxy-ß-phenethylamine).The primary natural sources of mescaline are peyote (Lophophora williamsii or Lophophora diffusa); San Pedro cactus (Trichocereus pachanoi); and Peruvian Torch (Trichocereus peruvianus).

Mescaline is found in many types of cacti, most prominently in peyote (lophophora williamsii), San Pedro (trichocerus pachanoi) and the Peruvian Torch (trichocerus peruvianus). The mescaline content of the various mescaline containing cacti varies greatly between species and individual samples. Following is an estimate of the mescaline contents of three species. Quantities obtained the various cacti which contain this compound are:

Lophophora williamsii - 300 mg / 27 g dried material
Trichocerus pachanoi - 300 mg / 100 g dried material
Trichocerus peruvianus - 300 mg / 37.5 g dried material

Structure:

Properties of 3,4,5-trimethoxybenzaldehyde:
- CAS Number : 000054-04-6
- Chem Name : MESCALINE
- Mol Formula: C11H17NO3
- Mol Weight : 211.26
- Melting Pt : 35.5 deg C
- Boiling Pt : 35-36 deg C at 12 mm Hg
Water Solubility:
- Value : 8.408E+004 mg/L
- Temp : 25 deg C
- Type : EST
- Ref : MEYLAN,WM ET AL. (1996)
Log P (octanol-water):
- Value : 0.78
- Type : EXP
- Ref : HANSCH,C ET AL. (1995)
Vapor Pressure:
- Value : 0.000322 mm Hg
- Temp : 25 deg C
- Type : EST
- Ref : NEELY,WB & BLAU,GE (1985)
Henry's Law Constant:
- Value : 1.68E-010 atm-m3/mole
- Temp : 25 deg C
- Type : EST
- Ref : MEYLAN,WM & HOWARD,PH (1991)
Atmospheric OH Rate Constant:
- Value : 2.353E-010 cm3/molecule-sec
- Temp : 25 deg C
- Type : EST
- Ref : MEYLAN,WM & HOWARD,pH (1993)

Mescaline Timeline:

1897 Mescaline is first isolated and identified by German chemist Arthur Heffter.

1919 Mescaline is first synthesized by Ernst Spath.

1927 An extensive study of mescaline's effects was published in Der Meskalinrausch (The Mescaline High).

Oct 1945 US Navy Technical Mission reports on mescaline experiments at the Nazi Dachau concentration camp.

1947 U.S. Navy initiates mescaline studies under the auspices of 'Project Chatter'.

1952 Dr. Humphry Osmond begins working with hallucinogens at a hospital in Saskatchewan, looking at the similarity        between mescaline and the adrenaline molecule.

May 1953 Aldous Huxley tries mescaline (400 mg) for the first time under the supervision of Dr. Humphrey Osmond. During the experience, he commented "This is how one ought to see, how things really are."

1954 The Doors of Perception by Aldous Huxley is published describing his 1953 experience with mescaline.

Oct 27, 1970 The Comprehensive Drug Abuse Prevention and Control Act is passed. Part II of this is the Controlled Substance Act (CSA) which defines a scheduling system for drugs and places most of the known hallucinogens (LSD, psilocybin, psilocin, mescaline, peyote, cannabis) in Schedule I.

Effects:

Both dopamine and norepinephrine have the exact carbon skeleton and an oxygenation pattern similar to mescaline.

The main metabolite of mescaline is 3,4,5 - trimethoxyphenylacetic acid, which appears to be produced enzymatically by something similar to diamine oxidase. Users experience a loss of spatial and temporal awareness and at higher dosages hallucinations.

Further Information:

Aldous Huxley: The Doors of Perception