Monograph Number:  5932
Title:  Mescaline
CAS Registry Number:  54-04-6
CAS Name:  3,4,5-Trimethoxybenzeneethanamine
Additional Names:  3,4,5-trimethoxyphenethylamine;  mezcaline
Molecular Formula:  C11H17NO3
Molecular Weight:  211.26.  
Percent Composition:  C 62.54%, H 8.11%, N 6.63%, O 22.72%
Literature References:  Psychotomimetic alkaloid isolated from peyote (mescal buttons), the flowering heads of Lophophora williamsii (Lemaire) Coult., Cactaceae.  Isoln:  A. Heffter, Ber. 29, 221 (1896).  Structure and synthesis:  E. Späth, Monatsh. 40, 129 (1919); K. H. Slotta, H. Heller, Ber. 63, 3029 (1930); E. Späth, F. Becke, Monatsh. 66, 327 (1935); M. U. Tsao, J. Am. Chem. Soc. 73, 5495 (1951); K. Banholzer et al., Helv. Chim. Acta 35, 1577 (1952).  Novel synthesis:  M. N. Aboul-Enein, A. I. Eid, Acta Pharm. Suec. 16, 267 (1979).  MS determn:  S. P. Jindal, T. Lutz, Eur. J. Mass Spectrom. Biochem. Med. Environ. Res. 2, 117 (1982).  Pharmacokinetics in rabbits:  C. Van Peteghem et al., Eur. J. Drug Metab. Pharmacokinet. 7, 1 (1982).  Mode of action study:  M. E. Trulson et al., Eur. J. Pharmacol. 96, 151 (1983).  Use in evaluating serotonin S2 antagonists:  C. J. E. Niemegeers et al., Drug Dev. Res. 3, 123 (1983).  Evaluation of use with chlorpromazine, q.v., in various psychoses:  H. C. B. Denber, S. Merlis:  J. Nerv. Ment. Dis. 122, 463 (1955).  Toxicity data:  L. B. Speck, J. Pharmacol. Exp. Ther. 119, 78 (1957); H. F. Hardman et al., Toxicol. Appl. Pharmacol. 25, 299 (1973).  Reviews:  A. R. Patel, Progress in Drug Research vol. 11, E. Jucker, Ed. (Birkhaüser Verlag, Basel, 196

 pp 11-47; G. J. Kapadia, M. B. E. Fayez, J. Pharm. Sci. 59, 1699-1727 (1970).
Properties:  Crystals, mp 35-36°.  bp12 180°.  Moderately sol in water; sol in alcohol, chloroform, benzene.  Practically insol in ether, petr ether.  Takes up CO2 from the air and forms a crystalline carbonate.  LD50 i.p. in rats:  370 mg/kg (Speck).
Melting point:  mp 35-36°
Boiling point:  bp12 180°
Toxicity data:  LD50 i.p. in rats:  370 mg/kg (Speck)
Derivative Type:  Hydrochloride 
Molecular Formula:  C11H17NO3.HCl
Molecular Weight:  247.72.  
Percent Composition:  C 53.33%, H 7.32%, N 5.65%, O 19.38%, Cl 14.31%
Properties:  Needles, mp 181°.  Sol in water, alcohol.  LD50 in mice, rats, guinea pigs (mg/kg):  212, 132, 328 i.p. (Hardman).
Melting point:  mp 181°
Toxicity data:  LD50 in mice, rats, guinea pigs (mg/kg):  212, 132, 328 i.p. (Hardman)
Derivative Type:  Sulfate dihydrate 
Molecular Formula:  (C11H17NO3)2.H2SO4.2H2O
Molecular Weight:  556.63.  
Percent Composition:  C 47.47%, H 7.24%, N 5.03%, O 34.49%, S 5.76%
Properties:  Prisms, mp 183-186°.  Sol in hot water, methanol; sparingly sol in cold water, ethanol.
Melting point:  mp 183-186°
Derivative Type:  Acid sulfate 
Molecular Formula:  C11H17NO3.H2SO4
Molecular Weight:  309.34.  
Percent Composition:  C 42.71%, H 6.19%, N 4.53%, O 36.20%, S 10.37%
Properties:  Crystals, mp 158°.
Melting point:  mp 158°
Derivative Type:  N-Benzoylmescaline 
Properties:  Needles from aq alc, mp 121°.  Very sol in alcohol, ether.
Melting point:  mp 121°
Derivative Type:  N-Methylmescaline 
Properties:  Occurs naturally, bp 130-140°.
Boiling point:  bp 130-140°
Derivative Type:  N-Acetylmescaline 
Properties:  Occurs naturally, mp 94°.
Melting point:  mp 94°
NOTE:  This is a controlled substance (hallucinogen):  21 CFR, 1308.11. 
"There are no differences but differences of degree between different degrees of difference and no difference."