Mescaline
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. Chem. 40, 129 (1919); K. H. Slotta, H. Heller, Ber. 63, 3029 (1930); E. Späth, F. Becke, Monatsh. Chem. 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, 1968) 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: 556.62
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.

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