5767. MDMA

Nomenclature

CAS number: 42542-10-9
N,α-Dimethyl-1,3-benzodioxole-5-ethanamine; (±)-3,4-methylenedioxymethamphetamine; N-methyl-3,4-methylenedioxyphenylisopropylamine; “Ecstasy”; “E”; “XTC”; “Adam”.
C11H15NO2; mol wt 193.24.
C 68.37%, H 7.82%, N 7.25%, O 16.56%.

Description and references

Entactogen; N-methyl derivative of MDA, q.v. (S)-Form possesses more potent CNS activity. Prepn: DE 274350 (1914 to E. Merck), C.A. 8, 3350 (1914); U. Braun et al., J. Pharm. Sci. 69, 192 (1980). Spectral and chromatographic analyses: K. Bailey et al., J. Assoc. Off. Anal. Chem. 58, 62 (1975). GC/MS determn in urine: B. K. Gan et al., J. Forensic Sci. 36, 1331 (1991). HPLC determn in whole blood: R. E. Michel et al., J. Neurosci. Methods 50, 61 (1993). Acute toxicity study: H. F. Hardman et al., Toxicol. Appl. Pharmacol. 25, 299 (1973). Series of articles on history, pharmacology, and neurotoxicity: Ann. N.Y. Acad. Sci. 600, 601-715 (1990). Review of biochemical actions: M. Rattray, Essays Biochem. 26, 77-87 (1991); of pharmacology, toxicology, and human experience: T. D. Steele et al., Addiction 89, 539-551 (1994); A. R. Green et al., Psychopharmacology 119, 247-260 (1995); H. Kalant, Can. Med. Assoc. J. 165, 917-928 (2001).

Chemical structure

Properties

Oil, bp0.4 100-110°.

Derivative

Hydrochloride.

Nomenclature

CAS number: 64057-70-1
C11H15NO2.HCl; mol wt 229.70.
C 57.52%, H 7.02%, N 6.10%, O 13.93%, Cl 15.43%.

Properties

Crystals from isopropanol/n-hexane, mp 147-148° (Bailey). Crystals from isopropanol/ether, mp 152-153° (Braun). uv max (ethanol): 286 nm (ε 3843). LD50 in mice, rats, guinea pigs (mg/kg): 97, 49, 98 i.p. (Hardman).

Note

This is a controlled substance (hallucinogen): 21 CFR, 1308.11.