5765. MDA

Nomenclature

CAS number: 4764-17-4
α-Methyl-1,3-benzodioxole-5-ethanamine; 3,4-methylenedioxyamphetamine; 3,4-methylenedioxy-α-methyl-β-phenylethylamine; 3,4-methylenedioxyphenylisopropylamine; “Love”; EA-1299.
C10H13NO2; mol wt 179.22.
C 67.02%, H 7.31%, N 7.82%, O 17.85%.

Description and references

Entactogen; synthetic amphetamine derivative with stimulant and hallucinogenic properties. Metabolite of MDMA, q.v. Prepn: C. Mannich, W. Jacobsohn, Ber. 43, 189 (1910); U. Braun et al., J. Pharm. Sci. 69, 192 (1980). Pharmacology: L. E. Markert, D. C. S. Roberts, Pharmacol. Biochem. Behav. 39, 569 (1991); K. M. Hegadoren et al., Psychopharmacology 118, 295 (1995). HPLC determn in whole blood: R. E. Michel et al., J. Neurosci. Methods 50, 61 (1993). GC/MS determn in hair: P. Kintz et al., J. Chromatogr. B 670, 162 (1995). Acute toxicity studies: P. N. Thiessen, D. A. Cook, Clin. Toxicol. 6, 193 (1973); H. F. Hardman et al., Toxicol. Appl. Pharmacol. 25, 299 (1973). Review of toxicity, mechanism of action, and psychoactive effects: R. P. Climko et al., Int. J. Psychiatry Med. 16, 359-372 (1986-1987).

Chemical structure

Properties

Almost colorless oil. bp22 157°. bp0.2 80-90°.

Derivative

Hydrochloride.

Nomenclature

CAS number: 6292-91-7
C10H13NO2.HCl; mol wt 215.68.
C 55.69%, H 6.54%, N 6.49%, O 14.84%, Cl 16.44%.

Properties

Crystals from isopropanol/ether, mp 187-188° (Braun); also reported as mp 180-181° (Mannich, Jacobsohn). Easily sol in water, alcohol. LD50 in mice, rats, guinea pigs (mg/kg): 68, 27, 28 i.p. (Hardman).

Note

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